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$686,000
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Property Description
Gated and guarded waterfront living in the exclusive community of Wyndham. This elegant waterfront residence sits on a large 0.80-acre lot with peaceful pond views, mature landscaping, and timeless architectural appeal. Stately wrought-iron gates, a brick-paved entry, and manicured grounds set the tone for the executive lifestyle this enclave is known for. Inside, the beautifully maintained 4-bedroom, 3-bath layout offers refined living spaces filled with natural light, soaring ceilings, crown moldings, upgraded wood flooring, and wide windows framing serene water views. A flexible executive office can easily function as a fourth bedroom. The chef-inspired kitchen features custom cabinetry, glass-front displays, granite countertops, stainless-steel appliances, and a built-in desk nook. The adjoining family room includes a cozy fireplace and custom wine storage, while the formal living and dining rooms add sophistication for gatherings. The private primary suite is a true retreat with room for a sitting area, dual walk-in closets, and a spa-like bath with jetted tub, walk-in shower, dual sinks, and elegant sconce lighting. Additional bedrooms are generously sized and well-separated for privacy. Step outside to enjoy resort-style Florida waterfront living. A covered lanai with audio/TV connections opens to an expansive paver patio, lagoon-style heated pool and spa, outdoor firepit, and tranquil pond and fountain views-ideal for entertaining or quiet evenings at home. The oversized two-car garage includes epoxy floors and extensive built-in storage. Recent upgrades include new wood flooring in all bedrooms and the office, new tile in both baths, expanded patios, upgraded irrigation, refreshed landscaping, and new interior/exterior paint. Wyndham residents enjoy tennis and pickleball courts, basketball, a playground, and manned security-all in a beautifully maintained lakefront setting near the Winter Haven Chain of Lakes, shopping, dining, medical care, and major highways. Disney World is under an hour away, with convenient access to Tampa and Orlando airports. A rare opportunity to own one of Wyndham's finest waterfront executive homes, offering luxury, privacy, and a stunning natural setting.
Full Property Details
Full Property Details for 105 Wyndham Dr
General
- Sold For: $686,000
- HOA FEE: $275/month
- HOA FEE FREQ.: Annually
- Taxes: $6,051 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: P4935887
- Added to Site: 134 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 12
- Interior Features: Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Wood Burning
- Appliances: Built-In Oven, Dishwasher, Dryer, Electric Water Heater, Range, Refrigerator, Washer
- Flooring: Ceramic Tile, Engineered Hardwood, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Gated, Park, Pickleball Court(s), Playground, Tennis Court(s), Vehicle Restrictions
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Screen Enclosure
- Spa: Yes
- Spa Description: Heated
- Security/Safety: Gated Community
Exterior
- Exterior Features: Irrigation System, Sliding Doors
- Deck/Patio: Covered, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Garage Faces Side
Location
- Area: 33884 - Winter Haven / Cypress Gardens
- County: Polk
- Development Name: 33884 - Winter Haven / Cypress Gardens
- Subdivision: WYNDHAM AT LAKE WINTERSET
- Driving Directions: Hwy 27 to Thompson Nursery Rd - West on Thompson Nursery to Wyndham Drive - Once through the gate make a right - Home will be down on your left
- Direction Faces: South
School Information
- Elementary School: Chain O Lakes Elem
- Middle School: Denison Middle
- High School: Lake Region High
Community
- Community Name: 33884 - Winter Haven / Cypress Gardens
- Community Features: Gated Community - Guard, Park, Playground, Tennis Court(s)
- Optional Amenities: Gated, Park, Pickleball Court(s), Playground, Tennis Court(s), Vehicle Restrictions
- Association: Yes
- Assoc. Name: Wyndham at Lake Winterset / Jonathan Turner
- Pet Restrictions: Must contact the HOA directly to confirm all pet rules and restrictions.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Propane, Sewer Connected, Water Connected
Structural Information
- Architectural Info: Custom
- Architectural Style: Custom
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: One
- Square Feet: 2,591
- Sq. Ft. Source: Public Records
- Living Area: 2,591 Sq. Ft.
- Year Built: 1998
Lot Features
- Property View: Water
- Lot Size (Acres): 0.8
- Lot Size (Sq. Ft.): 34,948
- Lot Size: 34948
- Frontage: Street Paved
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Pond
- Water Front Desc.: Pond
Financial Considerations
- Association Fee: $3,300
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $6,051
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WYNDHAM AT LAKE WINTERSET PB 100 PGS 34 THRU 38 LYING IN SECS 11 & 14 T29 R26 LOT 15
- Flood Zone Info: X
- APN: 262911687423000150
- Property ID: 262911687423000150
Listed by The Stones Real Estate Firm
Sold by Live Florida Realty
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Schools
Schools serving 105 Wyndham Dr
School District:Polk County School District
| Name | Grades | Distance |
|---|---|---|
Chain Of Lakes Elementary School 7001 State Highway 653, Winter Haven, FL 33884 | PK-5 | 1 mi |
Denison Middle School 400 Avenue A Southeast, Winter Haven, FL 33880 | 6-8 | 4.2 mi |
Lake Region High School 1995 Thunder Road, Eagle Lake, FL 33839 | 9-12 | 3.7 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 105 Wyndham Dr
Date
Details
Price
Change
Source
1/15/2026
Sold
$686,000
-4.06%
MLS
10/04/2025
Price Reduced
$715,000
-1.38%
MLS
9/04/2025
Listed
$725,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
105 Wyndham Drive, Winter Haven, FL 33884 (MLS# P4935887) is a Single Family property that was sold at $686,000 on January 15, 2026. Want to learn more about 105 Wyndham Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

