$269,000
446 Club Drive
Winter Springs, FL 32708
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
About this home
Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.
Local Insight
At $184/sqft, this 1994 townhouse is priced well below the broader Oviedo market median of $515K, which makes sense given its smaller footprint and age—but that $520 monthly HOA is meaningful over time and worth stress-testing against comparable rentals if you're weighing investment potential. The location itself is solid for commuters; you're in Winter Springs with clean schools and reasonable I-4 access, though you're not quite in the heart of Oviedo's tech corridor hotspots like Lago Mar or closer-in subdivisions. The tight 0.03-acre lot and townhouse format mean minimal exterior upkeep, which appeals to some buyers, but resale appeal will depend heavily on whether the floor plan and finishes compete with newer inventory at similar price points.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history114 days on market
- Status: ActiveFeb 12, 2026
- Listed$279,900Feb 12, 2026
- Price reduced$269,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Townhouse
- Status
- Active
- Days on market
- 114
- Subdivision
- Cypress Club
- County
- Seminole
- Year built
- 1994
- Living area
- 1,460 sq ft
- Price/sq ft
- $184
- Building area
- 1,512 sq ft (Public Records)
- Lot size
- 1,448 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12117C0160F)
- Annual taxes
- $886 (2024)
- Parcel #
- 33-20-30-5HY-0000-0380
- Zoning
- PUD
- MLS #
- O6380694
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Ceramic Tile, Laminate
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Split Bedroom
- Laundry
- Corridor Access, Laundry Closet, Upper Level
- Stories / Levels
- Two
- Direction faces
- East
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Attached garage
- No
- Parking features
- Covered, Guest, Reserved
- Carport
- Yes
HOA & Financial
- HOA fee
- $1,561 / Quarterly
- Monthly HOA
- $520/mo
- Total monthly fees
- $556/mo
- Total annual fees
- $6,669
- HOA name
- CYPRESS CLUB/CHRISTOPHER ANDERSON
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 7 Months
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- For updated information regarding lease tenant approval please contact the association directly.
Exterior & Construction
- Exterior features
- Basketball Court, Playground, Sidewalk, Sliding Doors, Tennis Court(s)
- Construction materials
- Stucco
- Roof
- Tile
- Foundation
- Block, Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Available, Electricity Connected, Phone Available, Public, Sewer Available, Sewer Connected, Underground Utilities, Water Available, Water Connected
Community
- Pets allowed
- Number Limit, Size Limit, Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 11x8 |
| Living Room | First | 18x9.5 |
| Primary Bedroom | Second | 15x14 |
| Bedroom 1 | First | |
| Bedroom 2 | Second | |
| Bathroom 1 | First | |
| Bathroom 2 | Second | |
| Laundry | Second | |
| Balcony/Porch/Lanai | First |
Listing Details
- Listing date
- 2026-02-07
- On market date
- 2026-02-12
- Original list price
- $279,900
- Occupant type
- Owner
- MLS area
- 32708 - Casselberrry/Winter Springs / Tuscawilla
- Listing AOR
- Orlando Regional
- Status changed
- 2026-02-12
- Tax legal description
- LOT 38 CYPRESS CLUB PB 33 PGS 25 & 26
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
FROM 17-92 TO SHEPARD RD - TURN RIGHT AT SHEOAH BLVD - GO OVER BRIDGE AND TAKE A LEFT ONTO MOREE LOOP - VEER LEFT INTO CYPRESS CLUB COMMUNITY AND TAKE A RIGHT ONTO CLUB DR
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information 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.
Based on information submitted to the MLS GRID as of June 6, 2026 at 9:48 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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