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- School = Winter Park
Single Family
- Price: $11,900,000.00
- Price sqft: $889.59 / sqft
- Days On Market: 64
- Bedrooms: 7
- Baths: 11
- Garage / Parking Spaces: 4
- Bldg sqft: 13377
- Acreage: 1.63 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 2009
MLS#: O6269585
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsongpreserve Point
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6 acre gated Mediterranean Estate is a true private oasis. With over 11,000 square feet of living area and a beauti
Single Family
- Price: $6,100,000.00
- Price sqft: $949.27 / sqft
- Previous Price: $6,250,000
- Last Price Change: 02/12/25
- Days On Market: 67
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 3
- Bldg sqft: 6426
- Acreage: 0.51 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 2008
MLS#: O6268853
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Timberlane Shores
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: HOMEVEST REALTY
- DMCA Notice
Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom built residence by Farina & Sons offers the perfect bl
Single Family
- Price: $5,700,000.00
- Price sqft: $761.73 / sqft
- Days On Market: 22
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 7483
- Acreage: 0.36 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6282425
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Comstock Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Experience refined luxury in this newly constructed 2024 Hamptons style residence, a seamless blend of elegance and modern sophistication. A remote operated gated entrance opens to a grand circular dr
Single Family
- Price: $5,400,000.00
- Price sqft: $797.05 / sqft
- Days On Market: 147
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 6775
- Acreage: 0.33 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2008
MLS#: O6250411
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Gorgeous Winter Park home beautifully curated with designer details and recently featured in Junes Orange Appeal and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of
Single Family
- Price: $4,875,000.00
- Price sqft: $671.49 / sqft
- Days On Market: 10
- Bedrooms: 4
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 7260
- Acreage: 0.27 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2012
MLS#: O6281892
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Alexander Place
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
One or more photo(s) has been virtually staged. Discover a stunning blend of modern luxury and award winning design in this architectural gem by Phil Kean. Originally the International Showcase Home f
Single Family
- Price: $4,500,000.00
- Price sqft: $1,223.82 / sqft
- Days On Market: 17
- Bedrooms: 4
- Baths: 5
- Bldg sqft: 3677
- Acreage: 0.35 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 1926
MLS#: O6277515
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Virginia Heights
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past whi
Single Family
- Price: $4,500,000.00
- Price sqft: $992.28 / sqft
- Days On Market: 52
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 4535
- Acreage: 0.23 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6273466
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Palmer Ave Lakeside Prop
- Elementary School: Lakemont Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: FLORIDIAN REALTY GROUP LLC
- DMCA Notice
Under Construction. New Custom Home in the Desirable Winter Park Vias Completion Expected May 2025
This exceptional residence, designed with European English Tudor inspired architecture, offers the
Single Family
- Price: $4,395,000.00
- Price sqft: $789.76 / sqft
- Days On Market: 2
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 5565
- Acreage: 0.58 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 1998
MLS#: O6289194
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Forest Hills
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: KELLY PRICE & COMPANY LLC
- DMCA Notice
Just Listed ~ Stunning lakefront home in Winter Park that has been completely remodeled and offers 4 bedrooms, a bonus room, and guest apartment! This home is exquisite from top to bottom and feature
Single Family
- Price: $4,100,000.00
- Price sqft: $820.49 / sqft
- Days On Market: 126
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 4997
- Acreage: 0.30 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6255877
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Forest Hills
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Under Construction. Exquisite new construction residence nestled in the heart of Winter Park, walking distance to Park Ave. This luxurious home boasts over 4,000 square feet of meticulously designed l
Single Family
- Price: $3,892,000.00
- Price sqft: $679.35 / sqft
- Days On Market: 158
- Bedrooms: 4
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 5729
- Acreage: 0.45 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Creek
- Year Built: 2001
MLS#: O6246352
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Virginia Heights
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: STOCKWORTH REALTY GROUP
- DMCA Notice
Welcome to 1391 Richmond Road, a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot rig

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