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- Englewood Homes for Sale
- 185 WINSON AVENUE
$399,900
185 WINSON AVENUE, ENGLEWOOD, FL 34223
Beds
3
Baths
2
Sq Ft
1,500 sq ft
Year Built
1973
Lot Size
0.21 acres
Garage
,
About This Property
Virtually Staged. ## **Short distance to Dearborn Street – Discover the Best of Old Englewood Living!** If you've been searching for the charm of **Old Englewood** with a location that truly embraces the Florida lifestyle, **185 Winson Avenue** is the one you've been waiting for. Imagine leaving your car at home and taking a short golf cart, bike ride, or walk to **historic Dearborn Street**—the heart of Englewood. Enjoy locally owned restaurants, sidewalk cafés, wine bars, boutique shopping, art galleries, live music, community events, and the popular weekly farmers market. From seasonal festivals to evening concerts, there's always something happening just minutes from your front door. For outdoor enthusiasts, you're only moments from **Indian Mound Park**, where you'll find a public boat ramp, kayak launch, fishing pier, picnic pavilions, and beautiful views of Lemon Bay. Spend your weekends boating, paddleboarding, fishing, or simply watching spectacular sunsets. **Englewood Beach** and **Manasota Key Beach** are just a short drive away, making every day feel like a vacation. Inside, this well-maintained 3-bedroom, 2-bath home blends classic Florida charm with thoughtful updates. Original terrazzo floors, plantation shutters, and an updated kitchen with butcher block countertops create a warm, inviting atmosphere that's both stylish and functional. A rare bonus is the **approximately 400-square-foot air-conditioned detached studio**, complete with a kitchenette and full bathroom. Whether you need a guest suite, private home office, in-law quarters, art studio, fitness room, workshop, or creative space, this flexible building offers endless possibilities. The fenced backyard provides room for all your Florida toys—including a boat, RV, golf cart, kayaks, and more—along with multiple storage buildings and plenty of space to build the custom pool you've always wanted. Whether you're looking for a primary residence, seasonal escape, vacation home, or investment property, **185 Winson Avenue** offers one of the most desirable combinations in Englewood: an unbeatable Old Englewood location, walkability to Dearborn Street, easy access to Lemon Bay and Gulf beaches, flexible living space, and the relaxed coastal lifestyle buyers are searching for. ** Come experience why so many fall in love with Old Englewood—and why you'll want to call 185 Winson Avenue home.**
Property Overview
Interior Features
Exterior & Lot
Utilities
Parking
HOA & Community
Financial Details
Schools
Directions
From Port Charlotte 41 North, turn left onto US 776 El Jobean Road for miles; turn left on S McCall Road; left on W Cowles St; right on Magnolia Ave; left on Fray St; and Left on Winson. 185 Winson is on left 150 ft.,
Location
185 WINSON AVENUE, ENGLEWOOD, FL 34223
Listing Information
Schedule a Tour
Pick a Day
Preferred Time
Home Price
$399,900
Loan Term
Nearby Schools
How to Buy This Home
Multiple financing options available for this $399,900 home in ENGLEWOOD.
🏛️
FHA Loan
$13,997 Down
Government-backed, low down payment. Credit scores as low as 580.
🏦
Conventional
$19,995 Down
Traditional financing. As low as 3-5% down with good credit.
Florida Down Payment Assistance Programs
You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.
Florida Hometown Heroes
Up to $35,000
First-time buyers working in FL
FL Assist
Up to $10,000
FHA, VA, or USDA borrowers
FL HLP Second Mortgage
Up to $10,000
First-time buyers, 0% deferred
Sarasota County SHIP
Varies
Income-qualifying Sarasota residents
Can You Afford This Home?
Quick check based on the 28% debt-to-income rule. Not a guarantee, just a starting point.
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Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. 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 last updated: September 4, 2026.