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  1. School = Maitland
Details for 2211 Azalea Place, Winter Park, FL 32789
Single Family
  1. Price: $6,180,000.00
  2. Price sqft: $674.23 / sqft
  3. Days On Market: 8
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 9166
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: CanalFront,Lake,LakePrivileges
  13. 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 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: 3
  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
  7. High School: Winter Park
  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 1742 Temple Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,975,000.00
  2. Price sqft: $951.87 / sqft
  3. Days On Market: 4
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4176
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6320054
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lake Knowles Terrace Add 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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In one of Winter Parks desirable neighborhoods, this stunning four bedroom, five bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and o
Details for 640 Old Horatio Avenue, Maitland, FL 32751
Single Family
  1. Price: $2,999,000.00
  2. Price sqft: $563.93 / sqft
  3. Previous Price: $3,199,000
  4. Last Price Change: 06/30/25
  5. Days On Market: 107
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5318
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalAccess,LakePrivileges
  15. Year Built: 2025
MLS#: O6290533
  1. County: ORANGE
  2. City: Maitland
  3. Zipcode: 32751
  4. Subdivision: Long Branch Sub
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: RE/MAX EXCLUSIVE COLLECTION
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PRICE IMPROVEMENT!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent res
Details for 1400 Place Picardy, Winter Park, FL 32789
Single Family
  1. Price: $2,725,000.00
  2. Price sqft: $454.32 / sqft
  3. Previous Price: $2,825,000
  4. Last Price Change: 06/11/25
  5. Days On Market: 58
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5998
  10. Acreage: 0.32 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2008
MLS#: O6305686
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Fontainebleau
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CORCORAN PREMIER REALTY
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1440 Place Picardy, Winter Park, FL Custom Built Elegance with Timeless Finishes A custom built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From th
Details for 1630 Lasbury Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,650,000.00
  2. Price sqft: $502.18 / sqft
  3. Previous Price: $2,795,000
  4. Last Price Change: 06/16/25
  5. Days On Market: 110
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5277
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2003
MLS#: O6289369
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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One or more photo(s) has been virtually staged. Nestled on a serene, brick paved street in the heart of Winter Park, this elegant 5 bedroom, 3.2 bathroom pool home is situated on a stunning oversized
Details for 2412 Chantilly Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,389,000.00
  2. Price sqft: $459.78 / sqft
  3. Days On Market: 139
  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: 2024
MLS#: O6278049
  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: COMPASS FLORIDA LLC
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Step into a realm of refined livingan architectural tour de force in the heart of Winter Park. Designed by a premier boutique builder and meticulously crafted with no detail spared, this 5 bedroom, 6.
Details for 1355 Hibiscus Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,925,000.00
  2. Price sqft: $347.47 / sqft
  3. Days On Market: 12
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5540
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2006
MLS#: O6313372
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Lake Knowles Terrace Add 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PALMANO GROUP RE BROKERAGE LLC
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Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single family home offering over 4,100 SF of living space. Ideally located on a tree lined street with Winter Parks signature br
Details for 2407 Lafayette Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,888,000.00
  2. Price sqft: $473.78 / sqft
  3. Days On Market: 48
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3985
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2018
MLS#: O6308139
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Fontainebleau
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
  9. Provided through
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Discover this exceptional custom designed modern pool home, ideally situated on a quiet street in Winter Park. This spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loftprovid
Details for 1299 Harding Street, Winter Park, FL 32789
Single Family
  1. Price: $1,869,000.00
  2. Price sqft: $432.04 / sqft
  3. Previous Price: $1,899,999
  4. Last Price Change: 06/10/25
  5. Days On Market: 82
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4326
  10. Acreage: 0.30 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1951
MLS#: O6298410
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
  9. Provided through
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Welcome to your private slice of paradisea beautifully renovated home with a brand new 2024 pied terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Mait