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!
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!
Property Details
Price:
$284,000
MLS #:
O6430560
Status:
Pending
Beds:
3
Baths:
2
Type:
Townhouse
Subdivision:
WINDWARD SQUARE
Neighborhood:
32792winterparkaloma
Listed Date:
Aug 4, 2026
Finished Sq Ft:
1,284
Total Sq Ft:
1,482
Lot Size:
3,135 sqft / 0.07 acres (approx)
Year Built:
1978
See this Listing
Schools
Elementary School:
Eastbrook Elementary
Middle School:
Tuskawilla Middle
High School:
Lake Howell High
Interior
Appliances
Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Central
Interior Features
Ceiling Fan(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
Exterior
Architectural Style
Other
Association Amenities
Clubhouse, Gated, Playground, Pool, Recreation Facilities, Shuffleboard Court, Tennis Court(s)
Community Features
Deed Restrictions, Gated Community – No Guard, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco, Wood Frame, Wood Siding
Direction Faces
West
Exterior Features
Private Yard, Sidewalk, Sliding Doors
Fencing
Wood
Lot Features
Cul-De-Sac, In County, Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Guest, Parking Pad
Patio And Porch Features
Porch, Rear Porch
Roof
Membrane, Shingle
View
Trees/Woods
Window Features
Window Treatments
Financial
HOA Fee
$99
HOA Fee Frequency
Monthly
HOA Includes
Common Area Taxes, Community Pool, Maintenance Grounds, Pool Maintenance, Private Road
HOA Name
GREAT COMMUNITIES
HOA Phone
SHARRI SCOTT
Tax Year
2025
Taxes
$3,297
Map
Community
- Address2653 CAYMAN WAY WINTER PARK FL
- SubdivisionWINDWARD SQUARE
- CityWINTER PARK
- CountySeminole
- Zip Code32792
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Townhouse in WINTER PARK as of Aug 29, 2026
37
Townhouse Listed
73
Avg DOM
405
Avg $ / SqFt
$988,330
Avg List Price
Property Summary
- Located in the WINDWARD SQUARE subdivision, 2653 CAYMAN WAY WINTER PARK FL is a Townhouse for sale in WINTER PARK, FL, 32792. It is listed for $284,000 and features 3 beds, 2 baths, and has approximately 1,284 square feet of living space, and was originally constructed in 1978. The current price per square foot is $221. The average price per square foot for Townhouse listings in WINTER PARK is $405. The average listing price for Townhouse in WINTER PARK is $988,330. To schedule a showing of MLS#o6430560 at 2653 CAYMAN WAY in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of RE/MAX TOWN & COUNTRY REALTY. 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 InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. 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. 2653 CAYMAN WAY
WINTER PARK, FL
