2653 CAYMAN WAY
WINTER PARK, FL 32792
About this home
All play and no work! This beautifully maintained 3-bedroom, 2-bath townhouse offers the perfect combination of comfort, convenience, low HOA fees, and an unbeatable Winter Park location. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle, this home checks all the boxes. Step inside to discover a bright, open floor plan highlighted by vaulted ceilings and dramatic clerestory windows that flood the home with natural light. The thoughtfully designed split-bedroom floor plan provides added privacy, while the spacious primary suite features a walk-in closet and sliding glass doors leading to your own private, fenced backyard. The kitchen offers a comfortable eat-in dining area, abundant cabinet space, and an oversized pantry for exceptional storage. An enclosed laundry room adds everyday convenience, while recent updates provide peace of mind, including a brand-new roof (2026), newer A/C, updated plumbing, updated electrical panels, and fresh interior paint. Step outside to your covered patio with a convenient storage closet, overlooking a fully fenced backyard—the perfect place to relax, entertain, or enjoy your morning coffee. With low HOA fees, you'll also enjoy outstanding community amenities, including three swimming pools, tennis courts, a playground, a clubhouse, and a private south gate providing quick and convenient access in and out of the community. Ideally located just minutes from Downtown Winter Park, you'll love being close to Park Avenue, shopping, dining, entertainment, top-rated schools, and major highways, making commuting throughout Central Florida quick and convenient. If you've been searching for an affordable, move-in-ready home with major system updates, fantastic amenities, low HOA fees, and an exceptional Winter Park location, this is the one you've been waiting for. Schedule your private showing today!
Facts & features
Interior
- Bedrooms
- 3
- Bathrooms
- 2
- Living area
- 1,284 sqft
- Heating
- Central
- Cooling
- Central Air
- Flooring
- Carpet, Ceramic Tile
- Features
- Ceiling Fans(s), High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s)…
- Appliances
- Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Washer
Exterior & lot
- Lot size
- 3,135 sqft (0.07 ac)
- Roof
- Membrane, Shingle
- Construction
- Block, Stucco, Frame, Wood Siding
- Exterior
- Private Yard, Sidewalk, Sliding Doors
Financial
- HOA dues
- $99 / monthly
- Annual tax
- $3,297 (2025)
- Price / sqft
- $221/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- Electricity Connected, Public, Sewer Connected, Water Connected
Property
- Property type
- Townhouse
- Year built
- 1978
- Subdivision
- WINDWARD SQUARE
- County
- Seminole
Assigned schools
- Elementary
- Eastbrook Elementary
- Middle
- Tuskawilla Middle
- High
- Lake Howell High
Listing
- Status
- Active
- Days on market
- Today
- MLS #
- MFR801819541
- Source
- Stellar MLS
Listed by Kyle Clark · RE/MAX TOWN & COUNTRY REALTY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 29 comparable sales within 2 miles of WINTER PARK, FL. priced in line with RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $1,512/mo
- Property tax
- $213/mo
- Home insurance
- $200/mo
Tax, insurance and HOA are editable estimates with Florida-typical defaults — Florida homeowners insurance in particular varies widely by location and elevation. Confirm exact figures with a lender and insurer.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price historySample data
Reference timeline for $284,000. Live MLS history swaps in with the Stellar feed.
| Date | Event | Price | Change |
|---|---|---|---|
| 2026-08 | Listing updated | $284,000 | — |
| 2026-05 | Price changed | $284,000 | — |
| 2026-03 | Listed | $284,000 | — |
NeighbourhoodSample data
Reference scores for WINTER PARK, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Location
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