43 Chessor Lane
Wilton, CT 06897
South Wilton
5 Beds
4.5 Baths
5,352 sqft (on 1.31 acres)
5 Beds
4.5 Baths
5,352 sqft
(on 1.31 acres)
Local Information
- Map ViewExplore the area around 43 Chessor Lane.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2004
Lot Size
1.31 acres
Living Area
5,352 sqft
Price/Sqft
$466
Parking
3 Car Garage
Description
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.
43 Chessor Lane, Wilton, CT 06897 is a 5 bedroom, 5 bathroom, 5,352 sqft single-family home in South Wilton, built in 2004. It last sold for $2,350,000 on Sep 5, 2025 (4% above the $2,250,000 asking price). It is currently off market. The Trulia Estimate is $2,494,300, with a rent estimate of $7,704/month.
Home Details for 43 Chessor Lane
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Interior Details Basement: Full,Heated,Storage Space,Cooled,Interior Entry,Partially FinishedNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 5352 Square Feet |
Appliances & Utilities Utilities: Underground Utilities, Cable AvailableAppliances: Gas Range, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Zoned,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 5Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane WindowsDoor: French Doors |
Security Security: Security System |
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Exterior Home Features Roof: AsphaltPatio / Porch: PatioExterior: Balcony, Garden, Lighting, Stone Wall, Underground SprinklerFoundation: Concrete PerimeterGardenNo Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage Door Opener |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 4872 Square FeetFinished Area (below surface): 480 Square Feet |
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Year Built Year Built: 2004 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Clapboard, StoneNot a New ConstructionDoes Not Include Home Warranty |
Property Information Not Included in Sale: Please see list of Inclusions/ExclusionsParcel Number: 1926674 |
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Price List Price: $2,250,000 |
Status Change & Dates Off Market Date: Thu Jul 03 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: WiltonCommunity: South Wilton |
School Information Elementary School: Miller-DriscollJr High / Middle School: MiddlebrookHigh School: Wilton |
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Building Area Building Area: 5352 Square Feet |
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Community Features: Golf, Health Club, Library, Medical Facilities, Playground, Shopping/Mall |
Other Playground |
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No HOA |
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Lot Area: 1.31 Acres |
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Energy Efficiency Features: Thermostat, Windows |
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BasementMls Number: 24104186Attic: Storage, Walk-upAbove Grade Unfinished Area: 4872 |
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GolfHealth ClubLibraryMedical FacilitiesPlaygroundShopping/Mall |
Last check for updates: about 3 hours ago
Listed by Cindy Raney, (203) 257-8320
Coldwell Banker Realty, (203) 227-8424
Co-Listing Agent: Adrienne Schoetz, (917) 826-5345
Coldwell Banker Realty, (203) 227-8424
Bought with: Cheryl Williams, (203) 981-5247, Brown Harris Stevens, (203) 655-1418
Source: Smart MLS, MLS#24104186
Price History for 43 Chessor Lane
| Date | Price | Event | Source |
|---|---|---|---|
| 09/05/2025 | $2,350,000 | Sold | Smart MLS #24104186 |
| 07/03/2025 | $2,250,000 | Pending | Smart MLS #24104186 |
| 06/19/2025 | $2,250,000 | Listed For Sale | Smart MLS #24104186 |
| 05/08/2006 | $2,075,000 | Sold | Smart MLS #98268194 |
Market trends in Wilton
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
66
7MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $32,691 |
| Assessment | $1,339,240 |
Home facts updated by county records
Comparable Sales for 43 Chessor Lane
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.04 | Single-Family Home | $2,650,000 | 03/04/26 | 5 | 5 | 5,288 | |
0.51 | Single-Family Home | $1,860,044 | 07/01/26 | 5 | 3.5 | 4,324 | |
0.26 | Single-Family Home | $1,300,000 | 06/29/26 | 5 | 3 | 2,452 | |
0.79 | Single-Family Home | $1,600,000 | 06/30/26 | 5 | 4 | 4,843 | |
0.23 | Single-Family Home | $1,003,000 | 10/22/25 | 3 | 3 | 1,854 | |
0.39 | Single-Family Home | $1,290,000 | 06/25/26 | 3 | 2.5 | 2,496 | |
0.84 | Single-Family Home | $1,450,000 | 10/08/25 | 6 | 4.5 | 4,548 | |
0.74 | Single-Family Home | $1,310,000 | 12/15/25 | 5 | 3.5 | 3,357 | |
0.10 | Single-Family Home | $525,000 | 05/29/26 | 3 | 2 | 2,296 |
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Assigned Schools
These are the assigned schools for 43 Chessor Lane.
- Cider Mill School
- 3-5
- Public
- 831 Students
9/10GreatSchools RatingParent Rating AverageGreat experience with 2 kids so farParent Review7y ago - Middlebrook School
- 6-8
- Public
- 852 Students
10/10GreatSchools RatingParent Rating AverageThe leadership and teachers at Middlebrook are the best I've known. This is so important for this age group. They really handle the challenges of middle school years so well. My children are very different from each other and they helped both of my children find their place and succeed academically. They had great middle school friends and and some of their favorite teachers. Not many can say that about middle school!Parent Review4y ago - Miller-Driscoll School
- PK-2
- Public
- 845 Students
NAGreatSchools RatingParent Rating AverageMy family has had terrible experiences with this school. The teachers cannot be bothered to communicate with parents or care about the kids enrolled. The curriculum is boring and does nothing to challenge the many bright kids at the school. The administrators care even less about the kids than the teachers do. They use screens to babysit the kids a lot. The only bright spot is the pretty building which does not make up for everything else. I actually don’t understand how this is a good school district.Parent Review5mo ago - Wilton High School
- 9-12
- Public
- 1202 Students
10/10GreatSchools RatingParent Rating AverageWe had an amazing experience with the Wilton school system. The AP classes offered helped us to get read for college and the teachers are incredibly helpful and kind. They educate the whole child, and care about the students. In today’s world, this is rare but the educators here are amazing educators and kind people. We moved to Wilton for the school system and it was a great decision.Parent Review1y ago 
Check out schools near 43 Chessor Lane.
Neighborhood Overview
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