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Find homes, townhouses and condos in Winter Park, Florida in a variety of styles.

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Hot Winter Park Properties

1020 Minnesota Avenue Unit 8, Winter Park image
1020 Minnesota Avenue Unit 8, Winter Park — Casa Cielo Condo Or 6314 6111 $389,000

Beautiful Mediterranean-Themed condominium conveniently located in the heart of Winter Park. Minutes from downtown Orlando, Rollins College, Park Ave, Winter Park Village...

  • 3 Beds
  • 3 Baths
  • Casa Cielo Condo Or 6314 6111 SubDv.
  • 32789 Zip Code
2615 Oglesby Avenue, Winter Park image
2615 Oglesby Avenue, Winter Park $2,600,000

Luxury lakefront custom home awaits. This Parade of Homes winner features spacious open floor plan with great attention to detail. Large gourmet kitchen opens to spacious...

  • 7 Beds
  • 8 Baths
  • Dudsdread Heights SubDv.
  • 32789 Zip Code
1421 Woodale Avenue, Winter Park image
1421 Woodale Avenue, Winter Park $529,800

This charming and updated split 3 bedroom 2 bath bungalow on an oversized fenced-in lot, It is located on a quiet cobblestone street in the heart of one of Florida’s mos...

  • 3 Beds
  • 2 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
654 Montego Bay Court, Winter Park image
654 Montego Bay Court, Winter Park — 654 $164,900

Updates galore in an amazing location, minutes from Downtown Winter Park. You enter a serene, welcoming, neighborhood ready to be your new home. Brand new Spanish tiled r...

  • 2 Beds
  • 2 Baths
  • Winter Park Villas SubDv.
  • 32792 Zip Code
2094 Laurelwood Way, Winter Park image
2094 Laurelwood Way, Winter Park $688,000

One or more photo(s) has been virtually staged. Prepare to be amazed by this ultra modern home. This incredible home is a true smart home with modern finishes, controlled...

  • 5 Beds
  • 4 Baths
  • Preserve At Hawks Crest SubDv.
  • 32792 Zip Code
1813 Harland Park Drive, Winter Park image
1813 Harland Park Drive, Winter Park $1,160,000

Gorgeous 4 bedroom pool home located in the exclusive Windsong neighborhood of Winter Park. This home features quality construction and attention to detail with open conc...

  • 4 Beds
  • 3 Baths
  • Windsong-Knowles Place SubDv.
  • 32789 Zip Code
5123 Lake Howell Road, Winter Park image
5123 Lake Howell Road, Winter Park $369,900

WOW! Come check out this amazing mid-century modern completely updated and remodeled home! Move-in ready, the effective date is 2016, in which it was completely refurbish...

  • 4 Beds
  • 2 Baths
  • Tanglewood Sec 3 Rep SubDv.
  • 32792 Zip Code
112 Oak Grove Road, Winter Park image
112 Oak Grove Road, Winter Park $199,000

LOCATION, LOCATION! 3/2 Block home located within the city limits of Winter Park, Florida in Orange County close to where 17/92 meets Lee Road. This newer home has grani...

  • 3 Beds
  • 2 Baths
  • Winter Park Oaks SubDv.
  • 32789 Zip Code
1784 Mondrian Circle Unit 14, Winter Park image
1784 Mondrian Circle Unit 14, Winter Park — 1784 $875,000

Lakefront Living in Winter park! Welcome to this fantastic end unit townhome on Lovely Lake Killarney. You'll be amazed at the architectural details that abound in these ...

  • 3 Beds
  • 3 Baths
  • Lake Killarney Townhomes SubDv.
  • 32789 Zip Code
2255 Chantilly Avenue, Winter Park image
2255 Chantilly Avenue, Winter Park $990,000

Captivating and Traditional Southern Home in Winter Park! Situated on a sizeable 0.26+acre lot, this storybook 4BR/4BA abode captures attention with a muted buttercream e...

  • 4 Beds
  • 3 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
7757 Fernbrook Way, Winter Park image
7757 Fernbrook Way, Winter Park — 7757 $235,000

One or more photo(s) has been virtually staged. This Winter Park home has two stories. This home has been virtually staged to illustrate its potential.

  • 3 Beds
  • 2 Baths
  • Fernbrook Trails Ph 3 SubDv.
  • 32792 Zip Code
2386 Sun Valley Circle, Winter Park image
2386 Sun Valley Circle, Winter Park — 2386 $183,000

MAITENANCE FREE LIVING IN SOUGHT-AFTER WINTER PARK! 1-story condo community centrally located with easy access to Park Ave, Rollins College, Full Sail and major highways....

  • 2 Beds
  • 2 Baths
  • Cedarwood Village 1 SubDv.
  • 32792 Zip Code
432 Fletcher Place, Winter Park image
432 Fletcher Place, Winter Park $829,000

Beautiful Mediterranean Ranch home in the heart of Winter Park. Fully renovated throughout. The 8-foot mahogany front door opens up to a stunning Barrel-Vaulted foyer. Lo...

  • 4 Beds
  • 3 Baths
  • Sorensen Heights SubDv.
  • 32789 Zip Code
1365 Grove Terrace, Winter Park image
1365 Grove Terrace, Winter Park $985,000

Beautifully renovated one-story home with charm and quality you will love. This 4-bedroom, 3-bath home sits on an oversized corner lot nestled on a quiet street and is a ...

  • 4 Beds
  • 3 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
3354 Coleus Court, Winter Park image
3354 Coleus Court, Winter Park $325,000

One or more photo(s) has been virtually staged. **EASY TO SHOW** Delightful Single Story 4BD/3BA HOME with *DOUBLE PRIMARY BEDROOMS, *NEWER ROOF 2017, *NEW ELECTRICAL 202...

  • 4 Beds
  • 3 Baths
  • Eastbrook Sub Unit 14 SubDv.
  • 32792 Zip Code
375 W Welbourne Avenue Unit 107, Winter Park image
375 W Welbourne Avenue Unit 107, Winter Park — Douglas Grand $850,000

This is your opportunity to own a two-story, three-bedroom, three and a half bathroom townhome with its own private street entrance in historic downtown Winter Park at th...

  • 3 Beds
  • 3 Baths
  • Douglas Grand SubDv.
  • 32789 Zip Code
1277 Michigan Avenue, Winter Park image
1277 Michigan Avenue, Winter Park — Na $459,900

Stunning new townhome community in the Heart of Winter Park! Multiple units available. Built by award-winning Osprey Custom Home Builders, this 3 bedroom, 2.5 bath interi...

  • 3 Beds
  • 2 Baths
  • Park Shore SubDv.
  • 32789 Zip Code
1712 Arbor Park Drive, Winter Park image
1712 Arbor Park Drive, Winter Park $493,200

Located in the highly desirable Winter Park Location. This 4 Bedroom/ 2 Bathroom recently renovated home features updates throughout. This beautiful charming newly remode...

  • 4 Beds
  • 2 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
690 Osceola Avenue Unit 401, Winter Park image
690 Osceola Avenue Unit 401, Winter Park — #401 $379,000

Beautiful Lake Virginia condo priced to sell. This well maintained 2 bedroom, 2 bath condo is very close to downtown Winter Park, Rollins College, the Alfond Inn, restaur...

  • 2 Beds
  • 2 Baths
  • Lake Virginia Condo SubDv.
  • 32789 Zip Code
1329 Buccaneer Court, Winter Park image
1329 Buccaneer Court, Winter Park $379,900

Lakefront with Pool in Winter Park! Begin and end your daily grind overlooking the natural serenity of Lake Deeks, right in your own backyard. Working from home these day...

  • 4 Beds
  • 2 Baths
  • Harbour Ridge SubDv.
  • 32792 Zip Code
1909 Natalen Road, Winter Park image
1909 Natalen Road, Winter Park $439,000

Do not miss out on this 4 bedroom 3 full bathroom pool home, located in the desired Kenilworth Shores neighborhood!!! This charmer is zoned Brookshire, Glenridge and WPH...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1120 Aragon Avenue, Winter Park image
1120 Aragon Avenue, Winter Park — 1120 $475,000

Welcome to your new residence in Winter Park! This home is practically perfect with its oversized owner’s suite (with walk-in closet and jetted tub), guest room (split be...

  • 2 Beds
  • 2 Baths
  • Seville Park SubDv.
  • 32789 Zip Code
1751 Goodrich Avenue, Winter Park image
1751 Goodrich Avenue, Winter Park $835,000

STATE-OF-THE-ART technology, TOP-OF-THE-LINE finishes, attention to DETAIL, and centrally LOCATED in historic WINTER PARK is where you will find this 2019 fully renovated...

  • 4 Beds
  • 3 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
1939 Azalea Avenue, Winter Park image
1939 Azalea Avenue, Winter Park $307,500

WELCOME HOME to this Mid-Century modern, 3 bedroom, 2 bathroom home with beautiful curb appeal, a spacious front patio and a wonderful Winter Park location. From the mome...

  • 3 Beds
  • 2 Baths
  • Temple Terrace Annex SubDv.
  • 32792 Zip Code
1624 Hibiscus Avenue, Winter Park image
1624 Hibiscus Avenue, Winter Park $1,150,000

Welcome to the heart of Winter Park. This beautiful 2-story, 4-bedroom, 3.5-bath home includes a backyard oasis with pool/spa. A home that was built in 2012 features "wee...

  • 4 Beds
  • 3 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
209 Lewfield Circle Unit 209, Winter Park image
209 Lewfield Circle Unit 209, Winter Park — Lewfield Circle #209 $114,900

Enter the foyer of this ground floor unit on wide plank vinyl flooring which runs throughout this two bedroom, two bath unit * Galley style kitchen with large pantry lead...

  • 2 Beds
  • 2 Baths
  • Stratford A Winter Park Condo SubDv.
  • 32792 Zip Code
1602 Alabama Drive Unit 404, Winter Park image
1602 Alabama Drive Unit 404, Winter Park — Alabama $2,490,000

Welcome to the largest penthouse unit at The Alabama Condos. This home is two units combined, and has been completely renovated from floor to ceiling by Z Properties, a s...

  • 3 Beds
  • 3 Baths
  • Alabama Condo SubDv.
  • 32789 Zip Code
215 Sandlewood Trail Unit 7, Winter Park image
215 Sandlewood Trail Unit 7, Winter Park — 215 $210,000

Excellent schools. Excellent location. Short drive to Park ave, Farmer's Market, Full Sail, Rollins College. TENANT IS ON MONTH TO MONTH.

  • 2 Beds
  • 2 Baths
  • Sandalwood Creek Condo Ph 13 SubDv.
  • 32789 Zip Code
140 Dana Way, Winter Park image
140 Dana Way, Winter Park $1,395,000

Welcome to this luxurious, one-of-a-kind Posada custom home located on a quiet street in a very desirable Winter Park neighborhood. The classic finishes and open floor pl...

  • 3 Beds
  • 2 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1762 Elizabeths Walk, Winter Park image
1762 Elizabeths Walk, Winter Park $1,250,000

Come see this beautiful custom home locate in the Windsong Community in Winter Park built by Keith Groninger of Groninger Custom Homes. This 3,775 sqft 4 bedroom 4 bath h...

  • 4 Beds
  • 4 Baths
  • Windsong SubDv.
  • 32789 Zip Code
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