For Sale
Price CutPrice Drop: $5K (10/07)
Single family home for sale at 1055 Chesterfield Cir, Winter Springs, FL 32708 | MLS# O6413841 | Listing updated on 2026-10-08
Photo 1 of Single family home for sale at 1055 Chesterfield Cir, Winter Springs, FL 32708 | MLS# O6413841 | Listing updated on 2026-10-08
Photo 2 of Single family home for sale at 1055 Chesterfield Cir, Winter Springs, FL 32708 | MLS# O6413841 | Listing updated on 2026-10-08
Photo 3 of Single family home for sale at 1055 Chesterfield Cir, Winter Springs, FL 32708 | MLS# O6413841 | Listing updated on 2026-10-08
Photo 4 of Single family home for sale at 1055 Chesterfield Cir, Winter Springs, FL 32708 | MLS# O6413841 | Listing updated on 2026-10-08
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$475,000

Monthly Est:$2,364

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,665sqft

1055 Chesterfield Cir, Winter Springs, FL 32708

$2,364/moEst:

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  • Single Family Residence

  • Built in 1984

  • $24.58/mo HOA

  • 14,600 sqft lot

  • $285/sq.ft

Description

Virtually Staged. 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.

  • Houzeo last checked: 1 minute ago
  • Listing updated: October 8, 2026 at 12:05 am
  • Listing Provided by: Brittany Zapitz (321) 230-4445 | LPT REALTY, LLC (877) 366-2213
  • Source: Stellar MLS-FL | MLS#: O6413841 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Seminole County

  • City

    Winter Springs

  • Neighborhood

    --

  • Year Built

    1984

  • HOA Fees

    $24.58/mo

  • Finished Area

    1,665 sqft

  • Lot Size

    14,600 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6413841

  • MLS Status

    Active

  • Days on Market

    125

  • Cumulative Days on Market

    79

Open House

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Location

HOA Management

Michael Blake

HOA Fees

$295/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

  • Family Room

    Level: First

    Area: 390.00 Square Feet

    Dimensions: 15x26

  • Living Room

    Level: First

    Area: 132.00 Square Feet

    Dimensions: 12x11

  • Kitchen

    Level: First

    Area: 90.00 Square Feet

    Dimensions: 10x9

  • Primary Bedroom

    Level: First

    Area: 208.00 Square Feet

    Dimensions: 13x16

  • Bedroom 2

    Level: First

    Area: 120.00 Square Feet

    Dimensions: 12x10

  • Bedroom 3

    Level: First

    Area: 132.00 Square Feet

    Dimensions: 12x11

  • Dinette

    Level: First

    Area: 48.00 Square Feet

    Dimensions: 8x6

  • Primary Bathroom

    Level: First

    Area: 108.00 Square Feet

    Dimensions: 9x12

Interior

  • Flooring

    Carpet, Ceramic Tile, Laminate

  • Heating

    Electric

  • Appliances

    Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator

  • Cooling

    Central Air

  • Exterior Features

    Rain Gutters

  • Interior Features

    Ceiling Fans(s), Split Bedroom, Vaulted Ceiling(s), Walk In Closet(s)

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 1984

  • Home type

    Single Family Residence

  • Construction Materials

    Stucco

  • Property Condition

    Completed

  • Foundation Details

    Slab

  • Roof

    Shingle

Utilities & Energy

  • Water Source

    Public

  • Fireplace Features

    Family Room, Wood Burning

  • Parking Features

    Driveway, Garage Door Opener

  • Laundry Features

    Inside, Laundry Room

  • Utilities

    Bb/hs Internet Available, Cable Available, Electricity Connected, Fiber Optics, Fire Hydrant, Phone Available, Public, Sewer Connected, Underground Utilities, Water Connected

  • Pool Features

    Gunite, In Ground, Screen Enclosure

Other Features

  • Community Features

    Deed Restrictions, Sidewalks, Street Lights

  • Patio And Porch Features

    Covered, Rear Porch, Screened

  • Lot Features

    In County, Sidewalk, Paved

  • Subdivision Name

    Amherst

Price History

DateEventPrice

10/07/2026

Source: mls_logoStellar MLS-FL #MFRO6413841

Listed for Sale

$475,000 -1.04%

$285/sqft

08/19/2026

Source: mls_logoStellar MLS-FL #MFRO6413841

Contingent (Active Under Contract)

$480,000

$288/sqft

08/19/2026

Source: mls_logoStellar MLS-FL #MFRO6413841

Listed for Sale

$480,000

$288/sqft

08/19/2026

Source: mls_logoStellar MLS-FL #MFRO6413841

Listing Removed

$480,000 -2.04%

$288/sqft

08/03/2026

Source: mls_logoStellar MLS-FL #MFRO6413841

Off Market

$490,000 -1.98%

$294/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 08, 2026, 09:45PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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