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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: 169
  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
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  9. mfrmls
  10. DMCA Notice
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: 300
  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
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. mfrmls
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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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2412 Chantilly Avenue
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Multi-Family
  1. Price: $7,150,000.00
  2. Days On Market: 34
  3. Garage / Parking Spaces: 8
  4. Acreage: 0.27 acres
  5. Pool: Yes
  6. Waterfront: No
  7. Year Built: 2026
MLS#: O6383456
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Provided by: REAL BROKER, LLC
  6. mfrmls
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This exclusive trifecta investment opportunity combines luxury real estate, dual lane income potential, and powerful tax advantagesall in one of the fastest growing markets in the country. Investors c
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40 Palmer Avenue
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Details for 40 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,950,000.00
  2. Price sqft: $799.03 / sqft
  3. Days On Market: 43
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8698
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6380444
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Elementary School: Lakemont Elem
  5. Middle School: Maitland
  6. High School: Winter Park
  7. Provided by: ONE LUXURY INTERNATIONAL LLC
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Under Construction. Opportunities like this rarely present themself, just a eight minute walk from the iconic shops, restaurants, and cafs of Park Avenue, 40 Palmer represents a rare convergence of ar
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1260 Alabama Drive
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Details for 1260 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $6,900,000.00
  2. Price sqft: $875.41 / sqft
  3. Days On Market: 21
  4. Bedrooms: 6
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7882
  8. Acreage: 0.57 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Freshwater
  14. Year Built: 1991
MLS#: O6387200
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of
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550 Palmer Avenue
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Details for 550 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,895,000.00
  2. Price sqft: $861.66 / sqft
  3. Previous Price: $7,200,000
  4. Last Price Change: 01/07/26
  5. Days On Market: 153
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8002
  10. Acreage: 0.48 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6349188
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Place
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining, and the iconic Winter Park 9 hole golf course,
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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: 09/08/25
  5. Days On Market: 483
  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: COMPASS FLORIDA LLC
  6. mfrmls
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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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1200 Via Salerno
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Details for 1200 Via Salerno, WINTER PARK, FL 32789
Single Family
  1. Price: $6,450,000.00
  2. Price sqft: $793.94 / sqft
  3. Days On Market: 39
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8124
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2001
MLS#: O6381761
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  9. mfrmls
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Along one of the cobblestone brick streets in the prestigious Vias of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke fini
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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: 09/08/25
  5. Days On Market: 274
  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
  7. High School: Winter Park
  8. Provided by: FORTUNE INTERNATIONAL REALTY
  9. mfrmls
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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: $4,995,000.00
  2. Price sqft: $765.64 / sqft
  3. Previous Price: $5,250,000
  4. Last Price Change: 03/12/26
  5. Days On Market: 68
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6524
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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
  9. mfrmls
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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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