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Overview

5 bd4 ba3,197 sqft2 car garageSingle Family
TypeSingle Family
HOA$1,100/yr
Built1999
Lot12,521 sqft
Living area3,197 sqft
Price / sqft$239
Garage2 car

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About this home

Ceiling Fans(s)High CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorWalk-in Closet(s)Private Mailbox

2157 Wintermere Pointe Dr is a 1999-built home in Wintermere Pointe, Winter Garden. Inside you'll find 5 bedrooms, 4 bathrooms, and 3,197 square feet of living space. Listed at $765,000 (about $239/sqft), 52 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $1,100 annually.

From the listing

Welcome to this beautifully renovated residence offering an additional den, approximately 3,197 square feet of comfortable living space, and a two-car garage. Set on an oversized 0.29-acre lot in the gated Wintermere Pointe community, this home blends generous living areas with thoughtful, contemporary upgrades. Inside, you’re greeted by a bright, open layout finished with fresh neutral colors, crown molding, updated lighting, and attractive flooring throughout the main living areas. The floor plan provides multiple spaces for entertaining, dining, working from home, or simply relaxing. The completely redesigned kitchen serves as the heart of the home, featuring:Extensive shaker-style cabinetry, Dramatic stone countertops, Classic subway-tile backsplash, Under-cabinet lighting, Stainless-steel appliances, Double wall ovens, Contemporary range hood, Oversized waterfall island with abundant workspace and storage, built-in window seat with additional cabinetry, Separate beverage area with wine storage and beverage refrigerators. The kitchen opens naturally to the expansive living and dining areas, creating an inviting atmosphere for everyday living and gatherings. Large windows and sliding glass doors bring in natural light and offer easy access to the outdoor living space and spacious backyard. The first-floor den provides a versatile area that can serve as a home office, study, media room, or guest retreat. With five bedrooms and four bathrooms, the home offers comfortable accommodations and a layout designed for both privacy and flexibility. The upstairs layout includes a spacious bonus area that can easily be converted into a movie theater room. With existing built-in cabinetry and space for a refrigerator or beverage center, it’s an ideal setup for a private entertainment space, gaming room, or family media lounge. This home is located in one of Winter Garden’s highly regarded school zones, serving: Lake Whitney Elementary School, SunRidge Middle School, West Orange High School. Families appreciate the strong academic reputation and convenient proximity to these schools. This area is Prime Winter Garden Location. Just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways—including SR 429, Florida’s Turnpike, and SR 408—this move-in-ready home offers space, style, and accessibility in one of Winter Garden’s established gated communities. Schedule Your Private Showing Come experience the comfort, upgrades, and welcoming atmosphere of this beautifully updated Winter Garden home.

The essentials

Built
1999
Price / sqft
$239
On market
52 days
Annual tax
$9,260
HOA
$1,100/yr
Flood zone
X · Low risk
Lot
12,521 sqft
Type
Single Family Residence

At a glance

Single family
Built 1999
2 car garage
0.29 acres
Lot size
3,197 sqft
Living area

Payment

Est. monthly payment
$5,236/mo
Down payment (20%)
$153,000
Property taxes
$772/mo
HOA
$1,100/yr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1999
Lot
12,521 sqft
Cooling
Central Air, Attic Fan
Heating
Central
Parking
-
Days on Market
52
Ceiling Fans(s)
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Open Floorplan
Primary Bedroom Main Floor
Walk-in Closet(s)
Private Mailbox
Sidewalk
Built-in Oven
Cooktop
Dishwasher
Microwave
Range Hood
Refrigerator
Wine Refrigerator
Homestead exemption on file Flood Zone X
Annual Tax (2025)
$9,260
Parcel #
02-23-27-8456-00-120

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
Wintermere Pointe
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
12,521 sqft
HOA
$1,100/yr
Shelby Hercules

Price history

Date
Event
Price
10/9/2026
Price change
Source: Stellar MLS #TB8532509
$765,000-3.8%
$239/sqft
8/20/2026
Listed for sale
Source: Stellar MLS #TB8532509
$795,000
$249/sqft

Neighborhood

2157 Wintermere Pointe Dr
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $765,000
$760,000 – $765,000
99.5% – 100% of listTops out right at the list price
80% of listList price
222 of the last 443 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 52 after a $30,000 cut.

Sample: 443 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
$5,236/mo
Principal & interest$3,990
Property taxes$772
Insurance$383
HOA$92
Down payment20% · $153,000
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 is the fee 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

$765,000

$239 per sq ft

Beds and baths

5 beds, 4 baths

Size

3,197 sq ft

Time on market

52 days

Year built

1999

Monthly payment

About $5,236/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $9,260 annual tax bill, insurance, and the $1,100/yr HOA fee.

HOA fee

$1,100/yr

Managed by Shelby Hercules.

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 bySOUTH EARTH REALTY LLCListing agent: Ting LiListing data from Stellar MLS, MLS# TB8532509.

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