Searching on:
- School = Maitland Middle
- Listing Status = Active
Single Family
- Price: $6,895,000.00
- Price sqft: $861.66 / sqft
- Previous Price: $7,200,000
- Last Price Change: 01/07/26
- Days On Market: 169
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 8002
- Acreage: 0.48 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6349188
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Osceola Place
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
Single Family
- Price: $4,197,000.00
- Price sqft: $624.28 / sqft
- Days On Market: 29
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 4
- Bldg sqft: 6723
- Acreage: 0.36 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6389039
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Conwill Estates
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: KELLER WILLIAMS ADVANTAGE REALTY
- DMCA Notice
Single Family
- Price: $3,295,000.00
- Price sqft: $523.27 / sqft
- Previous Price: $3,399,999
- Last Price Change: 02/18/26
- Days On Market: 302
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 6297
- Acreage: 0.39 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2017
MLS#: O6302616
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Green Oaks Rep 02
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: SCANLON REALTY GROUP LLC
- DMCA Notice
Single Family
- Price: $2,850,000.00
- Price sqft: $459.97 / sqft
- Days On Market: 14
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 4
- Bldg sqft: 6196
- Acreage: 0.45 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1958
MLS#: O6393777
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Temple Heights
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
Land
- Price: $2,790,000.00
- Days On Market: 1
- Acreage: 0.49 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: O6397264
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Sicilian Shores
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
Single Family
- Price: $2,650,000.00
- Price sqft: $515.06 / sqft
- Days On Market: 15
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 5145
- Acreage: 0.40 acres
- Pool: No
- Waterfront: No
- Year Built: 1968
MLS#: O6392394
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Park North
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Single Family
- Price: $2,395,000.00
- Price sqft: $460.93 / sqft
- Days On Market: 58
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 5196
- Acreage: 0.27 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6381552
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: REAL BROKER, LLC
- DMCA Notice
Single Family
- Price: $2,300,000.00
- Price sqft: $497.41 / sqft
- Days On Market: 2
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4624
- Acreage: 0.36 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1961
MLS#: O6396611
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Green Oaks Rep 02
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Single Family
- Price: $2,184,000.00
- Price sqft: $430.68 / sqft
- Previous Price: $2,350,000
- Last Price Change: 04/09/26
- Days On Market: 121
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 3
- Bldg sqft: 5071
- Acreage: 0.35 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2015
MLS#: O6365961
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Fontainebleau
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Single Family
- Price: $1,949,999.00
- Price sqft: $554.61 / sqft
- Previous Price: $1,950,000
- Last Price Change: 04/09/26
- Days On Market: 56
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3516
- Acreage: 0.18 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6381988
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: REAL BROKER, LLC
- DMCA Notice









