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  1. City = Winter Park
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: 281
  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 702 Via Bella, Winter Park, FL 32789
Single Family
  1. Price: $4,650,000.00
  2. Price sqft: $1,025.36 / sqft
  3. Days On Market: 0
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4535
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6335854
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Palmer Ave Lakeside Prop
  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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Welcome to 702 Via Bella, an impressive 2025 English Cottage Estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying transitional elegance and true artisan cra
Details for 850 Juanita Rael, Winter Park, FL 32789
Single Family
  1. Price: $3,950,000.00
  2. Price sqft: $833.33 / sqft
  3. Days On Market: 8
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4740
  8. Acreage: 0.34 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1966
MLS#: O6337162
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep 03
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PHIL KEAN REAL ESTATE LLC
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Pre Construction. To be built. This is that house. Location, Architecture and Layout. Designed on one level on an oversized corner lot on the North side of Winter Park which allows an ease of in and
Details for 1910 Glencoe Road, Winter Park, FL 32789
Single Family
  1. Price: $3,490,000.00
  2. Price sqft: $737.22 / sqft
  3. Days On Market: 141
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4734
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6294091
  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: COMPASS FLORIDA LLC
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Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of prestigious Winter Park. This brand new construction embodies the perfect fusion of contemporary desi
Details for 1860 Via Contessa, Winter Park, FL 32789
Single Family
  1. Price: $2,790,000.00
  2. Price sqft: $304.52 / sqft
  3. Previous Price: $2,750,000
  4. Last Price Change: 08/07/25
  5. Days On Market: 458
  6. Bedrooms: 8
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 9162
  10. Acreage: 0.26 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2003
MLS#: O6210791
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lugano Terrace
  5. Provided by: SIERRA REALTY GROUP LLC
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Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal ch
Details for 2550 Venetian Way, Winter Park, FL 32789
Single Family
  1. Price: $2,699,000.00
  2. Price sqft: $439.65 / sqft
  3. Previous Price: $2,799,000
  4. Last Price Change: 08/05/25
  5. Days On Market: 289
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6139
  10. Acreage: 0.27 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalAccess
  15. 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
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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 1341 Place Picardy, Winter Park, FL 32789
Single Family
  1. Price: $2,695,000.00
  2. Price sqft: $437.43 / sqft
  3. Previous Price: $2,800,000
  4. Last Price Change: 06/30/25
  5. Days On Market: 72
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6161
  10. Acreage: 0.32 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2016
MLS#: O6319556
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Fontainebleau
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: STOCKWORTH REALTY GROUP
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Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter
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: 203
  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 715 Via Bella, Winter Park, FL 32789
Single Family
  1. Price: $2,369,000.00
  2. Price sqft: $547.37 / sqft
  3. Days On Market: 9
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4328
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1976
MLS#: O6338650
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Palmer Ave Lakeside Prop
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
  9. Provided through
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Tucked away on a quiet cul de sac lined with multi million dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, t
Details for 1781 Pine Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,300,000.00
  2. Price sqft: $474.52 / sqft
  3. Previous Price: $2,497,000
  4. Last Price Change: 09/01/25
  5. Days On Market: 83
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4847
  10. Acreage: 0.24 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2017
MLS#: O6314404
  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: FLORIDA CONNEXION PROPERTIES
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Price Reduced to sell. An exceptional custom home by award winning Davila Homes, perfectly blending modern design and functionality. Located in sought after Conwill Estates, just minutes from Park Ave