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739 ROUGHBEARD ROAD

House For Sale
$800,000

BTC: 12.50000000

ETH: 458.19014891

30 days
5 bds
3 ba
2,194 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Driveway / Garage Door Opener / On Street / Oversized / Workshop in Garage
Year Built:
1968
Lot:
0.25 Acres
Heating:
Central
Price/sqft:
$365
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$575,000
$400K – $747K
Confidence Low
List vs. estimate
$225K above estimate
List $800,000 · +39.1%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$364
-20.4% vs. city median $458
Based on
29 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$6,179
2025
Pool
In Ground
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Tile

    Heating

    • Central

    Cooling

    • Central Air

    Appliances

    • Dishwasher

    • Dryer

    • Microwave

    • Range

    • Refrigerator

    • Washer

    Other interior features

    • 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)

    Bedrooms and bathrooms

    • Bedrooms: 5

    • Full bathrooms: 3

  • Parking

    • Driveway

    • Garage Door Opener

    • On Street

    • Oversized

    • Workshop in Garage

    Property

    • Levels: One

    • Pool Private: Yes

    • Exterior Features: French Doors / Lighting / Sidewalk

    Lot

    • Lot: 0.25 Acres

    Other Property Information

    • Parcel Number: 092230943800060

    • Zoning: R-1A

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Cable Available

    • Electricity Connected

    • Natural Gas Connected

    • Sewer Connected

    • Water Connected

  • Other financial information

    • Annual tax amount: $6,179

  • Source details

    • MLS ID: O6404545

    Other facts

    • Construction Materials: Block / Concrete

    • Foundation Details: Slab

    • Fireplace Features: Living Room / Wood Burning

    • Laundry Features: Inside / Laundry Room

    • Lot Features: In County / Near Golf Course / Sidewalk

    • Patio And Porch Features: Covered / Front Porch / Patio

    • Pool Features: In Ground

    • Direction Faces: East

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 2194

    • Water Source: Public

    • Subdivision Name: WINTER PARK PINES

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: SERHANT