$2,250,000
PENDING

43 Chessor Ln Wilton, CT 06897

Estimated payment $14,960/month

Total Views 2,055
5 Beds
4.5 Baths
5,352 Sq Ft
$420 Price per Sq Ft

Highlights

  • Open Floorplan
  • Colonial Architecture
  • 5 Fireplaces
  • Miller-Driscoll School Rated A
  • Attic
  • Bonus Room

About This Home

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.

Listing Agent

Cindy Raney

Coldwell Banker Realty License #RES.0766946 Listed on: 06/15/2025

Coldwell Banker Realty

Co-Listing Agent

Adrienne Schoetz

Coldwell Banker Realty License #RES.0806091

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $32,691

Year Built

  • Built in 2004

Lot Details

  • 1.31 Acre Lot
  • Stone Wall
  • Sprinkler System
  • Garden

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Clap Board Siding
  • Block Exterior
  • Stone Siding
  • Radon Mitigation System

Interior Spaces

  • Open Floorplan
  • Central Vacuum
  • Entertainment System
  • Built In Speakers
  • Sound System
  • 5 Fireplaces
  • Thermal Windows
  • French Doors
  • Mud Room
  • Entrance Foyer
  • Bonus Room
  • Home Gym
  • Home Security System

Kitchen

  • Built-In Oven
  • Gas Range
  • Range Hood
  • Microwave
  • Dishwasher
  • Wine Cooler

Bedrooms and Bathrooms

  • 5 Bedrooms

Laundry

  • Laundry on upper level
  • Dryer
  • Washer

Attic

  • Storage In Attic
  • Walkup Attic
  • Unfinished Attic

Partially Finished Basement

  • Heated Basement
  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Basement Storage

Parking

  • 3 Car Garage
  • Automatic Garage Door Opener

Outdoor Features

  • Balcony
  • Patio
  • Exterior Lighting

Location

  • Property is near shops
  • Property is near a golf course

Schools

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

Utilities

  • Zoned Heating and Cooling System
  • Heating System Uses Oil
  • Programmable Thermostat
  • Underground Utilities
  • Power Generator
  • Private Company Owned Well
  • Fuel Tank Located in Basement
  • Cable TV Available

Listing and Financial Details

  • Exclusions: Please see list of Inclusions/Exclusions
  • Assessor Parcel Number 1926674

Home Details

Home Type

Single Family

Est. Annual Taxes

$32,691

Year Built

Built in 2004

Lot Details

0

Listing Details

  • Neighborhood: South Wilton
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 4872
  • Sq Ft Est Heated Below Grade: 480
  • Total Sq Ft: 5352
  • Year Built: 2004
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot, Shopping/Mall
  • In Law Access: Second Floor
  • Exclusions: Please see list of Inclusions/Exclusions
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: Yes
  • Directions: Range Rd. Right on McFadden, Right on Chessor Ln, #43.
  • In Law Apartment: Possible
  • Living Area Sq Ft Per Public Record: 4872
  • Street Type: Lane
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 5
  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Fireplaces: 5
  • Attic Description: Unfinished, Storage Space, Walk-up
  • Basement Description: Full, Heated, Storage, Cooled, Interior Access, Partially Finished, Full With Walk-Out
  • Interior Amenities: Audio System, Auto Garage Door Opener, Cable - Available, Central Vacuum, Open Floor Plan, Security System
  • Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • Additional Rooms: Bonus Room, Exercise Room, Foyer, Mud Room, Roughed-In Bath
  • Laundry Room Info: Upper Level
  • Attic: Yes
  • Home Automation: Built In Audio, Entertainment System
  • Street Number Modifier: 43

Exterior Features

  • Exterior Features: Balcony, Underground Utilities, Garden Area, Lighting, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Exterior Siding: Clapboard, Stone
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: No
  • Construction Description: Frame, Block

Garage/Parking

  • Garages Number: 3
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air, Zoned
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Domestic
  • Water Source: Private Well
  • Sewer: Septic

Schools

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

Green Features

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

Lot Info

  • Acres: 1.31
  • Lot Description: Dry Level Lot Sloping Lot On Cul-De-Sac Professionally Landscaped
  • Flood Zone: No
  • Zoning: R-1
  • Parcel #: 1926674

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 32691
  • Total Assessed Value: 1339240
  • Mil Rate Total: 24.41

MLS Schools

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

Map

Range of Values:

Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $32,691 $1,339,240 $301,210 $1,038,030
2024 $32,061 $1,339,240 $301,210 $1,038,030
2023 $29,046 $992,670 $287,980 $704,690
2022 $28,023 $992,670 $287,980 $704,690
2021 $27,666 $992,670 $287,980 $704,690
2020 $27,259 $992,670 $287,980 $704,690
2019 $28,331 $992,670 $287,980 $704,690
2018 $28,633 $1,015,700 $302,610 $713,090
2017 $28,206 $1,015,700 $302,610 $713,090
2016 $27,769 $1,015,700 $302,610 $713,090
2015 $27,251 $1,015,700 $302,610 $713,090
2014 $26,926 $1,015,700 $302,610 $713,090
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/03/2025 07/03/25 Pending -- -- --
06/19/2025 06/19/25 For Sale $2,250,000 -- $420 / Sq Ft
Source: SmartMLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $2,075,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $573,618 Adjustable Rate Mortgage/ARM
Closed $606,893 Unknown
Closed $266,000 Credit Line Revolving
Closed $601,450 Adjustable Rate Mortgage/ARM
Source: Public Records

Similar Homes in Wilton, CT

  • 433 Belden Hill Rd, Wilton, CT 06897

    $2,499,000

    • 5 Beds
    • 4.5 Baths
    • 6,400 Sq Ft
    • 433 Belden Hill Rd
    • Wilton, CT

    NEW PRICE! Exceptional Custom Designed Contemporary Colonial Farmhouse Style Estate in South Wilton. Set on 3.1 pristine acres of flat, manicured land in coveted South Wilton, this newly constructed 6,400 +/- square foot masterpiece sets a new standard for luxury living. No expense has been spared in creating this exceptional residence, where thoughtful design meets uncompromising quality. The

    Alison Mark Berkshire Hathaway NE Prop.

    Section Image
  • 5 Deerfield Rd, Wilton, CT 06897

    $1,750,000

    • 5 Beds
    • 4.5 Baths
    • 3,830 Sq Ft
    • 5 Deerfield Rd
    • Wilton, CT

    This extraordinary property stands as a testament to thoughtful preservation and modern comfort with soaring 11-foot ceilings and walls of glass that flood the interior with natural light. Built in 1969 with portions dating to the 1700s, this dramatic barn home is perfect as a weekend retreat or multi-family residence. This artistically designed home balances historic character with contemporary

    Christine Oleynick Keller Williams Realty

    Section Image
  • 93 Graenest Ridge Rd, Wilton, CT 06897

    $2,650,000

    • 5 Beds
    • 7 Baths
    • 6,447 Sq Ft
    • 93 Graenest Ridge Rd
    • Wilton, CT

    Welcome to 93 Graenest Ridge Road - an extraordinary modern residence custom designed and built by master craftsman Roy Tolliver. Set gracefully at the end of a quiet cul-de-sac in one of Wilton's most sought-after central neighborhoods, this architectural gem is a stunning example of elevated design, meticulous detail, and timeless craftsmanship. Every inch of this home is infused with

    Kim Burke Berkshire Hathaway NE Prop.

    Section Image
  • 132 Belden Hill Rd, Wilton, CT 06897

    $2,750,000

    • 6 Beds
    • 8 Baths
    • 8,636 Sq Ft
    • 132 Belden Hill Rd
    • Wilton, CT

    Stunning South Wilton estate with extensive luxury renovations and separate guest house for in-laws, Au Pair suite or legal rental. Features brand-new chef's kitchen with Wolf and Sub-Zero appliances, completely remodeled basement with wine cellar, home gym, and media room, plus updated bedrooms and bathrooms throughout. The versatile guest addition offers a great room, full kitchen, and bath -

    Peter Hastings Hastings Real Estate

    Section Image
  • 66 Little Brook Rd, Wilton, CT 06897

    $1,829,000

    • 4 Beds
    • 3.5 Baths
    • 4,023 Sq Ft
    • 66 Little Brook Rd
    • Wilton, CT

    Stunning, One-of-a-Kind Architecturally Distinctive Home in a Coveted South Wilton Neighborhood Tucked at the end of a quiet cul-de-sac and abutting 53-acre Cherry Lane Park, this extraordinary four-bedroom, three-and-one-half-bath home offers a rare blend of timeless design, exceptional craftsmanship, and privacy. Custom-built with stone and shingle, copper gutters, and a mix of cedar and

    Susan Larsen William Raveis Real Estate

    Section Image
  • 33 Middlebrook Farm Rd, Wilton, CT 06897

    $2,595,000

    • 5 Beds
    • 7 Baths
    • 5,860 Sq Ft
    • 33 Middlebrook Farm Rd
    • Wilton, CT

    **REDUCED** Nestled in Wilton's most prestigious enclave, the home offers nearly 3 acrs of breathtaking beauty& privacy. Tree-lined drive winds along tranquil Comstock Brook, leading to the distinguished residence. Mature cherry, apple, maple, blue spruce, and pine trees enhance the idyllic setting, while an expansive stone terrace invites al fresco dining & offers potential for future pool.

    Shalini Madaras Silver Pine Real Estate

    Section Image
  • 125 Nod Hill Rd, Wilton, CT 06897

    $2,650,000

    • 5 Beds
    • 6 Baths
    • 6,046 Sq Ft
    • 125 Nod Hill Rd
    • Wilton, CT

    This stunning custom Colonial at 125 Nod Hill Road was crafted by renowned architect Rick Moisan. Nestled on 2.48 acres with peaceful water views, the 6,046 sq ft residence blends timeless architecture with modern comfort in an idyllic setting. A mahogany front porch welcomes you inside, where high ceilings, custom millwork, and sun-filled rooms create an atmosphere of refined elegance. The

    Benjamin Howell Coldwell Banker Realty

    Section Image
  • 211 Linden Tree Rd, Wilton, CT 06897

    $1,699,000

    • 5 Beds
    • 4.5 Baths
    • 5,382 Sq Ft
    • 211 Linden Tree Rd
    • Wilton, CT

    Price Reduction on Stunning Cape Cod Retreat in Wilton, CT-5 Bed | 4.5 Bath | Newly built in 2015 and nestled in the heart of scenic Wilton, this stunning open floorplan home blends timeless charm and parklike views with modern luxury and energy efficiency. Boasting 5 spacious bedrooms and 4.5 elegantly appointed bathrooms, this home is the perfect retreat for everyday comfort and unforgettable

    Jeffrey Kaplan William Raveis Real Estate

    Section Image
  • 319 Mountain Rd, Wilton, CT 06897

    $2,150,000

    • 5 Beds
    • 6 Baths
    • 5,600 Sq Ft
    • 319 Mountain Rd
    • Wilton, CT

    Stunning custom Colonial with timeless architecture and a sophisticated, transitional interior design. Thoughtfully crafted with rich hardwood floors, intricate millwork, and soaring ceilings, this elegant home offers a comfortable and effortless flow. A bluestone slate walk leads to the open Foyer. The private Library features French doors and custom built-ins. The formal Living Room with gas

    Karla Murtaugh Compass Connecticut, LLC

    Section Image

Source: SmartMLS

MLS Number: 24104186

SmartMLS

APN: WILT-000084-000015-000004