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Details for 1400 Alabama Drive, Winter Park, FL 32789
Single Family
  1. Price: $6,200,000.00
  2. Price sqft: $609.34 / sqft
  3. Previous Price: $6,500,000
  4. Last Price Change: 07/17/25
  5. Days On Market: 145
  6. Bedrooms: 5
  7. Baths: 9
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 10175
  10. Acreage: 0.70 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. 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
  9. Provided through
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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, and walking distance to historic Park Avenue. A t
Details for 2211 Azalea Place, Winter Park, FL 32789
Single Family
  1. Price: $6,180,000.00
  2. Price sqft: $674.23 / sqft
  3. Days On Market: 31
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 9166
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: CanalFront,Lake,LakePrivileges
  13. 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
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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
Details for 1761 Legion Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,544,999.00
  2. Price sqft: $562.97 / sqft
  3. Previous Price: $3,599,999
  4. Last Price Change: 07/05/25
  5. Days On Market: 42
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6297
  10. Acreage: 0.39 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2017
MLS#: O6302616
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: SCANLON REALTY GROUP LLC
  9. Provided through
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One of the most coveted neighborhoods in all of Winter Park! This custom built 5 bedroom, 5.5 bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and
Details for 575 Palmer Avenue, Winter Park, FL 32789
Single Family
  1. Price: $3,150,000.00
  2. Price sqft: $483.43 / sqft
  3. Days On Market: 5
  4. Bedrooms: 6
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6516
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6327058
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Palmer Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: DEVLIN INVESTORS & ASSOCIATES
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Step into elevated Winter Park living with this exceptional Mediterranean inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated,
Details for 640 Old Horatio Avenue, Maitland, FL 32751
Single Family
  1. Price: $2,999,000.00
  2. Price sqft: $563.93 / sqft
  3. Previous Price: $3,199,000
  4. Last Price Change: 06/30/25
  5. Days On Market: 130
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5318
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalAccess,LakePrivileges
  15. Year Built: 2025
MLS#: O6290533
  1. County: ORANGE
  2. City: Maitland
  3. Zipcode: 32751
  4. Subdivision: Long Branch Sub
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: RE/MAX EXCLUSIVE COLLECTION
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PRICE IMPROVEMENT!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent res
Details for 2550 Venetian Way, Winter Park, FL 32789
Single Family
  1. Price: $2,799,000.00
  2. Price sqft: $455.94 / sqft
  3. Days On Market: 248
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6139
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: CanalAccess
  13. Year Built: 2008
MLS#: O6258445
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores First Add
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
  9. Provided through
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"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Pa
Details for 2412 Chantilly Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,389,000.00
  2. Price sqft: $459.78 / sqft
  3. Days On Market: 161
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5196
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6278049
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
  9. Provided through
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An architectural tour de force in the heart of Winter Park. Designed by a premier builder of boutique homes and crafted with no detail spared, this 5 bedroom, 6.5 bathroom estate offers over 4,500 squ
Details for 1710 Oneco Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,200,000.00
  2. Price sqft: $486.40 / sqft
  3. Days On Market: 0
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4523
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6328878
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Winter Park Heights
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. Provided through
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Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5 bedroom, 4.5 bath
Details for 1840 Bryan Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,999,500.00
  2. Price sqft: $428.62 / sqft
  3. Previous Price: $2,095,000
  4. Last Price Change: 05/30/25
  5. Days On Market: 83
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4665
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2014
MLS#: O6304239
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lakeview Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  9. Provided through
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This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a s
Details for 1521 Chestnut Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,899,900.00
  2. Price sqft: $513.07 / sqft
  3. Previous Price: $1,999,900
  4. Last Price Change: 06/16/25
  5. Days On Market: 69
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3703
  10. Acreage: 0.17 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2022
MLS#: A4651868
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lake Knowles Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
  9. Provided through
  10. DMCA Notice
Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, located in one of Winter Parks most sought after neighborhoods. Designed with sleek sophistication