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    1. Subdivision Like Winter Park Pines
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    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: 6
    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 Middle
    7. High School: Winter Park High
    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
    Listing Details and 41 Additional Pictures
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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: 43
    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
    One or more photo(s) has been virtually staged. 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
    Listing Details and 29 Additional Pictures
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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: 05/03/26
    5. Days On Market: 45
    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 Middle
    7. High School: Winter Park High
    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
    Listing Details and 29 Additional Pictures
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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: 04/19/26
    5. Days On Market: 283
    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 Middle
    7. High School: Winter Park High
    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
    Listing Details and 58 Additional Pictures
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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: 04/30/26
    5. Days On Market: 68
    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 Middle
    7. High School: Winter Park High
    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
    Listing Details and 46 Additional Pictures
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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: 105
    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
    Listing Details and 40 Additional Pictures
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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: 238
    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 Middle
    7. High School: Winter Park High
    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
    Listing Details and 30 Additional Pictures
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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    Datafeed Last updated on May 11, 2026 @ 12:00 am
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