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  1. School = Dommerich Elem
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Details for 2211 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,250,000.00
  2. Price sqft: $572.77 / sqft
  3. Previous Price: $5,495,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 322
  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
  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
Details for 1441 Cardinal Court, WINTER PARK, FL 32789
Single Family
  1. Price: $4,285,000.00
  2. Price sqft: $772.77 / sqft
  3. Days On Market: 26
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5545
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2022
MLS#: O6399395
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winflor Court Pt Rep
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Beautifully built in 2022 by Lonnie Richardson, this custom one story home sits on a quiet cul de sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes pai
Details for 1761 Legion Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,270,000.00
  2. Price sqft: $519.30 / sqft
  3. Previous Price: $3,295,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 333
  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
  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
Details for 948 Poinciana Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $3,174,000.00
  2. Price sqft: $700.82 / sqft
  3. Previous Price: $3,199,000
  4. Last Price Change: 04/25/26
  5. Days On Market: 119
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4529
  10. Acreage: 0.30 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2001
MLS#: O6372165
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores First Add
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lan
Details for 670 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,895,000.00
  2. Price sqft: $554.92 / sqft
  3. Days On Market: 5
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5217
  8. Acreage: 0.31 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2016
MLS#: O6405256
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Park Grove
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Graceful and timeless, this classic Southern inspired residence by esteemed builder Charles Clayton sits on a generous lot in Winter Parks coveted Park Grove neighborhood and makes a striking first im
Details for 620 Pinetree Road, WINTER PARK, FL 32789
Land
  1. Price: $2,790,000.00
  2. Days On Market: 32
  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
  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.
Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,394,500.00
  2. Price sqft: $460.84 / sqft
  3. Previous Price: $2,395,000
  4. Last Price Change: 04/21/26
  5. Days On Market: 89
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5196
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  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
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: 33
  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
  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
Details for 1760 Legion Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,295,000.00
  2. Price sqft: $373.23 / sqft
  3. Previous Price: $2,395,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 82
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6149
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1964
MLS#: O6383603
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location
Details for 1885 Temple Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,265,000.00
  2. Price sqft: $504.12 / sqft
  3. Previous Price: $2,295,000
  4. Last Price Change: 03/21/26
  5. Days On Market: 180
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4493
  10. Acreage: 0.24 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1963
MLS#: O6359471
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Lugano Terrace
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: COMPASS FLORIDA LLC
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Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5 bedroom, 3.5 bath brick home effortlessly blends timeless charm with extensive