Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities — including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by — groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!
Property Details
Price:
$205,000
MLS #:
O6447987
Status:
Active
Beds:
2
Baths:
2
Type:
Townhouse
Subdivision:
CYPRESS CLUB
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Oct 13, 2026
Finished Sq Ft:
1,224
Total Sq Ft:
1,280
Lot Size:
1,294 sqft / 0.03 acres (approx)
Year Built:
1987
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Vaulted Ceiling(s)
Laundry Features
Laundry Closet, Upper Level
Levels
Two
Exterior
Association Amenities
Clubhouse, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Community Features
Clubhouse, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Tennis Court(s)
Construction Materials
Block, Stucco
Direction Faces
Northwest
Exterior Features
Sliding Doors
Patio And Porch Features
Covered, Patio, Screened
Roof
Shingle
Financial
HOA Fee
$1,561
HOA Fee 2
$424
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Quarterly
HOA Includes
Community Pool, Maintenance Structure, Maintenance Grounds
HOA Name
Michelle Pogue
HOA Name 2
The Highlands
HOA Phone
4077886700
HOA Phone 2
4077701748
Tax Year
2025
Taxes
$2,065
Map
Community
- Address499 CLUB DRIVE WINTER SPRINGS FL
- SubdivisionCYPRESS CLUB
- CityWINTER SPRINGS
- CountySeminole
- Zip Code32708
Market Summary
Current real estate data for Townhouse in WINTER SPRINGS as of Oct 19, 2026
41
Townhouse Listed
87
Avg DOM
222
Avg $ / SqFt
$331,974
Avg List Price
Property Summary
- Located in the CYPRESS CLUB subdivision, 499 CLUB DRIVE WINTER SPRINGS FL is a Townhouse for sale in WINTER SPRINGS, FL, 32708. It is listed for $205,000 and features 2 beds, 2 baths, and has approximately 1,224 square feet of living space, and was originally constructed in 1987. The current price per square foot is $167. The average price per square foot for Townhouse listings in WINTER SPRINGS is $222. The average listing price for Townhouse in WINTER SPRINGS is $331,974. To schedule a showing of MLS#o6447987 at 499 CLUB DRIVE in WINTER SPRINGS, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of BLOOM HOME GROUP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 499 CLUB DRIVE
WINTER SPRINGS, FL
