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  1. City = Winter Park
  2. Listing Status = Active
1120 Preserve Point Drive
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Details for 1120 Preserve Point Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $8,950,000.00
  2. Price sqft: $669.06 / sqft
  3. Days On Market: 124
  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 Front
  14. Year Built: 2009
MLS#: O6350054
  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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In the exclusive community of Windsong on Lake Berry, this magnificent 1.6 acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped
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1112 Preserve Point Drive
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Details for 1112 Preserve Point Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $8,500,000.00
  2. Price sqft: $928.05 / sqft
  3. Days On Market: 255
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 9159
  8. Acreage: 1.94 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2013
MLS#: O6312768
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Windsong Preserve Point 4376
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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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
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2661 Via Tuscany
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Details for 2661 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $6,600,000.00
  2. Price sqft: $1,261.71 / sqft
  3. Previous Price: $8,500,000
  4. Last Price Change: 09/16/25
  5. Days On Market: 438
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5231
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2024
MLS#: O6260493
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Provided by: PV LUXURY GROUP PA
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Calling highest and best by 09/26/2025!! Seller financing available with very attractive terms introducing a unique, stunning modern home a groundbreaking architectural masterpiece, this one of
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887 Georgia Avenue
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Details for 887 Georgia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $843.45 / sqft
  3. Previous Price: $5,900,000
  4. Last Price Change: 01/26/26
  5. Days On Market: 191
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6758
  10. Acreage: 1.07 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1924
MLS#: O6331715
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Dyer Susan Resub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless
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2211 Azalea Place
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Details for 2211 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $599.50 / sqft
  3. Previous Price: $5,950,000
  4. Last Price Change: 12/07/25
  5. Days On Market: 229
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 9166
  10. Acreage: 0.69 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal Front,Lake Privileges
  16. Year Built: 2008
MLS#: O6319674
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FORTUNE INTERNATIONAL REALTY
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Exquisite Waterfront Estate in the Heart of Winter Park Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Parks most prestigious neighb
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1221 Richmond Road
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Details for 1221 Richmond Road, WINTER PARK, FL 32789
Single Family
  1. Price: $5,250,000.00
  2. Price sqft: $804.72 / sqft
  3. Days On Market: 23
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6524
  8. Acreage: 0.34 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2024
MLS#: O6373743
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Virginia Heights Rep
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Now offered with a significant price improvement, this award winning custom residence presents a rare opportunity in Winter Parks sought after Virginia Heights neighborhood, prized for its proximity t
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1302 Raintree Place
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Details for 1302 Raintree Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,150,000.00
  2. Price sqft: $872.00 / sqft
  3. Previous Price: $5,300,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 114
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5906
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6353083
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Camwood Sub
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophisticationall just steps from Winter Parks iconic Park Avenue.
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1660 Palmer Avenue
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Details for 1660 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $4,950,000.00
  2. Price sqft: $661.50 / sqft
  3. Previous Price: $5,200,000
  4. Last Price Change: 01/30/26
  5. Days On Market: 352
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7483
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2024
MLS#: O6282425
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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New Hamptons style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exception
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1150 Via Salerno
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Details for 1150 Via Salerno, WINTER PARK, FL 32789
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $1,082.99 / sqft
  3. Days On Market: 224
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4386
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6321143
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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In the heart of Winter Parks coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean minimalist residence that blends architectural refinement w/ organic warmth. Designed and de
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1336 College Point
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Details for 1336 College Point, WINTER PARK, FL 32789
Land
  1. Price: $4,595,000.00
  2. Days On Market: 11
  3. Acreage: 0.35 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Privileges
  8. Year Built: Not Available
MLS#: O6376009
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Virginia Heights
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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A rare offering on the shores of Lake Virginia, this prime lakefront parcel presents a distinguished opportunity within Winter Parks most coveted waterfront corridor. Encompassing a significant Lake V
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