1055 CHESTERFIELD CIRCLE, WINTER SPRINGS, FL, 32708
Active60 days on marketListed Jun 4, 2026MLS #O6413841
About this home
1055 CHESTERFIELD CIRCLE
Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. Property has fiber optics, 50 amp car charger in garage, and nest thermostat for A/C. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,665
Sqft
0.34 ac
Lot size
2
Garage
1984
Year built
One
Levels
$300
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.
$3,770 /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
$3,770/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
+21.2%
$/sqft vs Winter Springs actives
$300 vs $240
Days on market
60 vs 38 typical
Where $300/sqft sits among the 128 Winter Springs 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 Amherst
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Springs. See the full Winter Springs guide →
Amherst — neighborhood snapshot
Population
2,411
Median age
39
Median income
$142,917
Median home value
$390,400
Avg household
3
Households w/ children
224
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Springs market
$420K → $462K
Winter Springs median sold, yr/yr
97.8%
Sale-to-list ratio (12 mo)
83 of 128
Winter Springs actives have cut their price
Median sold price, Winter Springs, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 33% above the WINTER SPRINGS 32708 median. See the full Winter Springs market guide →
Paper trail
This home's history
Reality check
What actually sold near 1055 CHESTERFIELD CIRCLE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’25$410,000
1003 CHESTERFIELD CIRCLE · same community
3 bd · 2 ba · 1,759 sqft · $233/sqft · 64 DOM
Sold · May ’26$535,000
1017 CHESTERFIELD CIRCLE · same community
3 bd · 3 ba · 1,882 sqft · $284/sqft · 0 DOM
Sold · Dec ’25$439,000
1073 CHESTERFIELD CIRCLE · same community
4 bd · 2 ba · 2,064 sqft · $213/sqft · 85 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 1055 CHESTERFIELD CIRCLE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1055 CHESTERFIELD CIRCLE — 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
1055 CHESTERFIELD CIRCLE FAQs
What would the monthly payment be for 1055 CHESTERFIELD CIRCLE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,770/mo — principal and interest, the actual property-tax bill, the $25/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 1055 CHESTERFIELD CIRCLE?+
The association fee works out to $25 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1055 CHESTERFIELD CIRCLE?+
The most recent tax bill on record (2025) was $5,048. 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 1055 CHESTERFIELD CIRCLE?+
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 Winter Springs?+
At $499,900, this home is listed about 19% above the Winter Springs median of $420,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1055 CHESTERFIELD CIRCLE?+
Rainbow Elementary School (elementary), Indian Trails Middle School (middle), Winter Springs High School (high) — Seminole County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$499,900 runs 33% above the WINTER SPRINGS 32708 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Rainbow Elementary School, Indian Trails Middle School, Winter Springs High School — Rainbow Elementary School rates 5 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $515,000, now $499,900 — a $15K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of LPT REALTY, LLC · Brittany Zapitz. MLS #O6413841.
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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