2653 CAYMAN WAY, Winter Park, FL 32792

• 3 beds |
• 2 baths |
• 1,284 sqft

Property Description

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!

Listing Status:

Pending

Date Added:

August 4, 2026

Data Last Updated:

August 13, 2026 at 12:23PM

Listing Office:

RE/MAX TOWN & COUNTRY REALTY : 407-695-2066

Listing Agent:

Kyle Clark : 407-921-3287

Contact:

407-695-2066

MLS ID:

O6430560

Interior

• General: Ceiling Fans(s)High CeilingsLiving Room/Dining Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsVaulted Ceiling(s)Walk-In Closet(s)Window Treatments
• Rooms: Inside UtilityStorage Rooms
• Appliances: DishwasherDisposalDryerRange HoodRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: CarpetCeramic Tile
• A/C: Central Air
• Heating: Central

Exterior

• General: Private YardSidewalkSliding Doors
• Style: Other
• Other Structures: PorchRear Porch
• Parking: DrivewayGuestParking Pad

Construction

• Roofing: MembraneShingle
• Windows: Window Treatments
• General: BlockStuccoFrameWood SidingOneSlab

Location

• Road/Access: Paved
• HOA Amenities: ClubhouseGatedPlaygroundPoolRecreation FacilitiesShuffleboard CourtTennis Court(s)Common Area TaxesPoolMaintenance GroundsPrivate Road98.8Monthly
• Originating MLS: Stellar MLS
• County: Seminole

Lot

• Zoning: RESLOT 186 WINDWARD SQUARE SEC 2 PB 20 PGS 34 & 3534-21-30-521-0000-1860
• View: Trees/Woods
• Fencing: Wood

Utilities

• Utilities: Electricity ConnectedPublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple