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Winter Park Real Estate Search

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In the Orlando Metro Area of Orange County, Florida, the community of Winter Park is home to approximately thirty thousand people. The community is well-known for its charming brick-lined streets, sparkling lakes, and majestic mature trees. It was chartered in 1887 and is therefore well-established with many incredible services and amenities. Conveniently located just north of Orlando, Winter Park offers a quiet, laid-back lifestyle with quick and easy access to world-class entertainment and attractions. Similarly, Winter Park residents enjoy local upscale conveniences like boutique shopping, high-end restaurants, and other little luxuries, many found along Park Avenue. 

In addition to its long list of award-winning dining options, the community hosts many exciting annual events and festivals. Among a few of the locals’ favorite festivities are the Winter Park Autumn Art Festival, the Florida Film Festival, the Bach Festival Society of Winter Park, and the Winter Park Sidewalk Art Festival. The community is also home to the second oldest golf club in Central Florida and the Winter Park Historical Museum, among many other remarkable destinations. Further contributing to its appeal, Winter Park encompasses many impressive neighborhoods and subdivisions, including Plymouth Apartments, Orwin Manor, Green Oaks, Northwood Circle, Hannibal Square, College Quarter, and Windsong, to name a few. 

Real estate in Winter Park is as desirable and diverse as the Metro Area. Homes for sale in Winter Park include condos, townhomes, pool homes, golf course homes, new construction, waterfront properties, and homes in gated communities. Because of the extraordinary diversity of Winter Park real estate, price points span a broad range with opportunities for homebuyers in all stages of life. We would love to assist you with your Winter Park home search. Please connect with us today and we will happily share specific details about available properties in Winter Park, Florida.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Winter Park real estate market? Sign up for a Winter Park Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest Winter Park Homes for Sale

423 Warrenton Road Unit 423, Winter Park image
423 Warrenton Road Unit 423, Winter Park — 9 $293,500

Beautiful Condo in Winter Park. Cathedral ceilings, wood floors throughout with ceramic tile in wet areas, kitchen and dining room. Updated appliances, cabinets and quar...

  • 2 Beds
  • 2 Baths
  • Winter Park Pines Condo SubDv.
  • 32792 Zip Code
2911 Antique Oaks Circle Unit GE, Winter Park image
2911 Antique Oaks Circle Unit GE, Winter Park — 2911 $199,000

WHAO LOCATION! GROUND FLOOR CONDO 1018 SQUARE FEET!. Two bedrooms and two full bathrooms with an open floor plan and walk-in closet in Master bedroom! Includes Fridge, Ra...

  • 2 Beds
  • 2 Baths
  • Parkview Village SubDv.
  • 32792 Zip Code
600 Maiden Lane, Winter Park image
600 Maiden Lane, Winter Park $1,575,000

Perched on a hill on a corner lot, nestled between Sylvan and Bonita along the brick streets of Winter Park, this home has so much to offer. With a privacy wall along Mai...

  • 4 Beds
  • 4.5 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
234 Scottsdale Square Unit 234, Winter Park image
234 Scottsdale Square Unit 234, Winter Park — 234 $145,000

INCREDIBLE OPPORTUNITY to own an updated two-story condo with lush garden views from BOTH BALCONIES! The unit underwent an enormous upgrade overhaul just a few years ago ...

  • 2 Beds
  • 1.5 Baths
  • Winter Park Woods Condo SubDv.
  • 32792 Zip Code
1769 Indiana Avenue Unit D, Winter Park image
1769 Indiana Avenue Unit D, Winter Park — Las Casas De Indiana $429,000

Mediterranean style Townhouse, granite counter tops, SS appliances, hardwood floors on first floor and carpet on second floor, private courtyard, detached one car garage ...

  • 3 Beds
  • 2.5 Baths
  • Las Casas De Indiana SubDv.
  • 32789 Zip Code
4033 Tenita Drive, Winter Park image
4033 Tenita Drive, Winter Park $559,000

Cozy Winter Park Pool Home in Orange County - Move-in Ready! Experience the outdoor oasis by relaxing in your screened Lanai or take a dip in the private pool. Great for ...

  • 4 Beds
  • 2 Baths
  • Lake Waunatta Woods SubDv.
  • 32792 Zip Code
1303 Alberta Drive, Winter Park image
1303 Alberta Drive, Winter Park $2,950,000

Welcome to this exquisite French Modern home that seamlessly blends classic architecture with modern amenities. With 4 bedrooms, 4.5 bathrooms, 4,055 s/f, and a detached...

  • 4 Beds
  • 4.5 Baths
  • Alberta Place SubDv.
  • 32789 Zip Code
3173 Crown Jewel Court, Winter Park image
3173 Crown Jewel Court, Winter Park $375,000

Wanting to live in Winter Park in a newer and beautiful property? Here it is. This beautiful property is so centrally located that has it all near by within less than 10 ...

  • 3 Beds
  • 2.5 Baths
  • Coronado Twnhms SubDv.
  • 32792 Zip Code
2827 Parkland Circle, Winter Park image
2827 Parkland Circle, Winter Park $1,995,000

Welcome home to this professionally decorated two-story custom French provincial pool home. No space or detail has been overlooked, and with an endless list of upgrades, ...

  • 4 Beds
  • 3.5 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1918 Summerfield Road, Winter Park image
1918 Summerfield Road, Winter Park $1,300,000

BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home br...

  • 5 Beds
  • 4.5 Baths
  • Kenilworth Shores Section Seven SubDv.
  • 32792 Zip Code
1554 Harris Circle, Winter Park image
1554 Harris Circle, Winter Park $1,220,000

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
1740 Via Palermo, Winter Park image
1740 Via Palermo, Winter Park $4,200,000

Nestled near the heart of Winter Park, this modern masterpiece exudes elegance and superb attention to detail throughout. This home was a Parade of Homes collaboration be...

  • 5 Beds
  • 5.5 Baths
  • Sicilian Shores Rep 02 SubDv.
  • 32789 Zip Code
656 Randy Lane, Winter Park image
656 Randy Lane, Winter Park $795,000

Located on a quiet, tree lined street in Timberlane, a neighborhood in Winter Park that is known for its beautiful homes and excellent proximity to great schools, amazing...

  • 3 Beds
  • 2 Baths
  • Timberlane SubDv.
  • 32789 Zip Code
2680 Oglesby Avenue, Winter Park image
2680 Oglesby Avenue, Winter Park $949,900

Dreams do come true! 2019 Newer Build Winter Park and College Park Adjacent Paradiso! No HOA! Modern Farmhouse style with almost 2600 sqft of spacious floorplan featurin...

  • 4 Beds
  • 2.5 Baths
  • Dubsdread Heights SubDv.
  • 32789 Zip Code
316 Scottsdale Square Unit 316, Winter Park image
316 Scottsdale Square Unit 316, Winter Park — 316 $145,000

Welcome to your new cozy and charming 2-story condo at Winter Park Woods! Tucked away just off SR-436, this delightful 2-bedroom, 1.5-bathroom home is perfectly situated ...

  • 2 Beds
  • 1.5 Baths
  • Winter Park Woods Condo SubDv.
  • 32792 Zip Code
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