739 ROUGHBEARD ROAD Winter Park, FL $ 800,000
739 ROUGHBEARD ROAD
$ 800,000
Recently Listed
Open House 5/16 3pm - 5pm
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739 ROUGHBEARD ROAD

Winter Park, FL, 32792
$ 800,000
Bedrooms5 Baths3.0 Sq 2,194

Monthly Estimate*

$ 4,926

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Single Family Home for sale in Winter Park, FL

for $800,000 with 5 bedrooms and 3 full baths. This 2,194 square foot home was built in 1968 on a lot size of 0.25.

Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.

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Open House

5/16/2026 3:00 PM - 5:00 PM
739 ROUGHBEARD ROAD Winter Park, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 800,000

Bedrooms

5

Full Bath

3

Property Type

Single Family

Taxes

$ 6,179

Style

Single Family Residence

Lot Size

0.25

Year Built

1968

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6404545

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Cable Available Electricity Connected Natural Gas Connected Sewer Connected Water Connected
Roof Shingle
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer
Zoning R-1A
Garage Spaces 2
Patio/Porch Features Covered Front Porch Patio
Pool Features In Ground
Construction Materials Block Concrete
Pets Allowed Yes
Year Built 1968
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Golf Carts OK Golf Sidewalks
County Orange
New Construction false
Property Type Residential
Association Amenities Park Playground Trail(s)
Attached Garage true
Subdivision Name WINTER PARK PINES
Facing Direction East
Garage Y/N true
Total Rooms 9
Full Baths 3
Status Active
Directions From downtown Orlando take FL-408 East to Exit 14 for FL-436/Semoran Blvd and head north. Continue on Semoran Blvd then turn left onto Aloma Ave. Turn right onto Ranger Blvd into Winter Park Pines then turn left onto Balfour Dr and follow to Roughbeard Dr; home will be on your right.
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32792 - Winter Park/Aloma
Lot Size Units Square Feet
Lot Size Square Feet 10799
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Aloma Elem
Land Lease Y/N false
Tax Annual Amount 6179
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6404545
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 6
Legal Description WINTER PARK PINES UNIT FOURTEEN 2/59 LOT6
Minimum Lease No Minimum
Water Access Y/N false
Additional Rooms Family Room Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Crown Molding Kitchen/Family Room Combo Living Room/Dining Room Combo Primary Bedroom Main Floor Thermostat Walk-In Closet(s)
Flooring Tile
Furnished Y/N Unfurnished
Fireplace Features Living Room Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Inside Laundry Room
Total Bedrooms 5
Total Baths 3
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Exterior
Exterior Amenities French Doors Lighting Sidewalk
Vegetation Mature Landscaping
Fencing Fenced Wood
Parking Features Driveway Garage Door Opener On Street Oversized Workshop in Garage
Lot Features In County Near Golf Course Sidewalk
Water Source Public
Lot Size Area 10799
Foundation Details Slab
Building Area Total 2784
Lot Size Acres 0.25
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
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* Excluded Features
List By
Serhant

Broker

johnharbuck@serhant.com

Email

Affordability Calculator

$5,441
Per Month
91%
9%
0%
Monthly Principal & Interest
$4,926
Monthly Property Taxes
$515
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
5/5/2026$800,000 Listed Price

Map


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739 ROUGHBEARD ROAD, Winter Park, FL, 32792 is a Single Family Home for sale at $800,000 with 2,194 sqft and a lot size of 0.25. 739 ROUGHBEARD ROAD has 5 bedrooms, 3.0 baths, and was built in 1968. The property's zip code is 32792 which is in Winter Park, FL