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: 170
- 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: 30
- 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: $2,650,000.00
- Price sqft: $515.06 / sqft
- Days On Market: 16
- 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: $1,925,000.00
- Price sqft: $427.02 / sqft
- Days On Market: 21
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 4508
- Acreage: 0.18 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6383092
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: The Enclave Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Single Family
- Price: $1,899,500.00
- Price sqft: $407.18 / sqft
- Days On Market: 21
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4665
- Acreage: 0.29 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2014
MLS#: O6391922
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Lakeview Terrace
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Single Family
- Price: $1,895,000.00
- Price sqft: $420.27 / sqft
- Days On Market: 21
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 4509
- Acreage: 0.15 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6391825
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: The Enclave Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Single Family
- Price: $1,645,000.00
- Price sqft: $384.26 / sqft
- Previous Price: $1,695,000
- Last Price Change: 03/26/26
- Days On Market: 59
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 1
- Bldg sqft: 4281
- Acreage: 0.42 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1935
MLS#: O6379927
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Osceola Shores Sec 1
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
Townhome
- Price: $1,495,000.00
- Price sqft: $434.47 / sqft
- Days On Market: 21
- Bedrooms: 3
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3441
- Acreage: 0.12 acres
- Pool: No
- Waterfront: No
- Year Built: 2026
MLS#: O6383679
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: The Enclave Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Townhome
- Price: $1,495,000.00
- Price sqft: $425.44 / sqft
- Days On Market: 21
- Bedrooms: 3
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3514
- Acreage: 0.12 acres
- Pool: No
- Waterfront: No
- Year Built: 2026
MLS#: O6383602
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: The Enclave Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Single Family
- Price: $975,000.00
- Price sqft: $447.25 / sqft
- Previous Price: $995,000
- Last Price Change: 04/09/26
- Days On Market: 38
- Bedrooms: 3
- Baths: 3
- Bldg sqft: 2180
- Acreage: 0.66 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 1958
MLS#: G5108209
- County: ORANGE
- City: MAITLAND
- Zipcode: 32751
- Elementary School: Lake Sybelia Elem
- Middle School: Maitland Middle
- High School: Edgewater
- Provided by: LISA REALTY PARTNERS
- DMCA Notice









