UNDER CONTRACT

Contingent

$630,000

Est. $4,036/mo —

•

1,968

sq ft

744 Cornwall Rd, Winter Park, FL 32792

About this home

Under contract-accepting backup offers. 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! Also listed for rent

Single-familyProperty Type

1968Year Built

10,146 sq ftLot Size

$320Price/Sq.Ft.

2 car garageParking

Listed by Tammy Cuddy • VERSALIS REALTY POWERED BY SELLSTATE

Contact: 407-608-9593

Listing updated: Aug 14, 2026 at 11:11pm

Redfin checked: a minute ago

•Source:Stellar MLS as Distributed by MLS Grid #O6332168

Payment calculator

$4,036 per month

Principal and interest$3,269

Property taxes

$447

HOA dues

Home insurance

$320

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

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$450,000
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208 Chichester Cv, Longwood, FL 32779
OPEN SAT, 11AM TO 1PM
$360,000
3 beds2 baths1,351 sq ft
1982 Water Ln, Maitland, FL 32751
OPEN SAT, 11:30AM TO 2PMVIDEO TOUR
$449,000
4 beds2 baths1,766 sq ft
1047 Kelly Creek Cir, Oviedo, FL 32765
OPEN SAT, 12PM TO 2PM
$799,000
4 beds2.5 baths2,637 sq ft
1319 Buckwood Dr, Orlando, FL 32806
OPEN SAT, 12PM TO 2PM
$365,000
2 beds2 baths1,231 sq ft
2895 Donaldson Dr, Orlando, FL 32812
OPEN SUN, 11AM TO 2PM3D WALKTHROUGH
$875,000
3 beds3 baths2,792 sq ft
11450 Fangorn Rd, Orlando, FL 32825
REDFIN OPEN SUN, 12PM TO 2PM3D & VIDEO TOUR
$875,000
4 beds4 baths2,688 sq ft
442 Briercliff Dr, Orlando, FL 32806
OPEN SUN, 12PM TO 3PM3D WALKTHROUGH
$525,000
3 beds2 baths2,151 sq ft
13627 Dornoch Dr, Orlando, FL 32828
REDFIN OPEN SUN, 1PM TO 4PM3D WALKTHROUGH
$360,000
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$485,000
3 beds2 baths1,248 sq ft
1017 N Glenwood Ave, Orlando, FL 32803

Around this home

Schools

K - 12
Preschool & daycare

Brookshire Elementary School

Public PreK-5 • Assigned • 0.4mi

4/10

Glenridge Middle School

Public 6-8 • Assigned • 1.4mi

7/10

Winter Park High School

Public 9-12 • Assigned • 0.5mi

7/10

Provided by GreatSchools

About Winter Park

Pines

Winter Park Pines, located between Semoran Boulevard (SR 436) and Howell Branch Road, is a residential and suburban Winter Park neighborhood with mid-century ranch streetscapes and a canopy of mature oaks. The neighborhood’s character concentrates around the Howell Branch Road and Semoran Boulevard crossroads, where everyday errands cluster beside steady traffic and pocket plazas. Single-story homes, screened lanais, and generous lots set a low-slung architectural rhythm, with sidewalks and cul-de-sacs shaping a calm, lived-in feel. Cady Way Trail adds a linear green corridor for walking and cycling. Ward Park and the Winter Park Library bring courts, lawns, and civic programming into the weekly routine. Nearby, Winter Park Village supplies a modern retail-and-dining hub without shifting the neighborhood’s quiet tone.

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Ceiling fans
Crown molding
Eat-in kitchen
Kitchen/family room combo
Living room/dining room combo
Open floorplan
Split bedroom layout
Skylights

Bedrooms
4 bedrooms

Bathrooms
2 full bathrooms

Kitchen
Cooktop
Dishwasher
Microwave
Refrigerator
Wine refrigerator
Electric water heater

Laundry & utility
Washer
Dryer
Laundry area in garage

Flooring
Tile flooring
Wood flooring

Heating & cooling
Natural gas heating
Central air conditioning
Attic fan

Sale and tax history for 744 Cornwall Rd

Sale History
Tax History

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O6332168

Aug 14, 2026

Contingent

—

Aug 10, 2026

Price Changed

$630,000

$320/sq ft

Aug 10, 2026

Price Changed

$63,000

$32/sq ft

Jun 29, 2026

Price Changed

$675,000

$343/sq ft

Jun 22, 2026

Relisted

—

Apr 15, 2026

Price Changed

$695,000

$353/sq ft

Mar 28, 2026

Price Changed

$715,000

$363/sq ft

Feb 6, 2026

Relisted

—

Jul 31, 2025

Listed

$750,000

$381/sq ft

Stellar MLS as Distributed by MLS Grid #O5513443

Aug 3, 2017

Sold

$375,000

$191/sq ft

Jul 6, 2017

Pending

—

Jun 22, 2017

Price Changed

$390,000

$198/sq ft

May 25, 2017

Listed

$400,000

$203/sq ft

The brand new kitchen and wood floors make this jewel shine! Four bedroom, 2 bath Winter Park home with beautiful HARDWOOD FLOORS. Brand NEW eat in Kitchen has a large breakfast bar that opens to family room. Master Bedroom has French doors that leads to screened porch which provides lots of natural sunlight! Nice open living room with hardwood floors. The family room has another set of French doors that lead to 26' x 10' screened in porch with an INSULATED ROOF that overlooks private fenced in yard. GREAT home for entertaining! Crown molding in many rooms. This home has ENERGY EFFICIENT double pane windows. This home is located on a large corner lot with an irrigation system. Nice side entry garage adds to curb appeal.

Stellar MLS as Distributed by MLS Grid #O5068089

Mar 5, 2012

Sold

$225,000

$114/sq ft

Oct 12, 2011

Listed

$225,000

$114/sq ft

SHORT SALE 4 bedroom home with beautiful HARDWOOD FLOORS. Master bath recently updated, master has newer french doors that leads to screened porch which provides lots of natural sunlight! Nice open living room with hardwood floor and nice picture windowthat overlooks well manicured yard. The kitchen has a large breakfast bar and plenty of space and is eat in which is open to familyroom. The familyroom has another set of newer french doors that lead to 26' x 10' screened in porch with a INSULATED ROOF that overlooks a PARK LIKE setting backyard. GREAT for entertaining!Crown molding in many rooms of this home adds to the quality workmanship. This home has ALL NEWER Pex pipe for supply lines hot & cold and a rare to find water shut off junction box for each hot & cold line. This home has "NEWER" ENERGY EFFICIENT double pane windows to help Lower your summer electric bills. Also a newer coil in the AC and a Newer hot water tank. This home is located on a large corner lot with a sprinkler system. Nice side entry garage adds to curb appeal. Three shelves in living room and all drapes do not convey except the Green velvet ones in living room stay. Come see this home !

Public Records

Aug 28, 2002

Sold

$210,000

$107/sq ft

Public Records

Jun 1, 1994

Sold

$120,500

$61/sq ft

Public Records

Jun 1, 1968

Sold

$29,900

$15/sq ft

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

10,146 Sq. Ft.

Year renovated

1990

Finished Sq. Ft.

1,968

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,968

Year built

1968

Style

Single Family Residential

County

Orange County

APN

302209943302010

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

R-1A

Single-Family Dwelling Districts

The areas included within R-1-A single-family dwelling districts are intended to be single-family residential areas with large lots and low population densities. Certain structures and uses required to serve educational, religious, utilities and noncommercial recreational needs of such areas are permitted within the districts as special exceptions.

Permitted uses

Include but are not limited to:

Livestock production
Housing-Single unit
Fire house
Police station

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 107° expected this year, 22 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winter Park, FL • 32792

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

98/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

11.2 hrs

8.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 744 Cornwall Rd

$606,350

$24K under list price of $630K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $605K to $740K.

SOLD DEC 30, 2025
$675,000 Last sold price
3 beds2 baths2,134 sq ft
2418 Whitehall Cir, Winter Park, FL 32792
$4/sq ft
smaller lot
6 years older
SOLD JUL 9, 2026
$699,000 Last sold price
3 beds2 baths1,827 sq ft
676 Dunblane Dr, Winter Park, FL 32792
$63/sq ft
6 years older
SOLD JAN 29, 2026
$615,000 Last sold price
4 beds2.5 baths2,046 sq ft
607 Dunblane Dr, Winter Park, FL 32792
$19/sq ft
4 years older
SOLD APR 8, 2026
$740,000 Last sold price
3 beds2.5 baths1,838 sq ft
5343 Brady Ln, Orlando, FL 32814
$83/sq ft
smaller lot
40 years newer
SOLD DEC 22, 2025
$605,000 Last sold price
3 beds2 baths2,256 sq ft
2478 Whitehall Cir, Winter Park, FL 32792
$52/sq ft
larger lot
3 years older
SOLD JUL 15, 2026
$725,000 Last sold price
4 beds3 baths2,038 sq ft
350 Cornwall Rd, Winter Park, FL 32792
$36/sq ft
smaller lot
5 years older

Rental earnings

Est. $2,784 per month, based on comparable rentals

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Details provided by Stellar MLS as Distributed by MLS Grid and may not match the public record. Learn more.

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About this home

Payment calculator

Open houses

Nearby open houses (10)

Around this home

Schools

Property details

Sale and tax history for 744 Cornwall Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 744 Cornwall Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 32792

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