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About this home
Set on a quarter-acre lot on a tree-lined street in Winter Park Pines, this 5-bedroom, 3-bath pool home offers 2,194 sq ft of single-story living with room for everyone. The split floor plan places a spacious primary suite on its own side of the home, with a walk-in closet and French doors that open directly to the covered patio. The four guest bedrooms are generously sized, and one pair shares a Jack-and-Jill bath. The kitchen has a breakfast bar, a pantry, and views of the pool. It opens to a family room anchored by a wood-burning fireplace and a built-in desk. The formal living and dining rooms, crown molding, and three sets of French doors bring in natural light and a connection to the outdoors. Outside, the large covered, insulated patio overlooks a sparkling pool and a fenced backyard with real yard space. There is no mandatory HOA, and the oversized 2-car garage includes workshop space. You're minutes from Winter Park Pines Golf Club, Aloma Ave shopping, and Park Avenue. Zoned for Winter Park High.
Winter Park Pines, located between Semoran Boulevard (SR 436) and Howell Branch Road, is a residential and suburban Winter Park neighborhood with mid-century ranch streetscapes and a canopy of mature oaks. The neighborhood’s character concentrates around the Howell Branch Road and Semoran Boulevard crossroads, where everyday errands cluster beside steady traffic and pocket plazas. Single-story homes, screened lanais, and generous lots set a low-slung architectural rhythm, with sidewalks and cul-de-sacs shaping a calm, lived-in feel. Cady Way Trail adds a linear green corridor for walking and cycling. Ward Park and the Winter Park Library bring courts, lawns, and civic programming into the weekly routine. Nearby, Winter Park Village supplies a modern retail-and-dining hub without shifting the neighborhood’s quiet tone.
Provided by Walk Score and Local Logic
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Built-in features
Ceiling fans
Crown molding
Kitchen/family room combo
Living room/dining room combo
Thermostat
Walk-in closets
Family room
Inside utility
Bedrooms
5 bedrooms
Bathrooms
3 full bathrooms
Kitchen
Dishwasher
Range
Microwave
Refrigerator
Laundry & utility
Washer
Dryer
Laundry room inside
Flooring
Tile
Heating & cooling
Central heating
Central air
Exterior features
Covered front porch and patio
Patio
Outdoor lighting
Sidewalks
Wood fencing
Mature landscaping
Near golf course
Paved roads
Home design
Single family residence
One story
Faces east
Residential zoning (R-1A)
Homestead exempt
Parking
Driveway
On-street parking
Oversized garage
Attached garage with garage door opener
Workshop space in garage
2 garage spaces
Construction
Block and concrete construction
Shingle roof
Slab foundation
Built-in 2000s (year not specified)
Utilities
Public water
Public sewer
Cable available
Electricity connected
Natural gas connected
Water connected
Sewer connected
HOA & community
No association fee required
Community features include golf, trails, park, playground, and sidewalks
Golf carts allowed
Pets allowed
Other
Private in-ground pool
Electricity and solar
View estimated energy costs and solar savings for this home
MULTIPLE OFFERS, PLEASE COME SEE DURING THE HOLIDAY WEEKEND AND SUBMIT YOUR BEST OFFER before 8PM on Monday 9/6/2021. Welcome to Winter Park Pines, with tree-lined streets and friendly neighbors! This 5 bed, 3 bath home is the one you've been looking for! Walk in and notice the SPLIT FLOOR-PLAN, generous room sizes, crown moulding and beautiful wood plank tile though out. The living room is immediately on your right and leads right into the dining room. The dining room has a stunning view of the pool through the first set of FRENCH DOORS in the home. To your right is the LARGE MASTER bedroom with en-suite bathroom, walk-in closet and another set of FRENCH DOORS that lead straight onto the HUGE covered patio. Heading into the kitchen, there's a LARGE BREAKFAST BAR and built-in pantry, with all white cabinets and appliance and POOL VIEWS. Cozy up in the family room with an EYE-CATCHING WOOD BURNING FIREPLACE and built-in desk. Tucked behind the living room is the INSIDE UTILITY/LAUNDRY ROOM, ADDITIONAL 4 guest BEDROOMS, and 2 of the bathrooms. Head into the first room, the guest bedroom, with a WALK-IN CLOSET and JACK AND JILL BATHROOM (with a tub) connected to another bedroom. All GUEST BEDROOMS are GENEROUS IN SIZE with excellent closet space too. The WOOD-PLANK TILE flooring continues throughout the remaining bedrooms. The hall bath leads out to the pool area and spacious, FENCED-IN backyard. There is plenty of yard space, NOT JUST A POOL. The kidney-shaped POOL is the perfect size for hosting, as is the large and plenty of surrounding patio space. Not to mention the HUGE COVERED INSULATED PATIO area which is ALSO accessible through the THIRD SET OF FRENCH DOORS off of the family room and service window off of the kitchen. Roof: 2005 HVAC: 2008
Public Records
Jul 23, 2002
Sold
$239,000
$109/sq ft
Public Records
Jun 5, 2000
Sold
$196,000
$89/sq ft
Public Records
Mar 1, 1994
Sold
$137,500
$63/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$6,634 (+4.4%)
2024
$6,355 (+7.4%)
2023
$5,918 (+3.4%)
2022
$5,720 (+110.0%)
2021
$2,724 (+5.2%)
2020
$2,590 (−2.5%)
2019
$2,657 (+0.9%)
2018
$2,633 (+1.8%)
2017
$2,586 (+1.2%)
2016
$2,556 (−1.6%)
2015
$2,598 (−1.9%)
2014
$2,647 (+2.1%)
2013
$2,592 (+0.2%)
2012
$2,586
Public record
Public record
Zoning
Beds
5
Baths
3
Stories
1
Lot width
—
Lot depth
—
Lot size
10,799 Sq. Ft.
Year renovated
1973
Finished Sq. Ft.
2,194
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,194
Year built
1968
Style
Single Family Residential
County
Orange County
APN
302209943800060
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1A
Single-Family Dwelling Districts
The areas included within R-1-A single-family dwelling districts are intended to be single-family residential areas with large lots and low population densities. Certain structures and uses required to serve educational, religious, utilities and noncommercial recreational needs of such areas are permitted within the districts as special exceptions.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Fire house
Police station
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
9/10 Heat Factor
7 days above 107° expected this year, 22 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winter Park, FL • 32792
Average low and high temperatures (°F)
68
48
74
54
80
60
84
64
90
72
91
75
93
76
91
76
89
75
83
68
78
60
74
55
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
96/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 20% for direct sun exposure in Winter Park. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.8 hrs
7.9 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 739 Roughbeard Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $635,000 and $830,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $635K to $830K.