739 Roughbeard Rd, Winter Park, FL 32792
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Property image
OFF MARKET

739 Roughbeard Rd
Winter Park, FL 32792

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

$753,600

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $5,263/mo*
Refinance Your Home

$753,600

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $5,263/mo*
Refinance Your Home
5 Beds
3 Baths
2,194 sqft
(on 0.25 acres)

Home Value

Trulia Estimate
$754K
Since last month
Decreased$18K (-2.3%)
Since last year
Increased$124K (+19.8%)
Since last sale
Increased$259K (+52.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +114% in the last 10 years
MonthEstimated value
2026
August 2026$754K
July 2026$755K
June 2026$772K
May 2026$780K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
729 MONMOUTH WAY, Winter Park, FL
0.06
Single-Family Home
$793,500
08/14/26
4
3
2,332
927 FAIRWAY DRIVE, Winter Park, FL
0.14
Single-Family Home
$660,000
06/29/26
4
3
1,918
2625 SUMMERFIELD ROAD, Winter Park, FL
0.31
Single-Family Home
$739,000
04/08/26
5
3
2,199
730 S RANGER BOULEVARD, Winter Park, FL
0.04
Single-Family Home
$849,990
10/15/25
4
4
2,759
2758 SANDWELL DRIVE, Winter Park, FL
0.23
Single-Family Home
$500,000
01/12/26
4
2
2,303
639 FRIAR ROAD, Winter Park, FL
0.17
Single-Family Home
$795,000
05/08/26
4
3
1,950
630 SAINT DUNSTAN WAY, Winter Park, FL
0.30
Single-Family Home
$710,000
04/01/26
5
2
2,240
2609 SUMMERFIELD ROAD, Winter Park, FL
0.34
Single-Family Home
$875,000
03/05/26
5
2
2,554
422 S RANGER BOULEVARD, Winter Park, FL
0.34
Single-Family Home
$495,000
02/17/26
4
2
1,680
517 ROUGHBEARD ROAD, Winter Park, FL
0.30
Single-Family Home
$576,000
07/17/26
3
2
1,873

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
729 MONMOUTH WAY, Winter Park, FL 32792
0.06
$793,500
4
3
2,332
Recently Sold
721 ROUGHBEARD ROAD, Winter Park, FL 32792
0.04
$574,500
4
2
1,964
Off Market
730 S RANGER BOULEVARD, Winter Park, FL 32792
0.04
$849,100
4
4
2,759
Off Market
722 S RANGER BOULEVARD, Winter Park, FL 32792
0.05
$795,000
4
3
2,164
For Sale
715 ROUGHBEARD ROAD, Winter Park, FL 32792
0.06
$501,600
4
2
2,250
Off Market
2923 SUMMERFIELD ROAD, Winter Park, FL 32792
0.07
$689,000
4
3
1,918
Off Market
2907 SUMMERFIELD ROAD, Winter Park, FL 32792
0.07
$741,400
5
2
2,532
Off Market
736 WARRENTON ROAD, Winter Park, FL 32792
0.13
$310,000
2
2
1,320
Recently Sold
715 S RANGER BOULEVARD, Winter Park, FL 32792
0.08
$695,000
4
3
2,312
For Sale
2845 SUMMERFIELD ROAD, Winter Park, FL 32792
0.09
$864,000
4
2
2,630
Off Market
Berrington, Winter Park, FL 32792
0.10
$976,125+
3
2.5
2,030
-
Clearpoint, Winter Park, FL 32792
0.10
$1,014,125+
4
2.5
2,466
-

Local Information

  • Map ViewExplore the area around 739 Roughbeard Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1968
Lot Size
0.25 acres
Living Area
2,194 sqft
Price/Sqft
$343
Parking
Garage

About this House

Beautifully refreshed home in a prime Winter Park location, just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course. Enjoy the convenience of being within walking distance to Winter Park High School and the hospital campus, and a short drive to downtown Orlando, major highways, both airports, as well as Disney and Universal.
This home has been thoughtfully updated inside and out.
Highlights include:
* New granite countertops
* Freshly painted exterior and garage
* Freshly painted patio and pool deck
* New roof (2022)
* New electric panel (2022)
* Updated outlets (2022)
* Water lines re-piped to CPVC by previous owner
* New dishwasher (2024)
* New water heater (2025)
* New fence (2023)
* Newer stove, washer, and dryer included
* New light fixtures throughout
* Bathrooms with updated fixtures and modern colors
Updated landscaping with many overgrown trees removed and trimmed
The backyard features a lovely pool and outdoor area, perfect for relaxing or entertaining.
This is not a must sell situation. Price will not drop. Don't miss your opportunity to be in a great area that is highly desirable. If this is your dream location and home, buy now and don't miss out. As interest rates start to drop this area will become increasingly in higher demand. Buy now to get here, you can always refinance later.

For showings or to submit an offer, please email: lofsfugate8@gmail.com
Wil py agt 2 pcnt
739 Roughbeard Rd, Winter Park, FL 32792 is a 5 bedroom, 3 bathroom, 2,194 sqft single-family home built in 1968. It last sold for $495,000 on Nov 3, 2021. It is currently off market. The Trulia Estimate is $753,600, with a rent estimate of $3,683/month.

Home Details for 739 Roughbeard Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, Electric, GasCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Laminate
Interior Details
AtticNumber of Rooms: 20Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop, Solarium Atrium, Sun RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Asphalt, CompositionExterior: Stucco, Cement ConcreteGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 7Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1968Year Updated: 2021
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 10799 sqft

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Additional Information

Sport Court

Price and Tax history

DateEventPrice
Jul 22, 2026
Source: Stellar MLS #O6404545
ListingRemoved
$780,000
Jul 14, 2026
Source: Stellar MLS #O6404545
PriceChange
$780,000
Price decreased by 3%
May 5, 2026
Source: Stellar MLS #O6404545
Listed For Sale
$800,000
Mar 28, 2026
Source: N/A
ListingRemoved
Dec 28, 2025
Source: N/A
PriceChange
$841,004
Price increased by 0%

Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM
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Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % 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

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • 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
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  • 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
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  • 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
  • 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
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  • 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
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  • 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
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Explore by feature - Pet Friendly

147 pet-friendly rentals in Winter Park, FL

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Homes for sale near 739 Roughbeard Rd

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Off Market Homes Near 739 Roughbeard Rd

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Frequently asked questions about 739 Roughbeard Rd

  • What is 739 Roughbeard Rd estimated to be worth?
    Trulia's estimated value for 739 Roughbeard Rd in Winter Park, FL is $753,600.
  • What is the price history for 739 Roughbeard Rd?
    739 Roughbeard Rd in Winter Park, FL last sold for $495,000 in November 2021.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $451K. That is down $833 from the prior month.
  • Does 739 Roughbeard Rd have air conditioning?
    Yes, 739 Roughbeard Rd in Winter Park, FL has air conditioning.
  • Does 739 Roughbeard Rd have a pool?
    Yes, 739 Roughbeard Rd in Winter Park, FL has a pool.