744 Cornwall Rd, Winter Park, FL 32792
FOR SALE

744 Cornwall Rd
Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,968 sqft

$695,000

Original price: $715,000
Est. Mortgage $4,743/mo*
Get Pre-Qualified

$695,000

Original price: $715,000
Est. Mortgage $4,743/mo*
Get Pre-Qualified
4 Beds
2 Baths
1,968 sqft

Local Information

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

Description

Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio
View
No Info
HOA
None
Price/Sqft
$353
Listed
88 days ago

Home Details for 744 Cornwall Rd

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Balcony Porch Lanai, Dining Room, Great Room, Kitchen
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1968 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Phone Available, Public, Sewer Connected, Water ConnectedAppliances: Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine RefrigeratorDishwasherDryerLaundry: In GarageMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Skylight(s)Door: Sliding DoorsFlooring: Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Tile, Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Patio, Rear Porch, ScreenedFencing: WoodVegetation: Mature LandscapingExterior: GardenFoundation: BlockGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 159Days on Market: 88

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 092230943302010

Price & Status

Price
List Price: $695,000Price Per Sqft: $353

Active Status

MLS Status: Active

Media

Location

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

Agent Information

Listing Agent
Listing ID: O6332168

Building

Building Area
Building Area: 2467 Square Feet

Community

Not Senior Community

HOA

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

Lot Information

Lot Area: 10146 sqft

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6332168Back On Market Date: Fri Feb 06 2026Showing Requirements: Call Listing AgentUniversal Property Id: US-12095-N-092230943302010-R-N
Last check for updates: about 1 hour ago
Listing Provided by: Tammy Cuddy, (407) 608-9593
VERSALIS REALTY POWERED BY SELLSTATE, (407) 608-9593
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6332168
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 744 Cornwall Rd

DatePriceEventSource
04/15/2026$695,000PriceChange
Stellar MLS #O6332168
03/28/2026$715,000PriceChange
Stellar MLS #O6332168
02/06/2026$730,000Listed For SaleStellar MLS #O6332168
10/27/2025$750,000ListingRemovedStellar MLS #O6332168
08/01/2025$750,000Listed For SaleStellar MLS #O6332168
08/08/2017$375,000Sold
N/A
07/06/2017$390,000PendingAgent Provided
06/22/2017$390,000PriceChange
Agent Provided
05/26/2017$400,000Listed For SaleAgent Provided
03/06/2012$225,000Sold
N/A
11/06/2011$225,000ListingRemovedAgent Provided
10/13/2011$225,000Listed For SaleAgent Provided
06/03/1994$120,500Sold
N/A

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Property Tax and Assessment

Year2024
Tax$5,359
Assessment$562,853
Home facts updated by county records

Comparable Sales for 744 Cornwall Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2758 Sandwell Dr, Winter Park, FL
0.10
Single-Family Home
$500,000
01/12/26
4
2
2,303
2421 Summerfield Rd, Winter Park, FL
0.14
Single-Family Home
$660,000
11/17/25
4
2
2,256
639 Friar Rd, Winter Park, FL
0.23
Single-Family Home
$450,000
12/29/25
4
3
1,950
630 Saint Dunstan Way, Winter Park, FL
0.15
Single-Family Home
$710,000
04/01/26
5
2
2,240
2609 Summerfield Rd, Winter Park, FL
0.05
Single-Family Home
$875,000
03/05/26
5
2
2,554
2478 Whitehall Cir, Winter Park, FL
0.15
Single-Family Home
$605,000
12/22/25
3
2
2,256
2433 Whitehall Cir, Winter Park, FL
0.12
Single-Family Home
$690,000
08/14/25
3
2
1,841
715 Roughbeard Rd, Winter Park, FL
0.33
Single-Family Home
$505,000
08/01/25
4
2
2,250
2774 Banchory Rd, Winter Park, FL
0.23
Single-Family Home
$417,000
03/09/26
3
2
1,560
2625 Summerfield Rd, Winter Park, FL
0.06
Single-Family Home
$739,000
04/08/26
5
3
2,199

Assigned Schools

These are the assigned schools for 744 Cornwall 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

Tammy Cuddy, VERSALIS REALTY POWERED BY SELLSTATE, (407) 608-9593
Agent Phone: (407) 608-9593
744 Cornwall Rd, Winter Park, FL 32792 is a 4 bedroom, 2 bathroom, 1,968 sqft single-family home built in 1968. This property is currently available for sale and was listed by Stellar MLS on Feb 6, 2026. The MLS # for this home is MLS# O6332168.