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$465,000 Just Listed
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Property Description
Welcome to a home that feels right the moment you arrive. Set beneath the shade of mature oak trees on a 100-foot-wide lot in Winter Garden's golf cart district, this beautifully maintained single-story home in Island Pointe invites you to slow down, breathe a little deeper, and truly enjoy where you live. The wide, covered front porch stretches across the entire front of the home, creating the perfect place for morning coffee, evening conversations, and everything in between. Step inside and you're greeted by soaring vaulted ceilings and natural light that pours in from every angle, giving the home an open, airy feel that lives larger than its footprint. The layout flows effortlessly with multiple living and dining spaces designed for both connection and flexibility. At the center of it all is a generously sized kitchen with abundant counter space and a center island that opens seamlessly to the family room. This is where life happens. Holidays, casual dinners, and late-night conversations all find their place here. The split floor plan offers privacy and comfort. The owner's suite is tucked away and serves as a peaceful retreat with a walk-in closet and a spacious en-suite bath featuring dual sinks, a garden tub, and a separate shower. On the opposite side of the home, two additional bedrooms provide the ideal setup for family, guests, or a home office. This home has been lovingly cared for and offers something buyers are always searching for but rarely find: solid construction with major system updates already done, including a newer roof, updated HVAC, and a brand new water heater. The finishes reflect its original character, giving you the opportunity to modernize at your own pace and build meaningful equity along the way. But what truly sets this home apart is the lifestyle. Located in the highly sought-after Golf Cart District of historic Downtown Winter Garden, you are just minutes from everything that makes this area so special. Hop on your golf cart or bike and head to Plant Street where you'll find charming boutiques, incredible dining, live music, festivals, and the beloved Saturday Farmers Market. Enjoy local favorites like Crooked Can Brewery and Food Hall and Scoops Ice Cream only a quick ride away. Spend your weekends exploring the West Orange Trail or relaxing at nearby Newton Park, the City Pool, playground, fishing pier, and public boat ramp. Whether it's a morning ride, an afternoon on the water, or an evening out, everything you need is right at your fingertips. Daily convenience is just as impressive, with multiple grocery options nearby and shopping along Highway 50. You are also close to top-rated schools, Winter Garden Village, AdventHealth, and have easy access to the 429 and Florida Turnpike. All of this, paired with low HOA dues and a welcoming, established neighborhood, makes this home not just a great purchase, but a smart investment in both lifestyle and long-term value. Homes like this do not come around often. A single-story layout, a prime location, strong bones, and the chance to make it truly your own. Come see it in person. Walk the space. Feel the openness. Sit on the front porch and imagine life unfolding here.
Full Property Details
Full Property Details for 1035 Chase Dr
General
- Price: $465,000
- HOA FEE: $44/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $3,336 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6396474
- Updated: 4/13/2026
- Added to Site: 4 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 10
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Vaulted Ceiling(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Wood Burning
- Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile, Laminate, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Washer Hookup
Additional Information
- Security/Safety: Security System, Smoke Detector(s)
Exterior
- Exterior Features: Irrigation System, Lighting, Sidewalk, Sliding Doors
- Deck/Patio: Covered, Front Porch, Patio, Porch
- Porch/Patio/Deck: Covered, Front Porch, Patio, Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Garage Faces Side
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: ISLAND POINTE SUB
- Driving Directions: Take FL-429 to exit for Plant St / FL-438 W. Turn west onto Plant St. Turn right onto Hennis Rd. Turn left onto E Division St. Turn right onto Hearthglen Blvd. Turn right onto E Crest Ave. Turn right onto Island Pointe Dr. Turn right onto Chase Dr. Home will be on the left.
- Direction Faces: South
School Information
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: Ocoee High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Community Mailbox, Deed Restrictions, Sidewalks
- Association: Yes
- Assoc. Name: Folio Association Management
- Assoc. Fees Include: Common Area Taxes
- Pet Restrictions: Dogs and cats may be kept as pets only. No other animals, poultry or livestock shall be kept or maintained on any lot in Island Pointe. As per HOA covenants and restrictions and Orange County ordinances.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Florida, Other, Ranch
- Architectural Style: Florida, Other, Ranch
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: One
- Square Feet: 1,793
- Sq. Ft. Source: Public Records
- Year Built: 1995
Lot Features
- Lot Size (Acres): 0.23
- Lot Size (Sq. Ft.): 10,026
- Lot Size: 10026
- Lot Dimensions: 98 x 102
- Frontage: Street Paved
- Street/Road Desc.: Paved
- Fencing (Description): Vinyl, Wood
Financial Considerations
- Association Fee: $266
- Assoc Fee Freq.: Semi-Annually
- Assoc Fee Desc.: Required
- Tax Amount: $3,336.58
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ISLAND POINTE SUB 28/22 LOT 56
- Flood Zone Info: X
- APN: 112227389700560
- Property ID: 112227389700560
Listed by Upwell Realty Llc
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Schools
Schools serving 1035 Chase Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.8 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 2 mi |
Ocoee High School 1925 Ocoee Crown Point Parkway, Ocoee, FL 34761 | 9-12 | 1.7 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 1035 Chase Dr
Date
Details
Price
Change
Source
4/10/2026
Listed
$465,000
190.62%
MLS
4/26/2002
Sold
$160,000
—
Public Record
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
Tax History for 1035 Chase Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$3,162
—
$273,822
3%
2024
$3,162
4%
$266,105
3%
2023
$3,029
4%
$258,354
3%
2022
$2,922
-12%
$250,829
3%
2021
$3,316
—
$243,523
6%
2021
$3,316
-11%
$229,881
3%
2019
$3,711
128%
$222,771
64%
2018
$1,631
3%
$135,878
2%
2017
$1,583
1%
$133,083
2%
2016
$1,574
-2%
$130,346
1%
2015
$1,602
-1%
$129,440
1%
2014
$1,612
3%
$128,413
2%
2013
$1,567
—
$126,515
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1035 Chase Dr
1035 Chase Drive, Winter Garden, FL 34787 (MLS# O6396474) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1035 Chase Drive is currently listed for $465,000 and was received on April 10, 2026. Want to learn more about 1035 Chase Drive? 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.

