1208 Castleport Rd, Winter Garden, FL 34787

Off Market Sep 2025 for $645K

$675,896

Est. refi paymentEst. refi $4,428/mo

•

3,074

sq ft

1208 Castleport Rd, Winter Garden, FL 34787

About this home

BACK ON MARKE!!! Buyers financing fell through. PRICE IMPROVEMENT! Introducing a stunning new addition to the real estate market! This extraordinary 5 bedroom, 3 1/2 Bath property offers a perfect blend of elegance, sophistication, and modernity. Nestled in a highly desirable Golf Community, this house presents an enviable lifestyle for families or individuals seeking luxury living. Step inside to the newly painted interior that welcomes you with an abundance of natural light. Adorned with NEW beautiful luxury vinyl floors throughout and high ceilings, every corner of this home exudes luxury and comfort. The fully equipped kitchen is a chef's delight, complete with top-of-the-line stainless steel appliances, ample storage space, updated cabinets and a breakfast nook perfect for entertaining guests. The family room is an inviting oasis, featuring a large slider that provides the magnificent views of the landscaped backyard with a complete vinyl fence for privacy. This property is perfect for those who love to entertain or simply enjoy a peaceful oasis away from the hustle and bustle. Adjacent to the living room is a formal dining area. The Primary suite is a true retreat, newly remodeled luxurious ensuite bathroom complete with a double vanity, soaking tub, and a spacious glass-enclosed shower. Step outside the owners suite to a screened balcony overlooking the restful backyard. Each additional bedroom is generously sized and offers plenty of closet space and all bathrooms have been completely updated. Located in a sought-after golf community of Stoneybrook West featuring a 24-HOUR GUARD GATE to include a Jr Olympic pool, splash zone, playground, tennis, basketball and pickle ball courts, and fitness center. This property is surrounded by premium amenities including A+ rated schools, parks, shopping centers, restaurants and easy access to major highways. Don't miss the opportunity to make this breathtaking property your own. Schedule a viewing today and start living the luxurious lifestyle you deserve!

Single-familyProperty Type

2001Year Built

7,200 sq ftLot Size

$220Est. Price/Sq.Ft.

2 car garageParking

Listed by Barbara Waltman • KELLER WILLIAMS CLASSIC

Contact: 407-292-5400

Bought with Sais Park • FLORIDA REALTY INVESTMENTS

Redfin checked: 2 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #O6312107

Redfin Estimate

$675,896

$31K since sold in September 2025$10K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.8% lower than the average sale price ($682K) of 6 comparable homes.

SOLD AUG 28, 2026
$620,000
A
5 beds3 baths2,812 sq ft
1209 Castleport Rd, Winter Garden, FL 34787
SOLD AUG 3, 2026
$750,000
B
5 beds3 baths3,082 sq ft
13722 Fox Glove St, Winter Garden, FL 34787
SOLD MAY 27, 2026
$635,000
C
4 beds3 baths3,359 sq ft
15543 Pebble Ridge St, Winter Garden, FL 34787
SOLD JUN 10, 2026
$615,000
D
5 beds3.5 baths3,148 sq ft
813 Marsh Reed Dr, Winter Garden, FL 34787
SOLD APR 21, 2026
$745,000
E
4 beds3 baths2,970 sq ft
14046 Fox Glove St, Winter Garden, FL 34787
SOLD MAY 21, 2026
$725,000
F
4 beds2.5 baths2,763 sq ft
15508 Pebble Ridge St, Winter Garden, FL 34787

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Earn from this home

Sell

$127,015

Est. take-home

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Refinance

Est. cash available

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Rent

$3,581/mo

Redfin rental estimate

List your home for rent

Market trends in 34787, FL

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.8%

0.0% MoM

Median sale price

$611K

$11K MoM

Avg. days on market

42d

4 days MoM

Recently sold homes

558

8 MoM

New listings for sale

OPEN SAT, 11AM TO 2PM
$499,900
3 beds2.5 baths1,770 sq ft
13953 Easdale Aly, Winter Garden, FL 34787
NEW 6 HRS AGO
$589,000
3 beds2 baths2,035 sq ft
1631 Charlemagne Ct, Winter Garden, FL 34787
OPEN SAT, 1PM TO 5PM
$1,275,000
3 beds3 baths3,887 sq ft
81 Millholland St, Oakland, FL 34760
NEW 24 HRS AGO
$453,000
2 beds2 baths1,574 sq ft
13418 Princess St, Winter Garden, FL 34787
NEW 26 HRS AGO
$659,990
4 beds2 baths2,115 sq ft
3019 Cherry Orchard Ln, Winter Garden, FL 34787
NEW 26 HRS AGO
$245,000
3 beds3 baths1,544 sq ft
14501 Grove Resort Ave #3201, Winter Garden, FL 34787
COMING SOON
$575,000
2 beds2 baths1,051 sq ft
325 W Newell St, Winter Garden, FL 34787
NEW 29 HRS AGO
$595,000
4 beds2.5 baths2,496 sq ft
14354 Orchard Hills Blvd, Winter Garden, FL 34787
NEW 29 HRS AGO
$460,000
4 beds2 baths2,009 sq ft
1118 Maidenmoor Rd, Winter Garden, FL 34787
OPEN SEP 27, 1PM TO 3PM
$479,900
3 beds2.5 baths2,082 sq ft
2273 Standing Rock Cir, Oakland, FL 34787
See all

Provided by Redfin

Sale history for 1208 Castleport Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O6312107

Sep 19, 2025

Sold

$645,000

$210/sq ft

Aug 18, 2025

Pending

—

Aug 12, 2025

Price Changed

$655,000

$213/sq ft

Aug 10, 2025

Relisted

—

Jul 23, 2025

Pending

—

Jul 7, 2025

Price Changed

$675,000

$220/sq ft

May 25, 2025

Listed

$699,000

$227/sq ft

Public Records

Dec 28, 2011

Sold

$245,000

$80/sq ft

Stellar MLS as Distributed by MLS Grid #O5046651

May 27, 2011

Listed

$91/sq ft

** Price available after signing in.

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Year

Property tax

Land + Additions

Assessment*

2025

$9,180 (+8.4%)

$125,000 + $447,200

$572,200

2024

$8,468 (+11.2%)

$125,000 + $447,200

$572,200

2023

$7,613 (+9.8%)

$125,000 + $426,180

$551,180

2022

$6,932 (+16.7%)

$125,000 + $303,912

$428,912

2021

$5,938 (+7.3%)

$125,000 + $303,912

$428,912

2020

$5,534 (−1.0%)

$90,000 + $237,051

$327,051

2019

$5,592 (+3.1%)

$65,000 + $240,782

$305,782

2018

$5,425 (+4.1%)

$65,000 + $240,782

$305,782

2017

$5,213 (+1.1%)

$55,000 + $228,633

$283,633

2016

$5,158 (+4.1%)

$55,000 + $228,633

$283,633

2015

$4,953 (+6.1%)

2014

$4,667 (+13.8%)

2013

$4,099 (+1.6%)

2012

$4,033

Tax history for 1208 Castleport Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,180 (+8.4%)

$125,000 + $447,200

$572,200

2024

$8,468 (+11.2%)

$125,000 + $447,200

$572,200

2023

$7,613 (+9.8%)

$125,000 + $426,180

$551,180

2022

$6,932 (+16.7%)

$125,000 + $303,912

$428,912

2021

$5,938 (+7.3%)

$125,000 + $303,912

$428,912

2020

$5,534 (−1.0%)

$90,000 + $237,051

$327,051

2019

$5,592 (+3.1%)

$65,000 + $240,782

$305,782

2018

$5,425 (+4.1%)

$65,000 + $240,782

$305,782

2017

$5,213 (+1.1%)

$55,000 + $228,633

$283,633

2016

$5,158 (+4.1%)

$55,000 + $228,633

$283,633

2015

$4,953 (+6.1%)

2014

$4,667 (+13.8%)

2013

$4,099 (+1.6%)

2012

$4,033

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

7,200 Sq. Ft.

Year renovated

2001

Sq. Ft.

3,074

Year built

2001

Style

Single Family Residential

County

Orange County

APN

272304823102090

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

Property details

Parking

Parking Information
Garage Spaces: 2
Has Attached Garage
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 5

Bathroom Information
# of Full Baths (Total): 3
# of Half Baths (Total): 1

Laundry Room Information
Laundry Features: Inside

Other Rooms Information
Additional Rooms: Bonus Room,Breakfast Room Separate,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility
# of Rooms: 4

Fireplace Information
Has Fireplace
Fireplace Features: Decorative, Family Room, Insert

Heating & Cooling
Heating Information: Central
Cooling Information: Central Air

Interior Features
Interior Features: Ceiling Fans(s), Kitchen/Family Room Combo, Split Bedroom, Walk-in Closet(s)
Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer

Exterior

Building Information
Construction Materials: Block, Stucco
Roof: Shingle

Exterior Features
Patio And Porch Features: Patio
Exterior Features: Balcony, Private Mailbox, Sidewalk, Sliding Doors
Fencing: Vinyl

Property Features
Universal Property Id: US-12095-N-042327823102090-R-N

Waterfront Information
Water Body Name: BLACK LAKE
Waterfront Feet Total: 0
Water View Y/N: 0
Water Access Y/N: 1
Water Access Description: Lake
Water Extras Y/N: 1
Water Extras Description: Boat Ramp - Private,Fishing Pier

Property Information
CDD Y/N: 1
Homestead Y/N: 0
Other Equipment: Irrigation Equipment
Property Type: Residential
Property Sub Type: Single Family Residence
Zoning: PUD

Land Information
Total Acreage: 0 to less than 1/4

Lot Information
Lot Size Acres: 0.17
Road Surface Type: Asphalt
Lot Size Square Meters: 669

Building Information
MFR_BuildingAreaTotalSrchSqM: 363.90

Financial

Assessment Information
Other Annual Assessment Amount: $775

Tax Information
Tax Annual Amount: $8,468.44
Tax Year: 2024

Lease / Rent Details
Lease Restrictions YN: 1

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: Cable Connected, Electricity Connected, Sewer Connected

Location

Multi-Family Financial Information
Total Annual Fees: $2,872
Total Monthly Fees: $239.33

Multi-Unit Information
Unit Number YN: 0

HOA Information
Association Name: Erin Lewis
Has HOA
MFR_Association2YN: 0
Association Fee Requirement: Required
Association Approval Required Y/N: 1
Monthly HOA Amount: 239.33
Association Amenities: Basketball Court, Cable TV, Fitness Center, Gated, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Association Fee: $718
Association Fee Frequency: Quarterly
Association Fee Includes: Guard - 24 Hour, Cable TV, Pool, Internet

Location Information
Directions: 429 to exit 18 Stoneybrook Parkway follow to main Entrance in Stoneybrook West, turn right at the light go through Guard Gate continue to the 2nd stop sign turn left follow to 2nd stop sign turn left take your first left (Castleport Rd) house on the right 1208

Community Information
Community Features: Fitness Center, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Playground, Pool, Sidewalks, Tennis Court(s), Street Lights
Pets Allowed: Dogs OK

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,074
Stories: 2.0
Lot Size: 7,200 square feet
Style: Single Family Residential
Year Built: 2001
Year Renovated: 2001
County: Orange County
APN: 272304823102090

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Attribution Contact: 407-292-5400
Previous Status: Pending
Backups Requested YN: 1

Listing Date Information
Days to Contract: 85
BOM Date: 2025-08-10T00:00:00.000
Status Contractual Search Date: 2025-09-19

Listing Price Information
Calculated List Price By Calculated Sq Ft: 213.08

Green Information
Green Verification Count: 0
Direction Faces: East

Home Information
Living Area: 3074
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 285.58
Building Area Total: 3917
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Stories Total: 2
Levels: Two

Around this home

Schools

Whispering Oak Elementary School

Public PreK-5 • Assigned • 0.5mi

10/10

SunRidge Middle School

Public 6-8 • Assigned • 1.2mi

8/10

West Orange High School

Public 9-12 • Assigned • 2.9mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

8/10 Heat Factor

7 days above 108° expected this year, 23 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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 6.7 hours in December, placing it above the U.S. average for solar exposure.

8.7 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$643,000 – $778,000

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OPEN SAT, 11AM TO 2PM

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NEW 6 HRS AGO

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OPEN SAT, 1PM TO 5PM

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NEW 24 HRS AGO

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NEW 26 HRS AGO

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NEW 26 HRS AGO

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COMING SOON

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NEW 29 HRS AGO

$595,000

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NEW 29 HRS AGO

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Home values near 1208 Castleport Rd

Data from public records.

Address	Redfin Estimate
1233 Castleport Road, Winter Garden, FL 4 Beds \| 2 Baths \| 2390 Sq. Ft.	$587,606
1221 Castleport Road, Winter Garden, FL 5 Beds \| 3 Baths \| 3243 Sq. Ft.	$790,280

Address	Redfin Estimate
1209 Castleport Road, Winter Garden, FL 5 Beds \| 3 Baths \| 2812 Sq. Ft.	$657,467
1227 Castleport Road, Winter Garden, FL 4 Beds \| 3 Baths \| 3851 Sq. Ft.	$715,469

Address	Redfin Estimate
1215 Castleport Road, Winter Garden, FL 4 Beds \| 3 Baths \| 3864 Sq. Ft.	$834,912
1226 Castleport Road, Winter Garden, FL 5 Beds \| 3 Baths \| 2864 Sq. Ft.	$667,412

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 34787, FL

Sale history for 1208 Castleport Rd

Tax history for 1208 Castleport Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 34787

Home values near 1208 Castleport Rd

More real estate resources