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  1. Subdivision Like Winter Park Pines
  2. Listing Status = Active
739 Roughbeard Road
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Details for 739 Roughbeard Road, WINTER PARK, FL 32792
Single Family
  1. Price: $800,000.00
  2. Price sqft: $287.36 / sqft
  3. Days On Market: 9
  4. Bedrooms: 5
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2784
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1968
MLS#: O6404545
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines
  5. Elementary School: Aloma Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: SERHANT
  9. mfrmls
  10. DMCA Notice
Welcome to Winter Park Pines, one of Winter Parks most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood plank tile flooring thro
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350 Cornwall Rd
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Details for 350 Cornwall Rd, WINTER PARK, FL 32792
Single Family
  1. Price: $775,000.00
  2. Price sqft: $357.14 / sqft
  3. Days On Market: 45
  4. Bedrooms: 4
  5. Baths: 3
  6. Bldg sqft: 2170
  7. Acreage: 0.21 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1963
MLS#: O6394524
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines Rep
  5. Provided by: RE/MAX TOWN & COUNTRY REALTY
  6. mfrmls
  7. DMCA Notice
Fully reimagined and COMPLETELY RENOVATED AND DESIGNED BY HGTV DESIGNER, this stunning 4 br, 3 ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury wit
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418 Gilbert Road
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Details for 418 Gilbert Road, WINTER PARK, FL 32792
Single Family
  1. Price: $729,000.00
  2. Price sqft: $346.98 / sqft
  3. Previous Price: $740,000
  4. Last Price Change: 05/01/26
  5. Days On Market: 48
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2101
  10. Acreage: 0.21 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1964
MLS#: O6385950
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines Ut 5
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: SOTERA LIVING
  9. mfrmls
  10. DMCA Notice
Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright ope
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744 Cornwall Road
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Details for 744 Cornwall Road, WINTER PARK, FL 32792
Single Family
  1. Price: $695,000.00
  2. Price sqft: $281.72 / sqft
  3. Previous Price: $715,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 285
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2467
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1968
MLS#: O6332168
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: VERSALIS REALTY POWERED BY SELLSTATE
  9. mfrmls
  10. DMCA Notice
Welcome to your dream home! This exceptional 4 bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park
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2708 Lion Heart Road
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Details for 2708 Lion Heart Road, WINTER PARK, FL 32792
Single Family
  1. Price: $625,000.00
  2. Price sqft: $240.57 / sqft
  3. Previous Price: $627,500
  4. Last Price Change: 05/01/26
  5. Days On Market: 70
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2598
  10. Acreage: 0.23 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1963
MLS#: O6387685
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines Rep
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: EQUITYPRO LLC
  9. mfrmls
  10. DMCA Notice
Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a s
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2756 Sheriff Way
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Details for 2756 Sheriff Way, WINTER PARK, FL 32792
Single Family
  1. Price: $625,000.00
  2. Price sqft: $261.73 / sqft
  3. Days On Market: 15
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2388
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1965
MLS#: O6402570
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines
  5. Elementary School: Aloma Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: PALM CIRCLE REALTY
  9. mfrmls
  10. DMCA Notice
Welcome to your beautifully updated slice of the florida dream here in winter park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and
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330 Elkhorn Court
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Details for 330 Elkhorn Court, WINTER PARK, FL 32792
Single Family
  1. Price: $554,900.00
  2. Price sqft: $261.87 / sqft
  3. Previous Price: $559,900
  4. Last Price Change: 05/01/26
  5. Days On Market: 108
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2119
  10. Acreage: 0.20 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1965
MLS#: O6376757
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines Merrie Oaks
  5. Provided by: LA ROSA REALTY CW PROPERTIES L
  6. mfrmls
  7. DMCA Notice
330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern
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346 Ranger Boulevard
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Details for 346 Ranger Boulevard, WINTER PARK, FL 32792
Single Family
  1. Price: $485,000.00
  2. Price sqft: $227.49 / sqft
  3. Previous Price: $495,000
  4. Last Price Change: 03/18/26
  5. Days On Market: 241
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2132
  10. Acreage: 0.22 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1965
MLS#: S5134662
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines
  5. Elementary School: Aloma Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: IMPERIAL REALTY OF FLORIDA INC
  9. mfrmls
  10. DMCA Notice
PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the
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