4401 LITTLE JOHN TRAIL, SARASOTA, FL, 34232
Active54 days on marketListed Jun 4, 2026MLS #A4695906
About this home
4401 LITTLE JOHN TRAIL
Nestled beneath majestic oak trees in the established Sherwood Forest community, this beautifully maintained home offers the perfect blend of privacy, character, and convenience. Situated on a spacious homesite, the property welcomes you with mature landscaping, abundant shade, and a tranquil setting rarely found in such a central Sarasota location. Inside, you'll find a thoughtfully designed floor plan featuring generous living spaces, abundant natural light, and comfortable accommodations for everyday living and entertaining. Brand new stainless steel appliances with a natural gas range. The home's layout flows seamlessly from the main living areas to the outdoor spaces, creating an inviting atmosphere for gatherings with family and friends. Step outside to enjoy the expansive yard, offering plenty of room for outdoor activities, gardening, or simply relaxing beneath the canopy of mature trees. Whether you're seeking a primary residence, seasonal retreat, or investment opportunity, this property provides exceptional flexibility and value. Conveniently located just minutes from I-75, shopping, dining, top-rated schools, golf courses, and Sarasota's world-famous beaches, this home combines peaceful neighborhood living with easy access to everything the Gulf Coast lifestyle has to offer. Don't miss this opportunity to own a charming Sarasota property in one of the area's most established and desirable communities. New HVAC
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,894
Sqft
0.38 ac
Lot size
2
Garage
1986
Year built
One
Levels
$279
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 and the real association fee — not generic estimates.
$3,915 /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
$3,915/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
−3.5%
$/sqft vs SHERWOOD FOREST
$279 vs $477
Days on market
54 vs 58 typical
Where $279/sqft sits among the 8 homes for sale in SHERWOOD FOREST
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 Sherwood Forest
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Sherwood Forest — neighborhood snapshot
Population
2,331
Median age
58
Median income
$70,625
Median home value
$398,300
Avg household
2
Households w/ children
166
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$470K → $470K
Sarasota median sold, yr/yr
95.1%
Sale-to-list ratio (12 mo)
3 of 8
SHERWOOD FOREST have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 95% above the SARASOTA 34232 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 4401 LITTLE JOHN TRAIL
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$455,000
4443 ROBIN HOOD TRAIL W · same community
3 bd · 2 ba · 1,930 sqft · $236/sqft · 202 DOM
Sold · Sep ’25$643,000
365 Sherwood Forest Drive, Delray Beach FL 33445 · same community
3 bd · 2 ba · 1,852 sqft · $347/sqft · 90 DOM
Sold · Dec ’25$885,000
Nearby listing · same community
3 bd · 2 ba · 1,852 sqft · $478/sqft · 0 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 4401 LITTLE JOHN TRAIL — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4401 LITTLE JOHN TRAIL — 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
4401 LITTLE JOHN TRAIL FAQs
What would the monthly payment be for 4401 LITTLE JOHN TRAIL?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,915/mo — principal and interest, the actual property-tax bill, the $50/mo association fee 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.
How much are the HOA fees at 4401 LITTLE JOHN TRAIL?+
The association fee works out to $50 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4401 LITTLE JOHN TRAIL?+
The most recent tax bill on record (2025) was $4,285. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 4401 LITTLE JOHN TRAIL?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Sarasota?+
At $529,000, this home is listed about 7% below the Sarasota median of $570,000. The market section on this page shows how the area is trending.
Which schools are assigned to 4401 LITTLE JOHN TRAIL?+
McIntosh Middle School (middle), Fruitville Elementary School (elementary), Sarasota High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of OSIPOV GROUP REAL ESTATE · Bogdan Osipov. MLS #A4695906.
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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