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Overview

4 bd5 ba4,010 sqft3 car garageSingle Family
TypeSingle Family
HOA$546.25/qtr
Built2005
Lot13,000 sqft
Living area4,010 sqft
Price / sqft$217
Garage3 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)Crown MoldingHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsSplit Bedroom

14411 Hampshire Bay Cir is a 2005-built home in Bay Isle 48 17, Winter Garden. Inside you'll find 4 bedrooms, 5 bathrooms, and 4,010 square feet of living space. Listed at $870,000 (about $217/sqft), 128 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $546.25 quarterly.

From the listing

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.

The essentials

Built
2005
Price / sqft
$217
On market
128 days
Annual tax
$11,924
HOA
$546.25/qtr
Flood zone
X · Low risk
Lot
13,000 sqft
Type
Single Family Residence

At a glance

Single family
Built 2005
Private pool
Gunite
3 car garage
Driveway
0.30 acres
Lot size
4,010 sqft
Living area

Payment

Est. monthly payment
$6,148/mo
Down payment (20%)
$174,000
Property taxes
$994/mo
HOA
$546.25/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
2005
Lot
13,000 sqft
Cooling
Central Air
Heating
Central, Electric, Heat Pump
Parking
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Garage
Pool
Gunite, In Ground, Salt Water, Screen Enclosure, Tile
Days on Market
128
Ceiling Fans(s)
Crown Molding
High Ceilings
Kitchen/Family Room Combo
Open Floorplan
Primary Bedroom Main Floor
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Walk-in Closet(s)
Outdoor Shower
Sidewalk
Association Recreation - Owned
Deed Restrictions
Irrigation-reclaimed Water
Park
Playground
Sidewalks
Street Lights
Built-in Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Microwave
Range Hood
Refrigerator
Elementary
SunRidge Elementary
Middle
SunRidge Middle
High
West Orange High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$11,924
Parcel #
34-22-27-0162-00-050

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Bay Isle 48 17
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
13,000 sqft
City LimitsLevelSidewalkPavedPrivate
HOA
$546.25/qtr
Bay Isle at Black Lake Homeowners Assn: c/o HMI

Price history

Date
Event
Price
8/21/2026
Price change
Source: Stellar MLS #O6413972
$870,000-1.7%
$217/sqft
-
Price change
Source: Stellar MLS #O6413972
$885,000-1.1%
$221/sqft
6/5/2026
Listed for sale
Source: Stellar MLS #O6413972
$895,000
$223/sqft

Neighborhood

14411 Hampshire Bay Cir
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $870,000
$865,000 – $870,000
99.5% – 100% of listTops out right at the list price
80% of listList price
222 of the last 442 home closings in 34787 landed at this number or higher (50%). The median one sat 22 days before it went under contract, and this one is on day 128 after a $25,000 cut.

Sample: 442 closed home sales in 34787 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$6,148/mo
Principal & interest$4,537
Property taxes$994
Insurance$435
HOA$182
Down payment20% · $174,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$870,000

$217 per sq ft

Beds and baths

4 beds, 5 baths

Size

4,010 sq ft

Time on market

128 days

Year built

2005

Monthly payment

About $6,148/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $11,924 annual tax bill, insurance, and the $546.25/qtr HOA fee.

HOA fee

$546.25/qtr

Managed by Bay Isle at Black Lake Homeowners Assn: c/o HMI.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered bySTOCKWORTH REALTY GROUPListing agent: Julie Bettosini, PAListing data from Stellar MLS, MLS# O6413972.

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