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2660 Wyndsor Oaks Way

WINTER HAVEN, FL 33884

4 beds
4 baths
3,633 sqft
~1/2 acre lot
$238 per sqft
2005 build
– on site

Welcome to luxury living in the exclusive gated community of Wyndsor at Lake Winterset! This exceptional 4-bedroom, 2 full bath, 2 half bath home offers 3,600 sq ft of beautifully upgraded space, thoughtfully designed for both comfort and high-end entertaining. From the moment you enter, you’ll be captivated by the soaring ceilings with custom painted and crafted detail, large sun-filled windows, and the seamless flow of the open layout. The great room features a cozy fireplace and built-in shelving, with the seamless integration of the formal dining area. The private movie room makes hosting effortless. At the heart of the home, the chef’s kitchen is outfitted with top-of-the-line built-in appliances, a 5-burner gas stove, and overlooks a bright family room and breakfast nook. Speakers and volume control throughout the home create the perfect atmosphere for entertaining.The primary suite is a private retreat featuring a spa-style tub, extra-large walk-in shower, and spacious walk-in closets. All bedrooms provide comfort, privacy, and generous space — including a versatile fourth bedroom that can function perfectly as a home office or guest room. Step outside into your private backyard oasis — enjoy a screened-in pool, built-in outdoor grill, covered back patio, lighting and ceiling fans, and lush, mature landscaping including fruit trees. There’s also a covered front porch, shutters throughout, and a 3-car garage with circular driveway. Additional highlights include a new roof (2022), whole-house water filtration system, ample front and backyard space, and a welcoming community with tennis courts, a playground, and convenient access to the Chain of Lakes. This home is the complete package — elegant, functional, and perfect for entertaining. Schedule your private showing today!

Listing courtesy of STELLAR_MLS / LPT REALTY, LLC

Last checked: Checking… • Last updated May 3, 2025 •

MLS# TB8380095 —

The Building

Year Built:

2005
New Construction:

false
Architectural Style:

Custom
Construction Materials:

Concrete
Levels:

One
Stories Total:

1
Roof:

Shingle
Foundation Details:

Slab
Window Features:

Shutters
Patio And Porch Features:

Covered
Security Features:

Gated Community
Building Area Total:

5382
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Cathedral Ceiling(s)
Flooring:

Carpet
Additional Rooms:

Attic
Fireplace:

true
Fireplace Features:

Gas

Room Dimensions

Living Area:

3633
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

SR 540 (Cypress Gardens Rd) to Helena Road to Wyndsor. Turn left after guard gate to house.
Latitude:

27.973239
Longitude:

-81.691503
Coordinates:

-81.691503, 27.973239

The Property

Parcel Number:

262911687424002050
Property Type:

Residential
Property Subtype:

Single Family Residence
Property Condition:

Completed
Property Attached:

false
Lot Size Acres:

0.6
Lot Size Area:

26341
Lot Size SqFt:

26341
Lot Size Units:

Square Feet
Total Acres:

1/2 to less than 1
Direction Faces:

South
View:

false
Exterior Features:

French Doors
Vegetation:

Fruit Trees
Water Source:

Public
Road Responsibility:

Private Maintained Road
Road Surface Type:

Asphalt
Flood Zone Code:

x
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

false
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

5
Tax Block:

B
Tax Legal Description:

WYNDSOR AT LAKE WINTERSET PB 116 PGS 2 & 3 BLOCK B LOT 5
Tax Book Number:

116-2
Tax Annual Amount:

$9,565.22

Beds

Bedrooms Total:

4

Baths

Total Baths:

3
Total Baths:

4
Full Baths:

2
Half Baths:

2

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/TB8380095
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

BB/HS Internet Available
Sewer:

Public Sewer

Appliances

Appliances:

Built-In Oven
Laundry Features:

Electric Dryer Hookup

Schools

Elementary School:

Chain O Lakes Elem
Middle Or Junior School:

Denison Middle
High School:

Lake Region High

The Community

Subdivision Name:

WYNDSOR AT LAKE WINTERSET
Senior Community:

false
Community Features:

Gated Community - No Guard
Waterview:

false
Water Access:

false
Waterfront:

false
Spa Features:

In Ground
Pool Private:

true
Pool Features:

Screen Enclosure
Pets Allowed:

Yes
Association:

true
Association Fee:

2800
Association Fee Frequency:

Annually
Association Fee Requirement:

Required
Monthly HOA Amount:

233.33
Ownership:

Fee Simple
Association Approval Required:

false

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

3
Carport:

false
Covered Spaces:

3
Open Parking:

true
Parking Features:

Circular Driveway

Monthly cost estimate

Asking price

$865,000

Expense	Monthly cost
Mortgage	$4,631
Taxes	$797
Insurance	$237
HOA fees	$233
Utilities	$248 See report
Total	$6,146/mo.^*
	^*This is an estimate

Explore the Area

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Sale history

Date	Event	Source	Price	% Change
5/2/25 May 2, 2025	Listed / Active	STELLAR_MLS	$865,000	44.8% (5.0% / YR)
4/28/16 Apr 28, 2016		STELLAR_MLS	$597,500

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This house located in Wyndsor at Lake Winterset, FL 33884 is currently for sale for $865,000. 2660 Wyndsor Oaks Way is a 3,633 square foot house with 4 beds and 4 baths that has been on Estately for 1 days. 2660 Wyndsor Oaks Way is in the Wyndsor at Lake Winterset neighborhood of WINTER HAVEN. This house is in the attendance area of Frank E. Brigham Academy, Jewett School Of The Arts, Denison Middle School, Lake Alfred Polytech Academy, Chain Of Lakes Elementary School, Lake Region High School, and Jewett Middle Academy Magnet.

Listing Courtesy of: STELLAR_MLS and LPT REALTY, LLC.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.