32789 Zip Code FL 2 Bedroom Real Estate, Homes, Condos for Sale

693 Minnesota Avenue Unit 693, Winter Park

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated second-floor corner unit nestled within the sought-after Aragon Condominium community in the heart of Winter Park. This bright and airy two-bedroom, one-bath home offers a perfect blend of comfort, style, and convenience. Step inside to discover freshly painted interiors and elegant laminate flooring that flows seamlessly throughout the space. The galley-style kitchen offers a functional layout and opens to a spacious living and dining area—ideal for both relaxed evenings at home and entertaining guests. Natural light fills the open-concept living space, while the cozy front patio invites you to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are generously sized with pool view and feature built-in closets for easy organization, while a hallway closet adds extra storage for linens or household essentials. The bathroom features modern finishes and thoughtful design, with a shower and tub. The Aragon community offers a host of amenities designed for easy living, including a tranquil central courtyard, a sparkling community pool, on-site laundry facilities, and ample parking with both assigned and guest spaces. Located in one of Winter Park’s most vibrant neighborhoods, this condo is just steps from shopping centers, grocery stores, restaurants, and retail boutiques. With quick access to I-4 and nearby parks, it offers both a peaceful retreat and a connected urban lifestyle. Whether you’re a first-time buyer, downsizing, or searching for an ideal investment opportunity, this delightful home provides the perfect combination of charm, location, and livability.

851 Miles Avenue Unit 8, Winter Park

$1,245,000

2 Beds ⋅ 2 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Come see this outstanding 15,000 sqft lot surrounded by multi-million dollar homes on one of Winter Parks picturesque tree lined brick streets just a short drive from Park Avenue. This property offers the option of updating and remodeling the existing charming 1,683 sqft 2 bedroom, 2 bath Cottage located on the property or building your dream home in one of the most beautiful residential areas that Winter Park has to offer. You will live just minutes away from top rated schools, healthcare, restaurants and shopping and just a few minutes' drive to boat ramp access to Winter Parks famous chain of lakes.

171 Cortland Avenue, Winter Park

$675,000

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Attention builders and investors! Here’s your chance to own a prime property in the coveted Tree Streets of Winter Park, one of Central Florida’s most desirable neighborhoods. Whether you’re looking for immediate rental income or planning to build your dream home in the future, this opportunity is not to be missed! Tucked away just minutes from Phelps Park, the Winter Park YMCA, Lake Knowles, and top-rated Lakemont Elementary, this home is ideally located for both convenience and lifestyle. Enjoy peaceful neighborhood strolls, bike rides to the boutiques and cafés of Park Avenue, or weekend outings at the Winter Park Farmers’ Market. Living here means being immersed in the charm and culture that makes Winter Park so special—historic homes, scenic lakes, a vibrant arts scene, and a strong sense of community. Step inside to find a well-maintained home full of character. Original hardwood floors bring warmth and timeless appeal to the living areas and bedrooms. A versatile bonus room offers endless possibilities—use it as a home office, playroom, gym, or cozy den. Outside, the backyard is made for Florida living, with a screened-in patio perfect for al fresco dining and a spacious yard ideal for gardening, entertaining, or weekend fun. Whether you're investing, living in, or planning to build new, this property offers exceptional potential in a premier location. Don’t miss your chance to become part of the Winter Park lifestyle!

1511 Chestnut Avenue, Winter Park

$530,000

2 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Investor / Builder special!! Prime land opportunity located just minutes from Park Avenue. Don't miss your chance to build your custom home in this highly desirable area, surrounded by multi-million dollar homes. Value is in the land. Schedule your showing today!

2525 Lafayette Avenue, Winter Park

$434,000

2 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Welcome to 1122 Washington Avenue – a delightful 2-bedroom, 2.5-bath townhome located in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue, Rollins College, the Winter Park Tennis Center, and the brand-new Seven Oaks Park, this home offers the perfect blend of lifestyle and location. This area is undergoing tremendous transformation, especially along the revitalized Orange Avenue corridor, with exciting new shops, galleries, restaurants, and community spaces opening regularly. It’s a rare opportunity to live in a neighborhood that blends established charm with vibrant new growth. The home has been freshly painted and offers a bright, clean interior that’s ready for your personal touch. With tons of potential for upgrades and customization, you can truly make this space your own. Both bedrooms feature en-suite baths, and the open living area offers great flow for entertaining. A 2-car garage with driveway provides valuable convenience and storage. Enjoy low-maintenance living in a location that continues to grow in value and appeal. Whether you’re looking for a primary residence, a lock-and-leave second home, or an investment in the future of Winter Park, this is an opportunity you won’t want to miss.

1122 Washington Avenue Unit 7, Winter Park

$489,020

2 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Here is the opportunity to own this beautiful remodeled bungalow in the desirable town of Winter Park. This meticulously maintained two-bedroom, 1.5-bath home is just steps from Hannibal Square and Park Avenue. Enjoy the convenience of Rollins College, shopping, dining and vibrant nightlife, all within short distance. Enter inside this charming bungalow to discover a newly updated kitchen that features granite countertops, stainless steel appliances and a center island. The enclosed Florida room is off the kitchen and is where you will entertain or just relax, as it provides sun all day. The fully fenced yard creates a delightful retreat, and the turf grass requires no maintenance but provides a year-round manicured look. In 2023, significant enhancements were made, including addition of a new rear deck and a new front porch, further enhancing the overall charm and appeal of the property. The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019.

674 Douglas Avenue, Winter Park

$234,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of paint. Central heat/air was also added by the current owner to the screened in patio/balcony, including a closed off air duct to the balcony/patio, should you want to enclose the area. With a partial lake view from the patio, all you have to do to embrace nature is step outside your front door. This unit includes 1 parking space and visitor parking as well. Other amenities include the community pool, which overlooks Lake Killarney, a private loading dock for the boating expert in you, shuffleboard courts, grilling stations, and scenic outdoor seating areas, perfect for picnics, romantic sunsets, and daily meditation. HOA options for boat parking and dedicated kayak storage based upon availability. Located next door to Trader Joe’s and across from Winter Park Village, this condo offers convenient access to premier shopping, dining, and entertainment. Take a boat ride to Hillstone for happy hour or a delicious meal, relax in the pool while watching the sunset, or read a book under one of the park trees. Book your showing today and begin your ultimate lake life living!

151 N Orlando Avenue Unit 204, Winter Park

$275,000

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Great Opportunity in Prime Location! Price adjustment below appraised value. Located just off the Fairbanks Avenue exit from I-4, this charming 2-bedroom, 1-bath fixer-upper sits on a generous 7,000 sq ft lot in a quiet, convenient neighborhood. With original hardwood floors in the living area and bedrooms, this home is full of character and ready for your personal touch. The enclosed front porch has been vented for A/C, creating a light-filled sunroom and entry foyer—perfect for a relaxing morning coffee or casual sitting area. The garage has been converted into a functional bonus room/office space and a large laundry but could easily be restored to a traditional garage if desired. The kitchen offers space for a small dining table, and the original tiled bathroom remains in great condition, preserving the home’s vintage charm. Many of the windows have been updated, enhancing both aesthetics and energy efficiency. The large backyard features a concrete pad with existing electrical service, ideal for a future shed, workshop, or outdoor living area. Recent major updates make this home even more attractive: New Central A/C installed in May 2023. $10,000 in crawl space improvements (vapor barrier, dehumidifiers, drainage matting, and new access door), with a transferable service plan. Whether you're looking to renovate, invest, or build new, this property offers flexible options in a rapidly appreciating area. Tear down and build your dream home, or restore this cottage to its former charm—the choice is yours. Don’t miss out—schedule your showing today!

849 Driver Avenue, Winter Park

$780,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$535,000

2 Beds ⋅ 1 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience. Upon entering this residence, you are greeted with a bright and open living area accentuated by abundant wide-plank oak hardwood flooring and complete with features such as crown molding, a Nest thermostat, recessed lighting, and plantation shutters. The primary bedroom provides ample space and natural lighting, while the updated kitchen boasts modern finishes, including new quartz countertops & backsplash, stainless steel appliances, and an induction oven. The bathroom has been upgraded with Kohler fixtures and porcelain tile. For added convenience, the home includes an in-unit washer and dryer, as well as a balcony providing access to the scenic views and spacious grounds. The electrical panel box has been updated, along with new electrical outlets throughout. Residents can enjoy the community's numerous amenities, including a heated pool, hosting events in the renovated social room with a full kitchen, boat dock, and putting green, all set against the tranquil backdrop of Lake Osceola. The association dues include cable TV, building insurance, internet, maintenance (grounds, exterior, pool), on-site management, sewer, trash collection and water, providing a maintenance-free lifestyle. Additional highlights include an assigned covered parking space, storage room and a lakefront seating area. This sophisticated condominium creates a welcoming and refined atmosphere, making this an ideal residence. The location is conveniently located within walking distance to the vibrant Park Avenue, offering access to boutique shopping, dining, Rollins College and the renowned Morse Museum.

100 S Interlachen Avenue Unit 410F, Winter Park

$217,500

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all overlooking the spacious great room. One of the property's standout features is the spacious private balcony overlooking the lush beauty Mead Gardens. The balcony offers privacy and tranquility as there are no rear neighbors. The primary suite offers a peaceful garden view, an ensuite bath with walk-in shower and a single vanity. The second bedroom features sliding doors to the front entry and has easy access to a full guest bathroom with a tub/shower combo. Residents enjoy access to a sparkling community pool, laundry facilities, and mailboxes just steps away. Enjoy this prime Winter Park location, located just minutes from Park Avenue and Rollins College.

1250 S Denning Drive Unit 230, Winter Park

$632,100

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

This beautifully updated 2-bedroom, 2-bathroom corner unit is located in the highly desirable Winterset Condominiums on East Canton Avenue, just one block from Park Avenue in the heart of Winter Park. The unit features hardwood floors, crown molding, plantation shutters, and an open floorplan filled with natural light. The kitchen is fully upgraded with GE stainless steel appliances, a wine fridge, soft-close cabinets, and quartz countertops. Additional highlights include a programmable thermostat, updated lighting and ceiling fans, and a private storage unit on the same floor. Offered fully furnished with designer pieces, the unit also includes an assigned covered parking spot and access to the community’s pool. Winterset is an owner-occupied building; no rentals or pets are permitted. Live the ultimate Winter Park lifestyle - just steps from Rollins College, the Winter Park Golf Course, beautiful lakes, and top-tier dining, shopping, and more. Rarely available - schedule your private showing today!

225 E Canton Avenue Unit 225, Winter Park

$570,000

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless charm. Inside, you’ll find a beautifully designed open-concept kitchen ideal for entertaining, two spacious primary suites—each with its own spa-inspired en-suite bathroom—and a bonus office space with sweeping lake views that make working from home feel like a retreat. From top to bottom, every detail has been thoughtfully curated for both comfort and style. Step outside to your private covered patio and soak in postcard-worthy sunsets, or head down to the dock for a quiet moment by the water. The community offers a serene lakeside pool, very low HOA fees, and a laid-back lifestyle just minutes from some of Winter Park’s best shopping and dining. Come discover a one-of-a-kind home where lakefront tranquility meets urban convenience—this is Winter Park's best kept secret.

640 Killarney Bay Court Unit 4, Winter Park

$520,000

2 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

***Premier Land Opportunity on Lafayette Avenue, Winter Park, FL** Take advantage of an exceptional opportunity to own a prime piece of land in the highly desirable area of Winter Park, FL. This 7,734 sq. ft. lot on Lafayette Avenue offers an unparalleled chance to build the custom home of your dreams in one of Central Florida's most sought-after neighborhoods. With generous dimensions and favorable R-1A zoning, this lot is ideal for constructing a spacious custom home. Prospective builders can fully utilize the lot's potential, creating a luxurious residence tailored to modern trends and requirements. Winter Park is a vibrant community known for its rich history and lively present. The area has seen a home appreciation of 23% over the last two years, making it an excellent investment opportunity. It offers the perfect setting for both growing families and professionals seeking a blend of comfort and convenience. Winter Park residents enjoy various amenities, including access to top-notch schools, abundant parks, and a dynamic downtown area filled with shops, Michelin-star restaurants, and cultural venues. The location is also ideal for those looking for a safe, walkable community. Don’t miss this chance to collaborate with our preferred custom home builders to bring your vision to life. Your future of luxury living in Winter Park awaits on Lafayette Avenue. --

2507 Lafayette Avenue, Winter Park

$1,450,000

2 Beds ⋅ 1 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Sold for Data Purposes Only.

141 W Lake Sue Avenue, Winter Park

$175,000

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

2500 Lee Road Unit 208, Winter Park

$260,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader Joes, Hillstone's and across the street from Winter Park Village! Lakefront Winter Park Condo Community Ground Floor Remodeled 2 Bedroom 1 Bath Condo, Remodeled Kitchen and Bath, Includes Washer Dryer Inside Unit. Wood Look Laminate and Tile Floors. Lake Front Amenities, Boat Launch, Pool, Shuffleboard, Park Like Setting on Lake Killarney. This property also has Fitness and Recreation Facilities Onsite. Across the street from Winter Park Village for all your shopping & dining needs. Just a few minutes to Park Avenue and I4.

151 N Orlando Avenue Unit 115, Winter Park

$259,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

LOCATION LOCATION!! Now is your chance to own this STUNNING NEWLY RENOVATED 2 bed / 2 full bath FIRST FLOOR condo in the highly desirable MEAD GARDEN COMMUNITY within WALKING/BIKING DISTANCE to Rollins College and the Park Ave Area! This unit was recently renovated to include it's own DEDICATED LAUNDRY CLOSET! (2024) WASHER/DRYER COMBO INCLUDED! NEW ROOF (2022) NEW WATER HEATER (2024) This beautiful condo features an OPEN CONCEPT floor plan with lots of NATURAL LIGHT and UPDATED FINISHES! The bright and airy kitchen features UPGRADED QUARTZ COUNTERTOPS and STAINLESS STEEL APPLIANCES. New DOUBLE PANE & LOW-E WINDOWS (2021) Step through the SLIDING GLASS DOORS out onto your SCREENED PATIO offering GORGEOUS VIEWS of the COURTYARD GARDEN or take a dip in the HEATED COMMUNITY POOL just steps away. FRESHLY PAINTED INTERIOR! There is also a LAUNDRY FACILITY located next to the pool. The community offers DEDICATED BIKE STORAGE, as well as a 3 cubit feet STORAGE AREA FOR EACH UNIT. Each unit has an ASSIGNED PARKING SPACE plus plenty of VISITOR PARKING AVAILABLE! With MEAD GARDENS RIGHT BEHIND THE COMPLEX, you’ll have access to some of the BEST WALKING PATHS in Winter Park. CONVENIENTLY LOCATED between Trader Joe's, Winter Park Village, Ivanhoe Row, and Mills restaurants, and just a short distance to Park Avenue, Winter Park Tennis Center, Seven Oaks Park, and Rollins College. Cats are allowed! This condo won't last long, so call to schedule your private showing today!

1250 S Denning Drive Unit 111, Winter Park

$243,800

2 Beds ⋅ 3 Baths ⋅ Sandalwood Creek Condo Ph 04 SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Dreams Do Come True! FHA, VA, and DPA approved, making it a smart choice for a wide range of buyers. Welcome to your next home in the heart of 32789—Winter Park’s hidden gem, Sandlewood Creek! This rare townhome-style condo offers unbeatable value in a prime location with NO neighbors above or below and a LOW HOA. Step inside and enjoy nearly 1,000 sq. ft. of comfortable living space with an open floorplan, tile flooring downstairs, a large kitchen, and a convenient half-bath and laundry area with washer and dryer included. The 2021 Lennox HVAC system keeps things cool and efficient year-round. Upstairs, you'll find two spacious bedrooms with plush carpeting, and two full bathrooms, making this home as practical as it is inviting. Step outside to your private fenced patio—perfect for relaxing or entertaining. The Sandlewood Creek community is well-maintained and features a sparkling pool for your enjoyment, all while offering a low-maintenance lifestyle. Located just minutes from Park Avenue, Downtown Maitland, and top-tier shopping, dining, and entertainment, this home is also zoned for Dommerich Elementary, Maitland Middle, and Winter Park High—some of the most sought-after schools in the area. Affordable, move-in ready, and packed with value, this is a rare find in Winter Park you don’t want to miss!

255 Sandlewood Trail, Winter Park

$417,100

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Beautifully Renovated Lakefront Condo with Partial Lake Virginia & Downtown Views. Located just minutes from Park Avenue and Rollins College, this fully renovated condo offers stylish, maintenance-free living with partial views of Lake Virginia and the downtown skyline. The open-concept layout features a brand-new kitchen with quartz countertops, stainless steel Samsung appliances, recessed lighting, and an oversized island with bar seating. The spacious primary suite includes a private dressing area, three closets (including a walk-in with custom storage), and a beautifully updated en-suite bath with dual sinks and a walk-in shower. The guest bedroom has generous closet space and is served by a renovated bath with a soaking tub/shower combo. Three additional hallway closets also has exceptional storage. Additional updates include new central A/C, new hot water heater, new flooring throughout, and an in-unit washer and dryer. Community amenities include: a lakefront pool and hot tub, boat dock, fitness center, kayak storage, fire pit, bike storage, elevator, and reserved covered parking. Don’t miss this rare opportunity to own a modernized lakefront unit in one of Winter Park’s most desirable locations!

690 Osceola Avenue Unit 502, Winter Park

$575,000

2 Beds ⋅ 1 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original hardwood flooring in the spacious living room as well as both bedrooms. The hall bathroom has been updated with a new vanity, granite countertop, and marble tile. The well-appointed kitchen has Italian travertine flooring, Shaker-style 42" wood cabinets, granite countertops with an under-mount sink bowl, and beautiful stainless-steel appliances. Just off the kitchen is a cozy dining room which is perfect for family gatherings. New roof in (2021) and a 1 car garage! The property is zoned for top rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Surrounded by Muti-Million Dollar homes this is a rare opportunity to move in now and wait for future appreciation, add on, or maximize the value of the land and build your dream home. The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today!

1230 N Denning Drive, Winter Park

$375,000

2 Beds ⋅ 1 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive to Park Maitland School and zoned Princeton Elementary School. The existing single family structure is being offered as is and the owner has no previous information on the home. Demolition date is now scheduled for 4/24/2025. 20k impact fee credit/verify exact when pulling new permit

2259 Minnesota Avenue, Winter Park

$540,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Situated in a prime location, this condominium presents an excellent opportunity for customization and renovation. Sold as-is, this residence offers a spacious layout with ample potential to reimagine its interiors to suit modern living. Positioned within The Cloisters sought-after community, residents enjoy access to desirable amenities and a convenient setting near shopping, dining, and local attractions. A rare chance to transform and tailor a space to individual preferences.

100 S Interlachen Avenue Unit 415, Winter Park

$412,000

2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code

Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

535 N Interlachen Avenue Unit 107, Winter Park

$478,000

2 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 4th Add SubDv. ⋅ 32789 Zip Code

FSBO

2877 Euston Road, Winter Park

$939,000

2 Beds ⋅ 2 Baths ⋅ Cloisters The SubDv. ⋅ 32789 Zip Code

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

100 S Interlachen Avenue Unit 502D, Winter Park

$130,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

SPECIAL FINANCING AVAILABLE! First Horizon Home Start w/ Diversity Grant available for this home while funds last. This grant funds up to 100% LTV, no PMI, Minimum borrower contribution of $500, and diversity grant of $8,000 (with no repayment) for an affordable home in a prime location? This budget-friendly 2-bedroom, 1-bath condo is move-in ready! Freshly painted ceilings, walls, trim, doors, and even a refreshed bathtub and tile give the space a bright and updated feel. Step out onto the shaded back deck, where a beautiful tree provides the perfect spot to unwind and enjoy Florida’s amazing weather or take a short walk to the community pool and club house. You can’t beat this location! With easy access to I-4, commuting is a breeze—whether you're heading to downtown Orlando, the beaches on either coast, two international airports, or world-famous attractions like Disney, Universal, SeaWorld, Legoland, and more. Don’t miss out on this opportunity! Call today to schedule your showing.

1695 Lee Road Unit E205, Winter Park

$260,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

This spacious 2-bedroom, 2-bathroom condo awaits you in a vibrant community. The mid-century modern complex offers the convenience of a community pool, on-site laundry, and picturesque pond views while being centrally located near Downtown Orlando, Downtown Winter Park, and Mead Gardens. Embrace a comfortable and active lifestyle in this desirable residence

700 Melrose Avenue Unit B-4, Winter Park

$411,250

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained Winter Park gem, offering exceptional curb appeal and bursting with charm, character and timeless style. Located in the highly desirable Dubsdread Heights neighborhood, bordering Little Lake Fairview and the Dubsdread Golf Course, this home places you just minutes from the boutique shops, dining options and festivals of Park Avenue, with easy access to I-4. As you step inside, you're greeted by a bright sunroom with warm, stylish Saltillo tile flooring which seamlessly flows into the spacious living room featuring stunning Red Oak hardwood floors. The eat-in kitchen boasts sleek quartz countertops, modern cabinets with crown molding, a built-in pantry with convenient slide-out drawers and newer appliances. This home has been thoughtfully updated with double-paned windows, a 2018 roof replacement and updated plumbing, ensuring peace of mind for years to come. Both bedrooms are generous in size and feature Red Oak wood flooring and modern ceiling fans, with a full bath conveniently situated in between that retains timeless charm with original custom tiling, a pedestal sink, and shower/tub combo. The private, fully fenced backyard is a true tropical retreat, perfect for relaxation or entertaining guests. The recently replaced wood deck with sail awnings and a concrete patio create ideal spaces to enjoy Florida's year-round beauty. A charming brick paver walkway leads to a separate laundry and storage shed, with additional cabinets and space to meet your storage needs. This home has gutters installed along with a rain barrel designed to capture and conserve water for your landscaping watering needs. Kitchen appliances, washer, dryer and lawn mower, edger, and blower are all included in sale. Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park!

767 Baffie Avenue, Winter Park

$380,000

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

350 Killarney Bay Court Unit 5, Winter Park

$635,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Fresh, modern and move-in ready. This pristine, first-floor condo is located in historic downtown Winter Park at the coveted Cloisters Condominiums. Professionally designed and remodeled in 2021, this two-bedroom, two-bathroom unit includes an open floor plan with marble tile throughout and a screened patio with built-in planters and mature garden views. The large, open kitchen includes a family-sized island with seating and storage, stone countertops, new cabinetry and stainless-steel appliances, and Clearly® water filtration system. Timeless features include southern plantation shutters, wainscoting and hand-carved ceiling fans in every room, plus spa-inspired bathrooms, custom closets and plenty of storage, and a full-sized Bosch washer and dryer. The frosted glass barn door glides shut for your master suite retreat overlooking internal garden courtyard. Unit comes with assigned covered parking and air-conditioned storage closet. The Cloisters lifestyle boasts lakefront seating, docks, kayak storage and boat slips; workout rooms, Swedish dry sauna and inside bike storage; a newly remodeled club house with full kitchen, lending library, putting green, grill station and pool; professional on-site management and custodial staff—all set within established landscaping for unparalleled leisure. Unit 111 is light, bright and quiet. Being on the ground floor, this unit is perfect for those with a pet. Offered at under $700K with optional turnkey package available. Welcome home.

100 S Interlachen Avenue Unit 111, Winter Park

$429,000

2 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

ATTENTION INVESTORS!!! DIAMOND LOCATION!! THIS IS THE MOST WONDERFUL OPORTUNITY FOR BUYING YOUR DREAM DUPLEX WITH 1 BED 1 BATH ON EACH OF TWO FLOORS IN THE MOST DISERABLE AREA FOR LIVING CALLED WINTER PARK IN THE 32789 ZIDE CODE. NO HOA NEITHER CDD. IT IS LOCATED JUST MINUTES FROM PARK AVE., ROLLING COLLEGE, AND TONE OF RESTAURANTS!! EACH UNIT HAS 1 BED 1 BATH WITH ITS COZY KITCHEN, AND NICE FAMILY ROOM. THIS DUPLEX HAS A ENORMEOUS POTENTIAL INCOME. GREAT SCHOOLS!!, NEAR TO HIGH-WAYS!! RIGHT PRICE!! IT WILL NOT LAST LONG!!

441 Clay Street, Winter Park

$685,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where expansive windows frame picturesque views of the lush gardens and pool, creating an inviting ambiance throughout the living space. Rich wood floors flow gracefully through the open layout, enhancing the home’s warm and sophisticated character. The primary suite is a private haven, featuring custom-built cabinetry and drawers, a dressing area with abundant closet space and a beautifully updated en-suite bath. A dedicated laundry closet with a built-in washer and dryer adds everyday convenience. The second bedroom offers a custom-built office setup and dual access from the hall and living area, providing effortless versatility as a bedroom, sitting room or private study. The Cloisters offers an array of exclusive amenities designed to elevate everyday living. Guest parking is immediately below the unit in the forward parking circle, as well as along Morse Boulevard, ensuring seamless accessibility for visitors. Additional perks include an assigned covered parking space near the elevator, a dock with boat slips available for lease, two well-appointed fitness rooms, and a beautifully redesigned community space featuring a newly remodeled kitchen and bath. Just steps from the vibrant energy of Park Avenue, this exceptional home provides unparalleled access to fine dining, boutique shopping, cultural attractions, fitness centers and the distinguished Rollins College. Every detail has been carefully curated to create an extraordinary living experience in the heart of Winter Park. Seize this rare opportunity to own a desirable residence at The Cloisters, schedule your private tour today and embrace a home where elegance meets effortless living.

100 S Interlachen Avenue Unit 203, Winter Park

$224,999

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Condominium Association, Inc. SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.

2500 Lee Road Unit 202, Winter Park

$305,000

2 Beds ⋅ 3 Baths ⋅ Sandalwood Creek Condo Ph 01 SubDv. ⋅ 32789 Zip Code

Completely Renovated from Top to Bottom – Best Value in Winter Park! Welcome to this stunning 2-bedroom, 2.5-bathroom condo has been fully renovated from top to bottom, offering modern style, comfort, and unbeatable value in one of Winter Park’s most desirable locations. It is situated more as a townhome, so you will never have to worry about neighbors above or below you. Every inch of this home has been updated, including brand-new luxury vinyl plank flooring, fresh interior paint, modern cabinetry, quartz countertops, and fully remodeled bathrooms with sleek new finishes. The kitchen shines with new stainless steel appliances, while the entire home is brightened by all-new recessed lighting and stylish light fixtures. Major upgrades like a new HVAC system, new plumbing, and a new water heater ensure worry-free living. All for a reasonable HOA, you get to enjoy a well-run community with a community pool, and a hassle-free low maintenance lifestyle. Located just minutes from Park Avenue and Downtown Maitland, you’ll have premier shopping, dining, and entertainment at your fingertips. Plus, it's zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. This is one of the most affordable, move-in-ready homes in Winter Park—a rare find in today’s market. Don’t miss out—schedule your private showing today!

311 Sandlewood Trail Unit 4, Winter Park

$230,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in 2018-2019, New Appliances within last 5 years. Spacious Room Sizes, Private Balcony. Perfect location! Easy walk to Shopping, Restaurants, Movie Theater, close to Park Avenue and Farmers Market, minutes to I-4. One of Winter Park's best kept secrets! Don't miss this opportunity to view and own in this lovely community!

1500 Gay Road Unit 10C, Winter Park

$385,000

2 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet street yet just minutes from downtown Winter Park, College Park, and downtown Orlando, this beautifully updated 1955 ranch offers the perfect blend of peaceful living and urban convenience. With 2 bedrooms, 2 baths, and 1,262 square feet of thoughtfully renovated space, this home is move-in ready and full of character. As you enter, you’re greeted by a large, open living space that’s filled with natural light from the many windows. The spacious living room flows seamlessly into the dining area, making it perfect for both everyday living and hosting gatherings. The recently renovated kitchen is the heart of the home, showcasing sleek gray shaker cabinetry, black stainless steel appliances, quartz countertops, and a Mediterranean tile floor. It’s a bright and functional space where cooking and entertaining come together. The kitchen opens to the dining area, which leads out to a massive paver patio and a large, fully fenced backyard—ideal for outdoor relaxation, grilling, or even future expansion. The master bedroom is generously sized with space for a king-sized bed and features a built-in closet. A small but mighty ensuite bathroom with original vintage pink and grey tile adds charm and character to this space. The second bedroom is perfect as a guest room, children’s room, or home office. The second bathroom also embraces the vintage aesthetic with its green and white tile, while the bathtub has been reglazed and is ready for your next soak. Built with durable concrete block construction, this home offers low maintenance and energy efficiency. The one-car garage, accessed from the kitchen, provides ample storage space and houses the laundry area. The HVAC system was replaced in 2019, ensuring comfort year-round. Repipe done in 2020. Water heater replaced in 2020. Located just minutes from Winter Park’s renowned dining, boutique shopping, and cultural attractions, as well as being close to AdventHealth, Downtown Orlando, and major highways, this home offers the perfect balance of suburban tranquility and urban accessibility. With thoughtful updates already completed, this home is ready for its new owner. Don’t miss out on this opportunity to own in one of Central Florida’s most desirable neighborhoods.

1930 Albert Lee Parkway, Winter Park

$280,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

HUGE PRICE CHANGE! Welcome to this beautifully updated second-floor unit, offering a fresh and modern living experience. Featuring brand-new luxury vinyl flooring, new appliances, granite countertops, as well as upgraded fans and light fixtures, this home combines style and comfort. Enjoy breathtaking, floor-to-ceiling pond views from the sunroom, creating the perfect spot to relax and unwind. The building has been fully replumbed for added peace of mind. CLICK ON VIRTUAL TOUR to get an overview of the complex. Nestled within over 8 acres of lush gardens, the complex boasts majestic live oaks, lighted walking paths, a serene pond, and a beautiful pool oasis – providing a tranquil, park-like setting. Winter Park Gardens is a vibrant 55+ community that also welcomes younger owners, offering an unparalleled location just a short walk from everything Winter Park has to offer. Come see why Winter Park Gardens is the best buy in Winter Park and experience the lifestyle you’ve been dreaming of!

700 Melrose Ave Unit A 22, Winter Park

$585,000

2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to 1424 Cavendish Road. This Beautiful 1940’s Pool Home is tucked between the tree-lined streets of highly desired, Orwin Manor, offering the perfect blend of classic appeal and modern convenience. Step into this charming home and experience its warm and inviting ambiance. The living room is bathed in natural light, with a cozy wood-burning fireplace that adds timeless character and comfort. Beyond, discover your personal backyard retreat—a serene oasis with mature landscaping, a spacious lounge area, and a private saltwater pool, perfect for summer relaxation. The refreshed kitchen is both stylish and functional, featuring granite countertops, newer appliances, updated sink and faucet, and GAS STOVE, complemented by an adjacent dining area. The two bedrooms are thoughtfully designed, separated by a fully remodeled bathroom boasting sleek modern tiles, a chic vanity, updated fixtures, and elegant lighting. This home also offers practical upgrades, including enhanced attic insulation, updated plumbing and electrical, natural gas, and a tankless water heater for endless energy-efficient hot showers. Every detail has been considered to blend modern convenience with timeless charm. Orwin Manor is one of Winter Park’s most cherished neighborhoods, known for its tree-lined streets, historic homes, and central location. Residents love the community’s proximity to Park Avenue, Downtown Orlando and College Park. Enjoy the convenience of walking to Orange Avenue’s restaurants or take a quick drive to Park Avenue, Winter Park’s premier shopping and dining destination, where you can explore boutiques, favorite local restaurants, and charming coffee shops. For professionals, the location couldn’t be better. Major hospitals such as Advent Health Orlando and Orlando Health are within close proximity, providing excellent career opportunities and peace of mind for healthcare access. The area is also conveniently located near Downtown Orlando, making commutes to major corporate offices and job hubs a breeze. Experience the best of Winter Park living in a neighborhood that combines a serene suburban feel with the vibrancy of city life. Don’t miss the opportunity to make this Gem your new home!

1424 Cavendish Road, Winter Park

$704,700

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

JUST LISTED – Beautiful 2-bedroom end unit at Winter Park’s Park West Condominiums! Tastefully remodeled this spacious 1,544 SF home features an open floor plan with a split-bedroom layout. The home offers dark, engineered wood flooring throughout the common living rooms, comfortable ceiling height, glass sliders that open to Juliet balconies, and windows on 3 sides of the unit, allowing an abundance of natural light throughout the day. The kitchen has been updated and features white cabinetry, Quartz countertops, stainless steel appliances, and a bar top for seating. The primary bedroom is oversized and offers a large, private en suite complete with double vanities, a standalone shower, garden bath, and two separate walk-in closets with built-ins. The second bedroom is also generously sized and has direct access to a guest bath with a tub/shower combo. An interior laundry closet houses a full-size, side by side, washer and dryer, with built-in storage and shelving. Additional interior amenities include plantation shutters, updated light fixtures, newer HVAC (2023), and more. This unit also comes with one reserved parking spot in the under-building garage. Park West offers its residents exclusive use of a community pool, tennis courts, a recreation room/clubhouse, and gated access. Located just one-block from Park Avenue, this luxury condo is a very short walk to award-winning dining and boutique shops. This unit is gem and units of this quality hardly come on market – schedule your showing today.

350 Carolina Avenue Unit 301, Winter Park

$310,000

2 Beds ⋅ 1 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Charming 3-Bedroom Home in the Heart of Winter Park! Welcome to 2259 Minnesota Avenue, a well-maintained 2-bedroom, 1-bathroom single-family home offering 1,015 sq. ft. of cozy and functional living space in the highly sought-after Winter Park area. Step into this inviting home, where the thoughtfully designed layout ensures comfort and ease. The kitchen is equipped with modern appliances and spacious counters, making meal preparation a breeze. Each of the three bedrooms provides a comfortable retreat, and the home’s meticulous upkeep ensures it’s move-in ready. Situated minutes from Park Avenue, Winter Park’s vibrant hub of shopping, dining, and cultural attractions. The property features a yard space perfect for gardening, entertaining, or relaxing under the Florida sun. Close to top-rated schools, lush parks, and convenient transportation options. Take a scenic boat tour through the Winter Park Chain of Lakes or enjoy outdoor adventures at Mead Botanical Garden. Stroll through Park Avenue, known for its upscale boutiques, cafes, and the beautiful Central Park. Immerse yourself in art and history at the renowned Morse Museum of American Art or the Winter Park History Museum. This home is a rare find in one of Central Florida’s most desirable neighborhoods, offering a perfect blend of suburban tranquility and urban convenience. Don’t miss this opportunity to own a piece of Winter Park charm. Schedule your private tour today!

2259 Minnesota Avenue, Winter Park

$315,000

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

Welcome to 690 Osceola Avenue, a lakefront complex in the heart of Winter Park. This sleek, modern residence offers the perfect blend of contemporary design and convenient urban living, just minutes (less than a mile) from the charming shops, restaurants and cultural attractions of Winter Park's renowned Park Avenue. This two-bedroom, two-bath condominium has a private screened balcony with sliding doors off the family room and primary suite, offering a peaceful retreat for enjoying the Florida sunshine and picturesque views of the Fern Canal. As you enter the unit off the courtyard, you will enjoy the newly painted interior with hardwood floors in the dining room and kitchen. The kitchen boasts granite countertops, stone backsplash, a new refrigerator, double oven, microwave, double stainless steel sink and ample cabinets for storage. The generously sized primary suite features a walk-in closet and en-suite bath with shower. This unit also features an in-unit laundry with stackable washer/dryer for ultimate convenience. Lake Virginia condominiums offer a one-bedroom guest suite that can be reserved and rented for the night. Amenities include but are not limited to the following: lake access to Lake Virginia, pool with jacuzzi, private dock (boat slips are available via waiting list per HOA approval at an extra fee), fitness center, ground-floor covered parking (one assigned space per unit), recently updated clubhouse with kitchen, outdoor gas grill and fire pit, sauna room, storage racks for canoes, kayaks or paddleboards, a gated pet run for those dog lovers out there, plus water, trash, city sewer and basic cable. With easy access to major highways and just a short drive to downtown Orlando/attractions, this property is a must-see. Whether you're looking for a stylish home or a low-maintenance vacation property, 690 Osceola Avenue, Unit 209 offers everything you need to enjoy the best of Winter Park living. Don’t miss the opportunity to make this exceptional condominium your new home!

690 Osceola Avenue Unit 209, Winter Park

$500,000

2 Beds ⋅ 1 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Pure potential. Tear down, renovate or move-in. Prime Winter Park location walking distance to Audubon Park.

2842 Eastern Parkway, Winter Park

$1,900,000

2 Beds ⋅ 2 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Come see this outstanding 20,997 sqft lakefront lot located on beautiful Lake Sylvan in the heart of Winter Parks’s Sylvan Lake Shores neighbor. This is a very desirable 125 foot wide lot located on a peaceful, tree-lined brick street, surrounded by br high-end homes and offers a 130 foot wide view of the lake. This is the perfect lot to build your dream home on. Top rated schools, healthcare, restaurants and shopping are nearby and downtown Winter Park are just minutes away.

1441 Grove Terrace, Winter Park

$315,000

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

Seller motivated!!! **Prime Location & Endless Potential!** Fantastic opportunity to make it your own Oasis with some updating. Transform this condo with your personal design. Situated in Winter Park's most sought-after zip code, this spacious 2-bedroom, 2-bath lakefront condo is an incredible opportunity to create your perfect retreat. Enjoy your dock—ideal for a boat or paddle board—and unwind on the large side porch while taking in the serene surroundings. Community amenities include a refreshing pool, relaxing spa, and a fully-equipped gym. Plus, you’ll have the convenience of a designated covered parking. Best of all, you're just a short stroll from Park Avenue’s vibrant shops, dining, and entertainment. Don't miss out on this rare combination of location, lifestyle, and potential!

690 Osceola Avenue Unit 308, Winter Park

$575,000

2 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Multiple Offers, please submit highest and best by Friday 1/10 4pm. Charming Winter Park Gem with Exceptional Opportunities! Nestled in the heart of Winter Park, this classic bungalow offers an incredible opportunity to either move right in or redevelop into your dream home. Located just off Park Avenue and one of the last remaining original homes on Oaks Blvd, this home combines charming character with updated features. Step inside to find beautiful original hardwood floors that exude timeless elegance, while the updated kitchen and bath ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain. The carport features a laundry/storage area, adding even more functionality to the property. The home is topped with a durable metal roof, further enhancing its appeal. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision. Located just a short distance from Winter Park's best attractions, you'll enjoy proximity to the Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location. Don’t miss the chance to make this rare property your own!

1137 Oaks Boulevard, Winter Park

$230,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

NEW WINDOWS AND SLIDING GLASS DOOR JUST INSTALLED!!! Discover unparalleled comfort in this stunning 2-bed, 2-bath Condominium, nestled in the sought-after Winter Park community with frontage on Lake Killarney. Immerse yourself in luxury with a sparkling community pool and a host of recent upgrades that include upgraded flooring, kitchen cabinets, counter-tops, bathrooms, and more. Positioned on the first floor just steps away from Winter Park Village, Trader Joe's and Park Avenue! The property offers a community boat ramp and a fishing pier on Lake Killarney whcih allows for skiing and other water sports. This home also features a charming covered rear porch, inviting you to create lasting memories while enjoying those beautiful winter and summer nights. Your ideal haven awaits in this meticulously updated gem! The property will not last so don't miss your chance to make this home you own.

1500 Gay Road Unit 7A, Winter Park

$464,000

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

How wonderful would it be to live in a location where you felt you were on vaction everyday? This lovely condo near Park Avenue in Winter Park is just that. Thoughtful design is central to the interior of this condominium. Outside it boasts its own mini patio. It also has a very unususal, very desirable feture. It has its own first floor private entrance in close proximity to its personal parking space. No need to go through the lobby for this particular condo.

215 E Canton Avenue Unit 215, Winter Park

$425,000

2 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Discover the charm of this beautiful 3-bedroom home in the heart of Winter Park, one of the most desirable areas in Central Florida! • Bedrooms: 3 bedrooms, offering comfort and functionality. • Location: Situated on a serene street, providing the quintessential Winter Park lifestyle. • Roof: Recently replaced, ensuring long-term durability and peace of mind. • Fireplace: Cozy wood-burning fireplace, perfect for relaxing evenings. • Lot Size: Expansive lot with endless possibilities for outdoor living, gardening. This stunning home is a must-see! Perfect as a cozy retreat or an exceptional investment opportunity in a prime location. all the information is intended to be accurate and must be verified by buyers / realtor agent.

1550 Indiana Avenue, Winter Park

$1,650,000

2 Beds ⋅ 2 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Rare opportunity to own this exclusive 2 bedrooms / 2 bathrooms condominium within the highly sought after Villa Siena. Nestled in the heart of quaint downtown Winter Park, Fl this meticulously maintained, 2nd floor, condo has been elegantly updated. Interior features include a split plan floorplan, travertine flooring, bright kitchen with quartz countertops, Sub-Zero refrigerator and Wolf gas stove, breakfast bar, dining area with custom built-in bar and wine refrigerator, crown molding within the living room, primary suite and guest bedroom offer tray ceilings, recessed lighting, walk-in closets, and french doors that lead out onto private balconies overlooking the tree lined brick street and award winning Alfond Inn and Spa, new primary bathroom with dual sinks, separate tub and shower and Toto toilet, spacious utility room with cabinetry and wash sink. Villa Siena offers secured underground parking, Club room with bar and outdoor sitting area great for entertaining guests, fitness center, roof top terrace, conference room, guest parking, and an onsite property manager to assist with Resident needs. Steps to the charming Park Avenue shopping District known for it’s celebrated restaurants, boutique stores, Central Park, 9 hole golf course, museums, train station, and Rollins College. Welcome Home! Video Tour: https://youtu.be/AMDbRupc4GM

315 E New England Avenue Unit 9, Winter Park

$380,000

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Charming 2-bedroom, 1-bathroom single-family home located in the desirable Winter Park area! This beautifully maintained property offers 1,150 sq ft of living space, master closet (9 by 8.5ft) and features several recent updates, including brand-new bamboo hardwood floors throughout the interior. The spacious, fenced-in backyard is perfect for outdoor living, with a new wood decking patio for relaxing or entertaining. Enjoy peace of mind with a newer AC condenser and air handler, along with new kitchen appliances and fresh exterior paint. Additional highlights include a well-maintained septic system with regular pump service every 2 years, public water utilities, and an encapsulated crawl space with a dehumidifier, French drain, and sump pump for added moisture control. The roof is set to be replaced within the next 30-60 days, ensuring long-term durability. This home combines comfort and functionality in a prime Winter Park location—don’t miss out on the opportunity to make it yours!

830 Overspin Drive, Winter Park

$775,000

2 Beds ⋅ 2 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Charming Opportunity in the Heart of Winter Park - 1520 Palmer Avenue Nestled in the highly coveted 32789 zip code, this property presents a rare chance to own a large lot in one of Winter Park's most desirable neighborhoods. Surrounded by stunning homes and mature tree-lined streets, this prime piece of real estate is a blank canvas for your vision. The value is truly in the land—imagine building your dream home from the ground up or embarking on a rewarding remodel to create your very own HGTV-worthy masterpiece. The spacious lot offers endless possibilities for outdoor living spaces, lush landscaping, or even a custom pool. Located just minutes from top-rated schools, boutique shopping, dining on Park Avenue, and beautiful lakes, 1520 Palmer Avenue is perfectly positioned to enjoy all that Winter Park has to offer. Opportunities like this don't come often—schedule your private tour today and take the first step toward bringing your dream home to life!

1520 Palmer Avenue, Winter Park

$600,000

2 Beds ⋅ 1 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

FIRST TIME OFFERING! Charming Bungalow in the heart of Winter Park. 50’ x 150’ lot offers limitless possibilities! Convenient to Rollins College, Park Avenue and all that this special community has to offer. Just down the street, you'll find Lake Virginia, where residents of Antonette Avenue are included in access to a private dock accessing the Winter Park Chain of Lakes, offering opportunities for boating, fishing, and enjoying all of the natural beauty of the area. Sure to attract a lot of attention (as homes in this area don’t come up for sale often) seize the opportunity to make it your own!

786 Antonette Avenue, Winter Park

$670,000

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This lovely 2 bedroom/2-bathroom condo is in the newest building in gated community of Park West Winter Park. The unit has 9ft ceilings, crown molding, and beautiful hardwood floors, and a private office. The primary bedroom is spacious with a large walk-in closet. The bathroom includes a large soaker tub and a walk-in shower with dual vanities. The second bedroom utilizes the hallway bathroom, which is complete with a shower/tub combination. The kitchen has wood cabinets, granite countertops, and newer stainless steel appliances. There is one covered parking space and additional open parking spaces. The community amenities include a large clubhouse, pool, and tennis/pickleball courts. Located just one block from beautiful Park Avenue, you're just steps away from an array of upscale boutiques, gourmet restaurants, and cultural attractions. <iframe src="https://my.matterport.com/show/?m=WqHS8ffboym&brand=0&mls=1&" width="640" height="360" style="border: 0;" allow="fullscreen"></iframe>

350 Carolina Avenue Unit 304, Winter Park

$170,000

2 Beds ⋅ 3 Baths ⋅ Sandalwood Creek Condo Ph 01 SubDv. ⋅ 32789 Zip Code

**INVESTOR SPECIAL! Cash Only Opportunity! This 2-bedroom, 2.5-bathroom CONDO, built in 1984, is a diamond in the rough waiting for your personal touch! The Sandlewood Creek complex affords residents a community pool, assigned and guest parking, and is zoned for top rated schools. With an unbeatable location, amidst a vibrant environment, cultural events, and only a few minutes to the Winter Park Village, Park Avenue, Maitland, numerous shopping, dining, and entertainment options, and with easy access to the main thoroughfares and all that Central Florida has to offer, this condo offers a CONVENIENT LIFESTYLE! Whether you're looking to make this your home, renovate and flip or add to your rental portfolio, this property has INCREDIBLE POTENTIAL... an excellent investment opportunity in desirable WINTER PARK! Don't miss out on this chance to bring your vision to life. Act fast — schedule your private showing today!

311 Sandlewood Trail Unit 4, Winter Park

$465,000

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

Experience the best of lakeside living in this stunning 2-bedroom, 2-bathroom condo on beautiful Lake Virginia, part of the Winter Park Chain of Lakes. Just a short walk from Park Avenue, Rollins College, top-notch dining, and vibrant cultural spots, this sparkling 6th-floor condo offers serene treetop views overlooking the Fern Canal. The light-filled space was renovated in 2020 with a thoughtfully designed kitchen featuring white cabinetry, quartz countertops, and Bosch appliances. Additional upgrades include updated bathrooms, new piping and flooring, crown molding, and a premium hurricane-rated patio door. A new Trane air conditioner was added in July 2023. The Lake Virginia Condominium amenities include a dock, sauna, pool and spa with lake views, fire pit, gas grill, rentable guest suite, party room, dog walk, and storage for small watercraft. The HOA fee covers water, cable, and internet.

690 Osceola Avenue Unit 610, Winter Park

$975,000

2 Beds ⋅ 2 Baths ⋅ The Cloisters SubDv. ⋅ 32789 Zip Code

Set within Winter Park's prestigious Cloisters, this refined third-floor condominium offers a rare blend of elegance and modern comforts in a location that combines natural beauty with prime convenience. Lovingly transformed with luxurious upgrades, this open-concept residence invites abundant natural light and showcases exquisite details throughout. Step into a world of sophistication with herringbone-patterned hardwood floors, a chef's kitchen featuring top-of-the-line stainless steel appliances and stone countertops, and solid wood doors adorned with brass hardware for an added touch of timeless class. The Cloisters' thoughtfully curated amenities include a serene heated pool nestled in lush gardens, a clubhouse ideal for social gatherings, a private boat dock with slips, and a putting green for leisurely afternoons. Every element of this residence speaks to a lifestyle marked by tranquility and convenience, making it an ideal haven for those who seek a blend of sophistication and serenity in the heart of Winter Park.

106 S Interlachen Avenue Unit 316D, Winter Park

$190,000

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Super cute, move-in-ready 2-bedroom, 1-bath condo, perfectly situated in the heart of Winter Park. This first-floor end unit offers modern upgrades and unbeatable convenience, making it an ideal place to call home. Inside you will find the tastefully renovated space, featuring a brand-new AC unit, updated windows, and a hot water heater, all installed in 2023 to ensure year-round comfort and peace of mind. The kitchen boasts new stainless steel appliances, granite countertops, and walnut cabinetry. Enjoy abundant natural light through energy-efficient double-hung windows, and admire the beautiful tile flooring throughout. The property has one assigned parking spot located close to the unit, with ample parking around for guests. Onsite laundry steps away from the unit. The Community screened pool is the perfect spot to sit back and relax. This condo’s prime location puts you close to Publix, Agave Azul, Chick-Fil-A, and other popular dining options. You’ll also be just minutes from Trader Joe’s, Whole Foods, Winter Park Library, and the gorgeous Mead and Leu Botanical Gardens. Plus, with nearby access to Rollins College, Full Sail University, Valencia College, and top-rated schools, you’ll enjoy a perfect blend of tranquility and urban convenience. Don’t miss your opportunity to see this beautifully updated condo in one of Winter Park’s most desirable areas. Schedule your private tour today!

851 Miles Avenue Unit 15, Winter Park

$650,000

2 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Discover this unique farmhouse chic home, just two blocks from renowned Park Avenue. This adorable two-bedroom, two-bath home is full of character, featuring a picturesque white picket fence. Originally built in 1925, this property has been transformed, blending historic charm with modern comforts. Step inside to an airy open floor plan where a spacious living room, dining area and kitchen flow seamlessly together. Relax by the electric fireplace in the living room or entertain in the kitchen, complete with whimsical, retro-style Big Chill appliances that add a bright and cheerful touch. The home is filled with vintage character and modern flair, featuring vibrant colors, shiplap walls and solid heart pine floors throughout. Both baths are tastefully designed with handcrafted cement tiles, and the two bedrooms are cozy yet surprisingly spacious, with ample closet space efficiently integrated into the design. The outdoor living space is just as inviting, with a 300-square-foot screened back porch, ideal for relaxing or entertaining year-round. A carport pergola featuring an electric car charger adds even more versatility to the indoor-outdoor living experience. Garfield will have you gushing with its storybook setting! Don’t miss your chance to own this one-of-a-kind Winter Park gem featured in Winter Park Magazine so schedule your visit today!

411 Garfield Avenue, Winter Park

$467,500

2 Beds ⋅ 2 Baths ⋅ Bungalow Park SubDv. ⋅ 32789 Zip Code

Welcome to your dream cottage! This adorable 2-bedroom, 2-bathroom charmer has serious curb appeal and tons of character. Step inside to find a cozy living/dining room combo with beautiful original wood floors and so much natural light pouring in from every window. The living room has an electric fireplace perfect for chilly evenings. The kitchen is ready for action with solid wood cabinets, granite counters, a stainless steel refrigerator, a Maytag dishwasher, and a range with hood. The second bedroom and full bathroom (hello, shower/tub combo!) are conveniently located right off the kitchen. Head upstairs to the spacious primary suite with built-in closets and cabinetry, plus a private bathroom. There’s even a bonus flex space off the primary suite that’s currently an office but could be anything you want—nursery, workout room, you name it! Tucked under the stairs, you’ll find a convenient inside laundry room. Outside, the fully fenced backyard is an absolute oasis, with mature trees and a covered back porch decked out in warm wood accents that make you feel like you’re on vacation. Located in the heart of Winter Park, this home is just minutes from all the fun on Orange Avenue and Park Avenue and zoned for top-rated Audubon K-8 and Winter Park High School. With a roof from 2018, AC from 2016, and updated plumbing and electrical, it’s move-in ready. Call today to schedule your private tour—this one won’t last long!

1001 Minnesota Avenue, Winter Park

$385,000

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

Largest unit at Killarney Bay, set up as a town home -bedrooms upstairs town house with large screened in area back porch, new washer and dryer - wood floors throughout, close to Winter Park Village - complex is a small great location with great access to I-4 - Killarney Bay sits on Lake Killarney with private pool overlooking. Only 5 rental units are allowed at KB at any given time. Super clean and ready for new owner. Beautiful wood ceilings in main living areas and wood floors and stairway! tastefully done, real fireplace. Current tenant has flexibility in moving. oversized bedrooms are located on the second floor, featuring suite bathrooms and walk-in closets. The primary bedroom also features its own balcony. This community is walking distance only minutes to 17-92, I-4, Winter Park Village, Trader Joe’s, Whole Foods, Publix, and downtown Winter Park’s retail and restaurants. Owner may hold a MTG-

740 #3 Killarney Bay Ct Unit 7-3, Winter Park

$405,000

2 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Don't miss this immaculate and move-in ready 2-bedroom/2-bath Winter Park home, with a 1-car garage, and a NEW ROOF coming soon! Recently updated, this home features fresh paint inside and out, improved landscaping, new lighting, a new dishwasher, and a new microwave. The desirable, open floorplan features a spacious family room/kitchen combo, separated by an island that offers extra storage and seating. Stainless steel appliances and a window overlooking the backyard enhance the kitchen, while an adjacent dining area flows into a bright Florida room, making this home ideal for entertaining. Both bedrooms have walk-in closets, and there’s plenty of extra storage with 2 hall closets. The backyard steals the show, featuring a large (22’x15’) covered porch with ceiling fans, two storage sheds, and raised garden boxes—perfect for your gardening projects! The freshly painted, attached 1-car garage offers washer & dryer hookups and shelving for more storage. Tucked away on a quiet street, yet minutes from downtown Winter Park, College Park, and downtown Orlando, this home is close to Trader Joe’s, Whole Foods, Publix, Home Depot, and more...and offers easy access to I-4 for commuting.

2113 Albert Lee Parkway, Winter Park

$475,000

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

Price Improvement! Welcome to the luxury of Winter Park condo living, just steps from the world famous Park Avenue! You will be delighted to step into elegance in this charming first-floor condo with 9' ceilings in the highly sought-after Villages of Winterset Condominiums. Picture this – a simple stroll from your doorstep leads you to Park Avenue's enticing shopping and dining delights, the Morse Museum's cultural treasures, the vibrant energy of Rollins College, the refreshing greenery of the Winter Park Golf course, and the convenience of Sun Rail's commuter train. Immerse yourself in the charm of Central Park, where art festivals, concerts, movies, and events unfold right before your eyes. The Winterset mid-rise building offers key-secured access and a convenient call box for welcoming visitors. The lobby extends a warm welcome with a lounge area, perfect for unwinding or greeting your guests. Indulge in the pristine amenities of this well maintained community – a generously sized private pool, sun deck, and a grilling area designed for your leisure. Now, let's talk about this freshly painted gem of a corner unit – bathed in natural light and adorned with stunning travertine floors. The fully remodeled kitchen (2024) features granite countertops, new cabinets, all new stainless steel appliances and overlooks the spacious dining space. The open-concept dining into living room leads you to the open-entry sunroom that features energy-efficient impact-resistant sliding glass doors that overlooks a paved patio and lush greenery. Both of the bedrooms feature brand new carpet and beautiful plantation shutters that offer privacy and energy efficiency. The welcoming primary suite, boasts a walk-in closet and elegant make-up vanity with a large walk-in tile shower, big enough for two! The guest bath exudes charm with warm wood cabinetry and a tub/shower combo. Live the carefree lifestyle you've been dreaming of in this exclusive Winter Park haven, surrounded by multi-million dollar condos and homes. A property like this will not be available long. Call for your private showing today!

213 E Canton Avenue Unit 213, Winter Park

$450,000

2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to this charming home in the highly sought after Orwin Manner. Situated on one of the most desirable streets in the neighborhood, this move in ready 2 bedroom 1 bathroom home holds onto classic details while boasting a beautifully updated and modern kitchen and bathroom. The exterior has been refreshed and re landscaped to offer beautiful curb appeal and low maintenance foliage. The large back deck has ample room for seating and grilling out with a beautiful open yard beyond. This lot provides the ability to enjoy plenty of space to enjoy as is or to add on in the future. This home has been well maintained and enjoyed by its owners and is a true gem that will serve the next owners well. Located minutes from I4 and within walking distance to Orange Avenues restaurants, shops, and parks this home effortlessly combines convenience and modern charm.

1401 Devon Road, Winter Park

$450,000

2 Beds ⋅ 3 Baths ⋅ Cherokee Park SubDv. ⋅ 32789 Zip Code

LOCATION, LOCATION, LOCATION! Tucked in a peaceful enclave of Winter Park, this distinctive 2-bedroom, 2.5-bathroom townhome blends mid-century modern charm with contemporary functionality. This home welcomes you inside with an open-concept floor plan featuring a charming wood-burning fireplace flanked by built-in shelving and classic brick flooring that seamlessly connects the living, dining, and kitchen areas, ideal for entertaining and everyday living. The spacious layout flows into the dining and kitchen area with a breakfast bar that invites casual dining, while the kitchen is outfitted with stainless steel appliances and countertops and plenty of cabinetry. The large windows allow for abundant natural light, especially in the upstairs bedrooms, where high ceilings create a sense of openness. Each bedroom offers a plethora of storage with a private ensuite framed by unique clerestory windows, providing privacy while welcoming sunlight and complementing the beautiful wood flooring. Outside, the private backyard offers a generous patio area perfect for hosting epic BBQs or simply relaxing. Experience the best of Winter Park living with this prime location, steps away from the Winter Park Tennis Club and a short stroll to Park Avenue’s acclaimed shops and restaurants, picturesque Rollins College campus, the vibrant Winter Park Farmers' Market, and the scenic shores of Lake Virginia. This home is also a stone’s throw from the exciting up-and-coming Seven Oaks Park, a 1.5-acre green space designed to promote community and wellness through its lush landscaping and thoughtfully curated spaces. Whether you are looking for a standout addition to your investment portfolio or a place to call your own, this property offers endless possibilities. Don’t miss the opportunity to make it yours—schedule a private showing today!

1102 Azalea Lane, Winter Park

$235,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Remodeled 2nd story, end unit, 2-bedroom, 2-bath condo in stunning Winter Park! Enjoy all the charm Winter Park has for you, just minutes from Park Avenue's shops and restaurants, or take a short bike ride to nearby parks and outdoor venues. This desirable end-unit condo has been upgraded with new kitchen cabinets, granite countertops, and stainless steel appliances. Recent 2023 improvements include a new AC, roof & gutters. The interior has been freshly painted, and the home boasts new outlets, wall switches, and light fixtures throughout. Enjoy new luxury vinyl floors and plush carpeting, as well as all-new door hardware for a polished look. The community offers a pool and an on-site laundry facility. With Mead Gardens right behind the complex, you’ll have access to some of the best walking paths in Winter Park. Conveniently located between Trader Joe's, Winter Park Village, Ivanhoe Row, and Mills restaurants, and just a short distance to Park Avenue, Winter Park Tennis Center, Seven Oaks Park, and Rollins College. With low monthly fees, this is a fantastic opportunity to live affordably in Winter Park!

1250 S Denning Drive Unit 205, Winter Park

$315,000

2 Beds ⋅ 1 Baths ⋅ Golfview SubDv. ⋅ 32789 Zip Code

HUGE PRICE REDUCTION! Welcome to this charming beautiful well maintained single family home located in Winter Park, FL with NO HOA. This home has it all! This property features a breezeway entrance / Mudroom that leads you to the front door of the home or to the door to enter the backyard. Presenting 2 bedrooms, 1 bathroom, 1 car garage shared with laundry room space, moving along to the living-room & open eat in kitchen combo. Your large backyard is fenced in to give you privacy while entertaining. It also boasts a covered patio that allows you to enjoy watching the rainfall or sip some lemonade during the sunshiny days. The owner has recently painted the entire exterior and revamped the curb appeal. This home is perfectly situated near downtown Orlando and just minutes from Dubsdread Golf Course and amazing local restaurants. Less than 30 minutes away from your funnest attractions such as Disney, Universal Studios and some great colleges !! Property is currently tenant occupied. Rest assured it’s very easy to show. Here’s your opportunity to own property in Winter Park so schedule your showing today because this won’t last! HVAC: Replaced in 2014 and outdoor unit is rebuilt in 2023 (new compressor) PLUMBING Completely re plumbed in 2009 ROOF- Replaced in 2019 ELECTRICAL replaced in 2009/ Main panel upgraded in 2017 Back Porch built in 2019/ Front Windows replaced in 2018 Exterior Completely repainted: Sept. 2024

1225 Formosa Avenue, Winter Park

$845,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to this enchanting 1935-built home nestled in the heart of Orwin Manor, a neighborhood known for its historic charm and serene ambiance and conveniently located off Orange Avenue with easy access to Park Avenue, Downtown Orlando, College Park, and Thorton Park. This charming residence features 2 spacious bedrooms and 2 bathrooms, perfect for modern living while retaining its historic allure. The original hardwood floors add warmth and character, flowing seamlessly throughout the home. The charming kitchen offers a cozy and inviting space for culinary adventures, complete with updated appliances. Gather around the wood-burning fireplace in the living room, creating the perfect setting for cozy evenings. The expansive yard provides ample space for outdoor activities and gardening. Additionally, the home boasts versatile flex spaces, ideal for a home office, a formal den, or even a nursery, ensuring it suits your lifestyle needs. This home is a true gem.

1423 Westchester Avenue, Winter Park

$330,000

2 Beds ⋅ 3 Baths ⋅ Huntington Condo SubDv. ⋅ 32789 Zip Code

Seize the opportunity to own this delightful townhouse within walking distance of downtown Winter Park, where the charm of Park Avenue and the vibrant Rollins College campus await just steps from your door. This two-bedroom, two-and-a-half-bathroom home presents an ideal canvas for creating your haven. As you enter, you'll be welcomed by a well-planned layout featuring a spacious great room with a cozy wood-burning fireplace, perfect for gathering with friends and family. The adjacent dining area flows seamlessly into a bright sunroom, offering a versatile space that could easily function as a home office or a tranquil retreat for reading and relaxation. Upstairs, discover two generously sized bedrooms, each boasting its covered balcony where you can enjoy peaceful mornings or unwind in the evening. The primary suite is a highlight, featuring a walk-in closet and a unique loft area that provides additional storage or a private nook for relaxation. The en-suite bath adds to the convenience and comfort. Step outside to a large, private backyard patio, ideal for hosting outdoor dinners, barbecues or simply soaking up the Florida sunshine in your secluded space. The property includes a covered, assigned parking space, with additional guest parking available for visitors. On a quiet dead-end street, this townhouse offers the ease of a lock-and-leave lifestyle, allowing you to fully embrace the vibrant offerings of Winter Park, from its eclectic dining and boutique shopping to the nearby SunRail station and bustling farmer’s market. Zoned for the highly regarded Audubon K-8 and Winter Park High School, this property combines convenience with potential to create the home you've always envisioned. Don’t let this rare opportunity pass you by.

647 Huntington Avenue Unit 8, Winter Park

$329,900

2 Beds ⋅ 1 Baths ⋅ Village Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Location.... Location.... Location.... First Floor Condo situated in the heart of Winter Park and walking distance to Park Avenue, Rollins College, Winter Park Village and Sun Rail. The condo has been recently renovated with new appliances, led lighting, wood, tile, and stone finishes and there are NO units above this one. You have access to a "new" private deck just right outside the unit back door to just relax and enjoy a quiet evening. No Condominium Assessments and All Major Building Components/Projects (Roof, Fencing, Driveway, Landscaping, Lighting, Painting) have been completed Within the Last 7 Years! This home is "wireless" from the doorbell to the electrical switches and ceiling lights which can be dimmed for a relaxing mood. It is set up on a Google Home Platform and can be controlled remotely. A nest thermostat, doorbell and a state of the art wireless Blue ADT alarm system that is self-monitored with backup capabilities to ensure notifications of events. There is a new all-in-one washer/dryer for a one-time load and done. The unlimited hot water system maintains constant temperature based on your convenient and easy dial setting and comfort. The kitchen has modern track lighting and granite counters. Custom white plantation shutters and crown molding throughout the home. There is one assigned parking space with ample parking for another vehicle and guest parking. The location in Winter Park is ideal and is located near the police and fire station. This home has everything you need to enjoy the Winter Park lifestyle and cultural events.

500 N Pennsylvania Avenue Unit E, Winter Park

$330,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

PRICE IMPROVEMENT – Best buy in Winter Park..........Motivated Sellers! CLICK ON VIRTUAL TOUR to get an overview of the complex. Step into this beautifully updated 2-bedroom, 2-bath condo located in the highly desirable Winter Park Gardens community. This move-in-ready unit has been thoughtfully upgraded with modern features, including brand-new plumbing, a tankless water heater, resealed windows, recessed lighting, and ceiling fans throughout. The entire home boasts stylish wood-look tile flooring, providing a sleek, modern look. The open-concept kitchen is a true highlight, with solid wood cabinets, pull-out shelving, glass display cabinets, and luxurious granite countertops – perfect for both cooking and entertaining. Both bathrooms have been tastefully updated with high-end finishes. The condo offers plenty of storage, including spacious closets with built-in organizers, ensuring your home is both functional and stylish. A standout feature is the secondary bedroom, which includes a built-in queen-size Murphy bed, offering incredible space-saving functionality for guests or additional uses. Winter Park Gardens is a vibrant 55+ community that also welcomes younger owners, making it an ideal location for anyone looking to enjoy the serene, park-like atmosphere. Located within walking distance to Winter Park's most coveted attractions like Mead Gardens, Rollins College, and Park Avenue, this condo is truly a hidden gem. The community amenities include a sparkling pool and peaceful pond, offering a tranquil retreat. This is a must-see property – come experience all the charm and comfort it has to offer!

700 Melrose Ave J 1 Avenue Unit J1, Winter Park

$493,000

2 Beds ⋅ 1 Baths ⋅ Selwyn Heights SubDv. ⋅ 32789 Zip Code

Discover the potential of 1411 Ridgewood Avenue, a charming 1949 bungalow located in the heart of Winter Park, walking distance to Park Avenue. This 2-bed, 1-bath home is set on a massive lot, offering a unique opportunity to either enjoy the vintage charm or create your dream home from the ground up. With plenty of space for expansion or a complete rebuild, this property is perfect for those looking to invest in one of Winter Park’s most desirable neighborhoods. Just minutes from top schools, shopping, and dining, this location offers both convenience and the chance to design your perfect oasis.

1411 Ridgewood Avenue, Winter Park

$1,000,000

2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Walk to Park Avenue! Experience upscale living in this fabulous condo on the famous Winter Park Chain of Lakes. Located on the fifth floor, you will enjoy breathtaking tree-top lake views from this beautifully updated, one story unit covering almost 2100 square feet. The open layout features expansive living and dining areas that seamlessly transition to an outdoor screened-in porch. The stylish kitchen is well equipped with custom wood cabinets, granite countertops, stainless steel appliances and a center island with breakfast bar. The condo features a spacious guest suite with double closets, and a dramatic guest bath, complete with a custom designer vanity and a large walk-in shower. The generous owners suite offers a lounging area with radiant natural lighting. The spa-like bathroom includes custom vanities, soaking tub and a large walk in closet with built-ins. Additionally, features include automated blinds in the living room and an indoor laundry closet. The well maintained complex located on the shores of Lake Osceola offers underground parking, storage closet, and amenities such as pool and community laundry room. Situated just steps away from vibrant Park Ave, residents will enjoy many fantastic restaurants, cafes, Museums, and Boat Tours, in addition to the convenience of the Sunrail/Amtrak station. The condo fee includes electricity, sewer, water, gas, maintenance, on-site manager, community pool, ground maintenance, roof, insurance, exterior and more.

311 E Morse Boulevard Unit 6-18, Winter Park

$540,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

OPPORTUNITY KNOCKS! To own and renovate this 4th floor unit with beautiful views of pool and lake from its large screened in patio! This 2 bedroom - 2 bath condo is located directly across from the elevator, includes storage space on property and 1 covered assigned carport space (C6). The Cloisters is located in the Heart of Downtown Winter Park: Just a short stroll to Alfond Inn, Sun Rail, Farmer's Market, Morse Museum, Scenic Boat Tour, Central Park plus all the boutiques, cafe's and everything else Park Avenue has to offer. Enjoy this delightful community featuring several elevators, heated pool, putting green, fitness center, on-site manager, lovely clubhouse & private LAKEFRONT PARK with boat slips (first come, first serve)

100 S Interlachen Avenue Unit 404D, Winter Park

$595,000

2 Beds ⋅ 2 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code

Prime Winter Park lot and/or home for sale - 2 bedrooms / 2 bathrooms 1,162 heated Sq. Ft. with single car garage 1,754 gross square feet Remodeled kitchen and large backyard Winter Park High School A grade school - Elementary and Middle Schools grade B

1848 Mizell Avenue, Winter Park

$372,500

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Fully remodeled ground floor 2/2 unit at the gorgeous Winter Park Gardens. Hickory finish floors through out. Bright sunroom is opened up creating a seamless living/dining expanse. Bright widened kitchen features white soft-close cabinets, white granite solid-surface counter tops, and stainless steel appliances. Both remodeled bathrooms are are clean and light with safety bars and easy entry standing showers. Stunning floor to ceiling views of pool and lush tranquil gardens douse the space with natural light. No step ground floor convenience and very close proximity to the user-friendly laundry room make it the best possible situation. Walking distance to Rollins, Orange Ave District, Mead Gardens, Park Avenue and everything that makes Winter Park so special.

700 Melrose Avenue Unit H 3, Winter Park

$520,000

2 Beds ⋅ 1 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters Condominiums, a sanctuary nestled between the serene Winter Park Chain of Lakes and the vibrant Park Avenue. This sophisticated condominium embodies the essence of Winter Park living, offering a perfect blend of elegance and convenience. As a resident, you'll enjoy a sought-after address that places you in the heart of this charming locale. This refined fourth-floor residence spans over 900 square feet and features two spacious bedrooms and one full bath. The moment you enter, you are greeted by a charming foyer that seamlessly connects to a well-appointed kitchen. Here, you will find stainless steel appliances, ample counter space, and abundant cabinetry, making it a dream for any culinary enthusiast. The inviting living area extends an open invitation to relax on the oversized balcony, covered in lush astroturf, where you can unwind while taking in the tranquil, scenic views. The Cloisters offers an array of amenities designed for the connoisseur of life. Enjoy leisurely days by the heated pool, surrounded by meticulously maintained grounds, or entertain in the social room. For boating enthusiasts, a boat dock with eight slips provides direct access to the picturesque Lake Osceola. Golfers can refine their skills on the private putting green. This exceptional home is just a short stroll from Park Avenue, where you can explore an array of dining and shopping options. Whether you prefer to meander through Hannibal Square or embark on a serene boat ride along the Winter Park Chain of Lakes, this location offers a lifestyle of sophistication and convenience. Notable features include European white oak wide-plank flooring, Carrera marble porcelain tile in the bath, new Kohler bath fixtures, designer light fixtures throughout, plantation shutters, and a Lutron system for select lights, all combining to create a harmonious living space. For the discerning buyer, The Cloisters offers a unique opportunity to experience the art of living in a serene yet connected environment. This is more than just a home – it's a statement of refined living. The condominium fee covers cable TV, common area taxes, an escrow reserves fund, building insurance, internet, maintenance (grounds, exterior, repairs, pool), a condominium association manager, sewer, trash collection, and water, ensuring a maintenance-free lifestyle.

100 S Interlachen Avenue Unit 410, Winter Park

$585,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Located in the highly sought-after neighborhood of Orwin Manor, where Winter Park meets Orlando, this inviting 2-bedroom, 2-bathroom home with a versatile den offers comfort, style, and an unbeatable location. From the moment you arrive, the bright exterior and welcoming pathway set the stage for what’s inside. Sitting on a spacious 0.20-acre corner lot, this home offers both curb appeal and plenty of outdoor space to enjoy. Step inside the living room, where a cozy wood-burning fireplace and a charming built-in cabinet add warmth and character. The living room flows seamlessly into the dining room, a bright space filled with natural light—perfect for everyday meals or hosting guests. Just off the dining room, you’ll find the kitchen, featuring stone countertops and white cabinets. The primary bedroom is a standout, with high ceilings, barn doors, and direct access to a covered patio with a brick floor. The ensuite bathroom is roomy, with double sinks, a soaking tub, a large shower, and a walk-in closet. The second bedroom is also generously sized, making it comfortable for guests or family. The Florida room, with its French doors and natural light, offers flexibility—whether you need a family room, office, or playroom. Outside, the oversized backyard is a great space for entertaining or just relaxing, with both a covered patio off the primary bedroom and an open patio with pavers. Just minutes from Downtown Winter Park, College Park, and Orlando, and with quick access to I-4, getting around town couldn’t be easier. You’ll love the convenience of this location, close to shopping, dining, AdventHealth, and the Orlando Science Center. This home is ready for you to make it your own—schedule a tour today and see all it has to offer!

1600 Berkshire Avenue, Winter Park

$750,000

2 Beds ⋅ 1 Baths ⋅ Fairbanks Park SubDv. ⋅ 32789 Zip Code

SPECTACULAR WINTER PARK OPPORTUNITY! This oversized corner lot in Fairbanks Park overlooking Lake Midget and Lake Midget Park is a rare opportunity to build your dream home in Winter Park. The 2-bedroom/1-bath home, original owners since 1941, is available for renovation or new construction. Serene views of Lake Midget from the front porch, that can’t be beat. New restaurant and retail space is being developed across the street on Fairbanks Ave. Close proximity to Rollins baseball field, and less than a mile from Park Avenue, Rollins College, restaurants, shopping, and so much more. Don’t miss this diamond in the rough – call today for your showing!!!

731 Midget Drive, Winter Park

$405,000

2 Beds ⋅ 1 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Gem Opportunity! Consumers choice! Own this charming 2 bedroom 1 bathroom property OR BUILD your dream home with this SPACIOUS LOT over a Quarter of an acre tucked in the serene Non HOA community just a stroll away to LAKE KILLARNEY. This property has close proximity to top-rated schools, vibrant dining, shopping, and cultural experiences. With its ideal location and abundant potential, 2420 Euston Rd is the perfect canvas for your next project. Don’t miss out on this rare chance to create something truly special in Winter Park. Lake Killarney is one of Winter Park's hidden gems, offering a peaceful retreat from the hustle and bustle of city life. Covering approximately 234 acres, this spring-fed lake is known for its clear waters and serene environment, making it a favorite spot for both residents and visitors. Whether you're into kayaking, paddleboarding, or simply enjoying a quiet afternoon by the water, Lake Killarney provides a variety of outdoor activities that cater to nature lovers and water enthusiasts alike. Lots in Winter Park are extremely hard to come by, but behold the opportunity you have been waiting for! A charming primary, profitable Rental Home, or start from scratch and BUILD. Come check out this Rare Opportunity before it's gone!

2420 Euston Road, Winter Park

$196,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This delightful end-unit condo offers the best of both convenience and style, just minutes away from the vibrant Park Avenue with its eclectic shops, fine dining, and local attractions. Whether you prefer a leisurely stroll to nearby parks or a quick bike ride to outdoor venues, this location has it all. The community recently installed a new roof and gutters in 2023, giving you added peace of mind. Step inside to this freshly painted, bright, and open living space, where the kitchen seamlessly overlooks the living and dining room, creating an inviting atmosphere ready for you to make your own. Just off the living space, you'll find a charming screened porch, the perfect spot to unwind with a book while enjoying the tranquil garden courtyard views. The complex amenities including a heated community pool and a convenient on-site laundry facility. Nature lovers will appreciate the proximity to Mead Gardens, with its scenic walking paths right at your doorstep. Additionally, a new outdoor event venue is under construction nearby, adding to the vibrant community atmosphere. Located within easy reach of Trader Joe's, Winter Park Village, Ivanhoe Row, Mills restaurants, and Park Avenue, this condo provides an ideal blend of affordability and prime location. Don't miss this exceptional opportunity to experience the best of Winter Park living with low monthly fees.

1250 S Denning Drive Unit 124, Winter Park

$775,000

2 Beds ⋅ 3 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

***VERY RARE CORNER DOUBLE CONDO WITH 2 COVERED PARKING SPACES*** Stunning is the first word that comes to mind when describing this casual but elegant 2 bedroom, 3 bath condominium in the highly sought after Winterset building. Designer touches and quality finishes are evident the minute you walk through the front door. The gracious owner's retreat is large with a spa-like bath and 2 walk-in closets with built-ins. The secondary bedroom offers a private bath and walk-in closet. The gourmet kitchen and breakfast area offers custom wood cabinetry, granite counter tops, tile backsplash, under cabinet lighting and high end appliances. Other features include beautiful hardwood flooring, built-in bar and cabinetry. The secured building requires a code to access the lobby, along with a call box for your guests to be buzzed into the building. This condo boasts wonderful closet spaces throughout along with a separate storage closet and 2 convenient covered carport spaces. Just steps away from the stylish shops and restaurants on Park Avenue and other popular Winter Park amenities this unique and spectacular condo will not disappoint! Call today for your private viewing! NOTE: NO RENTALS OR PETS.

233 E Canton Avenue Unit 233, Winter Park

$320,000

2 Beds ⋅ 1 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code

This lovely two bedroom, one bath, 904 sqft home in Winter Park is ready for you to call home! Upon entry, you will notice lovely hard wood flooring throughout the main livings of the home. You'll be greeted by the light and airy feel due to the expansive windows in this property. The kitchen features a fridge, range, and over the range oven. There's plenty of cabinetry space as well and there's a door that leads to the spacious backyard. Through the door you'll find a covered patio- a perfect spot to enjoy your cup of coffee. Both bedrooms are specious and provide plenty of closet space. The bedrooms have quick access to the bath. The bathroom has an upgraded vanity and a shower/tub combo. Rounding out this home is the laundry room off the back patio. This home is located in the heart of Winter Park- it's very close to the Winter Park Village, downtown Winter Park, Lee Road, Orlando Avenue, and I4. This home has easy access to I4, shopping, dining, entertainment, and more! *Photos are from 8-5-2020.

821 Carver Street, Winter Park

$465,000

2 Beds ⋅ 1 Baths ⋅ Osceola Heights SubDv. ⋅ 32789 Zip Code

Authentic 1930 bungalow with detached guest suite in prime Winter Park location, surrounded by $1m+ homes. Great opportunity to build new or renovate. The main house is 640sf with 2 bedrooms/1 bath and has a sunporch with built-ins, living room + dining room with original hardwood floors, kitchen, and utility porch with washer/dryer. The 576sf guest house is a converted garage with family room, kitchen that has cooktop, microwave & refrigerator, 1 bedroom/1 bathroom, and newer roof and AC. 9 x 13 shed is on the property. New fence. Great location within walking distance to the Winter Park YMCA and only minutes to Park Avenue’s shops and restaurants, Interlachen Country Club, Winter Park Racquet Club, the Winter Park Golf Course (WP9), Advent Hospital, and Rollins College. Lot size is 0.15 acres and 50x125sf. House being sold AS IS with no repairs.

1870 Walker Avenue, Winter Park

$505,000

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. GREAT LOCATION! This top floor unit is located in the gated community of Park West just one block from the cobblestoned Park Avenue in downtown Winter Park with acclaimed restaurants, museums, and shopping. This two-bedroom two-bathroom unit features a fireplace and stunning vaulted ceilings in the living room/dining room, primary bedroom, and second bedroom as well as two walk-out balconies. The second bedroom balcony was enclosed adding additional living space. The HVAC was replaced in 2022. The unit comes with a designated parking space in the ground level garage that has elevator access to the fourth floor and there is additional open/guest parking in the outside parking lot. Community amenities include clubhouse, pool, and tennis/pickleball courts.

250 Carolina Avenue Unit 406, Winter Park

$370,000

2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully renovated 2-bedroom, 1-bathroom home in a prime location just minutes from downtown Winter Park, and a short walk to restaurants, shops, and the picturesque Lake Killarney! Step inside to discover the large light-drenched dining room, featuring warm wood floors and open to the spacious living room. This space is perfect for both relaxation and entertaining. The stylish kitchen is equipped with 42-inch white shaker cabinets, quartz countertops, stainless steel appliances, and a sleek glass backsplash. Both bedrooms are generous in size, each with ample closet space, views of the peaceful backyard, and are split by the updated bathroom in between. Outside, you'll find an expansive fenced-in backyard, ideal for outdoor activities and gatherings, and ample parking in the long paver driveway. This home offers the perfect blend of modern updates and an unbeatable location with I4 close by for easy commuting to downtown Orlando and beyond. Schedule your private showing today!

1971 Karolina Avenue, Winter Park

$365,000

2 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge First Add SubDv. ⋅ 32789 Zip Code

Opportunity awaits with this 1956 block construction home, nestled on a spacious .34-acre lot in the desirable Winter Park neighborhood of 32789. Offering private lake access and stunning lake views from the backyard, this property presents an ideal canvas for a complete remodel, allowing the next owner to create their dream home in a picturesque setting. The home features a garage and is situated in a great community, providing the perfect foundation for a transformative renovation project. Don't miss the chance to bring new life to this charming property and make it your own. Roof is 2003. HVAC is 2023. Plumbing Repiped in 2016 to CPVC. Septic Replaced in 2012.

2345 Albert Lee Parkway, Winter Park

$1,145,000

2 Beds ⋅ 2 Baths ⋅ Interlachen Condo SubDv. ⋅ 32789 Zip Code

Experience Luxury and Charm! Discover an extraordinary residence nestled in the heart of Winter Park, where luxury meets location. This 2 bed / 2 bath (1,718 heated sq. ft.) is sure to charm you, spectacular wood parquet floors, Spanish/Mediterranean barrel roof tiles, inviting fireplaces, and walls of elegant French pane windows that flood the space with natural light. The impressive wood plank vaulted ceiling in the dining room adds a touch of European flair. The family room and dining room are adorned with floor-to-ceiling wood bookcases, adding to character and appeal. Tucked away for privacy: two charming patios overlook a secluded entryway, and meticulously re-paved brick paths wind through lush landscaping, ensuring utmost privacy and serenity. The expansive primary bedroom upstairs, offers views of Casa Feliz and the golf course. Plenty of space in large walk-in closet and its own cozy fireplace. Embrace the vibrant lifestyle of downtown Winter Park with a leisurely stroll to Park Avenue’s chic cafes, boutique shopping, and museums. The home is just steps away from the enchanting Charles H. Morse Park Moonlight Garden, known for its flower-covered archways and picturesque path leading to the historic Casa Feliz mansion. This property blends the best of both worlds: the privacy of a free-standing home and the convenience of condominium living. Recent high-end updates include a new water heater 2023, new electrical panel 2023, state-of-the-art Trane AC 2021, a stylishly remodeled kitchen with designer tile and stainless steel appliances, high-efficiency windows and doors, new tile roof 2021, and freshly painted exteriors. Trees have been trimmed and brick paths leveled as of May 2024. Only 6 distinctive units in this exclusive complex. All are unique with their own floorplans, personality, and charm. This home has two designated parking spots (1 covered parking) and offers unparalleled charm and sophistication. Maintenance-free lifestyle! Lock and leave for extended periods with no concerns. HOA handles maintenance and common areas. Don’t miss this rare opportunity—schedule your private tour today and make this Winter Park masterpiece yours!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src=https://my.matterport.com/show/?m=pi8AS8w5fcE&mls=1 frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

625 N Interlachen Avenue Unit A, Winter Park

$450,000

2 Beds ⋅ 1 Baths ⋅ 3212071-3212071 SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, Florida at 1501 Michigan Avenue, this charming home offers a perfect blend of comfort and convenience. This lovely home offers comfortable living space, featuring 2 bedrooms and 1 bathroom. The kitchen and bathroom were tastefully remodeled in 2023, complemented by new tile floors that were installed throughout the house in the same year. The interior walls received a fresh coat of paint in 2023, enhancing the home's modern appeal. Key updates include a new AC unit in 2020, a roof replacement in 2021, and updated electrical wiring with the main electrical panel replaced in 2019, ensuring peace of mind for the new owners. The property also features a cozy loft, stainless steel appliances, a large fenced backyard, a paver driveway, an attic for additional storage, and a carport for one vehicle. Situated in a quiet neighborhood without an HOA, this residence offers easy access to major conveniences. Just a 3-minute drive to I-4, a 6-minute drive to Advent Health and College Park, and in close proximity to large plazas, SunRail, Winter Park Village, and Park Avenue, residents will enjoy a lifestyle of comfort and accessibility. Don't miss the opportunity to make this meticulously maintained home your own in the sought-after Winter Park area.

1501 Michigan Avenue, Winter Park

$385,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability). Assigned parking space, community storage & mail just outside the back door. Walk to Trader Joe's, Hillstone's, Winter Park Village, Publix, movies, restaurants, shopping, etc. Bike or walk to Downtown Winter Park and Sunrail. Fully renovated unit with extra care to space planning. o Highest ceilings in the community. Solid bamboo wood flooring. Recessed lights. Surround sound & TV mount . Textured walls & ceiling . Custom trim . 4 panel sliding glass and transom windows looking over lakeview & lawn . Large renovated kitchen with glass tower cabinets . Drink bar and large island . Granite counters . Stainless steel appliances. Downlighting, under & over cabinet lighting o stainless steel appliances. End your day enjoy the lake views while making dinner. Shower cubbies & candle cubbie for baths . Italian space enhancing vanity . Upgraded fixtures . Frame mirrored medicine cabinet for hidden extra storage o Custom expanded master closet system. Community amenities include o Lakefront dock with boat slips o Private boat ramp o Lakeside pool & large lawn with Adirondacks o Grills & picnic tables o Paddle board / canoe / kayak racks o Bass fishing . Bike racks, shuffleboard . Assigned Parking space just outside the door . Storage Space o Gym, laundry rooms, community storage, and recycling. **Furniture is not inlcuded in the listing price**

151 N Orlando Avenue Unit 131, Winter Park

$1,340,000

2 Beds ⋅ 2 Baths ⋅ Lords Sub SubDv. ⋅ 32789 Zip Code

Welcome to Winter Park lakefront living at its finest. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity.

571 Lake Front Boulevard, Winter Park

$260,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Beautifully renovated 2 bedroom, 2 bath condo on the Ground Floor in gorgeous Winter Park!! Come enjoy all that Winter Park offers, with only a few minutes ride to Park Avenue and all of the shops and restaurants. Or, take a short bike ride to the many parks and outdoor venues. This END Unit condo has new cabinets, beautiful quartz countertops, and stainless steel appliances. The refrigerator is new. The electric water heater is new. The windows and slider have been replaced. This condo is just waiting for YOU!! Both bathrooms have updated tile, new vanities and quartz countertops! The luxury vinyl flooring is throughout the main living area and kitchen, tile flooring in bathrooms, with carpet in both bedrooms. A screen porch is the perfect place to relax with a good book while enjoying the courtyard - garden view! This complex has a heated community pool and on-site laundry facility! Mead Gardens is directly behind the condo's You have the best walking paths in all of Winter Park right next door! There is a new outdoor event venue currently being built nearby. You are perfectly located between Trader Joe's, Winter Park Village, Ivanhoe Row, Mills restaurants and Park Avenue! This is a great opportunity to live in Winter Park affordably with low monthly fees!! (New Roofs and Gutters - 2023)

1250 S Denning Drive Unit 105, Winter Park

$219,000

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, this charming home offers the perfect blend of comfort and convenience! Ideal for those seeking a cozy retreat, the home features an updated kitchen with a farmhouse sink, washer and dryer in unit, HVAC from 2024, and a water heater from 2019. Located in a vibrant neighborhood close to I4, restaurants and parks, this residence promises a delightful living experience in one of Winter Park’s most desirable locations.

851 Miles Avenue Unit 26, Winter Park

$1,005,000

2 Beds ⋅ 2 Baths ⋅ Interlachen Condo SubDv. ⋅ 32789 Zip Code

Discover the charm and downtown Winter Park ambiance with this two-bedroom plus office, two-bath Mediterranean villa, a true “hidden gem” out of the way to find off Interlachen Avenue! The quaint six-villa condominium community is adjacent to the historic Winter Park Golf Course & Casa Feliz. Just footsteps from the vibrant shopping and dining on Park Avenue, this peaceful, private retreat is a European style sanctuary right in the heart of downtown Winter Park. This 1,610-square-foot, two-level condominium is a unique find and wonderful opportunity to make it your own private oasis. On the main level there is a lovely kitchen open to dining room and gorgeous living area featuring vaulted wood ceilings, a wood-burning fireplace, and two walls of French doors opening to separate private courtyards, covered lanai and fountain... There is also a secondary bedroom suite that includes an ensuite bath, perfect for guests or family. Lastly, there is a secluded office/sunroom with gorgeous arched windows and a separate entrance that offers a versatile space for work or relaxation. Upstairs solely encompasses the spacious primary suite boasting a sitting area, French doors and windows and two balconies including an expansive covered balcony off the bedroom, a walk-in closet, and ensuite bath. Embrace the old-world feel of the Spanish/Mediterranean architecture, complete with a newer community tile roof, recent new exterior paint, and peaceful winding courtyards. A secretive brick drive leads to the unit's two designated parking spots including one in a covered carport. Enjoy the "Lock and Leave" lifestyle with the enjoyment of downtown living and the seclusion of this Winter Park treasure. Walk to the Winter Park Golf Course, Casa Feliz, and stroll through the iconic streets of downtown Winter Park. Don’t miss this incredible opportunity to own a piece of Winter Park's history.

627 N Interlachen Avenue Unit B, Winter Park

$475,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to Winter park! This 2/2 has a large den that could easily be a spacious 3rd bedroom as it has it's own closet. This is a charming, 1950's home with a very large master bedroom and a large en suit master bath, jacuzzi style tub and walk in shower. There is a great flow thru in the main living area with a fireplace and built in bookshelves . The remodeled kitchen has newer appliances and contemporary details. The Den /bonus room walks out to a large deck, perfect for entertaining and a great yard for pets or a pool! This location is so convenient as it is right in between Winter Park and the College Park Neighborhood. Museums, parks, shopping and restaurants are right in your neighborhood. Extremely convenient to all major highways. Less than a block away from I-4 entrance and exit. Take a look, make an offer!

1638 Berkshire Avenue, Winter Park

$240,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

This beautifully upgraded, 2 bedroom, 2 bath condo is a ground floor unit, boasts Winter Park Lake access, and is located just 0.4 miles from Winter Park Village. You’ll love the spacious, open floor plan, the natural lighting, the rustic wood plank tiles, and the updated kitchens and bathrooms! Kitchen features white cabinets, granite countertops, brushed nickel hardware, sleek black appliances, ample prep space, and a breakfast bar! The community is tucked back in a quiet corner of Winter Park and hugs Lake Killarney’s shoreline! Your community pool, laundromat, and patio all enjoy beautiful views of the lake! Bring your favorite book and chill by the pool while doing your laundry, or bird watch from your community's lakefront patio! The community also includes a boat ramp onto the lake and a watercraft parking area! You can’t beat this location! Winter Park’s best restaurants and amenities are all at your fingertips! Imagine kayaking to Trader Joe’s for a few groceries or biking to Hillstone for dinner and drinks on the water! Park Ave with all its boutique shopping and fine dining are within 2 miles! Rollins College and Full Sail University are within approximately 3 miles as well! Don’t let this opportunity to live in downtown Winter Park pass you by! Call me today to set up your private showing!

1500 Gay Road Unit 8B, Winter Park

$140,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove/Winter Park SubDv. ⋅ 32789 Zip Code

Great opportunity to make this 2 bedroom, 1 bathroom unit at Waterfall Cove your own. Located blocks to Winter Park Village with restaurants and shopping galore this location is PRIME!!! The unit has a spacious floorplan with a view of the pool from the second floor balcony. The unit has an open living/dining room with galley kitchen, inside laundry with stacked washer/dryer unit. The unit does need TLC and is priced to sell!!! Make your appointment to see this property today!

1695 Lee Road Unit D205, Winter Park

$145,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Discover this charming 2-bedroom, 1-bathroom condo in the tranquil community of Waterfall Cove. With a covered balcony and a walk-in closet in the primary bedroom, this home is ready for its new owner. The community offers a playground, a pool, and includes cable and internet in the HOA fees. Conveniently located near Rollins College and Winter Park's Park Ave, you'll have access to a variety of shops, restaurants, and art galleries. Just a short walk away, Winter Park Village has undergone a multimillion-dollar renovation, enhancing its shopping, dining, and entertainment options. In 2024, Seven Oaks Park will open, providing an exceptional outdoor experience. With downtown Winter Park only minutes away and I-4 less than a mile from your doorstep, commuting is effortless. Perfect for both homeowners and investors. Schedule your viewing today!

1695 Lee Road Unit D206, Winter Park

$152,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Discover this charming 2-bedroom, 1-bathroom condo in the tranquil community of Waterfall Cove. With a covered balcony and a walk-in closet in the primary bedroom, this home is ready for its new owner. The community offers a playground, a pool, and includes cable and internet in the HOA fees. Conveniently located near Rollins College and Winter Park's Park Ave, you'll have access to a variety of shops, restaurants, and art galleries. Just a short walk away, Winter Park Village has undergone a multimillion-dollar renovation, enhancing its shopping, dining, and entertainment options. In 2024, Seven Oaks Park will open, providing an exceptional outdoor experience. With downtown Winter Park only minutes away and I-4 less than a mile from your doorstep, commuting is effortless. Perfect for both homeowners and investors, this condo currently has a tenant generating a rental income of $1,400 per month (currently on a month to month lease agreement) with a 45 day lease agreement termination request. This opportunity won't last long—schedule your viewing today!

1695 Lee Road Unit E213, Winter Park

32789 Zip Code 2 Bedroom Real Estate & Homes

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