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$299,990 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1,467 Sq. Ft.
  • Updated 2 hours ago
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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! 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!

Full Property Details for 2275 Island Run

General

  • Price: $299,990
  • HOA FEE: $85/month
  • Taxes: $4,730 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6439848
  • Updated: Today (9/7/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 6
  • Interior Features: High Ceilings, Walk-In Closet(s)
  • Appliances: Convection Oven, Dishwasher, Electric Water Heater, Microwave, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Closet

Exterior

  • Exterior Features: Other

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Seminole
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: WINDWARD SQUARE SEC 3
  • Driving Directions: one side Gates are not open, please go from Howell Branch run and follow the GPS.
  • Direction Faces: South

Community

  • Community Name: 32792 - Winter Park/Aloma
  • Community Features: Playground
  • Association: Yes
  • Assoc. Name: winter park
  • Assoc. Fees Include: Maintenance Grounds, Maintenance Repairs

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

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

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,467
  • Sq. Ft. Source: Public Records
  • Year Built: 1980

Lot Features

  • Lot Size (Acres): 0.1
  • Lot Size (Sq. Ft.): 4,533
  • Lot Size: 4533
  • Street/Road Desc.: Concrete

Financial Considerations

  • Association Fee: $85
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,730
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 303 WINDWARD SQUARE SEC 3 PB 22 PGS 28 & 29
  • Flood Zone Info: X
  • APN: 34213052500003030
  • Property ID: 34213052500003030
  • Block/Lot/Section: 00/00

Listed by U Key Realty

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Listing agent

— 2275 Island Run —

  • U Key Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2275 Island Run

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
6-83 mi
Lake Howell High School
4200 Dike Road, Winter Park, FL 32792
9-122.6 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 2275 Island Run Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/07/2026
Listed
$299,990
185.7%
MLS
6/11/2014
Sold
$105,000
—
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 2275 Island Run

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,026
24%
$315,654
4%
2024
$4,066
7%
$304,287
6%
2023
$3,790
24%
$287,076
37%
2021
$3,050
-9%
$209,196
-12%
2022
$3,367
10%
$238,674
30%
2021
$3,050
19%
$183,306
37%
2019
$2,557
9%
$134,155
-13%
2018
$2,338
13%
$153,825
24%
2017
$2,073
8%
$124,497
15%
2016
$1,921
11%
$108,405
18%
2015
$1,725
33%
$91,630
25%
2014
$1,296
17%
$73,429
26%
2013
$1,111
—
$58,455
—
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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NMLS#: 1598647

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Listed by U Key Realty

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2275 Island Run, Winter Park, FL 32792 (MLS# O6439848) is a Townhouse property with 3 bedrooms and 2 full bathrooms. 2275 Island Run is currently listed for $299,990 and was received on September 07, 2026. Want to learn more about 2275 Island Run? 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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