Houses for sale in Winter Park

230,336 available properties
Sort by:
Most relevant first
Most relevant first
Most up-to-date first
Most recent published
Price: Lowest first
Price: Highest first
Bedrooms: Lowest first
Bedrooms: Highest first
Size: Lowest first
Size: Highest first
17 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 2,295,000
Winter Park, Orange County

3,295 sq.ft

Office roomTerraceEquipped kitchenSwimming pool

5 days + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Bertha, Winter Park
Request Details
Bertha, Winter Park

4 Bedrooms

3 Bathrooms

3,156 sq.ft

1 day + 7 hours ago

26 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 3,250,000
Winter Park, Orange County
GardenFireplaceEquipped kitchenSwimming pool

1 week + 1 day ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Williamsburgh, Winter Park
Request Details
Williamsburgh, Winter Park

3 Bedrooms

2 Bathrooms

2,133 sq.ft

1 day + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Winter Park, Seminole County
Request Details
Winter Park, Seminole County

3 Bedrooms

2 Bathrooms

2,029 sq.ft

1 day + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Detmar Terrace, Winter Park
Request Details
Detmar Terrace, Winter Park

4 Bedrooms

2 Bathrooms

2,148 sq.ft

1 day + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Winter Park Pines, Winter Park
Request Details
Winter Park Pines, Winter Park

3 Bedrooms

2 Bathrooms

2,117 sq.ft

1 day + 7 hours ago

25 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 3,500,000
Winter Park, Orange County

4,036 sq.ft

Office roomTerraceFireplaceEquipped kitchenSwimming poolLift

1 week + 3 days ago

45 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 950,000
Winter Park, Orange County
FireplaceEquipped kitchen

2 weeks + 6 days ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Winter Park, Seminole County
Request Details
Winter Park, Seminole County

3 Bedrooms

2 Bathrooms

2,139 sq.ft

1 day + 7 hours ago

37 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 3,075,000
Winter Park, Orange County
FireplaceEquipped kitchenSwimming pool

1 week + 7 hours ago

46 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,750,000
Winter Park, Orange County
Office roomTerraceEquipped kitchenSwimming pool

1 week + 1 day ago

35 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,495,000
Winter Park, Orange County
GardenTerraceDeck

1 week + 3 days ago

45 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 6,195,000
Winter Park, Orange County
Office roomEquipped kitchenSwimming pool

1 week + 3 days ago

44 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 899,900
Winter Park, Orange County
GardenEquipped kitchen

1 week + 4 days ago

40 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 2,000,000
Winter Park, Orange County
GardenFireplaceEquipped kitchenSwimming pool

Sep 26, 2026

32 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,595,000
Winter Park, Orange County
GardenOffice roomFireplaceEquipped kitchenSwimming pool

Sep 25, 2026

15 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,250,000
Winter Park, Orange County
GardenSwimming pool

5 days + 7 hours ago

39 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 4,250,000
USD 4,400,000
3%
Winter Park, Orange County
Equipped kitchenSwimming pool

1 week + 7 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 3,495,000
Winter Park, Orange County
Office roomEquipped kitchenSwimming pool

Sep 23, 2026

28 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 2,625,000
Winter Park, Orange County

3,048 sq.ft

Office roomParkingFireplaceEquipped kitchenLift

Sep 11, 2026

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Winter Park, Seminole County
USD 365,000
Winter Park, Seminole County

3 Bedrooms

1 Bathroom

1,185 sq.ft

1 day + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Winter Park, Orange County
Request Details
Winter Park, Orange County

4 Bedrooms

4 Bathrooms

4,421 sq.ft

1 day + 7 hours ago

View photo Arrow icon pointing to the right
Updated
Foreclosure
House
House for sale in Orwin Manor, Winter Park
Request Details
Orwin Manor, Winter Park

2 Bedrooms

1 Bathroom

948 sq.ft

1 day + 7 hours ago

15 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,275,000
Winter Park, Orange County
TerraceSwimming pool

5 days + 7 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,690,000
Winter Park, Orange County
TerraceEquipped kitchenSwimming pool

6 days + 7 hours ago

50 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,425,000
Winter Park, Orange County
TerraceEquipped kitchen

6 days + 7 hours ago

30 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 3,265,000
Winter Park, Orange County

4,949 sq.ft

GardenEquipped kitchenSwimming pool

1 week + 1 day ago

36 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 699,500
Winter Park, Orange County
GardenTerraceEquipped kitchen

1 week + 2 days ago

25 pictures Arrow icon pointing to the right
House
House for sale in Winter Park, Orange County
USD 1,495,000
Winter Park, Orange County
Equipped kitchenSwimming pool

1 week + 2 days ago

Give us your email and we'll notify you as soon as we have news about:
Houses winter park
By suscribing you agree to the terms and conditions and privacy policy Receive alerts
Property value in Winter Park
Average price per sq.feet
USD 354/sq.feet
0.4 %
Price evolution on August 2026
16.0 %
Price evolution on September 2025
Average property value
USD 669,900

Property value in Winter Park by number of bedrooms

USD 475,000 USD 330/sq.feet
Average price of 2 bedrooms Houses for sale with 2 bedrooms
USD 435,000 USD 294/sq.feet
Average price of 3 bedrooms Houses for sale with 3 bedrooms
USD 1,350,000 USD 435/sq.feet
Average price of 4 bedrooms Houses for sale with 4 bedrooms
Enter your email and be the first to know about updates on:
Houses winter park
By suscribing you agree to the terms and conditions and privacy policy Receive alerts
Your search Houses winter park has been saved
Close