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Sold · Single Family

14039 HAMPSHIRE BAY CIRCLE

WINTER GARDEN, FL 34787

Beds
4 beds
Baths
5 baths
Area
3,801 sqft
Single FamilyBuilt 200617,609 sqft lot2-car garageCentralCentral Air, Attic Fan$216/sqft572 days on market

About this home

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.

Facts & features

Interior

Bedrooms
4
Bathrooms
5
Living area
3,801 sqft
Heating
Central
Cooling
Central Air, Attic Fan
Flooring
Tile, Vinyl
Stories
2
Features
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor…
Appliances
Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave…

Exterior & lot

Lot size
17,609 sqft (0.4 ac)
Roof
Shingle
Construction
Block, Stucco
Exterior
French Doors, Lighting, Rain Gutters

Parking

Garage
2 spaces

Financial

HOA dues
$141 / monthly
Annual tax
$11,068 (2024)
Price / sqft
$216/sqft

Utilities

Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Cable Connected, Sewer Available, Sewer Connected, Water Available, Water Connected

Property

Property type
Single Family
Year built
2006
Subdivision
BAY ISLE 48 17
County
Orange

Listing

Status
Sold
Days on market
401 days
MLS #
MFR745993005
Source
Stellar MLS

Listed by Kelly De Lima Perez · SUMMERHILL REALTY GROUP LLC

Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.

Estimate your monthly cost

PITI + HOA
Estimated monthly payment$5,409/mo
Principal & interest
$4,146/mo
Property tax
$922/mo
Home insurance
$200/mo
HOA dues
$141/mo

Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own 2024 bill. Insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.

Ask about this property

Answered from this listing’s own figures and the sales around it.

Price history

From the property’s MLS record.

DateEventPriceChange
May 29, 2026Price reduced$819,900−$100,100
May 28, 2026Sold$819,900
Jan 24, 2025Listed$920,000

Neighbourhood

The schools below come from the MLS record for this home. Walking, transit and cycling figures for WINTER GARDEN, FL are not connected yet, so this page does not show them.

Elementary school
Not listed
Not named in the MLS record for this home
Middle school
Not listed
Not named in the MLS record for this home
High school
Not listed
Not named in the MLS record for this home

Location

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