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$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