Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous . 22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.
Single-familyProperty Type
1971Year Built
9,798 sq ftLot Size
$308Price/Sq.Ft.
2 car garageParking
Listed by Amy Turner• KELLER WILLIAMS WINTER PARK
Contact: 407-545-6430
Bought with Jo Ann Lamar• PREMIER SOTHEBY'S INTL. REALTY
Est. $2,733 per month, based on comparable rentals
Sale and tax history for 517 Roughbeard Rd
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6399029
Jul 17, 2026
Sold
$576,000
$308/sq ft
May 2, 2026
Pending
—
Apr 29, 2026
Listed
$565,000
$302/sq ft
Stellar MLS as Distributed by MLS Grid #O5219924
Jul 31, 2014
Sold
$250,000
$133/sq ft
Jul 24, 2014
Pending
—
Jul 24, 2014
Relisted
—
Jul 7, 2014
Contingent
—
Jun 25, 2014
Pending
—
Jun 14, 2014
Relisted
—
Jun 10, 2014
Listing Removed
—
Apr 30, 2014
Relisted
—
Apr 16, 2014
Pending
—
Apr 4, 2014
Listed
$245,000
$131/sq ft
Great Winter Park home in Golf Community. Home boasts new carpet, tile, windows, French doors, kitchen cabinets, air handler and paint in and out. This beautiful 3 bedroom, 2 bathroom split plan home has large rooms and lots of closet space. Large Master bedroom with walk-in closet, double vanity and French doors to porch. Living room has 18 x18 ceramic tile & crown moldings. Kitchen with 42" solid wood honey oak cabinets opens to Family room featuring brick wood burning fireplace, vaulted ceilings and French doors. Relax on the large screened and tiled 31x12 porch with fenced back yard and mature landscape with gorgeous shade trees. This home sits on a quiet tree lined street and provides great Orange Co. schools.
Public Records
May 27, 2004
Sold
$247,000
$132/sq ft
Public Records
Jun 1, 1977
Sold
$47,000
$25/sq ft
Public Records
Jun 1, 1972
Sold
$37,500
$20/sq ft
Public Records
Jun 1, 1971
Sold
$33,500
$18/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$4,323 (+5.3%)
2024
$4,107 (+7.4%)
2023
$3,823 (+3.9%)
2022
$3,678 (+1.9%)
2021
$3,612 (+5.1%)
2020
$3,437 (−2.7%)
2019
$3,534 (+0.9%)
2018
$3,504 (+1.6%)
2017
$3,449 (+0.8%)
2016
$3,420 (−1.6%)
2015
$3,477 (−6.0%)
$90,000 + $135,136
$225,136
2014
$3,697 (+55.0%)
2013
$2,386
2012
$2,384
Public record
Public record
Zoning
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
9,798 Sq. Ft.
Year renovated
1976
Sq. Ft.
1,873
Year built
1971
Style
Single Family Residential
County
Orange County
APN
302210944200090
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
Property details
Parking
Parking Information
Parking Features: Driveway, Garage Door Opener, On Street
Garage Spaces: 2
Has Attached Garage
Has Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 3
Bathroom Information
# of Full Baths (Total): 2
Laundry Room Information
Laundry Features: In Garage
Other Rooms Information
Additional Rooms: Formal Dining Room Separate,Formal Living Room Separate
# of Rooms: 14
Fireplace Information
Has Fireplace
Fireplace Features: Family Room, Wood Burning
Heating & Cooling
Heating Information: Central
Cooling Information: Central Air
Interior Features
Interior Features: Ceiling Fans(s), Crown Molding, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Split Bedroom, Stone Counters, Thermostat, Walk-in Closet(s)
Lot Features: In County, Landscaped, Near Golf Course, Sidewalk, Paved, Unincorporated
Lot Size Acres: 0.22
Road Surface Type: Asphalt
Lot Size Square Meters: 910
Zoning Compatible YN: 1
Planned Unit Development YN: 0
Other Exemptions YN: 0
Building Information
MFR_BuildingAreaTotalSrchSqM: 230.77
Financial
Tax Information
Tax Annual Amount: $4,323
Tax Year: 2025
Lease / Rent Details
Lease Restrictions YN: 1
Utilities
Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
Additional Water Information: Dinky Dock Public Boat Ramp to the Winter Park Chain of Lakes is less than 10 minutes away.
Location
Multi-Unit Information
Unit Number YN: 0
Furnished: Unfurnished
HOA Information
MFR_Association2YN: 0
Association Fee Requirement: None
Association Approval Required Y/N: 0
Association Fee Frequency: Annually
School Information
Elementary School: Aloma Elem
Middle Or Junior High School: Glenridge Middle
High School: Winter Park High
Location Information
Directions: From downtown Winter Park, travel east on Fairbanks Ave. At N Ranger Road, turn right. After about a mile, turn left on Bower Road, right on Warrenton Road, right on De Brocy Way and 517 Roughbeard Road will be on your right.
Community Information
Community Features: Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s), Street Lights
Pets Allowed: Cats OK, Dogs OK, Yes
Public facts
Beds: 3
Baths: 2.0
Sq. Ft.: 1,873
Stories: 1.0
Lot Size: 9,798 square feet
Style: Single Family Residential
Year Built: 1971
Year Renovated: 1976
County: Orange County
APN: 302210944200090
Home facts updated by county records on Aug 17, 2026
Other
Miscellaneous Information
Third Party YN: 1
Listing Information
Attribution Contact: 407-545-6430
Previous Status: Pending
Backups Requested YN: 1
Home Warranty YN: No
Listing Date Information
Days to Contract: 2
Status Contractual Search Date: 2026-07-17
Listing Price Information
Calculated List Price By Calculated Sq Ft: 301.66
Green Information
Green Verification Count: 0
Direction Faces: East
Green Indoor Air Quality: Ventilation
Home Information
Living Area: 1873
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 174.01
Building Area Total: 2484
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Levels: One
Security Features: Security System Owned, Smoke Detector(s)
Around this home
28/100 Car-Dependent45/100 Somewhat bikeable
Schools
Places
Transit
Aloma Elementary School
Public PreK-5 • Assigned • 0.5mi
4/10
Glenridge Middle School
Public 6-8 • Assigned • 1.8mi
7/10
Winter Park High School
Public 9-12 • Assigned • 0.9mi
7/10
Provided by GreatSchools
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, 23 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
92
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
In this area, properties receive around 8.6 hours in
June and 6.8 hours in December, placing it above the
U.S. average for solar exposure.
8.6 hrs
6.8 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$615,000 – $745,000
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