2653 CAYMAN WAY
Winter Park, FL 32792
$284,000
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, ...
Listing Courtesy of: RE/MAX TOWN & COUNTRY REALTY
407-695-2066
Buyer Represented by: KELLER WILLIAMS ADVANTAGE III
| Listing Id: | O6430560 |
|---|---|
| List Price: | $284,000 |
| Close Price: | $284,000 |
| Close Date: | 2026-09-09 |
| Property Type: | Residential |
| Property Sub Type: | Townhouse |
| Status: | Closed |
| Bedrooms Total: | 3 |
| Bathrooms Full: | 2 |
| Living Area: | 1,284 |
| Tax Annual Amount: | $3,297 |
| Lot Size Square Feet: | 3,135 |
| Lot Size Acres: | 0.07 |
| Architectural Style: | Other |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Seminole |
| Subdivision Name: | Windward Square |
| Postal Code: | 32792 |
| Year Built: | 1978 |
| Appliances: | Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Washer |
| Association Amenities: | Clubhouse, Gated, Playground, Pool, Recreation Facilities, Shuffleboard Court, Tennis Court(s) |
| Builder Name: | BABCOCK HOMES |
| Association Fee: | $99 |
| Association Fee Frequency: | Monthly |
| Association Fee Includes: | Common Area Taxes, Pool, Maintenance Grounds, Private Road |
| Bathrooms Total Integer: | 2 |
| Building Area Source: | Public Records |
| Building Area Total: | 1482 |
| Building Area Units: | Square Feet |
| Direction Faces: | West |
| Foundation Details: | Slab |
| Construction Materials: | Block, Stucco, Frame, Wood Siding |
| Cooling: | Central Air |
| 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 |
| Elementary School: | Eastbrook Elementary |
| Exterior Features: | Private Yard, Sidewalk |
| Fencing: | Wood |
| Flooring: | Carpet, Ceramic Tile |
| Furnished: | Unfurnished |
| Community Features: | Deed Restrictions, Gated Community - No Guard, Park, Playground, Pool, Sidewalks, Tennis Court(s) |
| Heating: | Central |
| High School: | Lake Howell High |
| 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 Features: | Inside, Laundry Room |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Features: | Cul-De-Sac, In County, Landscaped, Sidewalk, Paved, Private |
| Lot Size Acres: | 0.07 |
| Postal Code Plus4: | 1618 |
| Middle Or Junior School: | Tuskawilla Middle |
| MLS Area Major: | 32792 - Winter Park/Aloma |
| MLS Area Major: | 32792 - Winter Park/Aloma |
| Original List Price: | $284,000 |
| Other Equipment: | Private Yard |
| Parcel Number: | 34-21-30-521-0000-1860 |
| Parking Features: | Driveway, Guest, Parking Pad |
| Patio And Porch Features: | Porch, Rear Porch |
| Pets Allowed: | Yes |
| Township: | 21 |
| Road Surface Type: | Paved |
| Roof: | Membrane, Shingle |
| Listing Terms: | Cash, Conventional, FHA, VA Loan |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Utilities: | Electricity Connected, Public, Sewer Connected, Water Connected |
| View: | Trees/Woods |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 34 |
| Zoning: | RES |
| Possession: | Close Of Escrow |
| Vegetation: | Mature Landscaping, Trees/Landscaped |
| Window Features: | Window Treatments |
| Additional Lease Restrictions: | BUYER TO VERIFY WITH HOA 3 YEAR OWNER OCCUPANT BEFORE LEASING |
| Additional Rooms: | Inside Utility, Storage Rooms |
| Association Approval Required Yn: | No |
| Association Email: | SSCOTT@GREATCOMMUNITIES.COM |
| Association Fee Requirement: | Required |
| Association Url: | WWW.GREATCOMMUNITIES.COM |
| Available For Lease Yn: | No |
| Backups Requested Yn: | No |
| Building Area Total Srch Sq M: | 137.68 |
| Building Name Number: | 2653 |
| Calculated List Price By Calcula: | 221.18 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6430560?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6430560?w=Customer |
| Dpryn: | Yes |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 119.29 |
| Lot Size Square Meters: | 291 |
| Minimum Lease: | 1-2 Years |
| Monthly Hoa Amount: | $99 |
| Num Of Own Years Prior To Lse: | 3 |
| Pet Restrictions: | BUYER TO VERIFY WITH HOA/COUNTY |
| Realtor Info: | As-Is, Docs Available, Lease Restrictions, No Sign, See Attachments |
| Room Count: | 6 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Total Annual Fees: | $1,186 |
| Total Monthly Fees: | $99 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 1 |
| Association Name: | GREAT COMMUNITIES |
| Association Phone: | SHARRI SCOTT |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-695-2066 |
| Originating System Name : | Stellar MLS |
| Dock Yn: | No |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-08-04 |
Mortgage Calculator
Copyright 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. Information deemed reliable but is not guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of My Florida Regional MLS DBA Stellar MLS. Real estate listings held by brokerage firms other than the owner of this page include the name of the listing broker. Information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This site will be monitored for 'scraping' and any use of search facilities of data on the site other than by a consumer looking to purchase real estate is prohibited. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on October 21, 2026 12:22 AM - ET
Based on information submitted to the MLS GRID as of October 21, 2026 12:22 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. Properties displayed may be listed or sold by various participants in the MLS. Some listings have been excluded from this website.
IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.
Property Last Updated: October 21, 2026 12:22 AM - ET
