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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: 142
  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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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: 26
  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: 11/15/25
  5. Days On Market: 160
  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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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: 67
  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: 39
  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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1910 Glencoe Road
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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: 228
  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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1821 Englewood Road
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Details for 1821 Englewood Road, WINTER PARK, FL 32789
Single Family
  1. Price: $3,295,000.00
  2. Price sqft: $630.26 / sqft
  3. Previous Price: $3,495,000
  4. Last Price Change: 11/07/25
  5. Days On Market: 72
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5228
  10. Acreage: 0.28 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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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: 451
  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
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1411 Nottingham Street
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Details for 1411 Nottingham Street, ORLANDO, FL 32803
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $624.03 / sqft
  3. Days On Market: 27
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 5128
  8. Acreage: 0.31 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2010
MLS#: O6355930
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32803
  4. Subdivision: Beverly Shores
  5. Elementary School: Audubon Park K8
  6. High School: Edgewater High
  7. Provided by: FANNIE HILLMAN & ASSOCIATES
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This one of a kind, top tier custom contemporary home in coveted Beverly Shores/Rose Isle delivers true turnkey luxury with exceptional finishes, premium cabinetry, high end appliances, and fully inte
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457 New England Avenue
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Details for 457 New England Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,100,000.00
  2. Price sqft: $805.82 / sqft
  3. Days On Market: 65
  4. Bedrooms: 5
  5. Baths: 5
  6. Bldg sqft: 3847
  7. Acreage: 0.41 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1920
MLS#: O6345511
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  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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Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the
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