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$515,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,665 Sq. Ft.
  • Updated 1 hour ago

Next open house:

Open House: 12:00 PM - 3:00 PM

Sunday 6/7 12:00 PM - 3:00 PM

1055 Chesterfield Circle,Winter Springs, FL 32708

1055 Chesterfield CircleWinter SpringsFL32708

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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.

Full Property Details for 1055 Chesterfield Cir

General

  • Price: $515,000
  • HOA FEE: $25/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,048 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6413841
  • Updated: Today (6/4/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Wood Burning
  • Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Screen Enclosure, Solar Heat
  • Spa Description: In Ground

Exterior

  • Exterior Features: Irrigation System, Rain Gutters, Sliding Doors
  • Deck/Patio: Covered, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • County: Seminole
  • Development Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Subdivision: AMHERST
  • Driving 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.
  • Direction Faces: South

School Information

  • Elementary School: Rainbow Elementary
  • Middle School: Indian Trails Middle
  • High School: Winter Springs High

Community

  • Community Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Community Features: Fishing, Deed Restrictions, Sidewalks
  • Association: Yes
  • Assoc. Name: Michael Blake

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fire Hydrant, Phone Available, Public, Sewer Connected, Street Lights, Underground Utilities, Water Connected

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,665
  • Sq. Ft. Source: Public Records
  • Year Built: 1984

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 14,600
  • Lot Size: 14600
  • Lot Dimensions: 90 x 150
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $295
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • CDD: Yes
  • Tax Amount: $5,048
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 11 AMHERST PB 28 PGS 39 & 40
  • Flood Zone Info: x
  • APN: 13213050900000110
  • Property ID: 13213050900000110
  • Block/Lot/Section: 39

Listed by Lpt Realty, Llc

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Listing agent

— 1055 Chesterfield Cir —

  • Lpt Realty, Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1055 Chesterfield Cir

School District:Seminole County School District
NameGradesDistance
Rainbow Elementary School, Winter Springs, FL
1412 Rainbow Trail, Winter Springs, FL 32708
K-51.3 mi
Indian Trails Middle School, Winter Springs, FL
415 Tuskawilla Road, Winter Springs, FL 32708
6-82 mi
Winter Springs High School
130 Tuskawilla Road, Winter Springs, FL 32708
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1055 Chesterfield Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/04/2026
Listed
$515,000
66.13%
MLS
1/12/2021
Sold
$310,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1055 Chesterfield Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,048
-2%
$368,983
1%
2024
$5,157
1%
$364,324
2%
2023
$5,096
34%
$357,024
40%
2021
$3,798
-8%
$255,033
-21%
2022
$4,119
8%
$321,687
97%
2021
$3,798
101%
$163,398
4%
2018
$1,885
1%
$156,746
2%
2017
$1,867
-2%
$153,522
2%
2016
$1,900
—
$150,364
-6%
2019
$1,908
-1%
$159,724
7%
2015
$1,920
1%
$149,319
1%
2014
$1,899
-1%
$148,134
1%
2013
$1,915
—
$145,945
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Lpt Realty, Llc

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1055 Chesterfield Circle, Winter Springs, FL 32708 (MLS# O6413841) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1055 Chesterfield Circle is currently listed for $515,000 and was received on June 04, 2026. Want to learn more about 1055 Chesterfield Circle? Do you have questions about finding other Single Family real estate for sale in Winter Springs? You can browse all Winter Springs real estate or contact a Coldwell Banker agent to request more information.

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