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Search All Winter Park Homes For Sale

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Winter Park FL. Homes For Sale

Accurate Listings Updated Every 5 Minutes

Homes Under $300,000

$300,000-$500,000

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Located in Orange County, Florida, and just outside of the bustling city of Orlando, lies the town of Winter Park, where residents enjoy the beautiful scenery, fun recreation, and family-friendly community. Enjoy the peace of this suburban city, with its serene lakes and botanical gardens bringing a slow-paced atmosphere to the neighborhood. Founded as a resort community, Winter Park contains many recreational facilities, from a beach, boat launch, numerous museums, and golf courses, there is an endless array of things to do in Winter Park.

Bounded by numerous lakes, Winter Park residents enjoy boating, fishing and kayaking in vast stretches of blue water. With nature trails winding around the shores of Lake Virginia and Lake Maitland, outdoor enthusiasts enjoy biking, hiking, and observing nature along these beautiful paths. Additionally, residents will find many beautiful parks and gardens to enjoy, with Ward Park and the Mead Botanical Gardens hosting sports facilities, walking trails, and lovely scenery. Along with a vast array of recreation, Winter Park residents love the conveniences and amenities provided by the downtown district, from shopping malls, restaurants, and local cafes, you will find great shopping and dining options in the area. 

There is a variety of homes in Winter Park that range anywhere from humble beach cottages to elegant lakefront mansions. This suburban residential community consists of single-family homes, large estates, and condominiums. Depending on the property’s size, location, and age, the prices range anywhere from affordable starter homes to high-end extravagant residences. There really is a home for everyone here in Winter Park, Florida. 

 

If you would like more information regarding homes for sale in Winter Park, Florida, please allow us to assist you and contact us today.

Newest Winter Park Listings

1500 Grove Terrace, Winter Park image
1500 Grove Terrace, Winter Park $1,485,000

Looking for the quintessential Winter Park home? This exquisite, single story 3 bedroom, 3 bath, plus office home is located in the beautiful Lake Sylvan Shores neighbor...

  • 3 Beds
  • 3 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
128 Oak Grove Road, Winter Park image
128 Oak Grove Road, Winter Park $339,000

Welcome Home! Located only MINUTES from the luxury Winter Park Village and Park Avenue. This home is situated exactly where you need to be in order to make the most of e...

  • 3 Beds
  • 2 Baths
  • Winter Park Oaks SubDv.
  • 32789 Zip Code
550 Lake Front Boulevard, Winter Park image
550 Lake Front Boulevard, Winter Park $1,975,000

Welcome to 550 Lake Front Boulevard, a luxurious haven situated in Winter Park, Florida. This remarkable residence, built in 2019, embodies elegance, meticulous craftsman...

  • 5 Beds
  • 4.5 Baths
  • Lords Sub SubDv.
  • 32789 Zip Code
657 Worthington Drive, Winter Park image
657 Worthington Drive, Winter Park $780,000

Picturesque 4 Bedroom / 2 Bathroom Home on tranquil end of street. Don't Be fooled by the square footage. This home feels and lives much larger! Gorgeous Light and Bright...

  • 4 Beds
  • 2 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
431 Fletcher Place, Winter Park image
431 Fletcher Place, Winter Park $2,000,000

A stunning home in Winter Park ready for the next lucky family to move in! This charming four-bedroom, 3.5-bath home has it all. The moment you walk in the front door fro...

  • 4 Beds
  • 3.5 Baths
  • Sorensen Heights SubDv.
  • 32789 Zip Code
2352 Kestrel Perch Place, Winter Park image
2352 Kestrel Perch Place, Winter Park $795,000

Welcome to this newly constructed home in the beautiful, gated community of Hawks Crest. This stunning Anastasia model has 4 bedrooms 3.5 bathrooms that comes with 2 AC u...

  • 4 Beds
  • 3.5 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
1405 Lone Feather Trail, Winter Park image
1405 Lone Feather Trail, Winter Park $929,000

Distinctive, private, unique and full of character is what sets this estate apart from all other properties on the market. Welcome home to your freshly built and highly u...

  • 4 Beds
  • 3.5 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
1155 Wildmeadow Run, Winter Park image
1155 Wildmeadow Run, Winter Park $769,000

Welcome to the exclusive gated community, Meadows at Hawk's Crest, located in sought-after Winter Park northeast of Orlando. We promise that this house will not disappoin...

  • 4 Beds
  • 3.5 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
625 Brechin Drive, Winter Park image
625 Brechin Drive, Winter Park $749,900

A timeless home awaits among the tree canopies of Kenilworth Shores, a tried-and-true Winter Park neighborhood steeped in history. A pristine property and beautifully app...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
1612 Eastbrook Boulevard, Winter Park image
1612 Eastbrook Boulevard, Winter Park $399,900

Attention All Buyers and Investors…This is a Must See 3br/2bath single story home in one of Winter Parks highly sought out neighborhoods in Eastbrook. This property has N...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 05 SubDv.
  • 32792 Zip Code
428 S Phelps Avenue, Winter Park image
428 S Phelps Avenue, Winter Park $895,000

Located in the quaint, desirable Kenilworth Shores of Winter Park is where you will find this UPDATED traditional home that features over 2100 sq. ft., boasting 3 bedroom...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 02 SubDv.
  • 32789 Zip Code
1460 Sunset Drive, Winter Park image
1460 Sunset Drive, Winter Park $2,299,000

Welcome to Old Winter Park's coveted Tree Streets - a place where your dream home is waiting for you! This truly sustainable 5/3 property rests in a neighborhood teeming ...

  • 5 Beds
  • 2.5 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
2080 Sharon Road, Winter Park image
2080 Sharon Road, Winter Park $3,595,000

A truly stunning 2022 transitional, modern residence recently completed in the heart of the Vias by Z Properties Inc. Tremendous “off the charts” quality in this custom-d...

  • 4 Beds
  • 4.5 Baths
  • Tuscania SubDv.
  • 32789 Zip Code
2020 Strathaven Road, Winter Park image
2020 Strathaven Road, Winter Park $515,000

Terrific opportunity to renovate or restart and build new! Situated on a large .30 acre (13,035 sf) corner lot, the property offers lots of possibilities! Tucked away i...

  • 4 Beds
  • 2 Baths
  • Kenilworth Shores Section Seven SubDv.
  • 32792 Zip Code
870 Carver Street, Winter Park image
870 Carver Street, Winter Park $325,000

Great Investment Opportunity (SOLD AS IS) This three bedroom one bath home is in need of a total makeover, or tear down and build your own new home. Home is situated in ...

  • 3 Beds
  • 1 Baths
  • Magnolia Gardens Sub SubDv.
  • 32789 Zip Code
2156 Talman Court, Winter Park image
2156 Talman Court, Winter Park $2,495,000

Introducing a once-in-a-lifetime opportunity to own an exquisite multi-generational home in the coveted and exclusive neighborhood of Talman Mews, situated on not one, bu...

  • 5 Beds
  • 5.5 Baths
  • Talman Mews Ph 2 SubDv.
  • 32792 Zip Code
731 Williams Drive, Winter Park image
731 Williams Drive, Winter Park $1,189,000

Highly sought after community of Park Grove 3 bedroom 2.5 bath pool home now available! This beautiful home is located in highly sought after Park Grove community, just...

  • 3 Beds
  • 2.5 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
1640 Mayfield Ave, Winter Park image
1640 Mayfield Ave, Winter Park $1,725,000

Located in desirable Winter Park, this beautiful single-story home is situated on an oversized lot of 0.28 acres surrounded by mature oaks, magnolia and an array of lush ...

  • 3 Beds
  • 2.5 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
1451 Lyndale Boulevard, Winter Park image
1451 Lyndale Boulevard, Winter Park $1,750,000

**YOUR SEARCH STOPS HERE** POOL HOME** SEPARATE TWO BEDROOM GUEST HOUSE** MASTER BEDROOM ON MAIN LEVEL** Experience luxury living at its finest in this beautiful two-stor...

  • 5 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1321 Bridgeport Drive, Winter Park image
1321 Bridgeport Drive, Winter Park $759,900 ▼

Waterbridge of Winter Park! Rare opportunity to own in this fabulous Winter Park community being offered by the original owner. This one is ready for your special touch...

  • 4 Beds
  • 2 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
2112 Sycamore Drive, Winter Park image
2112 Sycamore Drive, Winter Park $599,999 ▼

Unbelievable opportunity to own this 4 bedroom, 3 bath home nestled within a charming and highly sought-after Winter Park neighborhood. This older home exudes timeless ap...

  • 4 Beds
  • 3 Baths
  • Northwood Terrace SubDv.
  • 32789 Zip Code
220 Blossom Lane, Winter Park image
220 Blossom Lane, Winter Park $699,500

Welcome to 220 Blossom Lane, an exquisite NEWLY RENOVATED single-family residence nestled in highly sought-after Winter Park, FL. This luxurious 3-bedroom, 2-bathroom hom...

  • 3 Beds
  • 2 Baths
  • Shores Lake Killarney SubDv.
  • 32789 Zip Code
2412 Chantilly Avenue, Winter Park image
2412 Chantilly Avenue, Winter Park $2,600,000

Under Construction. Breathtaking modern home just weeks away from completion. This sleek five-bedroom, six-and-a-half-bath residence abounds with high-end details through...

  • 5 Beds
  • 6.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1772 Chestnut Avenue, Winter Park image
1772 Chestnut Avenue, Winter Park $2,275,000

One or more photo(s) has been virtually staged. Welcome to Vimaro Homes newest completed Project! This listing showcases a stunning new construction project with an impre...

  • 5 Beds
  • 4.5 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
2246 King Henrys Court, Winter Park image
2246 King Henrys Court, Winter Park $563,250 ▲

!!!New Roof Coming soon!!! Welcome home to this 4 bedroom, 3 bathroom, single-family home located in the community of Winter Woods in Winter Park. All three bathrooms ha...

  • 4 Beds
  • 3 Baths
  • Winter Woods Unit 01 SubDv.
  • 32792 Zip Code
222 W Rockwood Way, Winter Park image
222 W Rockwood Way, Winter Park $3,600,000

New Construction Custom Built Masterpiece located in one of Winter Park’s most desirable neighborhoods, zoned for top-rated schools in the county and only minutes away fr...

  • 5 Beds
  • 5.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
730 Callahan Street, Winter Park image
730 Callahan Street, Winter Park $610,000

West Side Winter Park Investment Property

  • 3 Beds
  • 2 Baths
  • Carver Town SubDv.
  • 32789 Zip Code
1461 Via Tuscany, Winter Park image
1461 Via Tuscany, Winter Park $16,000,000

Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue...

  • 5 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
2819 Parkland Drive, Winter Park image
2819 Parkland Drive, Winter Park $2,395,000

Pre-Construction. To be built. Experience the perfect fusion of indoor-outdoor living, clean lines, and minimalist design in the heart of Winter Park. This California Mo...

  • 4 Beds
  • 4.5 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1038 Bradford Drive, Winter Park image
1038 Bradford Drive, Winter Park $449,000

You’ll be impressed with this well-cared for home in the desired Howell Estates Community of Winter Park. Extremely low yearly HOA fees of $25. You’ll notice the curb app...

  • 4 Beds
  • 2 Baths
  • Howell Estates Rep SubDv.
  • 32792 Zip Code
2918 Sanbina Street, Winter Park image
2918 Sanbina Street, Winter Park $495,000

This stunningly renovated ranch-style home is situated on a tranquil street in the charming Winter Park neighborhood, offering easy access to shopping and top-rated schoo...

  • 3 Beds
  • 2 Baths
  • Howell Heights SubDv.
  • 32789 Zip Code
1461 Palm Avenue, Winter Park image
1461 Palm Avenue, Winter Park $2,100,000

Under Construction. Under construction. Beautiful New Construction home in the heart of Winter Park. This upscale Magnolia Home features upscale design features throughou...

  • 4 Beds
  • 4.5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
544 Saint Dunstan Way, Winter Park image
544 Saint Dunstan Way, Winter Park $645,000 ▼

SOLAR HOME!!!!!Beautiful 4 bedroom 2 bath with a large pool located in the Winter Park Pine. Features large kitchen with large island, granite counter tops and 42" upper ...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
3471 Athena Drive, Winter Park image
3471 Athena Drive, Winter Park $425,900

Are you looking to live in a prestige Winter Park Pool Home! You have found one! It is located in a quiet Eastbrook Subdivision and in the heart of Winter Park! Only a sh...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 16 SubDv.
  • 32792 Zip Code
3409 Ferndell Drive, Winter Park image
3409 Ferndell Drive, Winter Park $415,000 ▼

Welcome home to the desirable Eastbrook community located in Winter Park and zoned for top-rated schools! Currently tenant occupied through 12/31/23 but seller will reque...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 8 SubDv.
  • 32792 Zip Code
424 Turkey Run, Winter Park image
424 Turkey Run, Winter Park $1,250,000 ▼

This lovingly cared for transitional pool home with oversized lot is situated on a quiet tree-lined street. This spacious home is perfect for family living or entertainin...

  • 4 Beds
  • 3.5 Baths
  • Quail Hollow SubDv.
  • 32789 Zip Code
2019 Natalen Road, Winter Park image
2019 Natalen Road, Winter Park $1,395,000

Under Construction. New CUSTOM pool home a short walk to Winter Park High School. Private keyed ACCESS to beautiful LAKE BERRY with boat dock and ramp is available for on...

  • 3 Beds
  • 4 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
617 Penn Place, Winter Park image
617 Penn Place, Winter Park $3,495,000

This exquisite French Country estate is a true masterpiece, boasting a grand total of 4900 square feet of luxurious living space. Located in the highly coveted Penn Place...

  • 4 Beds
  • 3.5 Baths
  • Pennsylvania Place Rep SubDv.
  • 32789 Zip Code
617 Balmoral Road, Winter Park image
617 Balmoral Road, Winter Park $1,250,000 ▼

New Price!! Beautifully renovated four-bedroom, three-full-bath Winter Park home. The incredible curb appeal begins with new landscaping, exterior lighting, paver drive,...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1530 Mayfield Avenue, Winter Park image
1530 Mayfield Avenue, Winter Park $2,995,000 ▲

Located in Winter Park this home was devised by architectural firm, Green Apple & built by E2 Homes. Contemporary living adheres to a few principles that define its simpl...

  • 4 Beds
  • 4 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
1863 Lake Spier Dr, Winter Park image
1863 Lake Spier Dr, Winter Park $1,175,000 ▼

RARE FIND - *** LAKE FRONTAGE on Private Lake Spier with DOCK, POOL,& CABANA which could never be built today!!!*** This home is in the perfect location only 0.7 miles or...

  • 4 Beds
  • 3 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
2015 N Park Avenue, Winter Park image
2015 N Park Avenue, Winter Park — Park Ave $1,925,000

Welcome to 2015 N. Park Avenue - your brand new modern construction home! This stunning property is designed with contemporary features and high-end finishes throughout....

  • 4 Beds
  • 4.5 Baths
  • N Park Ave SubDv.
  • 32789 Zip Code
2315 Janice Avenue, Winter Park image
2315 Janice Avenue, Winter Park $1,200,000 ▼

BACK ON THE MARKET!!! This beautiful, lovingly cared for move-in ready, one story 4-bedroom 2.5 bath home offers you a unique opportunity to own in Winter park for under...

  • 5 Beds
  • 3 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
1271 Via Capri, Winter Park image
1271 Via Capri, Winter Park $2,975,000 ▼

Luxurious and inviting, this custom one-owner home has it all and is on a quiet brick street in the desirable Via’s of Winter Park, elevated on a generous sized lot with ...

  • 5 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
1741 Glencoe Road, Winter Park image
1741 Glencoe Road, Winter Park $2,850,000

This beautiful 4-bedroom home (with a pool) sits close by between Lake Sue and Lake Virginia in one of the most sought-after neighborhoods of Winter Park. And in an area ...

  • 4 Beds
  • 4.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1503 Palmer Avenue, Winter Park image
1503 Palmer Avenue, Winter Park $1,499,000

Fabulous single story home in the heart of Winter Park! This 4 bed, 3 bath home is situated on a large CORNER lot with a highly desirable 3 car garage! Step inside the fo...

  • 4 Beds
  • 3 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
671 Via Lugano, Winter Park image
671 Via Lugano, Winter Park $4,500,000 ▼

Serene and private estate on a half acre lot in the Heart of Olde Winter Park. A custom built estate with amazing detail throughout boasts 6 bedrooms (downstairs master p...

  • 6 Beds
  • 6.5 Baths
  • Sicilian Shores SubDv.
  • 32789 Zip Code
2164 Crandon Avenue, Winter Park image
2164 Crandon Avenue, Winter Park $369,000

In the heart of Winter Park, next to 1-4 between Par and Fairbanks exits. This cute 2/1 house is ready for renovations which will make it a great home or rental. It is on...

  • 2 Beds
  • 1 Baths
  • Olympia Heights Annex SubDv.
  • 32789 Zip Code
5058 Seminole Avenue, Winter Park image
5058 Seminole Avenue, Winter Park $380,000 ▼

Winter Park charmer with short term/rental possibilities, a brand NEW ROOF (2023), NEW KITCHEN (2022), UPDATED A/C (2022), WATER HEATER (2023), WOOD LOOK TILE throughout ...

  • 3 Beds
  • 2 Baths
  • Suburban Homes SubDv.
  • 32792 Zip Code
2430 Roxbury Road, Winter Park image
2430 Roxbury Road, Winter Park $995,000

Under Construction. New construction in Winter Park, Florida. Nestled amongst million-dollar properties, with Lake Killarney just down the street, this single-story conte...

  • 4 Beds
  • 3.5 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
1619 Elizabeths Walk, Winter Park image
1619 Elizabeths Walk, Winter Park $2,250,000

! Attention Buyers! Live Your best life in the desirable Windsong Subdivision in Winter Park. This beautiful custom built home, with attention paid to every detail, wel...

  • 4 Beds
  • 3.5 Baths
  • Windsong Community Association, Inc. SubDv.
  • 32789 Zip Code
640 Dunblane Drive, Winter Park image
640 Dunblane Drive, Winter Park $776,900 ▼

PRICE REDUCTION! Simple Elegance! Just a stone's throw from Lake Baldwin! You will be captivated by this tastefully chic updated Home in the very sought after neighborho...

  • 3 Beds
  • 3 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
1022 Mckean Circle, Winter Park image
1022 Mckean Circle, Winter Park $2,395,000

This custom four bedroom, three and one half bathroom, 4,610 square foot pool home is located in the heart of Olde Winter Park. From the paver covered circular drive you...

  • 4 Beds
  • 3.5 Baths
  • Palmer Park SubDv.
  • 32789 Zip Code
465 N Phelps Avenue, Winter Park image
465 N Phelps Avenue, Winter Park $2,200,000

Pre-Construction. To be built. Modern Farmhouse with Pool is located in Winter Park and offers over 4500 sq. ft. of air-conditioned living space, with another 1,000 sq. ...

  • 7 Beds
  • 6 Baths
  • Ethel Park SubDv.
  • 32789 Zip Code
4091 Scarlet Iris Place, Winter Park image
4091 Scarlet Iris Place, Winter Park $1,800,000

Absolutely gorgeous, executive home, located in a gated community in the beautiful Bear Gully Pointe, in Winter Park!. Masterfully designed with exquisite details of cont...

  • 6 Beds
  • 5.5 Baths
  • Bear Gully Pointe SubDv.
  • 32792 Zip Code
780 Baffie Avenue, Winter Park image
780 Baffie Avenue, Winter Park $430,000 ▼

Deep lot one block from Dubsdread golf Course. You can use as your primary home or great for investor. Great location, minutes from Park Avenue, College Park and Downtown...

  • 3 Beds
  • 2 Baths
  • Dubsdread Heights SubDv.
  • 32789 Zip Code
4858 Seminole Avenue, Winter Park image
4858 Seminole Avenue, Winter Park $455,900 ▼

LOCATION, LOCATION, LOCATION!! in the hearth of winter park with no HOA, hard to find 1/2 Acres lot with a beautiful 3/2 move in ready, tile throughout. Roof was done in ...

  • 3 Beds
  • 2 Baths
  • Suburban Homes First Add SubDv.
  • 32792 Zip Code
1106 Palmer Avenue, Winter Park image
1106 Palmer Avenue, Winter Park $4,250,000

Elegant Charleston style residence secluded on a "private lane" in the heart of Olde Winter Park, just one property removed from Lake Osceola. Resting on over a ½ acre ma...

  • 4 Beds
  • 5.5 Baths
  • Winter Park Town Of SubDv.
  • 32789 Zip Code
643 Gilbert Road, Winter Park image
643 Gilbert Road, Winter Park $544,000 ▼

LOCATION, LOCATION, LOCATION!! Amazing opportunity to own in the highly sought after, well established neighborhood of WINTER PARK PINES. Zoned for great schools Brookshi...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
2512 Eastbrook Boulevard, Winter Park image
2512 Eastbrook Boulevard, Winter Park $389,000 ▼

Perfect 4/2.5 home in the well-established subdivision of Eastbrook in Seminole County! This lovely home has NEW laminated floors in the bedrooms, and recently painted wa...

  • 4 Beds
  • 2.5 Baths
  • Eastbrook Sub Unit 8 SubDv.
  • 32792 Zip Code
1231 Kenwood Avenue, Winter Park image
1231 Kenwood Avenue, Winter Park $799,000 ▼

Price Improvement on the Lowest Priced Pool Home in 32789!! Welcome to this stunning bungalow featuring 3 bedroom, 2 bathrooms with a Pool situated in the historic and ch...

  • 3 Beds
  • 2 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
7577 Dockside Street, Winter Park image
7577 Dockside Street, Winter Park $374,500 ▼

Fully remodeled home in Winter Park with no association and huge backyard space. New roof installed in 2021. This three-bedroom, two-bath, one-car garage home has new lam...

  • 3 Beds
  • 2 Baths
  • Woodcrest Unit 6 SubDv.
  • 32792 Zip Code
1714 Westchester Avenue, Winter Park image
1714 Westchester Avenue, Winter Park $850,000 ▲

Welcome to Orwin Manor, a timeless Orlando-Winter Park neighborhood established in 1924, offering lifestyle and prime location. Come see this designer dream! Solidly buil...

  • 3 Beds
  • 2.5 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1554 Harris Circle, Winter Park image
1554 Harris Circle, Winter Park $1,180,000 ▼

Pre-inspected. Offered for the first time in over 30 years! Winter Park’s only original, charming and completely remodeled historical farmhouse. Known as the “Harris-Edis...

  • 3 Beds
  • 2.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
526 Genius Drive, Winter Park image
526 Genius Drive, Winter Park $3,500,000 ▼

Magnificent lakeview estate in Windsong – 526 Genius Drive, Winter Park. For the first time, this stately residence is on the market and available for purchase. Custom bu...

  • 4 Beds
  • 4.5 Baths
  • Windsong North Shore 43/74 SubDv.
  • 32789 Zip Code
2627 Ambergate Road, Winter Park image
2627 Ambergate Road, Winter Park $599,000

This beautiful and remodeled home is turnkey and ready to move in. Investors -- You will love the cash flow upside with this property. Updated Roof, AC, Exterior Pain...

  • 4 Beds
  • 3 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
244 W Kings Way, Winter Park image
244 W Kings Way, Winter Park $939,000 ▼

Build your dream home in the desirable Lake Sue area. Nestled amongst the majestic oaks on a quaint brick street, current home is a three bedroom, two bath home with a g...

  • 3 Beds
  • 2 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
4 Isle Of Sicily, Winter Park image
4 Isle Of Sicily, Winter Park $10,950,000

Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… This spectacular residence is located on the Isle of Sic...

  • 5 Beds
  • 5.5 Baths
  • Isle Of Sicily SubDv.
  • 32789 Zip Code
1489 Lone Feather Trail, Winter Park image
1489 Lone Feather Trail, Winter Park $799,900 ▲

Stunning new two-story home in Winter Park’s exclusive gated community of Hawk’s Crest. This 4-bedroom, 3 bathroom home has a great floor plan that features open dining a...

  • 4 Beds
  • 3.5 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
2852 Sheriff Way, Winter Park image
2852 Sheriff Way, Winter Park $475,000 ▼

Click on link for walkthrough video Tour!!! Spacious well-kept home with over 2,036 SF of living space. Located on a quiet street, the property is set back on the lot wit...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
911 Osceola Avenue, Winter Park image
911 Osceola Avenue, Winter Park $1,099,000 ▼

PRICE IMPROVEMENT--Fabulous home in the Heart and Soul of Winter Park's Osceola Shores neighborhood. Walk to Polasek Museum, Rollins College, Dinky Dock Park and Park Ave...

  • 3 Beds
  • 3.5 Baths
  • Osceola Shores Sec 01 SubDv.
  • 32789 Zip Code
466 Henkel Circle, Winter Park image
466 Henkel Circle, Winter Park $4,500,000 ▼

*NOW READY TO SHOW*SCHEDULE TODAY*Welcome home to this Amazing Lake House situated just minutes away from the Charming and Historic Winter Park Avenue. This Wonderful Est...

  • 4 Beds
  • 5 Baths
  • Thomas M Henkels Add SubDv.
  • 32789 Zip Code
1150 Via Salerno, Winter Park image
1150 Via Salerno, Winter Park $3,495,000

Pre-Construction. To be built. Located on a rare “Vias” lot this new construction home was designed and developed by Scout + Company. In Pueblo Revival style, the home w...

  • 4 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
312 Fountain Lane, Winter Park image
312 Fountain Lane, Winter Park $474,900 ▼

Let yourself feel captivated by this Single-Family home recently remodeled, offering 3 bedrooms 2 bathrooms in the great neighborhood of Lake Killarney. Enjoy the opportu...

  • 3 Beds
  • 1.5 Baths
  • Shores Lake Killarney Sec 02 SubDv.
  • 32789 Zip Code
2741 Eastham Road, Winter Park image
2741 Eastham Road, Winter Park $699,900 ▲

Stunning Two-Story Home in Winter Park's exclusive neighborhood. House is offering 4 Spacious bedrooms and 2.5 bathrooms has a great floor plan. The gourmet kitchen wit...

  • 4 Beds
  • 3 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
1428 Holts Grove Circle, Winter Park image
1428 Holts Grove Circle, Winter Park $2,300,000 ▼

Residing in one of Winter Park’s most sought-after communities, this gorgeous Windsong Estate awaits. From the expansive layout and beautiful outdoor living space to the ...

  • 5 Beds
  • 5 Baths
  • Windsong Lakeside Sec 02 43/71 SubDv.
  • 32789 Zip Code
1410 Michigan Avenue, Winter Park image
1410 Michigan Avenue, Winter Park $499,000

This is YOUR NEW HOME located right in Winter Park. This THREE BEDROOM, ONE BATH home has over 1300 SQUARE FEET and is ready for YOU, its next owner! This home sits on a...

  • 3 Beds
  • 1 Baths
  • H Vanwies Sub SubDv.
  • 32789 Zip Code
2207 Kindel Avenue, Winter Park image
2207 Kindel Avenue, Winter Park $689,000 ▼

Lowest priced Waterfront in Winter Park! It’s rare to find. Plus, Seller to pay $10,000 toward buyers closing costs and/or interest rate buy down. This property is on L...

  • 3 Beds
  • 2 Baths
  • Albert Lee Ridge Annex SubDv.
  • 32789 Zip Code
1500 Harris Circle, Winter Park image
1500 Harris Circle, Winter Park $949,900

"THE TRIANGLE HOUSE" PROFESSIONALLY DECORATED! Has 2 fireplaces, one in the master bedroom and another in the living area. High ceilings throughout and a spectacular lot ...

  • 2 Beds
  • 2.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
281 Brewer Avenue, Winter Park image
281 Brewer Avenue, Winter Park $1,600,000 ▼

Stunning Custom Designed POOL Home - 5 Bedroom, 4.5 Bath located in Osceola Shores. Which is a neighborhood of luxury homes in Winter Park, Florida. WALKABLE TO PARK AVEN...

  • 5 Beds
  • 4.5 Baths
  • Osceola Shores Sec 02 SubDv.
  • 32789 Zip Code
2138 Lake Drive, Winter Park image
2138 Lake Drive, Winter Park $3,050,000 ▼

One or more photo(s) has been virtually staged. Lakefront luxury on the beautiful shores of Lake Killarney! Custom built with attention paid to every detail, this Mediter...

  • 4 Beds
  • 3.5 Baths
  • Killarney Point SubDv.
  • 32789 Zip Code
1531 Place Picardy, Winter Park image
1531 Place Picardy, Winter Park $1,895,000

Seller financing available on this incredible Winter Park home. An elegant custom home, designed & built by FG Shaub, is tucked away on a large corner lot on a pristine o...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
1131 Oxford Road, Winter Park image
1131 Oxford Road, Winter Park $730,000 ▼

***Location Location**Virginia Heights within Winter Park luxury living! Easy walk to Park Ave. and Rollins College. Lake Virginia is one block away with storage for you...

  • 3 Beds
  • 2 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
5080 Lake Howell Road, Winter Park image
5080 Lake Howell Road, Winter Park $380,000 ▼

Create your Winter Park dream home! This property is less than 1 minute to Interlachen Country Club with multiple million dollar homes in close proximity. Great to remode...

  • 3 Beds
  • 2 Baths
  • Tanglewood Sec 3 Rep SubDv.
  • 32792 Zip Code
170 S Phelps Avenue, Winter Park image
170 S Phelps Avenue, Winter Park $2,800,000

Under Construction. Brand new construction!! Ready to move in! A stunning modern transitional home located in the heart of Winter park minutes from Park Ave. As you enter...

  • 4 Beds
  • 4.5 Baths
  • Green Terrace SubDv.
  • 32789 Zip Code
2723 Norris Avenue, Winter Park image
2723 Norris Avenue, Winter Park $2,175,000 ▼

Pre-Construction. To be built. Pre-Construction. To be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park. Make...

  • 4 Beds
  • 3.5 Baths
  • Parklando 02 SubDv.
  • 32789 Zip Code
664 W Morse Boulevard, Winter Park image
664 W Morse Boulevard, Winter Park $4,299,000

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of August. This custom built Winter Park home is the epitome of l...

  • 4 Beds
  • 4.5 Baths
  • Morse And Pennsylvania SubDv.
  • 32789 Zip Code
2172 Temple Drive, Winter Park image
2172 Temple Drive, Winter Park $2,650,000

Under Construction. UNDER CONSTRUCTION; Elegance, comfort, and a welcoming environment blend cohesively at this modern West Indies new construction home in one of the mos...

  • 5 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
5609 Winterbrook Way, Winter Park image
5609 Winterbrook Way, Winter Park $629,999 ▲

*** PRICE ADJUSTMENT & BACK ON THE MARKET!! SADLY DUE TO BUYER'S FINANCING. PASSED INSPECTION & APPRAISED OVER ASK at $630K! *** Reports available upon request. NEW backy...

  • 4 Beds
  • 2.5 Baths
  • Winterbrook SubDv.
  • 32792 Zip Code
2726 Lake Howell Lane, Winter Park image
2726 Lake Howell Lane, Winter Park $1,800,000 ▼

Build your Dream Home ted on the shores of Lake Howell, this Lakefront property offers the potential buyer over 3.9 acres of High and Dry Land in a serene natural setting...

  • 3 Beds
  • 2 Baths
  • Lake Howell SubDv.
  • 32792 Zip Code
1318 Morton Road, Winter Park image
1318 Morton Road, Winter Park $1,700,000 ▼

"Welcome to this exclusive contemporary luxury home, showcasing an architectural design that sets it apart. The house is characterized by a robust structure, boasting...

  • 4 Beds
  • 3.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
3520 Wilde Avenue, Winter Park image
3520 Wilde Avenue, Winter Park $1,500,000

Pre-Construction. To be built. Custom transitional estate pool home on over 1 acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

  • 6 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
3580 Wilde Avenue, Winter Park image
3580 Wilde Avenue, Winter Park $1,500,000

Pre-Construction. To be built. Custom transitional estate pool home on over ¾-acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

  • 6 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
3540 Wilde Avenue, Winter Park image
3540 Wilde Avenue, Winter Park $1,200,000

Pre-Construction. To be built. Custom transitional estate pool home on over ¾-acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

  • 5 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
270 E Lake Sue Avenue, Winter Park image
270 E Lake Sue Avenue, Winter Park $1,699,900 ▲

Pre-Construction. To be built. RE-DESIGNED and BACK ON MARKET APRIL 21, 2023. Ready to break ground! INQUIRE NOW for more details about this gorgeous MODERN COUNTY pool ...

  • 5 Beds
  • 4.5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1190 N Park Avenue, Winter Park image
1190 N Park Avenue, Winter Park $8,500,000 ▼

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acre...

  • 8 Beds
  • 5.5 Baths
  • 0000 SubDv.
  • 32789 Zip Code
870 Georgia Avenue, Winter Park image
870 Georgia Avenue, Winter Park $2,095,000 ▼

NEW AND IMPROVED PRICE: Located in the heart of “The Golden Triangle” of Winter Park, this 0.43 acre property is approximately 125 feet wide by 150 feet deep. Discretely ...

  • 3 Beds
  • 2.5 Baths
  • Winter Park Old Town SubDv.
  • 32789 Zip Code
1816 Azalea Avenue, Winter Park image
1816 Azalea Avenue, Winter Park $475,000 ▼

Seller says "RANCH STYLE, ONE FLOOR 3/2 TOTAL AREA 2,382 SQ FEET, LIVING AREA 1,584 SQ FEET CONVENTIONAL AND CASH-ONLY SALE What I love about this home. Th...

  • 3 Beds
  • 2 Baths
  • Temple Terrace SubDv.
  • 32789 Zip Code
2056 Lake Drive, Winter Park image
2056 Lake Drive, Winter Park $3,999,999 ▼

Pre-Construction. To be built. Homes don’t come along like this very often! Here’s your opportunity to own a Magnificent Estate "Elanza on Lake Killarney." Enter through ...

  • 5 Beds
  • 5.5 Baths
  • Lords Sub SubDv.
  • 32789 Zip Code
1420 Holts Grove Circle, Winter Park image
1420 Holts Grove Circle, Winter Park $2,750,000 ▼

WINDSONG - WINTER PARK. Designed to perfection, this exquisite Spanish-Mediterranean home sits on an oversized lot overlooking the tranquil pond and fountain. Grand curb...

  • 4 Beds
  • 4.5 Baths
  • Windsong Lakeside Sec 02 43/71 SubDv.
  • 32789 Zip Code
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