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  1. Zipcode = 32789
Details for 2661 Via Tuscany, Winter Park, FL 32789
Single Family
  1. Price: $8,500,000.00
  2. Price sqft: $1,743.95 / sqft
  3. Previous Price: $8,799,000
  4. Last Price Change: 06/28/25
  5. Days On Market: 215
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4874
  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 4/30/2025!! Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one of a kind residence is built with reinforced concrete, st
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: 6
  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 1581 Forest Avenue, Winter Park, FL 32789
Single Family
  1. Price: $4,175,000.00
  2. Price sqft: $698.28 / sqft
  3. Days On Market: 32
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5979
  8. Acreage: 0.39 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1954
MLS#: O6298754
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Ellno Willo
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: BHHS FLORIDA REALTY
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An Exquisite Hollywood Regency style residence showcasing a meticulous architectural reconstruction by Master Custom Builder, Carlos Posada. Positioned on a 120x140 lot on a beautiful tree lined br
Details for 1742 Temple Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,975,000.00
  2. Price sqft: $951.87 / sqft
  3. Days On Market: 2
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4176
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6320054
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lake Knowles Terrace Add 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Nestled in one of Winter Parks most coveted neighborhoods, this stunning four bedroom, five bath modern masterpiece with Control4 automation offers the perfect blend of luxury and function. Designed w
Details for 1820 Glencoe Road, Winter Park, FL 32789
Single Family
  1. Price: $3,895,000.00
  2. Price sqft: $756.02 / sqft
  3. Days On Market: 6
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5152
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6317785
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: CORCORAN PREMIER REALTY
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Welcome to your dream homea masterfully designed, Dutch West Indies inspired custom residence that blends timeless elegance with modern luxury. Built by FG Schaub Custom Homes, this home features five
Details for 1761 Legion Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,599,999.00
  2. Price sqft: $571.70 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6297
  8. Acreage: 0.39 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
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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 141 Phelps Avenue, Winter Park, FL 32789
Single Family
  1. Price: $3,595,000.00
  2. Price sqft: $499.17 / sqft
  3. Days On Market: 53
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 7202
  8. Acreage: 0.28 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: LakePrivileges
  14. Year Built: 2006
MLS#: O6306273
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Windsong Lakeside Sec 01 43/70
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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**This stunning estate just became an unbeatable opportunity luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong communit
Details for 1820 Englewood Road, Winter Park, FL 32789
Single Family
  1. Price: $3,300,000.00
  2. Price sqft: $664.25 / sqft
  3. Days On Market: 24
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4968
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2015
MLS#: O6314354
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. High School: Winter Park High
  7. Provided by: KELLER WILLIAMS ADVANTAGE III
  8. Provided through
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Award winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Park Avenue, and East End Markethome to Michelin rated dining and upscale retail.
Details for 641 Virginia Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,250,000.00
  2. Price sqft: $794.23 / sqft
  3. Days On Market: 2
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4092
  8. Acreage: 0.48 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake,LakeFront,LakePrivileges
  13. Year Built: 1966
MLS#: O6321437
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Timberlane Shores
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: KELLER WILLIAMS WINTER PARK
  9. Provided through
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Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought after Timberlane Shores neighborhood of Winter Park. This expansive .48 acre lot offers approximate
Details for 1730 Winchester Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,150,000.00
  2. Price sqft: $666.39 / sqft
  3. Previous Price: $3,249,000
  4. Last Price Change: 05/27/25
  5. Days On Market: 310
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4727
  10. Acreage: 0.28 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2024
MLS#: O6235073
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Timberlane Shores
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: KELLER WILLIAMS WINTER PARK
  9. Provided through
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Welcome to this exquisite 5 bedroom, 5.5 bathroom home built by Lundev, perfectly situated in the highly sought after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this pr