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$285,000 Sale Pending
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Property Description
Under contract-accepting backup offers. Step into a storybook setting with this Enchanting, Turnkey Bungalow nestled in the heart of Winter Garden-a true must-see that captures both charm and modern comfort. From the welcoming front porch to the beautiful luxury vinyl plank flooring and picturesque backyard, every detail invites you to slow down and feel at home. Thoughtfully and completely remodeled, this darling residence offers 2 bedrooms, 1 bathroom, and a bright, airy layout designed for easy living and is staged to absolute perfection. Beyond the front door, discover a lifestyle that's simply unmatched. Take a short stroll to Plant Street or hop onto the scenic West Orange Trail, where the beauty of Winter Garden unfolds all around you. Winter Garden, Florida feels like a place where charm and sunshine quietly linger year-round. Brick-lined streets wind through a historic downtown filled with beautifully restored storefronts, local boutiques, and inviting cafés that spill out onto the sidewalks. Towering oak trees draped in Spanish moss provide shade as the West Orange Trail weaves its way through town, alive with cyclists, joggers, and families enjoying the breeze. Just steps away, the shimmering waters of Lake Apopka create a peaceful backdrop, where golden sunsets stretch across the horizon and birds glide effortlessly over the marshlands. The weekly farmers market brings the community together with fresh blooms, local flavors, and the kind of small-town warmth that's hard to find elsewhere. Blending old Florida charm with thoughtful growth, Winter Garden offers a lifestyle that feels both relaxed and vibrant-where every corner seems to invite you to slow down, take it in, and stay awhile. Back at home, enjoy peace of mind with extensive updates including a new roof, AC, flooring, kitchen, bathroom, plumbing, and electrical-truly move-in ready. With NO HOA and NO CDD, this property is ideal for a first-time buyer, downsizer, or anyone seeking a slice of charm close to it all. Step outside into an absolutely stunning outdoor retreat, where a beautifully landscaped gravel backyard sets the stage for relaxation and connection. Your private patio invites you to grill, unwind, and gather with loved ones-sharing stories, laughter, and unforgettable memories under the open sky. Opportunities like this don't come around often-schedule your private showing today before it's gone.
Full Property Details
Full Property Details for 345 Winter St
General
- Price: $285,000
- Taxes: $211 (2025)
- Status: Pending
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6402105
- Updated: 4/28/2026
- Added to Site: 27 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 4
- Interior Features: Ceiling Fan(s)
- Appliances: Microwave, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Luxury Vinyl
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: Laundry Room
Exterior
- Exterior Features: Fire Pit, Other, Private Mailbox
- Deck/Patio: Front Porch
- Porch/Patio/Deck: Front Porch
Parking
- Parking Features: Driveway
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: SHADOW LAWN
- Driving Directions: rom Orlando, take FL-408 West toward Ocoee and merge onto FL-429 North. Exit onto Plant Street/Winter Garden and head east toward downtown. Continue along Plant Street as it becomes Winter Garden–Vineland Road, then turn onto Winter Street. Follow Winter Street for a short distance, and 345 Winter Street will be on your right, nestled within the charming historic area of Winter Garden.
- Direction Faces: East
Community
- Community Name: 34787 - Winter Garden/Oakland
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electricity Available, Electricity Connected, Public, Sewer Available, Sewer Connected, Water Available, Water Connected
Structural Information
- Architectural Info: Bungalow, Cottage
- Architectural Style: Bungalow, Cottage
- Exterior Const.: Block, Concrete
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 700
- Sq. Ft. Source: Owner
- Year Built: 1951
Additional Structures
- Other Structures: Other
Lot Features
- Lot Size (Acres): 0.17
- Lot Size (Sq. Ft.): 7,506
- Lot Size: 7506
- Street/Road Desc.: Paved
- Fencing (Description): Chain Link
Financial Considerations
- Tax Amount: $211.44
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: SHADOW LAWN L/125 LOT 9 BLK G
- Flood Zone Info: x
- APN: 232227794807090
- Property ID: 232227794807090
- Block/Lot/Section: G
Listed by The Navy House
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Schools
Schools serving 345 Winter St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
William S Maxey Elementary School 1100 East Maple Street, Winter Garden, FL 34787 | PK-5 | 0.8 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.4 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.6 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 345 Winter St
Date
Details
Price
Change
Source
4/26/2026
Price Increased
$285,000
1.82%
MLS
4/24/2026
Listed
$279,900
127.93%
MLS
8/29/2025
Sold
$122,800
—
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 345 Winter St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$211
11%
$139,490
278%
2024
$190
10%
$36,906
3%
2023
$172
20%
$35,831
6%
2021
$143
-8%
$33,774
-3%
2022
$156
9%
$34,787
4%
2021
$143
13%
$33,308
2%
2019
$126
8%
$32,559
2%
2018
$117
10%
$31,952
2%
2017
$106
9%
$31,295
2%
2016
$97
1%
$30,651
1%
2015
$96
3%
$30,438
1%
2014
$93
11%
$30,196
1%
2013
$84
—
$29,750
—
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 345 Winter St
345 Winter Street, Winter Garden, FL 34787 (MLS# O6402105) is a Single Family property with 2 bedrooms and 1 full bathroom. 345 Winter Street is currently listed for $285,000 and was received on April 24, 2026. Want to learn more about 345 Winter Street? 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.

