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  1. School = Audubon Park K 8
1221 Richmond Road
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Details for 1221 Richmond Road, WINTER PARK, FL 32789
Single Family
  1. Price: $5,450,000.00
  2. Price sqft: $835.38 / sqft
  3. Previous Price: $5,575,000
  4. Last Price Change: 10/04/25
  5. Days On Market: 117
  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#: O6321906
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Virginia Heights Rep
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: KELLER WILLIAMS WINTER PARK
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An Award Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence locat
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1840 Fawsett Road
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Details for 1840 Fawsett Road, WINTER PARK, FL 32789
Single Family
  1. Price: $4,295,000.00
  2. Price sqft: $771.79 / sqft
  3. Previous Price: $4,395,000
  4. Last Price Change: 09/11/25
  5. Days On Market: 238
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5565
  10. Acreage: 0.58 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 1998
MLS#: O6289194
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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Experience the ultimate in luxury lakefront living in this meticulously renovated estate where every surface has been reimagined with the finest finishes and thoughtful design. This stunning property
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1751 Glencoe Road
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Details for 1751 Glencoe Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,895,000.00
  2. Price sqft: $695.78 / sqft
  3. Days On Market: 1
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5598
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6339739
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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Nestled just moments from the boutiques and cafs on Park Avenue, this newly completed Davila Homes masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30 acre lot,
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1820 Glencoe Road
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Details for 1820 Glencoe Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,825,000.00
  2. Price sqft: $742.43 / sqft
  3. Previous Price: $3,895,000
  4. Last Price Change: 11/02/25
  5. Days On Market: 136
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5152
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6317785
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: CORCORAN PREMIER REALTY
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Discover the ultimate in luxury real estate in Winter Park, Florida with this Dutch West Indiesinspired custom home built by FG Schaub Custom Homes. Ideally located just minutes from Park Avenues upsc
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1581 Forest Avenue
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Details for 1581 Forest Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,775,000.00
  2. Price sqft: $631.38 / sqft
  3. Days On Market: 22
  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#: O6347647
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Ellno Willo
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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Located just steps from Park Avenue, this extraordinary Winter Park residence was fully rebuilt in 2018 by master custom builder Posada Homes. Set on a 0.39 acre lot along one of Winter Parks most des
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207 Kings Way
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Details for 207 Kings Way, WINTER PARK, FL 32789
Single Family
  1. Price: $3,650,000.00
  2. Price sqft: $770.21 / sqft
  3. Days On Market: 43
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 4739
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6337304
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Charmont
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro
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2905 Parkland Drive
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Details for 2905 Parkland Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,499,900.00
  2. Price sqft: $543.72 / sqft
  3. Days On Market: 15
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6437
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6354029
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Lake Forest Park
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: UNITED REAL ESTATE PREFERRED
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Under Construction. Pre Construction. To be built. GROUND BROKEN OCTOBER 2025. Contact Builder quickly to customize to suite this gorgeous Alys Beach luxury home in Winter Park! Presented by Wooten B
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1821 Englewood Road
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New Construction
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Details for 1821 Englewood Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,495,000.00
  2. Price sqft: $668.52 / sqft
  3. Days On Market: 47
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5228
  8. Acreage: 0.28 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6345085
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This stunning new contemporary residence, a five bedroom, five and a half bath home by the renowned Rex Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury
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1910 Glencoe Road
New Construction
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Details for 1910 Glencoe Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,490,000.00
  2. Price sqft: $654.17 / sqft
  3. Days On Market: 204
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5335
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6294091
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Forest Hills
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  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
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300 Interlachen Avenue 403
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Details for 300 Interlachen Avenue 403, WINTER PARK, FL 32789
Condominium
  1. Price: $3,250,000.00
  2. Price sqft: $968.70 / sqft
  3. Previous Price: $3,350,000
  4. Last Price Change: 10/15/24
  5. Days On Market: 427
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3355
  10. Acreage: 0.40 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2005
MLS#: O6238504
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Residences
  5. Building: Residences
  6. Elementary School: Audubon Park K8
  7. Middle School: Audubon Park K 8
  8. High School: Winter Park High
  9. Provided by: FANNIE HILLMAN & ASSOCIATES
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Luxury, location, and lifestyle beautifully come together at The Residences, one of downtown Winter Parks premier condominium communities. The building offers 24 hour concierge service, a rooftop pool
Listing Details and 37 Additional Pictures
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