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- School = Brookshire Elem
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: $3,250,000.00
- Price sqft: $594.48 / sqft
- Days On Market: 2
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 5467
- Acreage: 0.30 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6286245
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Kenilworth Shores Sec 01
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, youre imm
Land
- Price: $1,950,000.00
- Days On Market: 52
- Acreage: 0.37 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: Not Available
MLS#: O6273464
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Sylvan Park
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- 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: $1,649,000.00
- Price sqft: $436.94 / sqft
- Previous Price: $1,674,999
- Last Price Change: 03/01/25
- Days On Market: 120
- 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 Middle
- High School: Winter Park High
- 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
Condominium
- Price: $1,575,000.00
- Price sqft: $740.13 / sqft
- Days On Market: 9
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 2128
- Acreage: 1.56 acres
- Pool: No
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 1969
MLS#: O6276777
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Lake Virginia Condo
- Building: Lake Virginia Condo
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
Gorgeous lakefront 2 story winter park penthouse, corner builders unit with panoramic views of lake virginia from almost every room and its expansive full width balcony. Welcome to lakefront luxury li
Single Family
- Price: $1,395,000.00
- Price sqft: $337.28 / sqft
- Days On Market: 1
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4136
- Acreage: 0.20 acres
- Pool: No
- Waterfront: No
- Year Built: 2018
MLS#: O6288366
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: Brookshire Heights 1st Add
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: PALMANO GROUP RE BROKERAGE LLC
- DMCA Notice
Welcome to 2536 Brookshire Ave, a spacious 4 bedroom, 3.5 bath modern farmhouse. The open floor plan enhances connectivity throughout, with a first floor primary suite featuring generous his and her c
Single Family
- Price: $1,350,000.00
- Price sqft: $389.72 / sqft
- Days On Market: 24
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3464
- Acreage: 0.33 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1948
MLS#: O6278498
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Sylvan Lake Shores
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: ORLANDO BROTHERS REAL ESTATE LLC
- DMCA Notice
Renovated and Charming One Story Home in the Heart of Winter Park
Nestled in the heart of Winter Park, this elegant one story home features a classic brick circular driveway and a welcoming covere
Single Family
- Price: $1,295,000.00
- Price sqft: $479.63 / sqft
- Previous Price: $1,395,000
- Last Price Change: 03/07/25
- Days On Market: 65
- Bedrooms: 5
- Baths: 4
- Bldg sqft: 2700
- Acreage: 0.15 acres
- Pool: No
- Waterfront: No
- Year Built: 2018
MLS#: O6270087
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park
- Elementary School: Brookshire Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park far
Single Family
- Price: $1,150,000.00
- Price sqft: $299.56 / sqft
- Days On Market: 99
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3839
- Acreage: 0.35 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1960
MLS#: O6262593
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Kenilworth Shores Sec 06
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, located in the desirable heart of Winter Park. This charming single story home boasts 4 bedrooms, 3 baths, and a generous
Single Family
- Price: $995,000.00
- Price sqft: $724.16 / sqft
- Previous Price: $1,050,000
- Last Price Change: 02/19/25
- Days On Market: 207
- Bedrooms: 2
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 1374
- Acreage: 0.45 acres
- Pool: No
- Waterfront: No
- Year Built: 1971
MLS#: O6232951
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32792
- Subdivision: Aloma
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
- Provided by: DAVEN REAL ESTATE INC
- DMCA Notice
This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property currently has a single family house that is Tenant Occupied and incom

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Listings provided courtesy of The Hernando County Association of Realtors MLS.
Listing Data ©2025 REALTOR® Association of Citrus County
Listing Data ©2025 Royal Palm Coast Realtor® Association
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Datafeed Last updated on March 15, 2025 @ 12:00 am
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