108 total properties
Did you mean the neighborhood Winter Park?
View 2809 BOWER ROAD Winter Park, FL MLS# R4910253
  • Virtual Tour
1 of 29
$2,995
3

Beds

2.0

Baths

1,488

Sq.Ft.

2809 BOWER ROAD

Winter Park, FL

Courtesy of STRAWBERRY FIELDS FOREVER REALY LLC
View 300 KILLARNEY DRIVE Winter Park, FL MLS# O6361584
$8,500
4

Beds

3.0

Baths

2,476

Sq.Ft.

300 KILLARNEY DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1580 OAKHURST AVENUE Winter Park, FL MLS# O6361638
$4,950
4

Beds

2.1

Baths

2,406

Sq.Ft.

1580 OAKHURST AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 148 OAK GROVE ROAD Winter Park, FL MLS# O6361640
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1 of 12
$2,095
3

Beds

2.0

Baths

1,156

Sq.Ft.

148 OAK GROVE ROAD

Winter Park, FL

Courtesy of THE CAVALIERI PROPERTY MANAGEMENT LLC
View 1350 LYNDALE BOULEVARD Winter Park, FL MLS# O6361248
$8,500
4

Beds

3.2

Baths

3,478

Sq.Ft.

1350 LYNDALE BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2862 KINGS DEER ROAD Winter Park, FL MLS# O6361314
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1 of 34
$3,000
3

Beds

2.0

Baths

1,763

Sq.Ft.

2862 KINGS DEER ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 367 HOLT AVENUE Winter Park, FL MLS# O6356610
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1 of 9
$2,100
2

Beds

1.0

Baths

850

Sq.Ft.

367 HOLT AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1565 MICHIGAN AVENUE Winter Park, FL MLS# O6360479
  • Virtual Tour
1 of 12
$1,575
2

Beds

1.0

Baths

900

Sq.Ft.

1565 MICHIGAN AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1055 CHEROKEE AVENUE Winter Park, FL MLS# O6360540
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1 of 45
$2,800
3

Beds

2.0

Baths

1,560

Sq.Ft.

1055 CHEROKEE AVENUE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 104 S INTERLACHEN AVENUE 114 Winter Park, FL MLS# O6360008
$4,850
2

Beds

2.0

Baths

1,143

Sq.Ft.

104 S INTERLACHEN AVENUE 114

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1436 MINNESOTA AVENUE Winter Park, FL MLS# O6359812
$1,295
2

Beds

1.0

Baths

805

Sq.Ft.

1436 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1730 ONECO AVENUE Winter Park, FL MLS# O6358524
  • Virtual Tour
1 of 52
$3,150
3

Beds

2.0

Baths

1,408

Sq.Ft.

1730 ONECO AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1436 MINNESOTA AVENUE Winter Park, FL MLS# O6359449
$15,588
805

Sq.Ft.

1436 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1807 N PARK AVENUE Winter Park, FL MLS# O6359356
  • Virtual Tour
1 of 42
$3,295
3

Beds

2.0

Baths

1,747

Sq.Ft.

1807 N PARK AVENUE

Winter Park, FL

Courtesy of THE REALTY MEDICS
View 690 OSCEOLA AVENUE 203 Winter Park, FL MLS# O6357444
$3,400
2

Beds

2.0

Baths

1,148

Sq.Ft.

690 OSCEOLA AVENUE 203

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 616 MONTEGO BAY COURT S Winter Park, FL MLS# S5137961
$1,800
2

Beds

2.0

Baths

1,037

Sq.Ft.

616 MONTEGO BAY COURT S

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View Address not provided Winter Park, FL MLS# TB8444168
$1,999
3

Beds

2.0

Baths

1,136

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TAH FLORIDA LLC
View 200 SAINT ANDREWS BOULEVARD 2903 Winter Park, FL MLS# O6357483
$1,895
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2903

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 2717 SCARLET ROAD Winter Park, FL MLS# O6357487
  • Virtual Tour
1 of 31
$2,795
3

Beds

2.0

Baths

1,240

Sq.Ft.

2717 SCARLET ROAD

Winter Park, FL

Courtesy of KUNERT REALTY INC
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
  • Virtual Tour
1 of 10
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

280

Estimated median home price

$675,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 6
$100K - 200K 37
$200K - 300K 19
$300K - 400K 16
$400K - 500K 25
$500K - 600K 22
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 162
Townhouse 19
Condo 70
Commercial 4
Rental 107
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/2/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 1/3/2026.