Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$800,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 2,194 Sq. Ft.
  • Updated 9 hours ago
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 739 Roughbeard Rd

General

  • Price: $800,000
  • Taxes: $6,179 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6404545
  • Updated: 5/5/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 9
  • Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room, Wood Burning
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Park, Playground, Trail(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: French Doors, Lighting, Sidewalk
  • Deck/Patio: Covered, Front Porch, Patio
  • Porch/Patio/Deck: Covered, Front Porch, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Orange
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: WINTER PARK PINES
  • Driving Directions: From downtown Orlando, take FL-408 East to Exit 14 for FL-436/Semoran Blvd and head north. Continue on Semoran Blvd, then turn left onto Aloma Ave. Turn right onto Ranger Blvd into Winter Park Pines, then turn left onto Balfour Dr and follow to Roughbeard Dr; home will be on your right.
  • Direction Faces: East

School Information

  • Elementary School: Aloma Elem
  • Middle School: Glenridge Middle
  • High School: Winter Park High

Community

  • Community Name: 32792 - Winter Park/Aloma
  • Community Features: Golf Carts OK, Golf, Sidewalks
  • Optional Amenities: Park, Playground, Trail(s)
  • Pet Restrictions: Buyer to verify.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Concrete
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,194
  • Sq. Ft. Source: Public Records
  • Year Built: 1968

Lot Features

  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 10,799
  • Lot Size: 10799
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced, Wood

Financial Considerations

  • Assoc Fee Desc.: None
  • Tax Amount: $6,179
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTER PARK PINES UNIT FOURTEEN 2/59 LOT6
  • Flood Zone Info: X
  • APN: 92230943800060
  • Property ID: 92230943800060

Listed by Serhant

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 739 Roughbeard Rd —

  • Serhant

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 739 Roughbeard Rd

School District:Orange County School District
NameGradesDistance
Aloma Elementary School
2949 Scarlet Road, Winter Park, FL 32792
K-50.8 mi
Glenridge Middle School
2900 Upper Park Road, Orlando, FL 32814
6-81.7 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-120.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 739 Roughbeard Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/04/2026
Listed
$800,000
61.62%
MLS
10/28/2021
Sold
$495,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 739 Roughbeard Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,634
4%
$436,015
6%
2024
$6,355
7%
$412,587
3%
2023
$5,918
117%
$400,570
107%
2021
$2,724
-52%
$193,694
-50%
2022
$5,720
110%
$388,903
104%
2021
$2,724
3%
$191,020
2%
2019
$2,657
1%
$186,725
2%
2018
$2,633
2%
$183,243
2%
2017
$2,586
1%
$179,474
2%
2016
$2,557
-2%
$175,783
1%
2015
$2,599
-2%
$174,561
1%
2014
$2,647
2%
$173,176
1%
2013
$2,592
—
$170,617
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 739 Roughbeard Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Serhant

Similar Properties near 739 Roughbeard Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1927 Eland Ave, Winter Park, FL 32789 - Photo 1
$825,000

1927 Eland Ave  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 11 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 2,242
    Sq. Ft.
Listed by Charles Rutenberg Realty Orlando
2072 Stone Cross Cir, Orlando, FL 32828 - Photo 1
$800,000

2072 Stone Cross Cir  Orlando, FL 32828

  • Single Family
  • Active
  • Updated 7 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,965
    Sq. Ft.
Listed by The Shugan Group Inc
2283 Stone Cross Cir, Orlando, FL 32828 - Photo 1 Price Reduced
-$20,000 (-2.5%)
$779,000

2283 Stone Cross Cir  Orlando, FL 32828

  • Single Family
  • Active
  • Updated 7 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,779
    Sq. Ft.
Listed by True Florida Realty Llc
14024 Cherry Bush Ct, Orlando, FL 32828 - Photo 1
$795,000

14024 Cherry Bush Ct  Orlando, FL 32828

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,390
    Sq. Ft.
Listed by Doug Woehr (407) 920-5201

Just Listed near 739 Roughbeard Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

653 Green Meadow Ave, Maitland, FL 32751 - Photo 1 Just Listed
$528,000

653 Green Meadow Ave  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,909
    Sq. Ft.
Listed by A+ Realty Professionals, Inc
775 Woodside Rd, Maitland, FL 32751 - Photo 1 Just Listed
$449,000

775 Woodside Rd  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,456
    Sq. Ft.
Listed by Fannie Hillman & Associates
814 Park Lake Cir, Maitland, FL 32751 - Photo 1 Just Listed
$216,000

814 Park Lake Cir  #8  Maitland, FL 32751

  • Condo
  • Active
  • Updated 4 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,432
    Sq. Ft.
Listed by Nexthome Neighborhood Realty
1928 South Blvd, Maitland, FL 32751 - Photo 1 Just Listed
$479,900
Open House

1928 South Blvd  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 21 hours ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,879
    Sq. Ft.
Listed by Lawhun Enterprises Iv, Llc Dba: Florida Realty Investments Iv

Price Reduced near 739 Roughbeard Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1321 Benevolent St, Maitland, FL 32751 - Photo 1 Price Reduced
-$5,900 (-1.57%)
$369,000

1321 Benevolent St  Maitland, FL 32751

  • Townhouse
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,751
    Sq. Ft.
Listed by Shirley Jones (407) 719-9180
106 Oakwood Dr, Maitland, FL 32751 - Photo 1 Price Reduced
-$900 (-0.14%)
$649,000

106 Oakwood Dr  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,877
    Sq. Ft.
Listed by Lpt Realty, Llc
502 Oak Ln, Maitland, FL 32751 - Photo 1 Price Reduced
-$30,000 (-4.77%)
$599,000

502 Oak Ln  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 1,966
    Sq. Ft.
Listed by Kressler Real Estate
1000 S Orlando Ave, Maitland, FL 32751 - Photo 1 Price Reduced
-$2,500 (-0.75%)
$332,500

1000 S Orlando Ave  #B25  Maitland, FL 32751

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 952
    Sq. Ft.
Listed by Kelly Price & Company Llc

Recent Sales near 739 Roughbeard Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2625 Summerfield Rd, Winter Park, FL 32792 - Photo 1 Sold
$739,000

2625 Summerfield Rd  Winter Park, FL 32792

  • Single Family
  • Closed
  • 5
    Beds
  • 3
    Total Baths
  • 2,199
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Palm Circle Realty
2609 Summerfield Rd, Winter Park, FL 32792 - Photo 1 Sold
$875,000

2609 Summerfield Rd  Winter Park, FL 32792

  • Single Family
  • Closed
  • 5
    Beds
  • 2
    Total Baths
  • 2,554
    Sq. Ft.
Listed and Sold by Karen Jacobs
630 St Dunstan Way, Winter Park, FL 32792 - Photo 1 Sold
$710,000

630 St Dunstan Way  Winter Park, FL 32792

  • Single Family
  • Closed
  • 5
    Beds
  • 2
    Total Baths
  • 2,240
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Stellar Non-Member Office
1712 Golfside Dr, Winter Park, FL 32792 - Photo 1 Sold
$750,000

1712 Golfside Dr  Winter Park, FL 32792

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 2,111
    Sq. Ft.
Listed by Era Grizzard Real Estate
Sold by Keller Williams Winter Park

739 Roughbeard Road, Winter Park, FL 32792 (MLS# O6404545) is a Single Family property with 5 bedrooms and 3 full bathrooms. 739 Roughbeard Road is currently listed for $800,000 and was received on May 04, 2026. Want to learn more about 739 Roughbeard Road? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

Tour this property