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$2,350,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 5,352 Sq. Ft.
  • 3 Car Garage
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Perched at the end of a peaceful South Wilton cul-de-sac, 43 Chessor Lane is a rare opportunity to own a custom-built masterpiece crafted by one of the area's most respected builders-for his own family. Designed with uncompromising quality and exceptional attention to detail, this home combines timeless elegance with cutting-edge technology for an elevated lifestyle. A new sweeping Belgian block-lined drive welcomes you to over 5,000 SF of refined living space, where thick crown moldings, coffered ceilings, and hand-finished millwork make a lasting impression. The sun-drenched chef's kitchen flows seamlessly into the family room, where a retractable projection screen and built-in surround sound create the ultimate home theater experience. A whole-house CAT 5 network, Control4 system, and six audio zones allow smart customization throughout. The primary suite features a spa-inspired bath, private sitting room, and balcony retreat. With five spacious bedrooms and 4.5 baths, every space is thoughtfully designed - with room for third floor expansion. A walk-out lower level with fireplace offers added living space and flexibility. Outside, professionally landscaped grounds offer room for pool, a bluestone patio, built-in fireplace, and intimate garden paths. Located within Wilton's award-winning school district and just minutes to shops, train, and town center-this home embodies both privacy and connection in one extraordinary setting.

Full Property Details for 43 Chessor Ln

General

  • Sold For: $2,350,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24104186
  • Added to Site: 216 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Bonus Room, Exercise Room, Foyer, Mud Room, Roughed-In Bath
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Central Vacuum, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 5
  • Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Full Bath: Upper
  • Partial Bath: Hardwood Floor, Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Balcony/Deck, Gas Log Fireplace, Full Bath, Sliders, W, Upper
  • Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Jack & Jill Bath, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Jack & Jill Bath, Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Cathedral Ceiling, Beams, Walk-In Closet, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Breakfast Bar, Dining Area, Island, Pantry, Patio/Terrace, Hard, Main
  • Formal Dining Room: Formal Dining Room - Fireplace, Hardwood Floor, Main
  • Office: Office - Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Fireplace, Wall/Wall Carpet, Lower
  • Rec Room: Fireplace, Wall/Wall Carpet, Lower
  • Laundry: Upper Level

Exterior

  • Exterior Features: Balcony, Underground Utilities, Garden Area, Lighting, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Color: Beige

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: South Wilton
  • Driving Directions: Range Rd. Right on McFadden, Right on Chessor Ln, #43.

School Information

  • Elementary School: Miller-Driscoll
  • Middle School: Middlebrook
  • High School: Wilton

Community

  • Community Name: South Wilton

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Zoned, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Stone
  • Basement Desc.: Full, Heated, Storage, Cooled, Interior Access, Partially Finished, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,352
  • Above Ground: 4,872 Sq. Ft.
  • Below Ground: 480 Sq. Ft.
  • Year Built: 2004

Lot Features

  • Lot Size (Acres): 1.31
  • Zoning: R-1
  • Lot Description: Dry, Level Lot, Sloping Lot, On Cul-De-Sac, Professionally Landscaped

Green Features

  • Energy Features: Generator Ready, Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $1,339,240
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Please see list of Inclusions/Exclusions
  • Property ID: 1926674

Meet the listing agent

Meet the listing agent
— 43 Chessor Ln —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 43 Chessor Ln

School District:Wilton School District
NameGradesDistance
Miller-Driscoll School
217 Wolfpit Road, Wilton, CT 06897
PK-20.8 mi
Cider Mill School
240 School Road, Wilton, CT 06897
3-52.5 mi
Middlebrook School, Wilton, CT
131 School Road, Wilton, CT 06897
6-82.4 mi
Wilton High School
395 Danbury Road, Wilton, CT 06897
9-122.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 43 Chessor Ln

Date
Details
Price
Change
Source
9/05/2025
Sold
$2,350,000
4.44%
MLS
6/19/2025
Listed
$2,250,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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43 Chessor Lane, Wilton, CT 06897 (MLS# 24104186) is a Single Family property that was sold at $2,350,000 on September 05, 2025. This property was listed by Cindy Raney & Team from our Westport Office.Want to learn more about 43 Chessor Lane? Do you have questions about finding other Single Family real estate for sale in Wilton? You can browse all Wilton real estate or contact a Coldwell Banker agent to request more information.