50 Chessor Lane, Wilton, CT 06897
OFF MARKET

$2,214,900

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 5,999 sqft (on 1.01 acres)

50 Chessor Lane, Wilton, CT 06897

South Wilton
Est. Refi. Payment $15,042/mo*
Refinance Your Home
Currently Off Market - Sold Sep 6, 2024 for $1,999,000

Home Value

Trulia Estimate
$2.21M
Since last month
Decreased$7K (-0.3%)
Since last year
Increased$135K (+6.4%)
Since last sale
Increased$234K (+11.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +101% in the last 10 years
MonthEstimated value
2026
September 2026$2.23M
August 2026$2.23M
July 2026$2.24M
June 2026$2.26M
May 2026$2.21M
April 2026$2.22M
March 2026$2.18M
February 2026$2.16M
January 2026$2.12M
2025
2024
2020

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
51 Chessor Lane, Wilton, CT
0.06
Single-Family Home
$2,650,000
03/04/26
5
5
5,288
18 Edith Lane, Wilton, CT
0.25
Single-Family Home
$1,300,000
06/29/26
5
3
2,452
58 Kent Road, Wilton, CT
0.39
Single-Family Home
$1,345,000
09/11/26
4
2.5
3,504
44 Old Nursery Drive, Wilton, CT
0.56
Single-Family Home
$1,860,044
07/01/26
5
3.5
4,324
53 Wolfpit Road, Wilton, CT
0.82
Single-Family Home
$1,600,000
06/30/26
5
4
4,843
183 Range Road, Wilton, CT
0.46
Single-Family Home
$1,610,000
08/10/26
5
3
2,937
112 Old Belden Hill Road, Norwalk, CT
0.82
Single-Family Home
$1,450,000
10/08/25
6
4.5
4,548
515 Belden Hill Road, Wilton, CT
0.74
Single-Family Home
$1,310,000
12/15/25
5
3.5
3,357
105 Danbury Road, Wilton, CT
0.48
Single-Family Home
$840,000
12/11/25
4
3.5
2,050
25 Arrowhead Road, Wilton, CT
0.39
Single-Family Home
$900,000
04/03/26
3
2.5
2,679

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
43 Chessor Lane, Wilton, CT 06897
0.05
$2,529,300
5
4.5
5,352
Off Market
51 Chessor Lane, Wilton, CT 06897
0.06
$2,650,000
5
5
5,288
Recently Sold
47 Chessor Road, Wilton, CT 06897
0.09
$1,377,500
4
2.5
3,650
Off Market
66 Kent Hills Lane, Wilton, CT 06897
0.14
$525,000
3
2
2,296
Recently Sold
60 Mcfadden Drive, Wilton, CT 06897
0.24
$1,124,800
4
3
2,610
Off Market
66 Mcfadden Drive, Wilton, CT 06897
0.26
$953,500
4
2
2,384
Off Market
18 Edith Lane, Wilton, CT 06897
0.25
$1,300,000
5
3
2,452
Recently Sold
65 Valeview Road, Wilton, CT 06897
0.26
$1,076,300
3
3
1,854
Off Market
60 Valeview Road, Wilton, CT 06897
0.30
$1,281,700
4
3
2,816
Off Market
134 Range Road, Wilton, CT 06897
0.33
$1,340,800
3
2
2,197
Off Market
21 Edith Lane, Wilton, CT 06897
0.31
$2,321,800
3
3.5
3,867
Off Market

Local Information

  • Map ViewExplore the area around 50 Chessor Lane.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
1.01 acre lot
5,999 sqft
$369/sqft
3 Car Garage

About this House

Custom built for the current owners, this 5,999 sq ft, 14 room, 5 bedroom, 4 full & 2 half bath, 3 car heated garage home was built with an "only the best will do" approach. The main floor boasts a beautiful open floor plan with 9ft high ceilings. The gourmet eat-in kitchen complete with Wolf, Subzero, Thermador and Bosch appliances flows beautifully to an open living space featuring a 12' stone fireplace in the family room, formal dining room and outdoor space, perfect for entertaining at any time of year. An office, living room, pantry, mudroom and two half-baths complete the first floor. On the second floor, enjoy your private primary bedroom with luxurious ensuite, large walk-in closet and fireplace. 3 large additional bedrooms all with walk in closets, two full baths and a bonus living space with dramatic cathedral ceilings complete the floor. The beautifully finished loft-style 3rd floor offers another office or crafting space option. Fully finished walk out lower level with guest bedroom and ensuite, exercise and game room offer tons of flexible options. Outside, peace and tranquility abound on your mahogany deck that leads to a heated inground swimming pool and is privately surrounded by a beautifully wooded 1 acre fully sprinklered lot. In addition, this home comes complete with tons of closet space, 2 gas and 1 wood fireplace, Generac whole house generator. Located on a cul-de-sac in South Wilton close to town center, restaurants and shopping.
50 Chessor Lane, Wilton, CT 06897 is a 5 bedroom, 6 bathroom, 5,999 sqft single-family home in South Wilton, built in 2005. It last sold for the $1,999,000 asking price on Sep 6, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,214,900, with a rent estimate of $11,199/month.
Last check for updates: about 2 hours ago
Listed by Kevin O'brien, (203) 943-9586
O'Brien Premier Properties, (203) 822-2524
Bought with: Lindsay Violette, (203) 769-9811, Houlihan Lawrence, (203) 869-0700
Source: Smart MLS, MLS#24026020

Home Details for 50 Chessor Lane

Interior Features

Interior Details
Basement: Full,Garage Access,Partially Finished,Liveable SpaceNumber of Rooms: 14Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Loft, Office, Other, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 5999 Square Feet
Appliances & Utilities
Appliances: Gas Range, Oven, Microwave, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached
Pool
Pool: Vinyl, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4777 Square FeetFinished Area (below surface): 1222 Square Feet

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1926680

Price & Status

Price
List Price: $1,999,000
Status Change & Dates
Off Market Date: Mon Aug 12 2024Possession Timing: Nego

Active Status

MLS Status: Closed

Location

Direction & Address
City: WiltonCommunity: South Wilton
School Information
Elementary School: Miller-DriscollJr High / Middle School: Middlebrook, Cider MillHigh School: Wilton

Building

Building Area
Building Area: 5999 Square Feet

HOA

No HOA

Lot Information

Lot Area: 1.01 Acres

Miscellaneous

BasementMls Number: 24026020Attic: Partially Finished, Walk-upAbove Grade Unfinished Area: 4777

Price and Tax history

DateEventPrice
Sep 6, 2024
Source: Smart MLS #24026020
Sold
$1,999,000
Aug 13, 2024
Source: Smart MLS #24026020
Pending
$1,999,000
Jun 20, 2024
Source: Smart MLS #24026020
Listed For Sale
$1,999,000
Sep 13, 2004
Source: N/A
Sold
$460,000

Market trends in Wilton

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$46.67KMoM
Sale-to-List Price
105.1%
0.7%MoM
Price per sq ft
$427
$4MoM
Available listings
49
15MoM

Around this home

Neighborhood Overview

South Wilton
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about South Wilton

  • Jelani37
    "It’s a small town, and traffic can be bad during rush hours on the Merritt "
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Frequently asked questions about 50 Chessor Lane

  • What is 50 Chessor Lane estimated to be worth?
    Trulia's estimated value for 50 Chessor Lane in Wilton, CT is $2,214,900.
  • What is the price history for 50 Chessor Lane?
    50 Chessor Lane in Wilton, CT last sold for $1,999,000 in September 2024.
  • Is Wilton a buyer's or seller's market?
    Wilton is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Wilton?
    The median sale price in Wilton is $1.47M. That is up $46.67K from the prior month.
  • Does 50 Chessor Lane have air conditioning?
    Yes, 50 Chessor Lane in Wilton, CT has air conditioning.
  • Does 50 Chessor Lane have a pool?
    Yes, 50 Chessor Lane in Wilton, CT has a pool.

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