185 WINSON AVENUE, ENGLEWOOD, FL, 34223
Active20 days on marketListed Jul 17, 2026MLS #C7528510
About this home
185 WINSON AVENUE
Virtually Staged. ## **Walk 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 people fall in love with Old Englewood—and why you'll want to call 185 Winson Avenue home.**
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,500
Sqft
0.21 ac
Lot size
1973
Year built
One
Levels
$280
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,097 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,097/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−0.5%
$/sqft vs Englewood actives
$280 vs $238
Days on market
20 vs 68 typical
Where $280/sqft sits among the 400 Englewood actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Old Englewood Village
Get to know Englewood. See the full Englewood guide →
Old Englewood Village — neighborhood snapshot
Population
3,260
Median age
64
Median income
$60,523
Median home value
$320,216
Avg household
2
Households w/ children
124
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Englewood market
$330K → $330K
Englewood median sold, yr/yr
94.6%
Sale-to-list ratio (12 mo)
179 of 400
Englewood actives have cut their price
Median sold price, Englewood, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 8% above the ENGLEWOOD 34223 median. See the full Englewood market guide →
Paper trail
This home's history
Reality check
What actually sold near 185 WINSON AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$464,000
108 WINSON AVENUE · same community
2 bd · 2 ba · 1,455 sqft · $319/sqft · 90 DOM
Sold · Mar ’26$795,000
918 EDGEWATER DRIVE
3 bd · 2 ba · 1,496 sqft · $531/sqft · 18 DOM
Sold · Feb ’26$309,900
1220 PUNTA NOVA TERRACE
2 bd · 2 ba · 1,493 sqft · $208/sqft · 53 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 185 WINSON AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 185 WINSON AVENUE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
185 WINSON AVENUE FAQs
What would the monthly payment be for 185 WINSON AVENUE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,097/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 185 WINSON AVENUE?+
The most recent tax bill on record (2025) was $3,346. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Englewood?+
At $420,000, this home is listed about 15% above the Englewood median of $365,000. The market section on this page shows how the area is trending.
Which schools are assigned to 185 WINSON AVENUE?+
Englewood Elementary School (elementary), Lemon Bay High School (high), L. A. Ainger Middle School (middle) — Sarasota County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX PALM REALTY · Natalie Dickerson. MLS #C7528510.
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 is deemed reliable but is not guaranteed accurate by Stellar MLS.
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