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$449,000
3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code
Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and flexibility. The true standout is the detached 1-bedroom, 1-bath guest house, a rare feature that's ideal for visitors, a private home office, fitness studio, creative space, or even an income-producing opportunity. The main home features two spacious bedrooms and a beautifully renovated bathroom, while timeless charm is showcased throughout with original hardwood floors, crown molding, custom built-ins, and an open-concept living space. The thoughtfully designed kitchen combines butcher block and custom concrete countertops with quality appliances, while the adjacent laundry and utility room adds extra functionality. Step outside to a backyard designed for year-round Florida living. The covered patio, complete with café lighting and ceiling fans, overlooks a fully equipped outdoor kitchen with custom concrete countertops, creating the perfect setting for entertaining. Lush tropical landscaping, an outdoor shower, and abundant storage complete the private outdoor oasis. Beyond its charm, this home is packed with practical upgrades including a metal roof, whole-house natural gas generator, and an exterior security camera system, providing comfort and peace of mind through every season.

2007 Cornell Avenue, Winter Park
$540,000
3 Beds ⋅ 2 Baths ⋅ Unrecorded Plat SubDv. ⋅ 32789 Zip Code
MULTIPLE OFFERS RECEIVED. SELLER WILL REVIEW OFFERS ON MONDAY, AUGUST 3RD. Welcome to Winter Park and the beautiful and desirable Lake Killarney Shores Neighborhood. Available for the first time in 25 years, this home is nestled on an oversized .35 acre lot with plenty of room to store a boat along with deeded lake access to Lake Killarney and NO HOA!! This Classic Florida Home is filled with natural light and features a spacious floorplan including 3 Bedrooms, 2 Full Bathrooms along with a bonus room perfect for a home office, home gym or play-room, a wood-burning fireplace, a spacious dining room overlooking the expansive screened and covered back porch area. The kitchen features solid wood cabinetry, stainless steel appliances and granite counter tops and provides additional space for storage or an eat-in kitchen arrangement. Updates include HVAC and Duct Work (2018) Newer Roof (2018), Updated Electrical (2018), Newer Plumbing (2018), New Water Main from Street to the house and Updated Master Bath (2018). The expansive fully fenced back yard includes two storage sheds and mature landscaping perfect for family gatherings and entertaining. This home is conveniently located near Winter Park Village, Downtown Winter Park and Park Avenue with access to an array of dining and shopping options. This home also has easy access to the I-4 corridor making it an easy commute to just about anywhere in Orlando/Central Florida Area. With a blend of tasteful updates, timeless character and charm this is the perfect place to call home! Call today to schedule a private viewing!

228 Rippling Lane, Winter Park
$429,900
4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Welcome to one of Orlando's most beloved neighborhoods, where tree-lined streets, golf course views, and a true sense of community create the lifestyle buyers are searching for. Perfectly positioned across from the 5th tee of historic Dubsdread Golf Course, this beautifully renovated home places you in the heart of the Dubsdread bubble—just minutes from the dining, shopping, and charm of both College Park and Winter Park. Set on an oversized .22-acre lot, this move-in-ready residence offers over 1,500 square feet of thoughtfully updated living space, blending classic character with today's most desired upgrades. Inside, you'll find refinished original hardwood floors, a fully renovated kitchen featuring stunning quartz countertops, new cabinetry, and new stainless steel appliances, plus two completely renovated bathrooms with fresh, timeless finishes. A 2023 rear addition adds valuable living space, while the inviting Florida room and screened porch provide the perfect spots to enjoy morning coffee, entertain friends, or unwind after a round of golf. Beyond the cosmetic improvements, the heavy lifting has already been done. Enjoy peace of mind with updated plumbing (2026) including removal of cast iron piping, updated electrical (2026), roof (2020), tankless water heater (2023), and energy-efficient windows (2023). Homes in the Dubsdread District rarely offer this combination of location, charm, lot size, and major renovations. Whether you're drawn to the golf course views, the walkable neighborhood feel, or the proximity to Orlando's best restaurants, parks, and entertainment, this home delivers the lifestyle that makes this area one of Orlando's most desirable places to call home. Move-in ready, extensively updated, and perfectly located—schedule your private showing today!

2249 Minnesota Avenue, Winter Park
$615,000
3 Beds ⋅ 2 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
Virtually Staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

1780 Goodrich Avenue, Winter Park
$375,000
2 Beds ⋅ 1 Baths ⋅ Glencoe SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready. But what truly sets this property apart is the location and land. With new construction and beautifully updated homes all around, this is the perfect spot for anyone looking to build something special. Enjoy the home as it is, rent it out for steady income, or start planning your future build in a prime Winter Park setting. A property with this kind of potential doesn’t come around often.

2482 Roxbury Road, Winter Park
$1,125,000
3 Beds ⋅ 3 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Virtually Staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or additional laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include Roof 2020, New HVAC System, New Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

1651 Westchester Avenue, Winter Park
$450,000
2 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES THE PERFECT SPACE TO UNWIND OR ENTERTAIN WHILE ENJOYING THE NATURAL SURROUNDINGS. THE KITCHEN FEATURES A REVERSE OSMOSIS SYSTEM TO FILTER THE DRINKING WATER. THIS PROPERTY IS A RARE OPPORTUNITY TO OWN A PIECE OF WINTER PARK HISTORY IN AN UNBEATABLE LOCATION NEXT TO FABULOUS SHOPPING AND DINING EXPERIENCES. ** SELLER HAS PLANS FOR ATTIC EXPANSION AVAILABLE.

518 Shoreview Avenue, Winter Park
$475,000
2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.

1036 Aragon Avenue, Winter Park
$450,000
2 Beds ⋅ 1 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Welcome to this charming 1935 Winter Park bungalow that blends timeless character with smart, modern upgrades in one of the city’s most walkable locations. This 2-bedroom, 1-bath home offers 1,002 square feet of thoughtfully updated living space, including a remodeled kitchen and bathroom (2021), newer ROOF (2021), Carrier A/C (2020), new flooring, and a tankless EcoSmart water heater. As you arrive, you’re welcomed by a charming old brick walkway with positive sayings painted along the bricks, adding warmth and personality to the curb appeal. The enclosed front porch creates a cozy bonus space with a swing—perfect for morning coffee or evening relaxation. The home features a separate dining area—a rare bonus in a bungalow this size—along with a surprisingly spacious kitchen offering abundant storage, modern appliances, butcher block counter, an over-the-stove microwave, and a space-saving 3-in-1 sink dishwasher. The bathroom showcases a luxury shower panel system with rainfall shower head and handheld spray. Additional upgrades include a GE electrical panel, ceiling fans in the living areas, and an interior utility room for added convenience. Walk to Hannibal Square, Park Avenue, Rollins College, SunRail, the Winter Park Library, and Rollins baseball field, with Trader Joe’s nearby and quick access to I-4. Whether you’re seeking a move-in-ready residence, income-producing investment, or a premium lot ideal for future luxury construction, this property offers exceptional flexibility and long-term value. Motivated seller—schedule your private showing today.

764 W Comstock Avenue, Winter Park
$315,000
4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code
Back on Market — Buyer’s financing fell through. This well-maintained Dubsdread District home is ready for its next owner! Previously under contract within 10 days, the property is back on the market due to a change in the buyer’s ability to secure finances — NO fault of the home. Featuring over 1,500 sq ft on a generous .22-acre lot across from the 5th tee at Dubsdread Golf Course, this updated 4-bedroom residence offers a 2023 rear addition, screened porch, and Florida room, along with major system upgrades including a 2020 roof, 2023 tankless water heater, new windows with transferrable warranty (2023), and updated electrical and plumbing. Move-in ready!! This is a rare opportunity to own a golf-adjacent home in one of Winter Park/College Park's most desirable neighborhoods—don’t miss it! — schedule your showing today. Seller welcomes clean, straightforward offers and is motivated to move efficiently.

2249 Minnesota Avenue, Winter Park
$415,000
2 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of MLK Park, made even better by our Florida sunsets, which can be seen right from the kitchen window! This home is perfect for anyone seeking a high-convenience and low-maintenance lifestyle. The location puts you right in the heart of town with scenic walks to Winter Park's famous Park Avenue, Hannibal Square, Winter Park Village, The WP9 Golf Course, Rollins College, and plenty more. There are endless options for shopping, entertainment, events, and dining. As the saying goes, "LOCATION, LOCATION, LOCATION!" Home Facts: Metal Roof (2019). AC (2018). Water Heater (2024). Vinyl Flooring (2025). Repiped supply and drain lines. Freshly painted living space. Washer and Dryer included. Spray foam insulation in attic to reduce energy bills. Turnkey and ready for her new Owner!

875 W Lyman Avenue, Winter Park
$1,000,500
3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Desired Winter Park address. A 1950s bungalow on a spacious lot surrounded by multi-million-dollar homes, this is the last untouched original home left on this block. Short distance to Lake Sue, Winter Park schools and many parks in the area. The value is in the land.

210 E Rockwood Way, Winter Park
$630,000
3 Beds ⋅ 2 Baths ⋅ Bungalow Park SubDv. ⋅ 32789 Zip Code
Welcome home to this charming 3-bedroom, 2-bath Mediterranean bungalow perfectly situated on a quiet brick street in the heart of Winter Park. You’ll feel tucked away from it all, yet you’re just blocks from restaurants, city parks & tennis courts, grocery shopping, Park Avenue, and Rollins College. Step inside to a warm and inviting atmosphere featuring 9-foot ceilings, a desirable split-bedroom layout, and an open great room that seamlessly blends the kitchen, dining, and living areas. Beautiful hardwood parquet floors add timeless character throughout. The primary suite offers a relaxing retreat with a deep soaking tub, separate shower, and windows overlooking the backyard. A convenient interior utility room doubles as a practical workspace with a built-in desk, perfect for paying bills or setting up a family computer center. Additional highlights: Top-rated Winter Park schools: Audubon K–8 & Winter Park High School and strong Four-Point: Tile Roof (2012), A/C (2021), Water Heater (2020), Electrical & Plumbing (2012). Easy access to I-4 for quick trips west to Downtown Orlando, the attractions, Tampa & I-75, or east to the beaches & I-95. This Winter Park gem combines charm, comfort, and convenience — the perfect place to call home.

1015 Bungalow Avenue, Winter Park
$312,000
3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code
$5K SELLER CONCESSION TOWARDS BUYER'S CLOSING COSTS AND PRE-PAIDS!!! Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that makes every square foot count! Nestled perfectly between Winter Park and College Park, this fully renovated gem blends modern upgrades with timeless charm. From the moment you arrive, the custom-built front pergola and all-new paver driveway invite you in with style. Step inside to discover a cozy yet efficient layout filled with thoughtful details: barn doors, built-ins, a cabinet pantry, and a linen closet in the guest bath that add character and storage throughout. The brand-new kitchen is compact but packed with quality—featuring granite countertops, stainless steel appliances, and custom cabinetry that maximizes function and charm. The spacious primary suite offers a walk-in closet and an en-suite bath with a very large walk-in shower. Other unique features include a charming barn door to separate the laundry area from the guest bath, optimizing flow and privacy, an extended and brand new paver driveway, along with a beautiful custom fence and storage sheds that provides added storage. This charming bungalow has been designed to live larger than its footprint. Don’t miss your chance to own this thoughtfully designed home in one of Central Florida’s most desirable locations!

1921 Dartmouth Avenue, Winter Park
$560,000
2 Beds ⋅ 1 Baths ⋅ Blk C Pt Rep 02 SubDv. ⋅ 32789 Zip Code
A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office & or additional Storage! Walking distance to Mead Gardens and the new Seven Oaks Park. Convenient to Rollins College, Park Avenue and Winter Park Village, featuring multiple local eateries and restaurants. Just one mile to Hospital, Science Center and Museum. Easy access to 17/92, I-4 and 408 Expressway. New Roofs (2022), Sewage Pipes Relined (2024), Hot Water Tank (2021) and Home Air Conditioner (2020). Don't miss this hidden gem in beautiful Winter Park, Florida. Submit all offers on "As Is" contract with proof of funds attached. All information is deemed to be correct. Buyer and buyer's agent should verify all prior to submission.

1339 Orchid Avenue, Winter Park
$228,000
1 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
This cozy 1-bedroom, 1-bath bungalow is your ticket into one of Winter Park’s most desirable neighborhoods—just steps from beautiful Lake Killarney and surrounded by some of the city’s best dining, shopping, and entertainment. Whether you’re looking for a charming personal retreat, a smart investment, or a renovation project with serious upside, this property delivers with its unbeatable location and potential. Sitting on one of the larger lots on the street and with no HOA to restrict your vision. What makes this opportunity truly special is the walkable lifestyle—Trader Joe’s, Winter Park Village, Park Avenue, Dubsdread Golf Course, and a full menu of local restaurants and shops are all just minutes away. Quick access to I-4 puts downtown Orlando, nearby attractions, and work commutes easily within reach, yet you’re tucked away in a serene, scenic pocket of town where lake breezes and neighborhood charm still reign. Homes in this area are rarely available at this price, making it a golden chance to get into a sought-after location and bring your dream renovation to life. Don’t miss the opportunity to own a slice of Winter Park with character, convenience, and curb appeal just waiting to be unlocked. Please allow up to 72 hours for a response. DO NOT SUBMIT OFFERS SITE UNSEEN!

1979 Staunton Avenue, 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
$600,000
3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code
Value is in the land.

1550 Palm Avenue, 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
$460,000
3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
Here's your opportunity to own a charming Winter Park bungalow with convenient access to 1792, I4, and all of the best shopping and dining in Winter Park, Maitland, and College Park. On the exterior of the home, you'll appreciate with the mature landscaping and the very low traffic, dead-end street that is Eland Ave. Notable systems include the roof, which was replaced in 2015, the 2018 windows, and the HVAC, which was replaced in 2022. In the backyard, the pool and hot tub provide an oasis environment that you're sure to fall in love with. The pool was resurfaced in 2023, along with new pavers, LED lighting, and tile so it looks and feels brand new! The hot tub was added in 2018 and will convey with the property. Inside, the space is perfect for entertaining and the layout is highly multifunctional. The kitchen overlooks the family room with all of its natural light and original wood flooring and there is a large bonus room, ideal for a home office or a playroom/secondary living space depending on the buyers' needs. 3 bedrooms and 2 bathrooms can be found down the hall. Additional upgrades to this property include windows, exterior LED lighting, and the irrigation system. This home is zoned for Hungerford Elementary, which is an OCPS Magnet Program for Advanced Curriculum (STEAM). In less than 10 minutes, you can get from this property to Park Avenue (6 minutes), Hannibal Square (7 minutes), Winter Park Village (5 minutes), Edgewater Drive (7 minutes), I-4 (3 minutes), Rollins College (10 minutes), and Lake Lily Park (6 minutes).

1937 Eland Avenue, Winter Park
$675,000
4 Beds ⋅ 3 Baths ⋅ Carver Town First Add SubDv. ⋅ 32789 Zip Code
This stunning property in historic Winter Park offers an excellent price point and is ideally situated near Park Avenue’s shops and restaurants, Rollins College, Winter Park Village, Winter Park Farmer's Market, and Hannibal Square. Completely renovated in 2021, this 4 bedroom, 3 bathroom home has been thoughtfully appointed with double primary suites, each with ensuite bathrooms and large closets. Split from these primary suites are 2 additional ample sized bedrooms and a full bathroom. The open floor plan boasts contemporary updates throughout, including light wood-like tile floors, LED recessed lighting and fresh paint. The kitchen is a chef's dream, featuring quartz countertops, a designer tile backsplash, stainless steel appliances, and a 5-burner gas stove complete with a pot filler. The primary ensuite bathroom is a luxurious retreat, showcasing dual vanities, an oversized tiled shower with multiple shower heads, and a built-in bench. The bathrooms are bright and fresh with contemporary black and white tile accents. Enjoy an expansive back yard with a large paved patio, perfect for entertaining. This home can also serve as an excellent investment opportunity for your Rollins student! Schedule your private showing today! HVAC - 2017 ROOF - 2021

678 Depugh Street, Winter Park
$500,000
3 Beds ⋅ 1 Baths ⋅ Lake Monte Sub SubDv. ⋅ 32789 Zip Code
HUGE PRICE ADJUSTMENT...NEARLY $100K!! Owner Is Highly Motivated and Ready To Work With You! This charming Winter Park Bungalow is centrally located in a highly desired area of Winter Park (32789) and is Ready for Immediate Occupancy! Featuring 3 full bedrooms, one bathroom, nearly 1,150 sqft of living area, a covered carport and storage rooms. Beautifully updated and maintained throughout the years with vintage style hardwood flooring which flows throughout. The renovated kitchen is sure to impress with modern 42-inch cabinets, granite countertops, stainless steel appliances and update hardware and finishes. The freshly painted interior and exterior makes this home feel “like new” again. Newer paddle fans and lighting fixtures have been added throughout the interior. This is the ideal opportunity for an investor looking to build new, a first-time home buyer or even a downsizing buyer. Setback nicely on a quiet, tree-lined street with a very spacious fenced back yard area that offers plenty of room for an outdoor living area, new pool and/or an additional dwelling or storage. Simply traditional Winter Park at its best! Conveniently located just moments from Winter Park shopping and fine dining, multiple grocery stores, beautiful parks, gyms, entertainment, hospitals, as well as A+ rated Winter Parks schools. Come and see for yourself before its gone! Act Now!

1810 Hollywood Avenue, 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
$615,000
3 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
*OFFERED BELOW APPRAISED VALUE* Charming Bungalow in Winter Park now Available. While originally built in 1932, this house has been completely renovated to today's standards. Upgrades/Improvements include New Roof (2024), New Windows (2024), New A/C and Ductwork (2024), New Flooring throughout (2024 - commercial grade LVP), New Appliances (2024), Completely Remodeled Kitchen and Bathrooms (2024), Whole House Repipe (2022), Upgraded from Septic to Sewer with New Sewer Line (2022), Exterior Paint (2024), and more. This property offers some very unique features. There is a Detached 280 sf Studio with a Full Kitchen and Bathroom. This unit is on a Separate Electrical Meter. There was also a Waterproofing System with Sump Pumps added around the foundation of this studio. This lot is just under 1/4 acre and zoned R-2, which offers a whole yard. The entire street is undergoing a major revitalization, the house next door (to the east), is currently scheduled to be torn down and replaced with 2 new luxury townhomes and priced at just under $1m a piece. This property offers the opportunity to live in the main house and AirBnb the studio, or rent both and hold indefinitely in an area that will only continue to appreciate. Don't miss your opportunity to own your piece of Winter Park. Schedule your private showing today.

1419 Miller Avenue, Winter Park
$414,900
2 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Welcome to this charming bungalow nestled in the highly sought after Dubsdread Heights neighborhood. A quaint covered front porch sets the stage for this delightful home. Inside, the fantastic open floor plan is flooded with natural light, creating an inviting space ideal for both relaxation and entertaining. The stylish kitchen is a chef's dream with custom cabinets, striking granite counters, stainless steel appliances, and a tasteful tile backsplash. A garden window above the kitchen sink is the ideal space for growing your very own herbs or just showcasing your favorite plants and flowers. Just beyond, a granite-topped coffee bar/sideboard adds a touch of elegance and practicality. The primary bedroom offers a serene retreat with a walk-in closet and a stunning en suite bath featuring a granite-topped vanity and a frameless glass enclosed shower with exquisite tilework and a convenient niche for toiletries, this bathroom is a spa-like oasis. An additional full bath with another granite-topped vanity and tub/shower combo serves the secondary bedroom. French doors from the kitchen's coffee bar/sideboard area lead to an expansive deck overlooking a large, open paver patio and fenced backyard, perfect for hosting gatherings or simply enjoying the amazing Florida weather. A brand new hurricane-proof shed provides ample storage space, while a magnificent mango tree offers fresh fruit and adds to the backyard's appeal. Located conveniently close to College Park, downtown Orlando, and Winter Park, and with easy access to I-4 and Fairbanks Avenue, this home ensures that getting around town is effortless. Meticulously maintained this beautiful bungalow is both spacious and modern while offering a cozy ambiance. The only item needed to complete this home is YOU!

760 Baffie Avenue, Winter Park
$950,000
3 Beds ⋅ 3 Baths ⋅ Hills SubDv. ⋅ 32789 Zip Code
Prepare to be impressed by this meticulously upgraded Winter Park home, where every detail has been carefully considered to offer the ultimate in comfort and convenience. Beautiful oversized and totally remodeled spit bedroom plan - 3 bed / 3 bath, single-story, brick construction with massive pool, wood-burning fireplace, and entertaining screened porch and patio. All on a private .32 acre lot. Step through the newly installed exterior door handles and locks into a home transformed by a comprehensive renovation. From the garage to the outside pool area, all new electrical wiring ensures safety and reliability. Transformation in 2021 includes - all new ELECTRICAL WIRING, PANELS, tankless gas water heater, chimney flume. Roof replaced in 2017. Added propane gas hookup opens up a world of possibilities, whether it's cooking on the gas oven or envisioning outdoor gatherings around a pizza oven or grill. In 2021- new flooring, interior doors, handles, and custom trim throughout. The laundry room has been thoughtfully expanded - new dryer venting. Brand new AC system, updated ducting, and added insulation for optimal climate control and energy efficiency. Recessed lighting illuminates the main areas. The open kitchen has undergone a stunning remodel, featuring NEWER APPLIANCES with a brand new LG gas range July 2024 and custom shelving. Eat-in island, quartz countertops, coffee bar, and designer tile backsplash. Two family rooms plus dining room that can also be used as an office! Bathrooms have been tastefully updated with new toilets and plumbing fixtures. Spacious primary suite overlooks pool area and has lots of closet space. Integrated wifi system including wifi boosters and hard-wired throughout the house for remote workability. Outside, the enhancements continue with new sod and mulch, an electronic wifi-controlled irrigation system, and a dedicated irrigation well for sustainable landscaping. The pool area has been expanded for entertaining. Pool light replaced and Spanish tile on screened-in porch. Perfect for large groups staying out of the sun and tons of dining and conversation area. Outdoor kitchen is ready to go once hooked up to gas. Porch is wonderful for pets too! Additionally, this home boasts a water softener, ensuring the highest quality water for your family. The outdoor patio off the master bedroom is prepped with 3 ft. slab to support future expansion, adding even more value and potential to this already remarkable property. Nestled within a friendly neighborhood on cul-de-sac and positioned atop a hill with excellent schools and a voluntary HOA offering community events, this home offers not just a place to live, but a lifestyle to embrace. Most coveted schools - Dommerich Elementary, Maitland Middle, and Winter Park High School Don't miss the opportunity to make this your forever home – schedule a viewing today!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src=https://my.matterport.com/show/?m=FKP12jRiFES&mls=1 frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

2421 Mandan Trail, Winter Park
$365,000
2 Beds ⋅ 1 Baths ⋅ Golfview Replat SubDv. ⋅ 32789 Zip Code
Ready for renovation to make it your own this bungalow is across the street from Dubsdread Golf Course. Midiron Drive is transitioning to million dollar homes so with a 150 FT X 60 FT Lot this is a good opportunity. The roof was installed in 2022 and the water heater is approx 7 years old. The floor plan includes 2 bedrooms/1 bath and a bonus room. Location, Location, Location! You’ll love the convenience of living in the hub of activity, with close proximity to winter Park Village, Advent Health, UCF Downtown Campur, Dr. Phillips Center for the Performing Arts and lots of shopping and dining options. Exciting developments on the horizon can be had with a short walk or bike to the future Packing District, which will feature a State-of-the-Art YMCA, walking/biking Paths and Trails, food halls and More. Whether you’re an avid golfer, a busy professional, or someone who loves being close to vibrant city life, this home offers the perfect location to enjoy it all.

3601 Midiron Drive, Winter Park
$925,000
3 Beds ⋅ 4 Baths ⋅ Orwin Manor SubDv. ⋅ 32789 Zip Code
Step back in time while indulging in contemporary comforts with this exquisite historic property boasting 3 bedrooms, 3 full baths, and 1 half bath. Take a dip in the luxurious inground swimming pool featuring a lavish Jacuzzi hot tub and a beautiful travertine deck surround. Elegant hardwood floors flow throughout the main areas of this home and stylish wood work is abundant throughout. Channel your inner chef in the fully remodeled gourmet kitchen equipped with gorgeous granite countertops, large eat-in island, stainless steel appliances, gas cook top, and ample storage space. Whether preparing a casual meal or hosting a dinner party, this kitchen is sure to inspire culinary creativity. Situated just minutes from downtown Winter Park and Orlando, this property offers unparalleled access to cultural landmarks, upscale dining establishments, boutique shops, and vibrant entertainment venues. Immerse yourself in the rich tapestry of history and culture while enjoying the convenience of modern urban living. Roof, HVAC, electrical, and plumbing were all replaced in 2016 during a renovation/addition. An inground swimming pool equipped with a Pentair automation package, led lighting, deck & spa jets, added in 2020. A 600 sq-ft guest-house/pool cabana was also added in 2021. Too many other upgrades to list. The Orwin Manor development dates back to the mid-1800’ and is located at the intersection of Orlando and Winter Park, hence the name "Orwin". Along with the residents, the convenient location, variety of architecture with many historic homes, mature street tree landscape and caring neighbors are what makes Orwin Manor such a great place to live. Come see this classic Orwin Manor upgraded historic home. To learn more about the history of Orwin Manor, visit https://orwinmanor.org/history/#_

1355 Pelham Road, Winter Park
$456,900
2 Beds ⋅ 1 Baths ⋅ Orwin Manor Stratford Sec SubDv. ⋅ 32789 Zip Code
Fall in love with this home - perfectly positioned on a beautiful, tree lined street, in the highly desirable Orwin Manor neighborhood in Winter Park. This warm, timeless and appealing 1947 bungalow has been lovingly updated and offers a seamless unique blend of yesteryear and modern updates. It is packed with charm and potential in every nook. As you step inside, you'll be greeted by original hardwood floors, updated kitchen and a view of your mature landscaped backyard from the light and airy sun room. The main bedroom does not disappoint with its larger size not found in these bungalows. You'll find the perfect balance of character and convenience in these key areas of the house. If you choose you can also enjoy the Florida sunshine in your spacious backyard or try your green-thumb – even room for expansion. It’s a home that invites you to live, laugh and grow. This home will simply fulfill your needs, indoors and outdoors. New roof, gutters, newer appliances, AC and double pane windows as well. Don't miss your opportunity to make this home yours. Minutes from Winter Park’s historic Park Avenue with Shopping and Restaurants galore, Orlando Museum of Art, The Orlando Science Center, Mead Gardens, AdventHealth Orlando Hospital, Downtown and the Sun Rail Station as well as easy access to the Interstate.

1434 Norfolk Avenue, Winter Park
$440,000
3 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
3 bedroom, 2 bathroom home with one car garage. New roof, remodeled kitchen and baths. Granite countertops, newer appliances including brand new washer and dryer all included. Lots of nice features including motion detection sink in the kitchen. New laminate flooring. Rolling island with seating and barstools stay. Laundry room located inside. Yard is fenced with white vinyl. Great location near Advent Health Hospital, Park Avenue, College Park, Rollins, Mead Gardens, and incredible restaurants.

1781 Michigan Avenue, Winter Park