$499,900
1055 Chesterfield Circle
Winter Springs, FL 32708
Listing updated: June 27, 2026 at 8:44 PM ET
Listing courtesy of Lpt Realty, Llc · Brittany Zapitz · MLS #O6413841 · Pending · 877-366-2213Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Under contract-accepting backup offers. 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. 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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history23 days on market
- Status: PendingJun 28, 2026
- Listed$515,000Jun 4, 2026
- Price reduced$499,900
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Pending
- Days on market
- 23
- Subdivision
- Amherst
- County
- Seminole
- Year built
- 1984
- Living area
- 1,665 sq ft
- Price/sq ft
- $300
- Building area
- 2,485 sq ft (Public Records)
- Lot size
- 14,600 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- x
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $5,048 (2025)
- Parcel #
- 13-21-30-509-0000-0110
- Zoning
- RES
- MLS #
- O6413841
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Carpet, Ceramic Tile, Laminate
- Appliances
- Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
- Interior features
- Ceiling Fans(s), Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- South
- Fireplace
- Yes
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener
HOA & Financial
- HOA fee
- $295 / Annually
- Monthly HOA
- $25/mo
- Total monthly fees
- $25/mo
- Total annual fees
- $295
- HOA name
- Michael Blake
- CDD
- Yes
- Min lease term
- 7 Months
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- No short term rentals
Exterior & Construction
- Exterior features
- Rain Gutters, Sliding Doors
- Construction materials
- Stucco
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Fire Hydrant, Phone Available, Public, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Family Room | First | 15x26 |
| Living Room | First | 12x11 |
| Kitchen | First | 10x9 |
| Primary Bedroom | First | 13x16 |
| Bedroom 2 | First | 12x10 |
| Bedroom 3 | First | 12x11 |
| Dinette | First | 8x6 |
| Primary Bathroom | First | 9x12 |
Listing Details
- Listing date
- 2026-06-02
- On market date
- 2026-06-04
- Original list price
- $515,000
- Occupant type
- Owner
- MLS area
- 32708 - Casselberrry/Winter Springs / Tuscawilla
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-28
- Tax legal description
- LOT 11 AMHERST PB 28 PGS 39 & 40
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
.From 417 head West on Red Bug Rd to Tuskawilla Rd North. Turn Right into Amherst at first light. Left at Stop sign home will be on your Left.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of June 27, 2026 at 8:44 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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