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Property Description
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!
Full Property Details
Full Property Details for 499 Club Dr
General
- Price: $205,000
- HOA FEE: $520/month
- HOA FEE FREQ.: Quarterly
- Taxes: $2,064 (2025)
- Status: Active
- Type: Townhouse
- Source: MidFloridaRegionalMLS
- MLS ID: O6447987
- Updated: Today (10/13/2026)
- Added to Site: Today
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 7
- Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Vaulted Ceiling(s)
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Laminate, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: Laundry Closet, Upper Level
Additional Information
- Shared Amenities: Clubhouse, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Exterior
- Exterior Features: Sliding Doors
- Deck/Patio: Covered, Patio, Screened
- Porch/Patio/Deck: Covered, Patio, Screened
Location
- Area: 32708 - Casselberrry/Winter Springs / Tuscawilla
- County: Seminole
- Development Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
- Subdivision: CYPRESS CLUB
- Driving Directions: 434 to North on Sheoh Blvd, to Right on 2nd Moree Loop, to Cypress Club entry, then left on to Club Drive. House will be on right.
- Direction Faces: Northwest
Community
- Community Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
- Community Features: Clubhouse, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Tennis Court(s)
- Optional Amenities: Clubhouse, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
- Association: Yes
- Assoc. Name: Michelle Pogue
- Assoc. Fees Include: Community Pool, Maintenance Structure, Maintenance Grounds
- Pet Restrictions: Buyer responsibility to independently verify with HOA and city/county any pet restrictions.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 1,224
- Sq. Ft. Source: Public Records
- Year Built: 1987
Lot Features
- Lot Size (Acres): 0.03
- Lot Size (Sq. Ft.): 1,294
- Lot Size: 1294
- Street/Road Desc.: Asphalt
Financial Considerations
- Association Fee: $1,561
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $2,064.58
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 72 CYPRESS CLUB PB 33 PGS 25 & 26
- Flood Zone Info: X
- APN: 3320305HY00000720
- Property ID: 3320305HY00000720
Listed by Bloom Home Group Realty Llc
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Price & Sales History for 499 Club Dr
Date
Details
Price
Change
Source
10/13/2026
Listed
$205,000
-24.07%
MLS
7/28/2022
Sold
$270,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 499 Club Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,987
6%
$165,128
3%
2024
$1,868
5%
$160,474
3%
2023
$1,786
-21%
$155,800
11%
2021
$2,258
-11%
$140,282
-20%
2022
$2,543
13%
$176,098
63%
2021
$2,258
111%
$108,271
2%
2019
$1,072
1%
$105,837
2%
2018
$1,057
1%
$103,864
2%
2017
$1,042
-38%
$101,728
6%
2016
$1,677
21%
$95,544
23%
2015
$1,385
3%
$77,400
3%
2014
$1,341
7%
$74,799
10%
2013
$1,249
—
$67,767
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 499 Club Dr
499 Club Drive, Winter Springs, FL 32708 (MLS# O6447987) is a Townhouse property with 2 bedrooms and 2 full bathrooms. 499 Club Drive is currently listed for $205,000 and was received on October 13, 2026. Want to learn more about 499 Club Drive? Do you have questions about finding other Townhouse real estate for sale in Winter Springs? You can browse all Winter Springs real estate or contact a Coldwell Banker agent to request more information.

