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$1,225,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,214 Sq. Ft.
  • Updated 5 days ago
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Charming & Spacious Lake-Community Home in Deer Island Welcome to 17556 Deer Isle Circle, a beautifully maintained 4-bed, 3.5-bath residence nestled on over one acre in the gated and highly desirable Deer Island community in Winter Garden. This classic Florida home combines generous living spaces with outdoor appeal - all just minutes from downtown shopping, dining, and parks. Step inside to discover an updated kitchen and an inviting layout that flows effortlessly for everyday living and entertaining. The flexible floor plan includes a detached guest room - perfect as a private space for visitors, a home office, or creative studio. Hardwood accents and plenty of natural light enhance the comfortable interior. Outdoors, enjoy classic Florida living with your own private screened-in pool and expansive grounds, ideal for gatherings, play, and relaxation. The inviting front porch welcomes you home and sets the tone for serene living. Located in a community with lake access to Johns Lake, a boat ramp & fishing pier, and recreational amenities including tennis and basketball courts, this property offers lifestyle and location in one rare package. Whether you're relaxing at home or exploring all Deer Island has to offer, this home delivers the space, comfort, and opportunity you've been looking for.

Full Property Details for 17556 Deer Isle Cir

General

  • Price: $1,225,000
  • HOA FEE: $207/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $9,281 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6332919
  • Updated: 1/12/2026
  • Added to Site: 166 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 4
  • Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Open Floorplan
  • Fireplace: Yes
  • Fireplace(s): Family Room
  • Appliances: Cooktop, Dishwasher, Disposal, Microwave, Range, Refrigerator
  • Flooring: Carpet, Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Basketball Court, Gated, Tennis Court(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Screen Enclosure

Exterior

  • Exterior Features: Lighting, Sidewalk, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: DEER ISLAND PH 02
  • Driving Directions: Heading North on Florida Turnpike, take exit 272 for FL-50 W toward Clermont. Turn left onto State Rte 50 W/W Colonial Dr. Turn left onto Deer Isle Dr. Turn left onto Deer Isle Circle. Home is on the right.
  • Direction Faces: North

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Community Boat Ramp, Dock, Fishing, Lake, Private Boat Ramp, Water Access
  • Optional Amenities: Basketball Court, Gated, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: Deer Island HOA / Sentry Management

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water District: JOHNS LAKE
  • Water: Well
  • Utility Description: Electricity Connected, Street Lights

Structural Information

  • Exterior Const.: Block, HardiPlank Type, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,214
  • Sq. Ft. Source: Appraiser
  • Year Built: 1998

Lot Features

  • Lot Size (Acres): 1.03
  • Lot Size (Sq. Ft.): 44,851
  • Lot Size: 1.0296
  • Street/Road Desc.: Asphalt

Water Features

  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: JOHNS LAKE
  • Water Front Desc.: Lake

Financial Considerations

  • Association Fee: $1,240
  • Assoc Fee Freq.: Semi-Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $9,281
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: DEER ISLAND PHASE 2 29/136 LOT 4
  • Flood Zone Info: X
  • APN: 302227202900040
  • Property ID: 302227202900040

Listed by Lakeside Realty Windermere Inc

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Listing agent

— 17556 Deer Isle Cir —

  • Lakeside Realty Windermere Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 17556 Deer Isle Cir

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-52.7 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-83.2 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-124.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 17556 Deer Isle Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/02/2025
Price Reduced
$1,225,000
-5.77%
MLS
9/15/2025
Price Reduced
$1,299,999
-3.7%
MLS
9/02/2025
Price Reduced
$1,349,900
-3.58%
MLS
8/04/2025
Listed
$1,400,000
126.35%
MLS
9/25/2018
Sold
$618,500
—
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 17556 Deer Isle Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,281
—
$615,082
3%
2024
$9,281
7%
$597,747
3%
2023
$8,648
4%
$580,337
6%
2021
$8,278
-1%
$547,023
-3%
2022
$8,388
1%
$563,434
5%
2021
$8,278
1%
$538,484
1%
2019
$8,217
14%
$531,797
25%
2018
$7,231
69%
$426,550
50%
2017
$4,288
1%
$283,790
2%
2016
$4,261
-2%
$277,953
1%
2015
$4,333
-1%
$276,021
1%
2014
$4,397
2%
$273,830
2%
2013
$4,301
—
$269,783
—
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Lakeside Realty Windermere Inc

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17556 Deer Isle Circle, Winter Garden, FL 34787 (MLS# O6332919) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 17556 Deer Isle Circle is currently listed for $1,225,000 and was received on August 04, 2025. Want to learn more about 17556 Deer Isle Circle? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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