405 Featured Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
- 1/12 12
4 Beds 6 Baths 4,205 SqFt$3,490,000Active1910 GLENCOE RD, Winter Park, FL 32789
Listed by Julie Christensen COMPASS FLORIDA LLC
Single Family Home
- 1/30 30
2 Beds 3 Baths 1,031 SqFt$214,900Active3254 OAK LAKE PL #137, Winter Park, FL 32792
Listed by Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP
Townhouse
- 1/49 49
2 Beds 2 Baths 956 SqFt$195,000Active2500 LEE RD #208, Winter Park, FL 32789
Listed by Debbie Jones KELLER WILLIAMS REALTY AT THE PARKS
Condo
- 1/23 23
2 Beds 1 Bath 881 SqFt$1,500Active - 1/32 32
3 Beds 2 Baths 2,268 SqFt$565,000Active701 DENTON RD, Winter Park, FL 32792
Listed by Liz Boyce CHARLES RUTENBERG REALTY ORLANDO
Single Family Home
- 1/26 26
2 Beds 2 Baths 949 SqFt$649,000Active101 S INTERLACHEN AVE #104, Winter Park, FL 32789
Listed by Kelly Price KELLY PRICE & COMPANY LLC
Condo
- 1/26 26
3 Beds 3 Baths 1,890 SqFt$625,000Active - 1/17 17
3 Beds 1 Bath 1,140 SqFt$450,000Active1564 CAVENDISH RD, Winter Park, FL 32789
Listed by Julie Wright CHARLES RUTENBERG REALTY ORLANDO
Single Family Home
- 1/17 17
5 Beds 4 Baths 3,598 SqFt$918,000Active5325 CYPRESS RESERVE PL, Winter Park, FL 32792
Listed by Dori Estrada PLLC LPT REALTY, LLC
Single Family Home
- 1/68 68
3 Beds 2 Baths 2,114 SqFt$950,000Active250 CORTLAND AVE, Winter Park, FL 32789
Listed by Alexandra Nordine EXP REALTY LLC
Single Family Home
- 1/19 19
1 Bath 549 SqFt$89,900Active3071 GEORGE MASON AVE #5, Winter Park, FL 32792
Listed by Katherine Bordelon CASTLE & COTTAGE REALTY LLC
Condo
- 1/44 44
4 Beds 3 Baths 2,046 SqFt$675,000Active607 DUNBLANE DR, Winter Park, FL 32792
Listed by Khozaif Merali CHARLES RUTENBERG REALTY ORLANDO
Single Family Home
- 1/57 57
4 Beds 3 Baths 3,121 SqFt$999,950Active1444 PELICAN BAY TRL, Winter Park, FL 32792
Listed by Jacob Hara TRANSCEND REALTY
Single Family Home
3 Beds 2 Baths 1,149 SqFt$210,000Active- 1/19 19
3 Beds 2 Baths 1,230 SqFt$245,000Active - 1/84 84
5 Beds 9 Baths 7,916 SqFt$5,895,000Active1400 ALABAMA DR, Winter Park, FL 32789
Listed by Rachel Peters, LLC THE AGENCY ORLANDO
Single Family Home
- 1/21 21
2 Beds 2 Baths 1,056 SqFt$135,000Active - 1/48 48
5 Beds 7 Baths 6,406 SqFt$4,950,000Active1660 PALMER AVE, Winter Park, FL 32789
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
Single Family Home
- 1/22 22
2 Beds 2 Baths 1,105 SqFt$200,000Active2923 ANTIQUE OAKS CIR #39, Winter Park, FL 32792
Listed by Michell Carrasquero GLOBALWIDE REALTY LLC
Condo
- 1/49 49
6 Beds 4 Baths 2,284 SqFt$1,215,000Active726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY
Multi-Family
- 1/49 49
6 Beds 4 Baths 2,284 SqFt$1,215,000Active726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY
Single Family Home
- 1/30 30
3 Beds 2 Baths 1,167 SqFt$695,000Active726 N PENNSYLVANIA AVE, Winter Park, FL 32789
Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY
Single Family Home
- 1/26 26
3 Beds 2 Baths 1,115 SqFt$550,000Active720 N PENNSYLVANIA AVE, Winter Park, FL 32789
Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY
Single Family Home
- 1/42 42
3 Beds 2 Baths 1,827 SqFt$765,000Active625 BRECHIN DR, Winter Park, FL 32792
Listed by Kelly Price KELLY PRICE & COMPANY LLC
Single Family Home
- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- List
- Mixed
- Map
0 Properties
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
- Zoom Out
- Clear the map boundary
- Reset all filters or remove one of your filters above to see more properties
- Winter Park, FL
- Listing Status: Active

