
14411 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL, 34787
Active4 days on marketListed Aug 4, 2026MLS #O6430003
About this home
14411 HAMPSHIRE BAY CIRCLE
Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
4,010
Sqft
0.3 ac
Lot size
3
Garage
2005
Year built
Two
Levels
$1
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$203 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$203/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Winter Garden actives
$1 vs $261
Days on market
4 vs 40 typical
Where $1/sqft sits among the 400 Winter Garden actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Bay Isle At Black Lake
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Bay Isle At Black Lake — neighborhood snapshot
Population
411
Median age
34
Median income
$119,458
Median home value
$417,800
Avg household
3
Households w/ children
85%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$585K → $620K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
168 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 14411 HAMPSHIRE BAY CIRCLE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’25$890,000
14003 HAMPSHIRE BAY CIRCLE · same community
4 bd · 4 ba · 4,015 sqft · $222/sqft · 88 DOM
Sold · May ’26$780,000
14039 HAMPSHIRE BAY CIRCLE · same community
4 bd · 4 ba · 3,801 sqft · $205/sqft · 401 DOM
Sold · Jul ’26$1,125,200
14255 HAMPSHIRE BAY CIRCLE · same community
4 bd · 4.5 ba · 4,625 sqft · $243/sqft · 73 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Steeve Cadeau
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 14411 HAMPSHIRE BAY CIRCLE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14411 HAMPSHIRE BAY CIRCLE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Steeve's phone and CRM.
Straight answers
14411 HAMPSHIRE BAY CIRCLE FAQs
What would the monthly payment be for 14411 HAMPSHIRE BAY CIRCLE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $203/mo — principal and interest, estimated property taxes and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
Are pets allowed at 14411 HAMPSHIRE BAY CIRCLE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Garden?+
At $6,000, this home is listed about 99% below the Winter Garden median of $584,500. The market section on this page shows how the area is trending.
Which schools are assigned to 14411 HAMPSHIRE BAY CIRCLE?+
Sunridge Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Under the WINTER GARDEN 34787 market on paper
$6,000 is 99% below the WINTER GARDEN 34787 median of $530,000, and at $1/sqft it sits under the Winter Garden average of $279.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 4 days on market in a Winter Garden market that averages 40 — if it fits, move quickly.
04Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of STOCKWORTH REALTY GROUP · Julie Bettosini, PA. MLS #O6430003.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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