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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: 30
  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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  10. DMCA Notice
**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 532 Worthington Drive, Winter Park, FL 32789
Single Family
  1. Price: $3,295,000.00
  2. Price sqft: $605.59 / sqft
  3. Days On Market: 52
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5441
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2023
MLS#: O6298838
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Kenilworth Shores Sec 01
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: FLORIDA ONE REAL ESTATE LLC
  9. Provided through
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Nestled in peaceful Winter Park, your new contemporary home boasts expansive open living areas featuring 12 foot ceilings, five en suite bedrooms, and outdoor living spaces spanning two levels. T
Details for 185 Sylvan Boulevard, Winter Park, FL 32789
Single Family
  1. Price: $2,590,000.00
  2. Price sqft: $622.60 / sqft
  3. Days On Market: 18
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4160
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6304627
  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: COMPASS FLORIDA LLC
  9. Provided through
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Under Construction. Brand new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning
Details for 104 Cortland Avenue, Winter Park, FL 32789
Single Family
  1. Price: $2,375,000.00
  2. Price sqft: $516.87 / sqft
  3. Days On Market: 22
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4595
  8. Acreage: 0.28 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1926
MLS#: O6307403
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Cortland Park
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  9. Provided through
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Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and res
Details for 1327 Bridgeport Drive, Winter Park, FL 32789
Single Family
  1. Price: $1,599,000.00
  2. Price sqft: $326.66 / sqft
  3. Days On Market: 8
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4895
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
  9. Provided through
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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 171 Cortland Avenue, Winter Park, FL 32789
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $620.53 / sqft
  3. Days On Market: 5
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2095
  8. Acreage: 0.34 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1940
MLS#: O6313622
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Cortland Park
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
  9. Provided through
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Come see this outstanding 15,000 sqft lot surrounded by multi million dollar homes on one of Winter Parks picturesque tree lined brick streets just a short drive from Park Avenue. This property offers
Details for 2536 Brookshire Avenue, Winter Park, FL 32792
Single Family
  1. Price: $1,275,000.00
  2. Price sqft: $308.27 / sqft
  3. Days On Market: 84
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4136
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2018
MLS#: O6288366
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Brookshire Heights 1st Add
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: PALMANO GROUP RE BROKERAGE LLC
  9. Provided through
  10. DMCA Notice
Welcome to 2536 Brookshire Ave, a spacious 4 bedroom, 3.5 bath modern farmhouse located in the heart of Winter Park. The open floor plan enhances connectivity throughout, with a first floor primary su
Details for 2260 Hawick Lane, Winter Park, FL 32792
Single Family
  1. Price: $995,000.00
  2. Price sqft: $724.16 / sqft
  3. Days On Market: 290
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 1374
  8. Acreage: 0.45 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1971
MLS#: O6232951
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Aloma
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: DAVEN REAL ESTATE INC
  9. Provided through
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This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property is currently vacant as the home and trees are recently demo'ed. The f
Details for 627 Darcey Drive, Winter Park, FL 32792
Single Family
  1. Price: $795,000.00
  2. Price sqft: $256.95 / sqft
  3. Days On Market: 9
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3094
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. 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
  10. DMCA Notice
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 625 Brechin Drive, Winter Park, FL 32792
Single Family
  1. Price: $795,000.00
  2. Price sqft: $327.97 / sqft
  3. Days On Market: 112
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2424
  8. Acreage: 0.21 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1961
MLS#: O6280564
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Kenilworth Shores Sec 04
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. Provided through
  10. DMCA Notice
PICTURE PERFECT HOME IN WINTER PARKS KENILWORTH SHORES! Homes of this quality and preservation hardly come on the market this immaculately kept, 3 bedroom, 2 bath home offers 1,827 SF and a stunning