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1400 Alabama Drive
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Details for 1400 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $6,500,000.00
  2. Price sqft: $638.82 / sqft
  3. Days On Market: 94
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10175
  8. Acreage: 0.70 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake
  14. Year Built: 1996
MLS#: O6285791
  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: THE AGENCY ORLANDO
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Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes
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1660 Palmer Avenue
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Details for 1660 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $5,200,000.00
  2. Price sqft: $694.91 / sqft
  3. Days On Market: 102
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7483
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Experience refined luxury in this newly constructed 2024 Hamptons style residence, a seamless blend of elegance and modern sophistication. A remote operated gated entrance opens to a grand circular dr
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421 Lakewood Drive
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Details for 421 Lakewood Drive, Winter Park, FL 32789
Single Family
  1. Price: $4,500,000.00
  2. Price sqft: $556.72 / sqft
  3. Days On Market: 580
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8083
  8. Acreage: 0.72 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake
  13. Year Built: 1957
MLS#: O6153641
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Osceola Shores Sec 03
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and me
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421 Lakewood Drive
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Details for 421 Lakewood Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $4,500,000.00
  2. Price sqft: $556.72 / sqft
  3. Days On Market: 580
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8083
  8. Acreage: 0.72 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 1957
MLS#: O6153641
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Shores Sec 03
  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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This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and me
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1782 Pine Avenue
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Details for 1782 Pine Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $4,100,000.00
  2. Price sqft: $609.85 / sqft
  3. Days On Market: 54
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6723
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6297161
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Conwill Estates
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: EXP REALTY LLC
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Under Construction. UNDER CONSTURCTION.....Step into this stunning West Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiec
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861 Bonita Drive
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Details for 861 Bonita Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,850,000.00
  2. Price sqft: $440.45 / sqft
  3. Days On Market: 61
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8741
  8. Acreage: 0.59 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1999
MLS#: O6287490
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Nestled on one of Winter Parks most picturesque brick lined streets, this stunning Mediterranean residence offers a refined blend of timeless elegance and modern luxury. With six bedrooms, six full ba
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4654 Thornlea Road
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Details for 4654 Thornlea Road, ORLANDO, FL 32817
Single Family
  1. Price: $3,615,000.00
  2. Price sqft: $499.93 / sqft
  3. Previous Price: $3,629,000
  4. Last Price Change: 05/24/25
  5. Days On Market: 82
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7231
  10. Acreage: 1.06 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2026
MLS#: O6286235
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32817
  4. Elementary School: Lakemont Elem
  5. Middle School: Maitland
  6. High School: Winter Park
  7. Provided by: BLUE CRAB REALTY LLC
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Pre Construction. To be built. Unparalleled Lakefront Luxury on Lake Waunatta, a private Ski Lake in Central Florida. Nestled at the end of a quiet cul de sac, this custom built 5,290 sq. ft. estate o
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1020 Mayfield Avenue
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Details for 1020 Mayfield Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,195,000.00
  2. Price sqft: $891.21 / sqft
  3. Days On Market: 45
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3585
  8. Acreage: 0.26 acres
  9. Pool: No
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: O6296230
  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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Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single story residence, customized and remodeled by Phil Kean Design Group. Open and spacious, 2,600 + SF interior layout which boasts
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541 Canton Avenue
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Details for 541 Canton Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,150,000.00
  2. Price sqft: $796.06 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3957
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6307816
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLER WILLIAMS WINTER PARK
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Timeless elegance meets boutique craftsmanship at 541 W Canton Avenuean exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Located just steps from
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940 Lincoln Circle
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Details for 940 Lincoln Circle, Winter Park, FL 32789
Single Family
  1. Price: $3,095,000.00
  2. Price sqft: $693.79 / sqft
  3. Previous Price: $3,350,000
  4. Last Price Change: 05/21/25
  5. Days On Market: 24
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4461
  10. Acreage: 0.33 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1995
MLS#: O6306740
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Robert Dhu Macdonald Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Located in Winter Parks highly sought after Golden Triangle, 940 Lincoln Circle is a beautifully renovated West Indies/Key West style home offering character, comfortable elegance, and functionality o
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