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$780,000
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Property Description
Fully Renovated 4BR Luxury Home | Bay Isle Gated | Private Cinema | Grand Primary Suite | Corner Lot Fully renovated 4-bedroom, 3.5-bath plus additional upstairs half bath, home located in the desirable Bay Isle gated community in Winter Garden. Residents enjoy access to a private lake, park, sidewalks, and gated security. HOA covers landscaping, private roads, amenities, and security. This premium corner-lot property features an oversized paved courtyard with ample space for a future pool and custom outdoor living area, ample parking, irrigation system, rain gutters, and a whole-house water filtration system (owned, no lease). Spacious layout includes open kitchen/family room, living/dining room combo, extended loft, private cinema room with reclining theater seating, 120" screen, short-throw projector, and surround sound system, and enclosed lanai ideal for entertaining. Interior features include porcelain tile flooring in main living areas and kitchen, high ceilings, crown molding, solid wood cabinetry, solid surface countertops, walk-in closets, and showers in all full bathrooms. The grand primary suite on the main level features a spa-style bathroom with jetted soaking tub and dual shower, along with two walk-in closets and an exceptional bonus area with three separate rooms and independent entrance, currently used as additional closets, offering flexible potential for a home office, gym, studio, or private retreat. Recent updates include roof replaced in 2021 and three A/C units (one brand new) for enhanced efficiency and reliability. The floor plan offers: "¢ Primary suite on the main level "¢ Upstairs private suite with bathroom and walk-in closet "¢ Two additional upstairs bedrooms with shared full bathroom "¢ Additional upstairs half bath (powder room) Prime location near Winter Garden Village, new hospital, and just minutes from charming Downtown Winter Garden, with easy access to major highways, theme parks, and Orlando International Airport.
Full Property Details
Full Property Details for 14039 Hampshire Bay Cir
General
- Sold For: $780,000
- HOA FEE: $141/month
- Taxes: $11,068 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6274785
- Added to Site: 529 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 10
- Interior Features: Attic Fan, Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Walk-In Closet(s), Window Treatments
- Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator
- Flooring: Porcelain Tile, Vinyl
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Exterior
- Exterior Features: French Doors, Irrigation System, Lighting, Rain Gutters
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: BAY ISLE 48 17
- Driving Directions: Take Winter Garden Vineland Rd to Hampshire Bay Cir Use the left lane to turn left onto Winter Garden Vineland Rd Slight left to stay on Winter Garden Vineland Rd At the traffic circle, take the 2nd exit and stay on Winter Garden Vineland Rd Turn left onto Bristol Isle Ln Turn right onto Hampshire Bay Cir
- Direction Faces: Southeast
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Water Access, Gated Community - Guard, Park, Playground, Sidewalks
- Association: Yes
- Assoc. Name: SINDI KLEIN-HAMIL
- Assoc. Fees Include: Maintenance Grounds, Private Road, Recreational Facilities, Security
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Cable Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 3,801
- Sq. Ft. Source: Public Records
- Living Area: 3,801 Sq. Ft.
- Year Built: 2006
Lot Features
- Lot Size (Acres): 0.4
- Lot Size (Sq. Ft.): 17,609
- Lot Size: 17609
- Street/Road Desc.: Asphalt
Financial Considerations
- Association Fee: $141
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- Tax Amount: $11,068.48
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: BAY ISLE 48/16 LOT 42
- Flood Zone Info: x
- APN: 342227016200420
- Property ID: 342227016200420
Listed by Summerhill Realty Group Llc
Sold by The Simon Simaan Group
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Schools
Schools serving 14039 Hampshire Bay Cir
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Sunridge Elementary School 14455 Sunridge Boulevard, Winter Garden, FL 34787 | PK-5 | 0.9 mi |
SunRidge Middle School 14955 Sunridge Boulevard, Winter Garden, FL 34787 | 6-8 | 0.9 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 14039 Hampshire Bay Cir
Date
Details
Price
Change
Source
5/28/2026
Sold
$780,000
-4.87%
MLS
2/20/2026
Price Reduced
$819,900
-0.01%
MLS
2/02/2026
Price Reduced
$820,000
-3.3%
MLS
11/16/2025
Price Reduced
$848,000
-0.12%
MLS
10/21/2025
Price Reduced
$849,000
-0.12%
MLS
10/15/2025
Price Increased
$850,000
0.01%
MLS
10/01/2025
Price Reduced
$849,900
-1.29%
MLS
9/28/2025
Price Increased
$861,000
0.23%
MLS
9/18/2025
Price Reduced
$859,000
-0.12%
MLS
9/09/2025
Price Reduced
$860,000
-5.39%
MLS
8/20/2025
Price Increased
$909,000
4.6%
MLS
7/30/2025
Price Reduced
$869,000
-2.25%
MLS
7/29/2025
Price Reduced
$889,000
-1.1%
MLS
6/26/2025
Price Reduced
$898,900
-0.01%
MLS
6/09/2025
Price Reduced
$899,000
-1.74%
MLS
5/13/2025
Price Reduced
$914,900
-1.08%
MLS
5/04/2025
Price Reduced
$924,900
-0.11%
MLS
4/16/2025
Price Reduced
$925,900
-0.54%
MLS
4/11/2025
Price Reduced
$930,900
-0.21%
MLS
4/07/2025
Price Reduced
$932,900
-0.11%
MLS
4/03/2025
Price Reduced
$933,900
-0.11%
MLS
3/21/2025
Price Increased
$934,900
1.64%
MLS
2/10/2025
Price Reduced
$919,800
-0.02%
MLS
1/24/2025
Listed
$920,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
14039 Hampshire Bay Circle, Winter Garden, FL 34787 (MLS# O6274785) is a Single Family property that was sold at $780,000 on May 28, 2026. Want to learn more about 14039 Hampshire Bay Circle? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

