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  1. School = Brookshire Elem
1120 Preserve Point Drive
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Details for 1120 Preserve Point Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $11,900,000.00
  2. Price sqft: $889.59 / sqft
  3. Days On Market: 64
  4. Bedrooms: 7
  5. Baths: 11
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 13377
  8. Acreage: 1.63 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake
  14. Year Built: 2009
MLS#: O6269585
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Windsongpreserve Point
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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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
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1833 Loch Berry Road
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Details for 1833 Loch Berry Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,250,000.00
  2. Price sqft: $594.48 / sqft
  3. Days On Market: 2
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5467
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6286245
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Kenilworth Shores Sec 01
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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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
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313 Sylvan Drive
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Details for 313 Sylvan Drive, WINTER PARK, FL 32789
Land
  1. Price: $1,950,000.00
  2. Days On Market: 52
  3. Acreage: 0.37 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake
  8. Year Built: Not Available
MLS#: O6273464
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sylvan Park
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: FLORIDIAN REALTY GROUP LLC
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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
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1429 Chapman Circle
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Details for 1429 Chapman Circle, WINTER PARK, FL 32789
Single Family
  1. Price: $1,649,000.00
  2. Price sqft: $436.94 / sqft
  3. Previous Price: $1,674,999
  4. Last Price Change: 03/01/25
  5. Days On Market: 120
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3774
  10. Acreage: 0.14 acres
  11. Pool: No
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 2014
MLS#: O6257912
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Windsong
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: CORCORAN PREMIER REALTY
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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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690 Osceola Avenue 604
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Details for 690 Osceola Avenue 604, WINTER PARK, FL 32789
Condominium
  1. Price: $1,575,000.00
  2. Price sqft: $740.13 / sqft
  3. Days On Market: 9
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2128
  8. Acreage: 1.56 acres
  9. Pool: No
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake
  14. Year Built: 1969
MLS#: O6276777
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Lake Virginia Condo
  5. Building: Lake Virginia Condo
  6. Elementary School: Brookshire Elem
  7. Middle School: Glenridge Middle
  8. High School: Winter Park High
  9. Provided by: COLDWELL BANKER RESIDENTIAL RE
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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
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2536 Brookshire Avenue
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Details for 2536 Brookshire Avenue, WINTER PARK, FL 32792
Single Family
  1. Price: $1,395,000.00
  2. Price sqft: $337.28 / sqft
  3. Days On Market: 1
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4136
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2018
MLS#: O6288366
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Brookshire Heights 1st Add
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: PALMANO GROUP RE BROKERAGE LLC
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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
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181 Phelps Avenue
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Details for 181 Phelps Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,350,000.00
  2. Price sqft: $389.72 / sqft
  3. Days On Market: 24
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3464
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1948
MLS#: O6278498
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sylvan Lake Shores
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: ORLANDO BROTHERS REAL ESTATE LLC
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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
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433 Carolina Avenue
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Details for 433 Carolina Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,295,000.00
  2. Price sqft: $479.63 / sqft
  3. Previous Price: $1,395,000
  4. Last Price Change: 03/07/25
  5. Days On Market: 65
  6. Bedrooms: 5
  7. Baths: 4
  8. Bldg sqft: 2700
  9. Acreage: 0.15 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 2018
MLS#: O6270087
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Brookshire Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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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
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708 Balmoral Road
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Details for 708 Balmoral Road, WINTER PARK, FL 32789
Single Family
  1. Price: $1,150,000.00
  2. Price sqft: $299.56 / sqft
  3. Days On Market: 99
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3839
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1960
MLS#: O6262593
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Kenilworth Shores Sec 06
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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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
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2260 Hawick Lane
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Details for 2260 Hawick Lane, WINTER PARK, FL 32792
Single Family
  1. Price: $995,000.00
  2. Price sqft: $724.16 / sqft
  3. Previous Price: $1,050,000
  4. Last Price Change: 02/19/25
  5. Days On Market: 207
  6. Bedrooms: 2
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 1374
  10. Acreage: 0.45 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1971
MLS#: O6232951
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Aloma
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: DAVEN REAL ESTATE INC
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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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Tropic Shores Realty - Crystal River
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Listing Data ©2025 Greater Fort Lauderdale REALTORS®
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
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on March 15, 2025 @ 12:00 am
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