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.
For sale
$800,000
739 Roughbeard Rd, Winter Park, FL 32792
5beds
2,194sqft
Single Family Residence
Built in 1968
10,799 Square Feet Lot
$-- Zestimate®
$365/sqft
$-- HOA
What's special
Kidney-shaped poolLarge breakfast barBuilt-in pantryNew light fixtures throughoutEn-suite bathPlenty of deck spaceFenced backyard
- 33 days |
- 1,327 |
- 71 |
Zillow last checked:
Listing updated:
Listed by:
John Harbuck 407-538-2841,
SERHANT 786-296-8626
Source: Stellar MLS,MLS#: O6404545
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Family Room, Utility Room
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Makeup/Vanity Space, Shower No Tub, Walk-In Closet(s)
- Level: First
- Area: 192 Square Feet
- Dimensions: 12x16
Bedroom 5
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 120 Square Feet
- Dimensions: 12x10
Bathroom 2
- Features: Ceiling Fan(s), Jack & Jill Bathroom, Walk-In Closet(s)
- Level: First
- Area: 143 Square Feet
- Dimensions: 13x11
Bathroom 3
- Features: Ceiling Fan(s), Jack & Jill Bathroom
- Level: First
- Area: 121 Square Feet
- Dimensions: 11x11
Bathroom 4
- Features: Ceiling Fan(s)
- Level: First
- Area: 110 Square Feet
- Dimensions: 11x10
Dining room
- Level: First
- Area: 168 Square Feet
- Dimensions: 14x12
Family room
- Features: Ceiling Fan(s), Built-in Features, Other
- Level: First
- Area: 294 Square Feet
- Dimensions: 21x14
Kitchen
- Features: Breakfast Bar, Pantry
- Level: First
- Area: 143 Square Feet
- Dimensions: 13x11
Living room
- Level: First
- Area: 273 Square Feet
- Dimensions: 13x21
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Laundry: Inside, Laundry Room
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)
- Flooring: Tile
- Doors: French Doors
- Has fireplace: Yes
- Fireplace features: Living Room, Wood Burning
Interior area
- Total structure area: 2,784
- Total interior livable area: 2,194 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Front Porch, Patio
- Exterior features: Lighting, Sidewalk
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Fenced,Wood
Lot
- Size: 10,799 Square Feet
- Features: In County, Near Golf Course, Sidewalk
- Residential vegetation: Mature Landscaping
Details
- Parcel number: 092230943800060
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Concrete
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1968
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Features: Golf Carts OK, Golf, Sidewalks
- Pet fee: $0 monthly
- Subdivision: WINTER PARK PINES
HOA
- Has HOA: No
- Amenities included: Park, Playground, Trail(s)
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $365/sqft
- Tax assessed value: $521,494
- Annual tax amount: $6,179
- Date on market: 5/4/2026
- Cumulative days on market: 34 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/5/2026 | Listed for sale | $800,000-4.9%$365/sqft |
Source:  Stellar MLS #O6404545 Report a problem | ||
| 3/28/2026 | Listing removed | -- |
Source: Owner Report a problem | ||
| 12/28/2025 | Price change | $841,004+0%$383/sqft |
Source: Owner Report a problem | ||
| 12/26/2025 | Price change | $841,003+0%$383/sqft |
Source: Owner Report a problem | ||
| 12/19/2025 | Price change | $841,002+0%$383/sqft |
Source: Owner Report a problem | ||
| 12/17/2025 | Price change | $841,001+0%$383/sqft |
Source: Owner Report a problem | ||
| 12/16/2025 | Price change | $841,000+0.1%$383/sqft |
Source: Owner Report a problem | ||
| 12/11/2025 | Price change | $840,000+1.8%$383/sqft |
Source: Owner Report a problem | ||
| 11/22/2025 | Listed for sale | $825,000$376/sqft |
Source: Owner Report a problem | ||
| 11/23/2024 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/12/2024 | Listed for sale | $825,000+73.7%$376/sqft |
Source: Owner Report a problem | ||
| 10/29/2024 | Listing removed | $475,000-4%$216/sqft |
Source: Stellar MLS #O5970079 Report a problem | ||
| 10/29/2023 | Listing removed | -- |
Source: Stellar MLS #O5970079 Report a problem | ||
| 11/3/2021 | Sold | $495,000+4.2%$226/sqft |
Source: Public Record Report a problem | ||
| 9/3/2021 | Pending sale | $475,000$216/sqft |
Source: Stellar MLS #O5970079 Report a problem | ||
| 9/2/2021 | Listed for sale | $475,000+98.7%$216/sqft |
Source: Stellar MLS #O5970079 Report a problem | ||
| 7/23/2002 | Sold | $239,000+21.9%$109/sqft |
Source: Public Record Report a problem | ||
| 6/5/2000 | Sold | $196,000+42.5%$89/sqft |
Source: Public Record Report a problem | ||
| 3/10/1994 | Sold | $137,500$63/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $6,355 +7.4% | $412,587 +3% |
| 2023 | $5,918 +3.4% | $400,570 +3% |
| 2022 | $5,720 +110% | $388,903 +100.8% |
| 2021 | $2,724 +1% | $193,694 +1.4% |
| 2020 | $2,698 +1.5% | $191,020 +2.3% |
| 2019 | $2,657 +0.9% | $186,725 +1.9% |
| 2018 | $2,633 | $183,243 -35.2% |
| 2017 | $2,633 +1.8% | $282,907 +11.6% |
| 2016 | $2,586 +1.1% | $253,470 +5.5% |
| 2015 | $2,557 -3.4% | $240,143 +16% |
| 2014 | $2,647 +2.1% | $207,049 +21.4% |
| 2013 | $2,592 +0.2% | $170,617 +0.9% |
| 2012 | $2,586 -12.8% | $169,119 -11% |
| 2011 | $2,965 -9.7% | $190,070 -11.3% |
| 2010 | $3,284 | $214,300 -4.3% |
| 2009 | -- | $223,833 -11.7% |
| 2008 | $3,141 -2.1% | $253,381 -2.6% |
| 2007 | $3,208 -5.8% | $260,256 -2.2% |
| 2006 | $3,405 +0.8% | $266,096 +25.5% |
| 2005 | $3,378 +4.6% | $212,081 +10.5% |
| 2004 | $3,229 -0.2% | $191,880 +1.4% |
| 2003 | $3,234 +25.9% | $189,260 +16.7% |
| 2002 | $2,569 -0.9% | $162,196 +7.3% |
| 2001 | $2,592 +34.2% | $151,214 +15% |
| 2000 | $1,932 | $131,445 |
Find assessor info on the county website
Monthly payment
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 32792
Nearby schools
GreatSchools rating
- 3/10Aloma Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 7/10Glenridge Middle SchoolGrades: 6-8Distance: 1.7 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Aloma Elem
- Middle: Glenridge Middle
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Orange County
- Winter Park
- 32792
- 739 Roughbeard Rd
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