739 Roughbeard Rd, Winter Park, FL 32792
FOR SALE
NEW - 1 DAY AGO
0.25 ACRES

739 Roughbeard Rd
Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 2,194 sqft (on 0.25 acres)

$800,000

Est. Mortgage $5,448/mo*
Get Pre-Qualified

$800,000

Est. Mortgage $5,448/mo*
Get Pre-Qualified
5 Beds
3 Baths
2,194 sqft
(on 0.25 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Pool
View
No Info
HOA
None
Price/Sqft
$365
Listed
1 day ago

Home Details for 739 Roughbeard Rd

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 5, Bathroom 2, Bathroom 3, Bathroom 4, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2194 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, PatioFencing: Fenced, WoodVegetation: Mature LandscapingExterior: Lighting, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,On Street,Oversized,Workshop in Garage
Pool
Pool: In GroundPool
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 1Days on Market: 1

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, ConcreteNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 092230943800060

Price & Status

Price
List Price: $800,000Price Per Sqft: $365

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER PARKCommunity: WINTER PARK PINES
School Information
Elementary School: Aloma ElemJr High / Middle School: Glenridge MiddleHigh School: Winter Park High

Agent Information

Listing Agent
Listing ID: O6404545

Building

Building Area
Building Area: 2784 Square Feet

Community

Community Features: Golf Carts OK, Golf, SidewalksNot Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 10799 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6404545Universal Property Id: US-12095-N-092230943800060-R-N

Additional Information

HOA Amenities: Park,Playground,Trail(s)
Last check for updates: about 3 hours ago
Listing Provided by: John Harbuck, (407) 538-2841
SERHANT, (786) 296-8626
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6404545
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price History for 739 Roughbeard Rd

DatePriceEventSource
05/05/2026$800,000Listed For SaleStellar MLS #O6404545
03/28/2026ListingRemovedN/A
12/28/2025$841,004PriceChange
N/A
12/26/2025$841,003PriceChange
N/A
12/19/2025$841,002PriceChange
N/A
12/17/2025$841,001PriceChange
N/A
12/16/2025$841,000PriceChange
N/A
12/11/2025$840,000PriceChange
N/A
11/22/2025$825,000Listed For SaleN/A
11/23/2024ListingRemovedN/A
11/12/2024$825,000Listed For SaleN/A
10/29/2024$475,000ListingRemovedStellar MLS #O5970079
10/29/2023ListingRemovedStellar MLS #O5970079
11/03/2021$495,000Sold
N/A
09/03/2021$475,000PendingStellar MLS #O5970079
09/02/2021$475,000Listed For SaleStellar MLS #O5970079
07/23/2002$239,000Sold
N/A
06/05/2000$196,000Sold
N/A
03/10/1994$137,500Sold
N/A

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Property Tax and Assessment

Year2024
Tax$6,355
Assessment$521,494
Home facts updated by county records

Comparable Sales for 739 Roughbeard Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
715 Roughbeard Rd, Winter Park, FL
0.06
Single-Family Home
$505,000
08/01/25
4
2
2,250
639 Friar Rd, Winter Park, FL
0.17
Single-Family Home
$450,000
12/29/25
4
3
1,950
2907 Summerfield Rd, Winter Park, FL
0.07
Single-Family Home
$749,000
06/16/25
5
2
2,532
2625 Summerfield Rd, Winter Park, FL
0.31
Single-Family Home
$739,000
04/08/26
5
3
2,199
730 S Ranger Blvd, Winter Park, FL
0.04
Single-Family Home
$849,990
10/15/25
4
4
2,759
2758 Sandwell Dr, Winter Park, FL
0.23
Single-Family Home
$500,000
01/12/26
4
2
2,303
630 Saint Dunstan Way, Winter Park, FL
0.30
Single-Family Home
$710,000
04/01/26
5
2
2,240
901 Golfside Dr, Winter Park, FL
0.36
Single-Family Home
$920,000
05/09/25
5
3
2,392
2756 Summerfield Rd, Winter Park, FL
0.20
Single-Family Home
$750,000
06/09/25
3
2
1,740
2609 Summerfield Rd, Winter Park, FL
0.34
Single-Family Home
$875,000
03/05/26
5
2
2,554

Assigned Schools

These are the assigned schools for 739 Roughbeard Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 593 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 85 % Say car is needed

  • 84 % Say there are sidewalks

  • 79 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Learn more about our methodology.
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
    Flag
  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
    Flag
  • Supak77
    "I just moved here and so far I feel very safe walking my dog early in the morning and late in the evening. Neighbors are very friendly and greet you. "
    4
    Flag
  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
    Flag
  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
    Flag
  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
    Flag
  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
    Flag
  • Oviedohome
    "Need to drive to work. Can walk to local parks. Walking or biking other places does not feel so friendly even though there are restaurants and grocery stores nearby. There are two commuter train stations close by. "
    2
    Flag

LGBTQ Local Legal Protections

John Harbuck, SERHANT, (786) 296-8626
Agent Phone: (407) 538-2841
739 Roughbeard Rd, Winter Park, FL 32792 is a 5 bedroom, 3 bathroom, 2,194 sqft single-family home built in 1968. This property is currently available for sale and was listed by Stellar MLS on May 5, 2026. The MLS # for this home is MLS# O6404545.