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  1. School = Maitland Middle
  2. Listing Status = Active
Details for 2203 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $12,900,000.00
  2. Price sqft: $713.85 / sqft
  3. Days On Market: 44
  4. Bedrooms: 6
  5. Baths: 9
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 18071
  8. Acreage: 2.18 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2002
MLS#: O6367595
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Elementary School: Dommerich Elem
  5. Middle School: Maitland Middle
  6. High School: Winter Park High
  7. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor cour
Details for 550 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,895,000.00
  2. Price sqft: $861.66 / sqft
  3. Previous Price: $7,200,000
  4. Last Price Change: 01/20/26
  5. Days On Market: 100
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8002
  10. Acreage: 0.48 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6349188
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Place
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining, and the iconic Winter Park 9 hole golf course,
Details for 1400 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $5,895,000.00
  2. Price sqft: $579.36 / sqft
  3. Previous Price: $6,200,000
  4. Last Price Change: 01/27/26
  5. Days On Market: 336
  6. Bedrooms: 5
  7. Baths: 9
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 10175
  10. Acreage: 0.72 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. 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 Middle
  7. High School: Winter Park High
  8. Provided by: THE AGENCY FL
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Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72 acre corner lot in one of Winter Park's most sought after locations. This 7,916 SF property includes a main residence of ov
Details for 887 Georgia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $843.45 / sqft
  3. Previous Price: $5,900,000
  4. Last Price Change: 01/26/26
  5. Days On Market: 183
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6758
  10. Acreage: 1.07 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1924
MLS#: O6331715
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Dyer Susan Resub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless
Details for 2211 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $599.50 / sqft
  3. Previous Price: $5,950,000
  4. Last Price Change: 12/07/25
  5. Days On Market: 221
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 9166
  10. Acreage: 0.69 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal Front,Lake Privileges
  16. 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 Middle
  7. High School: Winter Park High
  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 1302 Raintree Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,150,000.00
  2. Price sqft: $872.00 / sqft
  3. Previous Price: $5,300,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 106
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5906
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6353083
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Camwood Sub
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophisticationall just steps from Winter Parks iconic Park Avenue.
Details for 1150 Via Salerno, WINTER PARK, FL 32789
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $1,082.99 / sqft
  3. Days On Market: 216
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4386
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6321143
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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In the heart of Winter Parks coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean minimalist residence that blends architectural refinement w/ organic warmth. Designed and de
Details for 1161 Valencia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $4,395,000.00
  2. Price sqft: $803.03 / sqft
  3. Previous Price: $4,445,000
  4. Last Price Change: 01/27/26
  5. Days On Market: 163
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5473
  10. Acreage: 0.32 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2021
MLS#: O6330736
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Valencia Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: THE REAL ESTATE COLLECTION LLC
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Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2
Details for 1417 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $4,199,000.00
  2. Price sqft: $682.76 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6150
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6368668
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Park Grove
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: ONE LUXURY INTERNATIONAL LLC
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Under Construction. Tucked away on a quiet cul de sac in the coveted Park Grove community, this home sits on an expansive 0.37 acre lot, just moments from the boutiques, dining, and charm of Park Aven
Details for 1250 Maitland Avenue, MAITLAND, FL 32751
Land
  1. Price: $3,990,900.00
  2. Previous Price: $4,490,900
  3. Last Price Change: 10/23/25
  4. Days On Market: 553
  5. Acreage: 7.82 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front
  10. Year Built: Not Available
MLS#: O6222186
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Woodbridge
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: AG REALTY SERVICES LLC
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Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately 8 acres