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  1. School = Maitland Middle
887 Georgia Avenue
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Details for 887 Georgia Avenue, Winter Park, FL 32789
Single Family
  1. Price: $5,900,000.00
  2. Price sqft: $873.04 / sqft
  3. Previous Price: $6,500,000
  4. Last Price Change: 10/09/25
  5. Days On Market: 97
  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
  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
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2211 Azalea Place
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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: 08/18/25
  5. Days On Market: 135
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 9166
  10. Acreage: 0.69 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalFront,Lake,LakePrivileges
  15. 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
  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
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1120 Palmer Avenue
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Details for 1120 Palmer Avenue, Winter Park, FL 32789
Single Family
  1. Price: $4,250,000.00
  2. Price sqft: $1,088.35 / sqft
  3. Days On Market: 92
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3905
  8. Acreage: 0.42 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1951
MLS#: O6332795
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: 3223171 3223171
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PHIL KEAN REAL ESTATE LLC
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One or more photo(s) has been virtually staged. Now available to view. Fully furnished (all furniture and artwork available for additional pricing) Spectacular Phil Kean Design Group whole home remo
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1661 Palm Avenue
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Details for 1661 Palm Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,598,000.00
  2. Price sqft: $556.56 / sqft
  3. Days On Market: 5
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4668
  8. Acreage: 0.24 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6356760
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Winter Park Heights
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood.This residence combines timeless elegance with modern l
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1560 Woodland Avenue
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Details for 1560 Woodland Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,999,000.00
  2. Price sqft: $385.54 / sqft
  3. Previous Price: $2,150,000
  4. Last Price Change: 08/29/25
  5. Days On Market: 223
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5185
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1990
MLS#: O6293517
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: LOKATION
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You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick paved street. There are five bedrooms and four and a ha
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1861 Taylor Avenue
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Details for 1861 Taylor Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,975,000.00
  2. Price sqft: $493.01 / sqft
  3. Days On Market: 19
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4006
  8. Acreage: 0.19 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2023
MLS#: O6353448
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Orange Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Built by Meridian Homes in 2023, this newer construction, five bedroom, five full and two half bath residence combines timeless coastal architecture with a fresh, modern sensibility. Designed by Laur
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1710 Oneco Avenue
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Details for 1710 Oneco Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,945,000.00
  2. Price sqft: $430.02 / sqft
  3. Days On Market: 105
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4523
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6328878
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Winter Park Heights
  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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Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5 bedroom, 4.5 bath
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1660 Walnut Avenue
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Details for 1660 Walnut Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,759,000.00
  2. Price sqft: $536.12 / sqft
  3. Days On Market: 281
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3281
  8. Acreage: 0.15 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6275164
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lake Knowles Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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Under Construction. Elegant and modern new construction home perfectly situated in beautiful Winter Park. Scheduled for completion in December 2025, this brand new construction home offers a perfect b
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1150 Kenwood Avenue
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Details for 1150 Kenwood Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,290,000.00
  2. Price sqft: $411.09 / sqft
  3. Days On Market: 6
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3138
  8. Acreage: 0.15 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1988
MLS#: O6355666
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Dixie Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Wonderful opportunity homes rarely come available on this street! Located in the heart of Winter Park, this elegantly designed 3 bedroom, 2.5 bathroom residence offers 2,557 square feet of living sp
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2550 Big Bend Trail
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Details for 2550 Big Bend Trail, Maitland, FL 32751
Single Family
  1. Price: $799,999.00
  2. Price sqft: $271.65 / sqft
  3. Days On Market: 7
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2945
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1967
MLS#: O6348541
  1. County: ORANGE
  2. City: Maitland
  3. Zipcode: 32751
  4. Subdivision: Dommerich Hills Fifth Add
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: FLORIDA REALTY INVESTMENTS
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Sought after Dommerich Hills POOL Home with no HOA! This spacious block construction residence sits on an oversized lotover a quarter acreand offers nearly 3,000 square feet of living space with a rar
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