$284,000
2653 Cayman Way
Winter Park, FL 32792
Listing updated: August 4, 2026 at 5:56 PM ET
Listing courtesy of Re/Max Town & Country Realty · Kyle Clark · MLS #O6430560 · Active · 407-695-2066Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
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!
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 history0 days on market
- Status: ActiveAug 4, 2026
- Listed$284,000Aug 4, 2026
- Price increased$284,000
Facts & features
- Property type
- Residential
- Sub type
- Townhouse
- Status
- Active
- Days on market
- 0
- Subdivision
- Windward Square
- County
- Seminole
- Year built
- 1978
- Living area
- 1,284 sq ft
- Price/sq ft
- $221
- Building area
- 1,482 sq ft (Public Records)
- Lot size
- 3,135 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X
- Annual taxes
- $3,297 (2025)
- Parcel #
- 34-21-30-521-0000-1860
- Zoning
- RES
- MLS #
- O6430560
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Carpet, Ceramic Tile
- Appliances
- Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- West
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Attached garage
- No
- Parking features
- Driveway, Guest, Parking Pad
HOA & Financial
- HOA fee
- $99 / Monthly
- Monthly HOA
- $99/mo
- Total monthly fees
- $99/mo
- Total annual fees
- $1,186
- HOA name
- GREAT COMMUNITIES
- CDD
- No
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- No
- Lease restrictions
- Yes
- Additional lease restrictions
- BUYER TO VERIFY WITH HOA 3 YEAR OWNER OCCUPANT BEFORE LEASING
Exterior & Construction
- Exterior features
- Private Yard, Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco, Frame, Wood Siding
- Roof
- Membrane, Shingle
- Foundation
- Slab
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Connected, Public, Sewer Connected, Water Connected
Community
- Pets allowed
- 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 |
|---|---|---|
| Living Room | First | 18x13 |
| Dinette | First | 10x9 |
| Kitchen | First | 11x18 |
| Primary Bedroom | First | 15x12 |
| Bedroom 2 | First | 13x10 |
| Bedroom 3 | First | 12x10 |
Listing Details
- Listing date
- 2026-08-04
- On market date
- 2026-08-04
- Original list price
- $284,000
- Occupant type
- Vacant
- MLS area
- 32792 - Winter Park/Aloma
- Listing AOR
- Orlando Regional
- Status changed
- 2026-08-04
- Tax legal description
- LOT 186 WINDWARD SQUARE SEC 2 PB 20 PGS 34 & 35
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
SEMORAN TO EAST ON HOWELL BRANCH COMMUNITY IS ON THE RIGHT AND USE SECOND ENTRANCE ON ANTILLES AND CAYMAN IS FIRST RIGHT AND UNIT IS ON THE RIGHT SIDE
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Listing provided by Stellar MLS
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 August 4, 2026 at 5:56 PM 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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