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  1. School = Maitland Middle
  2. Listing Status = Active
550 Palmer Avenue
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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: 01/07/26
  5. Days On Market: 169
  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
  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,
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1782 Pine Avenue
New Construction
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Details for 1782 Pine Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $4,197,000.00
  2. Price sqft: $624.28 / sqft
  3. Days On Market: 29
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6723
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6389039
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Conwill Estates
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: KELLER WILLIAMS ADVANTAGE REALTY
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Step into this stunning West Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This
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1761 Legion Drive
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Details for 1761 Legion Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,295,000.00
  2. Price sqft: $523.27 / sqft
  3. Previous Price: $3,399,999
  4. Last Price Change: 02/18/26
  5. Days On Market: 301
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6297
  10. Acreage: 0.39 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2017
MLS#: O6302616
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: SCANLON REALTY GROUP LLC
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One of the most coveted neighborhoods in all of Winter Park! This custom built 5 bedroom, 5.5 bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and
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1300 Mayfield Avenue
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Details for 1300 Mayfield Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,850,000.00
  2. Price sqft: $459.97 / sqft
  3. Days On Market: 13
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6196
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1958
MLS#: O6393777
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Temple 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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Tucked behind towering hedges on a coveted brick lined street, this estate sits on an approximately acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination o
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620 Pinetree Road
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Details for 620 Pinetree Road, WINTER PARK, FL 32789
Land
  1. Price: $2,790,000.00
  2. Days On Market: 0
  3. Acreage: 0.49 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6397264
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sicilian Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Vias, this .48 acre homesite offers a fantastic combination of location, scale, and design potential.
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1130 Park North Place
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Details for 1130 Park North Place, WINTER PARK, FL 32789
Single Family
  1. Price: $2,650,000.00
  2. Price sqft: $515.06 / sqft
  3. Days On Market: 15
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5145
  8. Acreage: 0.40 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1968
MLS#: O6392394
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Park North
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: CORCORAN PREMIER REALTY
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Located on a quiet cul de sac in the heart of Winter Park, this traditional two story home offers a functional, well designed floorplan for both everyday living and entertaining. From the moment you s
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2412 Chantilly Avenue
New Construction
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,395,000.00
  2. Price sqft: $460.93 / sqft
  3. Days On Market: 57
  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: 2026
MLS#: O6381552
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: REAL BROKER, LLC
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Exceptional design meets refined luxury in this brand new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for bo
Listing Details and 60 Additional Pictures
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800 Juanita Rael
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Details for 800 Juanita Rael, WINTER PARK, FL 32789
Single Family
  1. Price: $2,300,000.00
  2. Price sqft: $497.41 / sqft
  3. Days On Market: 1
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4624
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1961
MLS#: O6396611
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one story residence ideally situated just moments from the vibrant shops and dining of Park Av
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2503 Versailles Avenue
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Reduced
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Details for 2503 Versailles Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,184,000.00
  2. Price sqft: $430.68 / sqft
  3. Days On Market: 121
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5071
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2015
MLS#: O6365961
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Fontainebleau
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
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Back on the marketan exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhanceme
Listing Details and 52 Additional Pictures
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2501 Lafayette Avenue
New Construction
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Details for 2501 Lafayette Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,949,999.00
  2. Price sqft: $554.61 / sqft
  3. Days On Market: 56
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3516
  8. Acreage: 0.18 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6381988
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park
  8. Provided by: REAL BROKER, LLC
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Under Construction. GENEROUSLY APPOINTED LUXURY HOME at $1,875.000 with sound and water walls at $1,950,000.Exceptional design meets refined luxury in this brand new architectural masterpiece by DaVin
Listing Details and 2 Additional Pictures
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