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Winter Park Real Estate Search

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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

640 Penn Place, Winter Park image
640 Penn Place, Winter Park $2,049,000

Welcome home to the highly desirable and sought-after community of Pennsylvania Place! This immaculate home boasts more than 4,000 SF with a resort inspired outdoor area ...

  • 4 Beds
  • 3 Baths
  • Pennsylvania Place Rep SubDv.
  • 32789 Zip Code
7765 Broken Arrow Trail, Winter Park image
7765 Broken Arrow Trail, Winter Park $775,000

LAKEFRONT! Charming Winter Park neighborhood on Lake Nan. Enjoy all the watersports like Jet skiing, fishing, swimming and boating on this spring fed lake as well as watc...

  • 3 Beds
  • 2 Baths
  • Arrowhead Cove Voluntary SubDv.
  • 32792 Zip Code
2609 Temple Trail, Winter Park image
2609 Temple Trail, Winter Park $475,000

Winter Park Vacant Land Available for Residential Development. This cleared 0.25-acre lot is zoned R-3 and will accommodate up to 3,800 square foot single family home or...

  • Temple Trail Village SubDv.
  • 32789 Zip Code
617 Dunraven Drive, Winter Park image
617 Dunraven Drive, Winter Park $650,000

WINTER PARK - NEW ROOF (2022), NEW A/C (2022) - Renovated in 2019, this beautiful one-story Winter Park 4BR - 3.5 Bath ranch is located in the sought-after Kenilworth Sho...

  • 4 Beds
  • 3.5 Baths
  • Kenilworth Shores Sec 05 SubDv.
  • 32792 Zip Code
1224 S Pennsylvania Avenue Unit 4, Winter Park image
1224 S Pennsylvania Avenue Unit 4, Winter Park — Casa Jardin $839,900

The long hunt is over! Step inside and immerse yourself in the modern Mediterranean space found in this 3 bed, 2 bath townhome in the heart of Winter Park. Mere minutes f...

  • 3 Beds
  • 2.5 Baths
  • Casa Jardin Condo SubDv.
  • 32789 Zip Code
2126 Woodcrest Drive, Winter Park image
2126 Woodcrest Drive, Winter Park $490,000

Great potential and the sky's the limit for this three bedroom, two bath home in desirable Kenilworth Shores. New roof, updated kitchen, and a little TLC to the beautifu...

  • 3 Beds
  • 2 Baths
  • Kenilworth Ests 1st Add SubDv.
  • 32792 Zip Code
233 Cambridge Boulevard, Winter Park image
233 Cambridge Boulevard, Winter Park $499,990

Location Location Location !! located in the Heart of Orlando This Freshly Remodeled has it all and NO HOA!! You don't have to look any further because your new home awa...

  • 3 Beds
  • 2 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
2158 Whitehall Drive, Winter Park image
2158 Whitehall Drive, Winter Park $548,000

This is a must see 3 bedroom 2 bath home located in Winter Parks most highly sought after communities - Winter Park Pines. Sitting on ¼ acre with top rated schools just...

  • 3 Beds
  • 2 Baths
  • Brookshire Heights 4th Add SubDv.
  • 32792 Zip Code
1822 Temple Drive, Winter Park image
1822 Temple Drive, Winter Park $799,000

Incredible opportunity in the Heart of Winter Park. This charming 3 bedroom, 3 bath garden cottage is ready to be moved-in, renovated, or potentially torn down to build y...

  • 3 Beds
  • 3 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
326 Scottsdale Square Unit 326, Winter Park image
326 Scottsdale Square Unit 326, Winter Park — 326 $155,000

Located just off SR-436 in Winter Park makes this a great location for easy access to all that Winter Park and the surrounding areas have to offer. Conveniently located n...

  • 2 Beds
  • 1.5 Baths
  • Winter Park Woods Condo SubDv.
  • 32792 Zip Code
1250 S Denning Drive Unit 109, Winter Park image
1250 S Denning Drive Unit 109, Winter Park — 109 $215,000

Welcome Home! Beautiful well-maintained first floor, end unit, 1 bedroom / 1 bath Winter Park condo at the sort after Mead Gardens with screened-in porch overlooking quie...

  • 1 Beds
  • 1 Baths
  • Mead Garden SubDv.
  • 32789 Zip Code
345 W Welbourne Avenue Unit 104, Winter Park image
345 W Welbourne Avenue Unit 104, Winter Park — Na $1,094,000

A Douglas Grand brownstone in the heart of Winter Park. This townhome style condo is located catty-corner from Central Park and one block off the shops and restaurants of...

  • 3 Beds
  • 3.5 Baths
  • Winter Park Residential SubDv.
  • 32789 Zip Code
1702 Glenridge Way, Winter Park image
1702 Glenridge Way, Winter Park — 1702 $699,000

Come see this hidden Winter Park gem! Immaculately maintained lakefront townhome with tw bedrooms, two baths, two-car carport and community pool! Lakeridge Townhomes, a t...

  • 2 Beds
  • 2 Baths
  • Orlando Park Rep SubDv.
  • 32789 Zip Code
315 E New England Avenue Unit 8, Winter Park image
315 E New England Avenue Unit 8, Winter Park — Villa Siena $1,200,000

Known as the Jewel of Winter Park, Villa Siena is located 2 blocks from Park Avenue and is directly across from the Alfond Inn. Amenities include assigned garage parking,...

  • 2 Beds
  • 2 Baths
  • Trovillion Condo SubDv.
  • 32789 Zip Code
2625 Aloma Avenue, Winter Park image
2625 Aloma Avenue, Winter Park — 2625 $460,000

Winter Park Pool Home!!! NEW ROOF! FRESH PAINT! Massively updated, this stunning property will be your retreat away from the world. The floor plan includes 3 bedrooms, 3 ...

  • 3 Beds
  • 3 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
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