Beautiful 2 bedroom 2 bathroom townhome within The Highlands Community. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New A/C 2023. Upstairs flexible loft space makes for a nice home office. Large primary bedroom has beautiful laminate floors and plenty of closet space and updated bathroom. Two assigned parking spaces directly in front of your townhome makes coming home convenient. Cypress Club residents enjoy their own private community pool in addition to All Highlands amenities. They include Audibon Park with BBQ/Picnic Area, Playgrounds, Olympic Size Pool, Kiddie Pool, Nature Walking Trails & Tennis & Pickleball Courts and a Clubhouse. Zoned for highly rated Seminole County Schools with The Highlands elementary school located within the community. Nearby Cross Seminole Trail and Central Winds Park. Located close to 17-92, SR417, grocery stores, fitness clubs.
Property Details
Price:
$247,500
MLS #:
O6391855
Status:
Active
Beds:
2
Baths:
2
Type:
Townhouse
Subdivision:
CYPRESS CLUB
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Mar 20, 2026
Finished Sq Ft:
1,224
Total Sq Ft:
1,334
Lot Size:
1,687 sqft / 0.04 acres (approx)
Year Built:
1987
See this Listing
Schools
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central
Interior Features
Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Thermostat, Vaulted Ceiling(s)
Laundry Features
Inside, Upper Level
Levels
Two
Exterior
Architectural Style
Contemporary
Association Amenities
Pickleball Court(s), Trail(s)
Community Features
Community Mailbox, Deed Restrictions, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Direction Faces
Northwest
Exterior Features
Irrigation System, Lighting, Sidewalk, Sliding Doors
Patio And Porch Features
Rear Porch, Screened
Roof
Tile
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, Pool Maintenance
HOA Name
Michelle Pogue
HOA Name 2
The Highlands
HOA Phone
407)788-6700
HOA Phone 2
(352)366-0234
Tax Year
2025
Taxes
$1,987
Map
Community
- Address499 CLUB DRIVE WINTER SPRINGS FL
- SubdivisionCYPRESS CLUB
- CityWINTER SPRINGS
- CountySeminole
- Zip Code32708
Subdivisions in WINTER SPRINGS
- ARROWHEAD AT TUSCAWILLA UNIT 1
- ARROWHEAD AT TUSCAWILLA UNIT 2
- AVERY PARK
- BAHAMA RANCHES
- BARCLAY RESERVE TWNHMS
- BARRINGTON ESTATES
- BARRINGTON ESTS
- BAY TREE SEC 09
- BAY TREE SEC 10
- BAYTREE VILLAGE
- BENTLEY GREEN UNIT 1
- CASA PARK VILLAS PH 1
- CASA PARK VILLAS PH 2
- CHESTNUT ESTATES PH 1
- COUNTRY CLUB VILLAGE UNIT 1
- COUNTRY CLUB VILLAGE UNIT 3
- CREEKS RUN
- CYPRESS CLUB
- CYPRESS VILLAGE 3RD REP TR C PH 1
- D R MITCHELLS SURVEY OF THE LEVY GRANT
- DEER RUN UNIT 19A
- DEER RUN UNIT 21A
- DEERSONG
- DEERSONG 2
- EAGLES POINT PH 6
- EAGLES WATCH PH 1
- ENTZMINGER FARMS ADD 2
- FAIRWAY OAKS UNIT 1
- FLAMINGO SPGS
- FOX GLEN AT CHELSEA PARC TUSCAWILLA PH 2
- FOXMOOR UNIT 2
- FOXMOOR UNIT 3
- GEORGETOWNE UNIT 1
- GEORGETOWNE UNIT 2
- GEORGETOWNE UNIT 3
- GLEN EAGLE UNIT 4
- GOLFSIDE VILLAS
- GREENBRIAR SUB PH 1
- GREENBRIAR SUB PH 2
- GREENS AT TUSCAWILLA
- GREENSPOINTE
- HACIENDA VILLAGE
- HARBOR WINDS
- HERITAGE COMMONS
- HERITAGE PARK TOWNHOMES
- HERITAGE PARK TWNHMS
- HICKORY GROVE
- HIGHLAND VILLAGE 1
- HIGHLAND VILLAGE 2
- HIGHLANDS SEC 1
- HIGHLANDS SEC 4
- HIGHLANDS SEC 6
- HIGHLANDS SEC 6 BEDS: 3
- HOWELL CREEK RESERVE PH 2
- HOWELL CREEK RESERVE PH 3
- INDIAN RIDGE
- INDIAN RIDGE PH 2
- JESUPS LANDING
- JESUPS RESERVE TWNHMS REP
- MOUNT GREENWOOD UNIT 2 OF
- MOUNT GREENWOOD UNIT 4
- NORTH ORLANDO
- NORTH ORLANDO 1ST ADD
- NORTH ORLANDO 2ND ADD
- NORTH ORLANDO RANCHES SEC 02
- NORTH ORLANDO RANCHES SEC 02A
- NORTH ORLANDO RANCHES SEC 06
- NORTH ORLANDO RANCHES SEC 09
- NORTH ORLANDO RANCHES SEC 10
- NORTH ORLANDO TERRACE UNIT 1 SEC 4
- NORTH ORLANDO TERRACE UNIT 2 SEC 8
- NORTH ORLANDO TERRACE UNIT 2 SEC 9
- NORTH ORLANDO TOWNSITE 4TH ADD REP
- OAK FOREST UNIT 3
- OAK FOREST UNIT 4
- OAK FOREST UNIT 6
- OAK FOREST UNIT 7
- PARKSTONE
- PARKSTONE UNIT 3
- PARKSTONE UNIT 4
- RESERVE AT TUSCAWILLA PH 2
- SEASONS THE
- SEMINOLE CROSSING TWNHMS
- SEVEN OAKS
- SEVEN OAKS TWO
- SEVILLE CHASE
- SHEOAH A CONDO SEC 2
- SHEOAH SEC 1
- STONE GABLE
- SUNRISE UNIT 2-A
- SUNRISE UNIT 2-B
- SUNRISE UNIT 2C
- SUNRISE UNIT 2D
- SUNRISE UNIT TWO C
- SUNRISE VILLAGE UNIT 1
- SUNRISE VILLAGE UNIT 6
- SUSAN WOODS
- TALMO SUB
- TUSCA OAKS
- TUSCANY PLACE PH 1
- TUSCAWILLA
- TUSCAWILLA PARCEL 90
- TUSCAWILLA UNIT 06
- TUSCAWILLA UNIT 12
- TUSCAWILLA UNIT 14A
- TUSCAWILLA UNIT 14B
- TUSKABAY PH 1
- TUSKAWILLA CROSSINGS 34’S
- TUSKAWILLA CROSSINGS PH 1
- TUSKAWILLA CROSSINGS PH 2
- TUSKAWILLA POINT
- TUSKAWILLA TRAIL SUBD
- WATTS FARMS
- WEDGEWOOD TENNIS VILLAS
- WILDWOOD
- WILLIAMSON HEIGHTS
- WILLOW RUN
- WINDING HOLLOW UNIT 2
- WINTER SPGS
- WINTER SPGS TOWN CENTER A REP
- WINTER SPGS UNIT 3
- WINTER SPGS UNIT 4
- WINTER SPGS VILLAGE PH 2
- WINTER SPRINGS UNIT 4
Market Summary
Current real estate data for Townhouse in WINTER SPRINGS as of Apr 23, 2026
46
Townhouse Listed
70
Avg DOM
222
Avg $ / SqFt
$340,522
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 $247,500 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 $202. The average price per square foot for Townhouse listings in WINTER SPRINGS is $222. The average listing price for Townhouse in WINTER SPRINGS is $340,522. To schedule a showing of MLS#o6391855 at 499 CLUB DRIVE in WINTER SPRINGS, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
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Courtesy of FLORIDA HOME TEAM 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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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
