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.
Sold for $2,350,000
$2,350,000
43 Chessor Lane, Wilton, CT 06897
5beds
5,352sqft
Single Family Residence
Built in 2004
1.31 Acres Lot
$2,377,800 Zestimate®
$439/sqft
$7,704 Estimated rent
Home value
$2,377,800
$2.14M - $2.64M
$7,704/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: September 06, 2025 at 08:03am
Listed by:
Cindy Raney & Team,
Cindy Raney 203-257-8320,
Coldwell Banker Realty 203-227-8424,
Co-Listing Agent: Adrienne Schoetz 917-826-5345,
Coldwell Banker Realty
Bought with:
Cheryl Williams, RES.0800406
Brown Harris Stevens
Source: Smart MLS,MLS#: 24104186
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Balcony/Deck, Gas Log Fireplace, Full Bath, Sliders, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Cathedral Ceiling(s), Beamed Ceilings, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bathroom
- Features: Hardwood Floor
- Level: Main
Bathroom
- Level: Upper
Dining room
- Features: Fireplace, Hardwood Floor
- Level: Main
Family room
- Features: Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Breakfast Bar, Dining Area, Kitchen Island, Pantry, Patio/Terrace, Hardwood Floor
- Level: Main
Living room
- Features: Hardwood Floor
- Level: Main
Office
- Features: Hardwood Floor
- Level: Main
Rec play room
- Features: Fireplace, Wall/Wall Carpet
- Level: Lower
Heating
- Forced Air, Zoned, Oil
Cooling
- Central Air
Appliances
- Included: Gas Range, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Upper Level, Mud Room
Features
- Sound System, Central Vacuum, Open Floorplan, Entrance Foyer
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Heated,Storage Space,Cooled,Interior Entry,Partially Finished
- Attic: Storage,Walk-up
- Number of fireplaces: 5
Interior area
- Total structure area: 5,352
- Total interior livable area: 5,352 sqft
- Finished area above ground: 4,872
- Finished area below ground: 480
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 3
Features
- Patio & porch: Patio
- Exterior features: Balcony, Garden, Lighting, Stone Wall, Underground Sprinkler
Lot
- Size: 1.31 Acres
- Features: Dry, Level, Sloped, Cul-De-Sac, Landscaped
Details
- Parcel number: 1926674
- Zoning: R-1
- Other equipment: Generator Ready, Entertainment System
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard, Stone
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2004
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Cable Available
Green energy
- Energy efficient items: Thermostat, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Health Club, Library, Medical Facilities, Playground, Shopping/Mall
Location
- Region: Wilton
- Subdivision: South Wilton
Price history
| Date | Event | Price |
|---|---|---|
| 9/5/2025 | Sold | $2,350,000+4.4%$439/sqft |
Source:  Smart MLS #24104186 Report a problem | ||
| 7/3/2025 | Pending sale | $2,250,000$420/sqft |
Source: Smart MLS #24104186 Report a problem | ||
| 6/19/2025 | Listed for sale | $2,250,000+8.4%$420/sqft |
Source: Smart MLS #24104186 Report a problem | ||
| 5/8/2006 | Sold | $2,075,000$388/sqft |
Source: Smart MLS #98268194 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $32,691 +2% | $1,339,240 |
| 2024 | $32,061 +10.4% | $1,339,240 +34.9% |
| 2023 | $29,046 +3.7% | $992,670 |
Find assessor info on the county website
Neighborhood: South Wilton
Nearby schools
GreatSchools rating
- NAMiller-Driscoll SchoolGrades: PK-2Distance: 0.8 mi
- 9/10Middlebrook SchoolGrades: 6-8Distance: 2.4 mi
- 10/10Wilton High SchoolGrades: 9-12Distance: 2.9 mi
Schools provided by the listing agent
- Elementary: Miller-Driscoll
- Middle: Middlebrook
- High: Wilton
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.