2275 ISLAND RUN, WINTER PARK, FL, 32792
Active35 days on marketListed Sep 7, 2026MLS #O6439848
About this home
2275 ISLAND RUN
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,467
Sqft
0.1 ac
Lot size
1980
Year built
One
Levels
$204
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.
$2,538 /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
$2,538/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
+41.1%
$/sqft vs Winter Park actives
$204 vs $343
Days on market
35 vs 58 typical
Where $204/sqft sits among the 339 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
$470K → $530K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
162 of 339
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 18% 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 2275 ISLAND RUN
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$217,000
2400 DOMINICA RUN · same community
2 bd · 1 ba · 854 sqft · $254/sqft · 48 DOM
Sold · Nov ’25$250,000
2399 ANTILLES DRIVE · same community
2 bd · 1 ba · 854 sqft · $293/sqft · 7 DOM
Sold · Oct ’26$401,200
2015 TAYLOR AVENUE
3 bd · 2 ba · 1,439 sqft · $279/sqft · 5 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
Leila Sabat
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 2275 ISLAND RUN — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2275 ISLAND RUN — before you fall in love.
See it in person
Schedule a tour
Live availability from Leila's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2275 ISLAND RUN FAQs
What would the monthly payment be for 2275 ISLAND RUN?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,538/mo — principal and interest, the actual property-tax bill, the $85/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 2275 ISLAND RUN?+
The association fee works out to $85 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2275 ISLAND RUN?+
The most recent tax bill on record (2025) was $4,730. 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 2275 ISLAND RUN?+
The listing reports pets: No. 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 $299,990, this home is listed about 50% below the Winter Park median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2275 ISLAND RUN?+
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 U KEY REALTY · Yukey Hoo. MLS #O6439848.
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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