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- School = Brookshire Elem
Single Family
- Price: $10,900,000.00
- Price sqft: $814.83 / sqft
- Previous Price: $11,900,000
- Last Price Change: 05/21/25
- Days On Market: 156
- 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 Front
- Year Built: 2009
MLS#: O6269585
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsongpreserve Point
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- 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: $8,500,000.00
- Price sqft: $928.05 / sqft
- Days On Market: 17
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 9159
- Acreage: 1.94 acres
- Pool: Yes
- Community Pool: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: LakeFront,LakePrivileges
- Year Built: 2013
MLS#: O6312768
- County: ORANGE
- City: Winter Park
- Zipcode: 32789
- Subdivision: Windsong Preserve Point 43/76
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
- Provided through
- DMCA Notice
Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2 acre lakefront estate, is absolutely gorgeous and is available for the first time! Cus
Single Family
- Price: $8,500,000.00
- Price sqft: $928.05 / sqft
- Days On Market: 17
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 9159
- Acreage: 1.94 acres
- Pool: Yes
- Community Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 2013
MLS#: O6312768
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsong Preserve Point 4376
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
- DMCA Notice
Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2 acre lakefront estate, is absolutely gorgeous and is available for the first time! Cus
Single Family
- Price: $3,595,000.00
- Price sqft: $499.17 / sqft
- Previous Price: $3,980,000
- Last Price Change: 06/07/25
- Days On Market: 38
- Bedrooms: 6
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 7202
- Acreage: 0.28 acres
- Pool: Yes
- Community Pool: Yes
- Waterfront: No
- Year Built: 2006
MLS#: O6306273
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsong Lakeside Sec 01 4370
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
**This stunning estate just became an unbeatable opportunity luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong communit
Single Family
- Price: $3,295,000.00
- Price sqft: $605.59 / sqft
- Days On Market: 60
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 5441
- Acreage: 0.26 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2023
MLS#: O6298838
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Kenilworth Shores Sec 01
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: FLORIDA ONE REAL ESTATE LLC
- DMCA Notice
Nestled in peaceful Winter Park, your new contemporary home boasts expansive open living areas featuring 12 foot ceilings, five en suite bedrooms, and outdoor living spaces spanning two levels.
T
Single Family
- Price: $2,590,000.00
- Price sqft: $622.60 / sqft
- Days On Market: 25
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 4160
- Acreage: 0.21 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6304627
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Sylvan Lake Shores
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Under Construction. Brand new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning
Single Family
- Price: $2,375,000.00
- Price sqft: $516.87 / sqft
- Days On Market: 30
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 4595
- Acreage: 0.28 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1926
MLS#: O6307403
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Cortland Park
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and res
Land
- Price: $1,750,000.00
- Previous Price: $1,850,000
- Last Price Change: 06/10/25
- Days On Market: 144
- Acreage: 0.37 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: Not Available
MLS#: O6273464
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Sylvan Park
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: FLORIDIAN REALTY GROUP LLC
- DMCA Notice
Desirable Winter Park, Lake Sylvan lakefront homesite, Sunset views, Lot dimensions 72 x 220 high and dry, .37+ acres custom home building site, quiet brick road, surrounded by other custom homes. FA
Single Family
- Price: $1,695,000.00
- Price sqft: $411.51 / sqft
- Days On Market: 38
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4119
- Acreage: 0.25 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2016
MLS#: O6305970
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Lake Monte Sub
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: EXP REALTY LLC
- DMCA Notice
Stunning contemporary home in Winter Park is close to Park Avenue and all of the wonderful restaurants, shops and the historic farmer's market. This luxurious home exudes a crisp, pristine setting wi
Single Family
- Price: $1,599,999.00
- Price sqft: $423.95 / sqft
- Days On Market: 211
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3774
- Acreage: 0.14 acres
- Pool: No
- Community Pool: Yes
- Waterfront: No
- Year Built: 2014
MLS#: O6257912
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsong
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Exceptional Phil Kean designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophisticated 4 bedroom, 4 bathroom residence seamlessly blends modern luxury with practic

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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on June 15, 2025 @ 12:00 am
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