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$284,000 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1,284 Sq. Ft.
  • Updated 5 hours ago
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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!

Full Property Details for 2653 Cayman Way

General

  • Price: $284,000
  • HOA FEE: $99/month
  • Taxes: $3,297 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6430560
  • Updated: Today (8/4/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 6
  • 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
  • Appliances: Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Gated, Playground, Pool, Recreation Facilities, Shuffleboard Court, Tennis Court(s)

Exterior

  • Exterior Features: Private Yard, Sidewalk, Sliding Doors
  • Deck/Patio: Porch, Rear Porch
  • Porch/Patio/Deck: Porch, Rear Porch

Parking

  • Parking Features: Driveway, Guest, Parking Pad

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Seminole
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: WINDWARD SQUARE
  • Driving 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
  • Direction Faces: West

School Information

  • Elementary School: Eastbrook Elementary
  • Middle School: Tuskawilla Middle
  • High School: Lake Howell High

Community

  • Community Name: 32792 - Winter Park/Aloma
  • Community Features: Deed Restrictions, Gated Community - No Guard, Park, Playground, Pool, Sidewalks, Tennis Court(s)
  • Optional Amenities: Clubhouse, Gated, Playground, Pool, Recreation Facilities, Shuffleboard Court, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: GREAT COMMUNITIES
  • Assoc. Fees Include: Common Area Taxes, Community Pool, Maintenance Grounds, Pool Maintenance, Private Road
  • Pet Restrictions: BUYER TO VERIFY WITH HOA/COUNTY

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Other
  • Architectural Style: Other
  • Builder: BABCOCK HOMES
  • Exterior Const.: Block, Stucco, Wood Frame, Wood Siding
  • Roof: Membrane, Shingle
  • Windows: Window Treatments
  • Stories/Levels: One
  • Square Feet: 1,284
  • Sq. Ft. Source: Public Records
  • Year Built: 1978

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.07
  • Lot Size (Sq. Ft.): 3,135
  • Lot Size: 3135
  • Frontage: Street Paved, Private Road
  • Street/Road Desc.: Paved
  • Fencing (Description): Wood

Financial Considerations

  • Association Fee: $99
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $3,297
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 186 WINDWARD SQUARE SEC 2 PB 20 PGS 34 & 35
  • Flood Zone Info: X
  • APN: 34213052100001860
  • Property ID: 34213052100001860

Listed by Re/Max Town & Country Realty

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— 2653 Cayman Way —

  • Re/Max Town & Country Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2653 Cayman Way

School District:Seminole County School District
NameGradesDistance
Eastbrook Elementary School
5525 Tangerine Avenue, Winter Park, FL 32792
K-51 mi
Tuskawilla Middle School
1801 Tuskawilla Road, Oviedo, FL 32765
6-82.9 mi
Lake Howell High School
4200 Dike Road, Winter Park, FL 32792
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2653 Cayman Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/04/2026
Listed
$284,000
379.73%
MLS
2/02/2011
Sold
$59,200
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2653 Cayman Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,246
49%
$235,808
3%
2024
$2,856
7%
$228,910
7%
2023
$2,660
24%
$214,759
38%
2021
$2,146
-9%
$155,959
-12%
2022
$2,364
10%
$177,698
28%
2021
$2,146
30%
$138,637
21%
2018
$1,650
-9%
$114,626
28%
2019
$1,818
24%
$89,900
-4%
2017
$1,469
7%
$94,011
15%
2016
$1,367
12%
$81,749
19%
2015
$1,223
15%
$68,570
23%
2014
$1,067
10%
$55,821
9%
2013
$973
—
$51,185
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Re/Max Town & Country Realty

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2653 Cayman Way, Winter Park, FL 32792 (MLS# O6430560) is a Townhouse property with 3 bedrooms and 2 full bathrooms. 2653 Cayman Way is currently listed for $284,000 and was received on August 04, 2026. Want to learn more about 2653 Cayman Way? Do you have questions about finding other Townhouse real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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