2535 LEEWARD WAY, WINTER PARK, FL, 32792
Active5 days on marketListed Nov 1, 2026MLS #O6454266
About this home
2535 LEEWARD WAY
A rare opportunity in Windward Square! This spacious 3-bedroom, 2-bath home offers 1,783 square feet of living space and 2,107 total square feet, along with sought-after features that are hard to find: a covered carport, a bright sunroom with its own A/C, and a private outdoor space. Engineered hardwood floors run throughout, and the kitchen was updated in 2011. Major updates include plumbing and electrical improvements in 2011, a roof replaced in June 2022, a 2022 hot water heater, and an HVAC system installed in January 2019. The covered carport and an additional uncovered space provide parking for three vehicles. Washer and dryer convey; the dryer was replaced in 2026. Enjoy Windward Square amenities including two pools, tennis courts, a clubhouse, and a playground, plus remote gate access to SR 436. The HOA includes exterior lawn maintenance; owners maintain the area inside their small fence.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,783
Sqft
0.1 ac
Lot size
1977
Year built
One
Levels
$182
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.
$2,677 /mo · 3.5% down FHA, 30-yr fixed at 7.5%
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
$2,677/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.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
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
−9.8%
$/sqft vs Winter Park actives
$182 vs $342
Days on market
5 vs 51 typical
Where $182/sqft sits among the 326 Winter Park actives
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 Windward Square
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Windward Square — neighborhood snapshot
Population
567
Median age
31
Median income
$61,250
Median home value
$219,300
Avg household
2
Households w/ children
85%
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$510K → $515K
Winter Park median sold, yr/yr
96.7%
Sale-to-list ratio (12 mo)
156 of 326
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 3% below the WINTER PARK 32792 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 2535 LEEWARD WAY
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’26$324,000
2676 BARBADOS DRIVE · same community
3 bd · 2 ba · 1,743 sqft · $186/sqft · 17 DOM
Sold · Oct ’26$250,000
2651 CAYMAN WAY · same community
2 bd · 2 ba · 1,020 sqft · $245/sqft · 63 DOM
Sold · Apr ’26$275,000
2612 EXUMA WAY · same community
2 bd · 2 ba · 1,020 sqft · $270/sqft · 7 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
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
Chad Creech
President, Commercial and Development Services · CENTURY 21 Edge
Tours, negotiation, and every question about 2535 LEEWARD WAY — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2535 LEEWARD WAY — before you fall in love.
See it in person
Schedule a tour
Live availability from Chad's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2535 LEEWARD WAY FAQs
What would the monthly payment be for 2535 LEEWARD WAY?+
With 3.5% down on a 30-year FHA loan at 7.5%, the all-in payment lands around $2,677/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 2535 LEEWARD 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 2535 LEEWARD WAY?+
The most recent tax bill on record (2025) was $513. 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 2535 LEEWARD 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 $325,000, this home is listed about 48% below the Winter Park median of $624,750. The market section on this page shows how the area is trending.
Which schools are assigned to 2535 LEEWARD WAY?+
Eastbrook Elementary School (elementary), Lake Howell High School (high), Tuskawilla Middle School (middle) — Seminole County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO · Angela Amy. MLS #O6454266.
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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