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  1. School = Brookshire Elem
Details for 141 Phelps Avenue, Winter Park, FL 32789
Single Family
  1. Price: $3,595,000.00
  2. Price sqft: $499.17 / sqft
  3. Days On Market: 55
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 7202
  8. Acreage: 0.28 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: LakePrivileges
  14. Year Built: 2006
MLS#: O6306273
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Windsong Lakeside Sec 01 43/70
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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**This stunning estate just became an unbeatable opportunity luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong communit
Details for 617 Worthington Drive, Winter Park, FL 32789
Single Family
  1. Price: $1,976,000.00
  2. Price sqft: $402.61 / sqft
  3. Days On Market: 7
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4908
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2018
MLS#: O6320955
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Kenilworth Shores Sec 06
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. Provided through
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Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5 bedroom, 4.5 bathroom pool residence showcases absolute perfection and modern elegance. Built
Details for 1780 Mizell Ave., Winter Park, FL 32789
Single Family
  1. Price: $1,795,000.00
  2. Price sqft: $487.37 / sqft
  3. Days On Market: 11
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3683
  8. Acreage: 0.17 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6319166
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Tangerine Court
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary Hancock and ideally in the heart of Winter Park. Offering nearly 2,800 square fee
Details for 1394 Grove Terrace, Winter Park, FL 32789
Single Family
  1. Price: $1,575,000.00
  2. Price sqft: $435.69 / sqft
  3. Days On Market: 1
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3615
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2002
MLS#: O6319510
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Sylvan Lake Shores
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 bath, plus office hom
Details for 1327 Bridgeport Drive, Winter Park, FL 32789
Single Family
  1. Price: $1,499,000.00
  2. Price sqft: $306.23 / sqft
  3. Previous Price: $1,599,000
  4. Last Price Change: 06/18/25
  5. Days On Market: 33
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4895
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1979
MLS#: O6311216
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Waterbridge
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: RE/MAX TOWN & COUNTRY REALTY
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This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking a
Details for 627 Darcey Drive, Winter Park, FL 32792
Single Family
  1. Price: $775,000.00
  2. Price sqft: $250.49 / sqft
  3. Previous Price: $789,000
  4. Last Price Change: 06/28/25
  5. Days On Market: 33
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3094
  10. Acreage: 0.21 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 1967
MLS#: O6306441
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Brookshire Heights 4th Add
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
  9. Provided through
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Nestled in the heart of sought after Winter Park, this beautifully updated 4 bedroom, 2 bathroom home offers 2,509 square feet of versatile living space designed for comfort, functionality, and style.
Details for 1116 Fairway Drive, Winter Park, FL 32792
Single Family
  1. Price: $549,900.00
  2. Price sqft: $231.25 / sqft
  3. Days On Market: 169
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2378
  8. Acreage: 0.23 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1978
MLS#: O6265989
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Golfside Sec 03
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: TURN-KEY MOVES REALTY
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One or more photos has been virtually staged. Welcome to this beautiful, single family home in the Golfside Community in Winter Park! This stunning 3 bedroom, 2 bathroom residence offers a living s
Details for 2244 Brookshire Avenue, Winter Park, FL 32792
Single Family
  1. Price: $549,000.00
  2. Price sqft: $273.68 / sqft
  3. Days On Market: 13
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 2006
  8. Acreage: 0.23 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1958
MLS#: O6316745
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Brookshire Heights
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: EXP REALTY LLC
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Welcome to this delightful 3 bedroom, 2 bathroom single family home located in the highly sought after Brookshire Heights neighborhood of Winter Park. Step inside to discover an open concept living ar
Details for 1913 Woodcrest Drive B, Winter Park, FL 32792
Condominium
  1. Price: $240,000.00
  2. Price sqft: $243.16 / sqft
  3. Previous Price: $245,000
  4. Last Price Change: 06/30/25
  5. Days On Market: 133
  6. Bedrooms: 2
  7. Baths: 2
  8. Bldg sqft: 987
  9. Acreage: 0.64 acres
  10. Pool: Yes
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1973
MLS#: O6281772
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Oaks Condo
  5. Building: Oaks Condo
  6. Elementary School: Brookshire Elem
  7. Middle School: Glenridge
  8. High School: Winter Park
  9. Provided by: FUTURE HOME REALTY INC
  10. Provided through
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Winter Park gem! Tastefully updated 2 bedroom, 2 bathroom corner condominium with a spacious patio is your rare chance ! This one of a kind residence boasts high quality enhancements such
Details for 1000 Semoran Boulevard 604, Winter Park, FL 32792
Condominium
  1. Price: $195,000.00
  2. Price sqft: $185.89 / sqft
  3. Days On Market: 22
  4. Bedrooms: 2
  5. Baths: 2
  6. Bldg sqft: 1049
  7. Acreage: 0.02 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 1969
MLS#: O6316635
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Golfside Villas Condo
  5. Building: Golfside Villas Condo
  6. Elementary School: Brookshire Elem
  7. Middle School: Glenridge
  8. High School: Winter Park
  9. Provided by: WEICHERT REALTORS HALLMARK PROPERTIES
  10. Provided through
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This second floor Winter Park Condo has been beautifully renovated. The kitchen renovation includes beautiful cabinets, newer stainless steel appliances, granite counter tops, and removing two walls f