2653 CAYMAN WAY, WINTER PARK, FL, 32792
Active1 days on marketListed Aug 4, 2026MLS #O6430560
About this home
2653 CAYMAN WAY
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!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,284
Sqft
0.07 ac
Lot size
1978
Year built
One
Levels
$221
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$2,331 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$2,331/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+8.1%
Days on market
1 vs 41 typical
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Winter Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
WINTER PARK 32792 — neighborhood snapshot
Population
52,794
Median age
34.7
Median income
$66,176
Median home value
$343,500
Avg household
2.34
Households w/ children
5,372
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 11% below the WINTER PARK 32792 median. See the full Winter Park market guide →
Paper trail
This home's history
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Tommy Trainer
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2653 CAYMAN WAY — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2653 CAYMAN WAY — before you fall in love.
See it in person
Schedule a tour
Live availability from Tommy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2653 CAYMAN WAY FAQs
What would the monthly payment be for 2653 CAYMAN WAY?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,331/mo — principal and interest, the actual property-tax bill, the $99/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 2653 CAYMAN WAY?+
The association fee works out to $99 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2653 CAYMAN WAY?+
The most recent tax bill on record (2025) was $3,297. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 2653 CAYMAN WAY?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $284,000, this home is listed about 51% below the Winter Park median of $577,450. The market section on this page shows how the area is trending.
Which schools are assigned to 2653 CAYMAN WAY?+
Brookshire Elementary (elementary), Winter Park High (high), Glenridge Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Under the WINTER PARK 32792 market on paper
$284,000 is 11% below the WINTER PARK 32792 median of $320,000, and at $221/sqft it sits under the Winter Park average of $433.
02Trees/Woods views
The trees/woods view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 1 day on market in a Winter Park market that averages 41 — if it fits, move quickly.
04Strong assigned schools
Brookshire Elementary, Winter Park High, Glenridge Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
Listing courtesy of RE/MAX TOWN & COUNTRY REALTY · Kyle Clark. MLS #O6430560.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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