1251 Castleport Rd, Winter Garden, FL 34787

Off Market Sep 2020 for $395K

$653,512

Est. refi paymentEst. refi $2,617/mo

•

2,819

sq ft

1251 Castleport Rd, Winter Garden, FL 34787

About this home

This spectacular golf front residence sits on a large green area before the golf course, with scenic views from every room. Open and spacious floor plan with RICH WIDE PLANK WOOD FLOORS, rounded entryways, and a dual-sided stairway. Enormous eat-in kitchen with center island, breakfast bar, and dinette. Rare 4 bd 2 1/2 bath with BONUS ROOM AND LOFT. Office/bonus room downstairs. .2nd story screened balcony is the perfect place to sit and relax while gazing at fireworks. Second screened patio downstairs and plenty of room for a pool. This exclusive gated and guarded subdivision features a community pool, fitness area, private ski lake, tennis, basketball, in-line hockey rink, dock and boat ramp

Single-familyProperty Type

2001Year Built

7,245 sq ftLot Size

$232Est. Price/Sq.Ft.

2 car garageParking

Listed by Kristi Matthew • CENTURY 21 PROFESSIONAL GROUP

Bought with Judson Osbon • TOP LISTING REALTY LLC

Redfin checked: 2 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #O5870026

Redfin Estimate

$653,512

$259K since sold in September 2020$7,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.1% higher than the average sale price ($622K) of 6 comparable homes.

SOLD MAY 21, 2026
$725,000
A
4 beds2.5 baths2,763 sq ft
15508 Pebble Ridge St, Winter Garden, FL 34787
SOLD AUG 28, 2026
$620,000
B
5 beds3 baths2,812 sq ft
1209 Castleport Rd, 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 APR 21, 2026
$745,000
D
4 beds3 baths2,970 sq ft
14046 Fox Glove St, Winter Garden, FL 34787
SOLD SEP 4, 2026
$495,000
E
3 beds2 baths2,170 sq ft
1343 Castleport Rd, Winter Garden, FL 34787
SOLD NOV 12, 2025
$511,500
F
4 beds2.5 baths2,754 sq ft
1134 Harbor Hill St, Winter Garden, FL 34787

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Earn from this home

Sell

$335,916

Est. take-home

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Refinance

Est. cash available

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Rent

$3,290/mo

Redfin rental estimate

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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

NEW 3 HRS AGO
$1,924,999
4 beds3 baths3,789 sq ft
15210 E Oakland Ave, Winter Garden, FL 34787
EARLY ACCESS
$879,000
4 beds4 baths3,424 sq ft
16513 Silver Brk Way, Winter Garden, FL 34787
COMING SOON
$1,650,000
5 beds4.5 baths3,506 sq ft
1032 Galston Aly, Winter Garden, FL 34787
NEW 10 HRS AGO
$399,000
3 beds2.5 baths1,727 sq ft
15579 Honeybell Dr, Winter Garden, FL 34787
NEW 20 HRS AGO
$899,000
4 beds3.5 baths3,042 sq ft
14961 Lebeau Loop, Winter Garden, FL 34787
NEW 25 HRS AGO
$700,000
3 beds2 baths2,066 sq ft
14371 Shocklach Dr, Winter Garden, FL 34787
COMING SOON
$399,900
3 beds2.5 baths1,860 sq ft
8049 Basilica Ln, Winter Garden, FL 34787
3D WALKTHROUGH
$585,000
2 beds2 baths1,051 sq ft
325 W Newell St, Winter Garden, FL 34787
NEW 29 HRS AGO
$515,000
3 beds2.5 baths1,811 sq ft
2696 Bobcat Chase Blvd, Oakland, FL 34787
NEW 30 HRS AGO
$409,000
3 beds2 baths1,539 sq ft
1606 Beulah Rd, Winter Garden, FL 34787
See all

Provided by Redfin

Sale history for 1251 Castleport Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5870026

Sep 18, 2020

Sold

$395,000

$140/sq ft

Jul 21, 2020

Pending

—

Jul 16, 2020

Price Changed

$415,000

$147/sq ft

Jun 25, 2020

Price Changed

$422,500

$150/sq ft

Jun 10, 2020

Listed

$425,000

$151/sq ft

Public Records

Oct 7, 2009

Sold

$270,000

$96/sq ft

Stellar MLS as Distributed by MLS Grid #O4713696

Sep 29, 2006

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4684494

Sep 11, 2006

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #R4584855

May 22, 2006

Listing Removed

—

Public Records

Apr 21, 2006

Sold

$365,000

$129/sq ft

Stellar MLS as Distributed by MLS Grid #O4663392

Apr 2, 2006

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4648711

Mar 3, 2006

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4625336

Dec 30, 2005

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4614347

Aug 17, 2005

Listing Removed

—

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Tax history for 1251 Castleport Rd

*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

7,245 Sq. Ft.

Year renovated

2001

Sq. Ft.

2,819

Year built

2001

Style

Single Family Residential

County

Orange County

APN

272304823102055

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

Property details

Parking

Parking Information
Garage Dimensions: 20x20
Parking Features: Garage Door Opener
Garage Spaces: 2
Has Attached Garage
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 4

Bathroom Information
# of Full Baths (Total): 2
# of Half Baths (Total): 1

Laundry Room Information
Laundry Features: Inside, Laundry Room

Other Rooms Information
Additional Rooms: Breakfast Room Separate,Family Room,Formal Living Room Separate,Inside Utility
# of Rooms: 10

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

Interior Features
Interior Features: Eat-in Kitchen, Kitchen/Family Room Combo, Split Bedroom, Walk-in Closet(s)
Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Range
Flooring: Carpet, Tile, Wood

Exterior

Building Information
Construction Materials: Block, Stucco, Wood Frame
Roof: Shingle

Exterior Features
Patio And Porch Features: Covered, Enclosed, Screened
Exterior Features: Irrigation System, Sidewalk, Sliding Doors, Sprinkler Metered

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: 0

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

Land Information
Vegetation: Oak Trees, Trees/Landscaped
Total Acreage: Up to 10,889 Sq. Ft.

Lot Information
Lot Features: Conservation Area, City Limits, Level, On Golf Course, Sidewalk, Paved, Private
Lot Size Acres: 0.17
Lot Size Square Meters: 673
Planned Unit Development YN: 1
Other Exemptions YN: 0

Building Information
MFR_BuildingAreaTotalSrchSqM: 354.15

Financial

Assessment Information
Other Annual Assessment Amount: $498

Tax Information
Tax Annual Amount: $3,222.11
Tax Year: 2019

Lease / Rent Details
Lease Restrictions YN: 1

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: Cable Available, Cable Connected, Electricity Available, Electricity Connected, Public, Sewer Available, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities
Additional Water Information: Community boat ramp to Black Lake

Location

Multi-Family Financial Information
Total Annual Fees: $2,040
Total Monthly Fees: $170

Multi-Unit Information
Unit Number YN: 0

HOA Information
Association Name: Michelle Arditi
Has HOA
Association Fee Requirement: Required
Association Approval Required Y/N: 1
Monthly HOA Amount: 170.00
Association Amenities: Basketball Court, Cable TV, Clubhouse, Fence Restrictions, Fitness Center, Gated, Lobby Key Required, Park, Playground, Pool, Private Boat Ramp, Tennis Court(s), Vehicle Restrictions
Association Fee: $510
Association Fee Frequency: Quarterly
Association Fee Includes: Guard - 24 Hour, Cable TV, Common Area Taxes, Pool, Management, Pool, Private Road

School Information
Elementary School: Whispering Oak Elem
Middle Or Junior High School: SunRidge Middle
High School: West Orange High

Location Information
Directions: County Road 535 to Stoneybrook West Pkwy to the guard gate.Enter through the gate turn left at Tour Point, then 2nd left at Pebble Ridge then turn left at Castleport home on left

Community Information
Community Features: Boat Ramp, Deed Restrictions, Fishing, Fitness Center, Gated, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Park, Playground, Pool, Sidewalks, Tennis Courts, Water Access, Waterfront
Pets Allowed: Yes

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,819
Stories: 2.0
Lot Size: 7,245 square feet
Style: Single Family Residential
Year Built: 2001
Year Renovated: 2001
County: Orange County
APN: 272304823102055

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Previous Status: Pending
Backups Requested YN: 0
Home Warranty YN: No

Listing Date Information
Days to Contract: 40
Status Contractual Search Date: 2020-09-18

Listing Price Information
Calculated List Price By Calculated Sq Ft: 147.22

Green Information
Direction Faces: North

Home Information
Living Area: 2819
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 261.89
Building Area Total: 3812
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Builder Name: US Homes
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 • 1.3mi

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

$621,000 – $752,000

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Listing provided by Zillow

New listings for sale in 34787

NEW 3 HRS AGO

$1,924,999

4 beds3 baths3,789 sq ft

15210 E Oakland Ave, Winter Garden, FL 34787

EARLY ACCESSCOMPASS COMING SOON

$879,000

4 beds4 baths3,424 sq ft

16513 Silver Brk Way, Winter Garden, FL 34787

COMING SOON

$1,650,000

5 beds4.5 baths3,506 sq ft

1032 Galston Aly, Winter Garden, FL 34787

NEW 10 HRS AGO

$399,000

3 beds2.5 baths1,727 sq ft

15579 Honeybell Dr, Winter Garden, FL 34787

NEW 20 HRS AGO

$899,000

4 beds3.5 baths3,042 sq ft

14961 Lebeau Loop, Winter Garden, FL 34787

NEW 25 HRS AGO

$700,000

3 beds2 baths2,066 sq ft

14371 Shocklach Dr, Winter Garden, FL 34787

COMING SOON3D WALKTHROUGH

$399,900

3 beds2.5 baths1,860 sq ft

8049 Basilica Ln, Winter Garden, FL 34787

3D WALKTHROUGH

$585,000

2 beds2 baths1,051 sq ft

325 W Newell St, Winter Garden, FL 34787

NEW 29 HRS AGO

$515,000

3 beds2.5 baths1,811 sq ft

2696 Bobcat Chase Blvd, Oakland, FL 34787

Home values near 1251 Castleport Rd

Data from public records.

Address	Redfin Estimate
1245 Castleport Road, Winter Garden, FL 4 Beds \| 4 Baths \| 2551 Sq. Ft.	$643,378
1301 Castleport Road, Winter Garden, FL 4 Beds \| 3 Baths \| 2583 Sq. Ft.	$604,566

Address	Redfin Estimate
1308 Castleport Road, Winter Garden, FL 4 Beds \| 2 Baths \| 2420 Sq. Ft.	$521,140
1307 Castleport Road, Winter Garden, FL 4 Beds \| 2 Baths \| 2267 Sq. Ft.	$605,345

Address	Redfin Estimate
1263 Castleport Road, Winter Garden, FL 5 Beds \| 3 Baths \| 3394 Sq. Ft.	$656,964
1233 Castleport Road, Winter Garden, FL 4 Beds \| 2 Baths \| 2390 Sq. Ft.	$587,606

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2020. 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 1251 Castleport Rd

Tax history for 1251 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 1251 Castleport Rd

More real estate resources