For sale

$749,000

Est. $5,511/mo —

•

3,673

sq ft

1349 Castleport Rd, Winter Garden, FL 34787

About this home

SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

Single-familyProperty Type

2001Year Built

7,200 sq ftLot Size

$204Price/Sq.Ft.

$243/moHOA Dues

2 car garageParking

Listed by Erika Castellani • WRA BUSINESS & REAL ESTATE

Contact: 407-512-1008

Listing updated: Oct 14, 2026 at 12:53pm

Redfin checked: 2 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #O6449173

Payment calculator

$5,511 per month

Principal and interest$4,088

Property taxes

HOA dues

Home insurance

Utilities

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
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OPEN SAT, 11AM TO 2PM
$535,000
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651 Autumn Oaks Loop, Winter Garden, FL 34787
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OPEN SAT, 11AM TO 2PM3D WALKTHROUGH
$375,000
3 beds2.5 baths1,944 sq ft
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$531 HOA • Garage • Community pool
OPEN SAT, 11AM TO 2PM3D & VIDEO TOUR
$720,000
4 beds3 baths2,195 sq ft
1184 Palm Cove Dr, Orlando, FL 32835
0.54 acre lot • 2 garage spots • Pool
OPEN SAT, 11AM TO 3PM
$650,000
4 beds3 baths2,869 sq ft
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0.38 acre lot • 3 garage spots • Pool
OPEN SAT, 1PM TO 3PM3D WALKTHROUGH
$265,200
3 beds2 baths1,757 sq ft
135 Brigadoon Pt, Orlando, FL 32835
8,969 sq ft lot • 2 garage spots • Built 1986
OPEN SUN, 11AM TO 2PM3D WALKTHROUGH
$675,000
4 beds2.5 baths2,834 sq ft
580 First Cape Coral Dr, Winter Garden, FL 34787
9,182 sq ft lot • Garage • Pool
REDFIN OPEN SUN, 12PM TO 2PM3D WALKTHROUGH
$740,000
5 beds4.5 baths3,663 sq ft
3275 Buoy Cir, Winter Garden, FL 34787
7,000 sq ft lot • 2 garage spots • Community pool

Around this home

Schools

K - 12
Preschool & daycare

Whispering Oak Elementary School

Public PreK-5 • Assigned • 0.4mi

10/10

SunRidge Middle School

Public 6-8 • Assigned • 1.4mi

8/10

West Orange High School

Public 9-12 • Assigned • 3.0mi

6/10

Provided by GreatSchools

About Stoneybrook

West

Stoneybrook West, located between Florida’s Turnpike and Lake Apopka, is a master-planned and golf-centered Winter Garden neighborhood with a gated layout and a broad lake-country backdrop. The scene concentrates around the Stoneybrook West Golf Club clubhouse, where cart paths, practice greens, and the first tee set the daily rhythm. Streets of stucco-and-tile Mediterranean-inspired homes and newer two-story builds curve around ponds, palms, and fairway views. Sidewalk loops and pocket greens shape a walk-and-roll routine, with community amenities clustered near the main entrance. For local culture, Plant Street Market, the Garden Theatre, and Crooked Can Brewing Company in Downtown Winter Garden serve as familiar gathering spots beyond the gates.

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Ceiling fans
Eat-in kitchen
High ceilings
Kitchen/family room combo
Living room/dining room combo
Open floor plan
Solid wood cabinets
Stone counters
Thermostat
Walk-in closets

Bedrooms
5 bedrooms

Bathrooms
3 full bathrooms
1 half bathroom

Kitchen
Dishwasher
Microwave
Range
Refrigerator

Laundry & utility
Inside laundry room
Washer
Dryer

Flooring
Ceramic tile
Vinyl

Heating & cooling
Central heating
Central air conditioning

Sale and tax history for 1349 Castleport Rd

Sale History
Tax History

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O6449173

Oct 12, 2026

Listed

$749,000

$204/sq ft

Stellar MLS as Distributed by MLS Grid #O6377923

Aug 11, 2026

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O6258370

Oct 13, 2025

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #G5020814

May 22, 2020

Sold

$390,000

$106/sq ft

Mar 23, 2020

Pending

—

Jan 2, 2020

Price Changed

$439,000

$120/sq ft

Sep 20, 2019

Listed

$474,900

$129/sq ft

Public Records

Aug 23, 2011

Sold

$265,000

$72/sq ft

Stellar MLS as Distributed by MLS Grid #S4673330

Nov 23, 2010

Listing Removed

—

Public Records

Aug 15, 2006

Sold

$475,000

$129/sq ft

Public Records

Jan 8, 2004

Sold

$300,000

$82/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$9,894 (+8.5%)

$125,000 + $502,430

$627,430

2024

$9,122 (+11.6%)

$125,000 + $502,430

$627,430

2023

$8,171 (+10.2%)

$125,000 + $478,621

$603,621

2022

$7,417 (+16.9%)

$125,000 + $338,770

$463,770

2021

$6,342 (+7.0%)

$125,000 + $338,770

$463,770

2020

$5,930 (−1.4%)

$90,000 + $261,928

$351,928

2019

$6,015 (+3.0%)

$65,000 + $266,141

$331,141

2018

$5,840 (+4.0%)

$65,000 + $266,141

$331,141

2017

$5,613 (+0.2%)

$55,000 + $252,437

$307,437

2016

$5,599 (+2.9%)

$55,000 + $252,437

$307,437

2015

$5,442 (+6.4%)

2014

$5,115 (+14.0%)

2013

$4,488 (+1.6%)

2012

$4,415

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

7,200 Sq. Ft.

Year renovated

2001

Finished Sq. Ft.

3,673

Unfinished Sq. Ft.

—

Total Sq. Ft.

3,673

Year built

2001

Style

Single Family Residential

County

Orange County

APN

272304823102066

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 5, 2026.

Climate risks

1/10 Flood Factor

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

9/10 Heat Factor

7 days above 108° expected this year, 24 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

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

Provided by First Street

Historical weather

Winter Garden, FL • 34787

Average low and high temperatures (°F)

68°

49°

74°

54°

80°

60°

84°

65°

89°

72°

91°

75°

92°

76°

91°

76°

88°

74°

81°

68°

78°

60°

72°

55°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

74/ 100

Good sunlight

Sunscore

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

7.5 hrs

5.7 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 1349 Castleport Rd

$731,768

$17K under list price of $749K

Nearby comparable homes

The Redfin Estimate uses 5 recent nearby sales, priced between $765K to $888K.

SOLD AUG 4, 2026
$765,000 Last sold price
5 beds3 baths3,902 sq ft
15162 Spinnaker Cove Ln, Winter Garden, FL 34787
$8/sq ft
larger lot
4 years newer
SOLD NOV 9, 2026
$842,000 Last sold price
5 beds5 baths3,935 sq ft
2716 Gorst Rd, Winter Garden, FL 34787
$10/sq ft
larger lot
2 years newer
SOLD JUN 29, 2026
1432 Marble Crest Way, Winter Garden, FL 34787
$824,500 Last sold price
5 beds4 baths3,734 sq ft
1432 Marble Crest Way, Winter Garden, FL 34787
$17/sq ft
larger lot
4 years newer
SOLD SEP 2, 2026
$887,500 Last sold price
5 beds4 baths3,505 sq ft
15878 Citrus Grove Loop, Winter Garden, FL 34787
$49/sq ft
larger lot
15 years newer
SOLD JUL 2, 2026
$775,000 Last sold price
5 beds3.5 baths3,598 sq ft
1157 Vinsetta Cir, Winter Garden, FL 34787
$11/sq ft
larger lot
13 years newer

Rental earnings

Est. $3,879 per month, based on comparable rentals

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Make a winning offer with the help of a local agent

Ask a question

(407) 972-1810

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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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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Property details

Sale and tax history for 1349 Castleport Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 1349 Castleport Rd

Early Access listings

Nearby similar homes

New listings for sale in 34787

More real estate resources