381 Chestnut Hill Road

Closed 4/10/26Virtual Tour
Closed 4/10/26Virtual Tour
Gallery Image 1
Sold
Last Sold Price
$1,325,000
4 beds3,438 sqft

381 Chestnut Hill Rd, Norwalk, CT 06851

Single FamilyProperty Type
1.11 acresLot Size
1999Year Built
$385/sq ftPrice per sq ft
6 carsParking Spaces

Description

Set on a private acre in the sought-after Four Winds Farm community, this turnkey colonial offers a peaceful, country setting with exceptional convenience. The sunny, open floor plan centers around an upscale kitchen with a large island and generous cabinetry, flowing seamlessly into a spacious family room with coffered ceilings and fireplace that's ideal for everyday living and entertaining. A wraparound deck extends the living space outdoors, overlooking a peaceful, private setting ideal for dining,...Set on a private acre in the sought-after Four Winds Farm community, this turnkey colonial offers a peaceful, country setting with exceptional convenience. The sunny, open floor plan centers around an upscale kitchen with a large island and generous cabinetry, flowing seamlessly into a spacious family room with coffered ceilings and fireplace that's ideal for everyday living and entertaining. A wraparound deck extends the living space outdoors, overlooking a peaceful, private setting ideal for dining, alfresco, relaxing, and entertaining. The thoughtfully designed layout balances open living with privacy, featuring a luxurious primary suite with sitting area and ample closets, along with three additional well-proportioned bedrooms. Additional highlights include formal living and dining rooms, a first-floor private home office with nearby full bath, and a high-ceiling walk-out basement offering flexible living space and attached garage equipped with a ChargePoint Home Flex Level 3 EV charger for modern energy conscience living. Conveniently located near Wilton Center, Westport town center, Cranbury Market, and Merritt Parkway access, this home feels like a retreat without sacrificing ease of living.
Listing closed: 04/10/2026 12:00 AM • Source: SMARTMLS, MLS#: 24147896
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Location

Listing Courtesy of William Raveis Real Estate, Michelle Genovesi
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$8,669 per month

30 year fixed, 7.03% Interest

Principal and Interest

$7,074

Property Taxes

$1,596

HOA Dues

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Property Information for 381 Chestnut Hill Road

Property Details

  • Taxes: $19,146 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Full, Storage, Concrete Floor, Full With Walk-Out
  • Direct Waterfront: No
  • Expected Active Date: 02-07-2026
  • Garages Number: 2
  • Neighborhood: Cranbury
  • Style: Colonial
  • Garage Parking Info: Attached Garage, Driveway
  • Swimming Pool: No
  • Expected On Market Date: 02-07-2026

Building Information

  • Year Built: 1999
  • Lot Size: 1.11 AC / 48,351 SF

Summary

Property and Location
  • Acres Source: Public Records
  • Directions: Please use GPS
  • Elementary School: Cranbury
  • High School: Norwalk
  • Latitude: 41.170969
  • Longitude: -73.395882
  • Middle Jr High School: West Rocks
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Private School(s), Stables/Riding, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 6
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $19,146

Interior and Exterior Features

Exterior Features
  • Exterior Features: Grill, Deck, Gutters, Lighting, Stone Wall
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Disposal, Washer, Dryer
  • Attic Description: Unfinished, Storage Space, Floored, Pull-Down Stairs
  • Cooling System: Ceiling Fans, Central Air, Zoned
  • Heat Type: Hot Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Built In Audio, Security System, Thermostat(s), Wired For Audio
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Humidifier, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: Laundry room off kitchen
  • Rooms Additional: Laundry Room, Workshop
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Tile Floor
  • Room Level: Main
  • Room Type: Full Bath
Room 3
  • Room Entry Order: 11
  • Room Features: Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Room 4
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 47E3520F6615A58AE0631A01100AC2E1
  • Room Entry Order: 3
  • Room Features: Vaulted Ceiling,Ceiling Fan,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 6
  • Room Entry Order: 4
  • Room Features: Granite Counters,French Doors,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 7
  • Room Entry Order: 5
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Level: Main
  • Room Type: Office
Room 8
  • Room Entry Order: 6
  • Room Features: Vaulted Ceiling,Ceiling Fan,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 9
  • Listing Key: 47E3520F6615A58AE0631A01100AC2E1
  • Room Entry Order: 7
  • Room Features: Ceiling Fan,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 8
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 9
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom

Property

Property and Assessments
  • Color: Grey
  • Construction Description: Frame
  • Driveway Type: Paved
  • Exclusions: Please see list on Documents
  • Exterior Siding: Clapboard, Cedar
  • Foundation Type: Concrete
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1999
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Living Area SQFT Per Public Records: 3438
Lot Information
  • Lot Description: Rear Lot, Treed, Sloping Lot, Professionally Landscaped
  • Parcel Number: 1941713
  • Sq Ft Est Heated Above Grade: 3438.0
  • Sq Ft Total: 3438.0
  • Zoning: AAA
Utilities
  • Energy Features: Generator Ready, Humidistat, Programmable Thermostat
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 50 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well

Multi Family

Income and Expenses
  • Estimated Annual Heat Cost: 3400
  • Occupied By: Owner

Property History for 381 Chestnut Hill Road

DateEvent & SourcePriceAppreciation
Apr 8, 2026

Closed (Public Record)

Public Record #1936245766

$1,325,000

+2.1% / yr

Jun 22, 2000

Closed (Public Record)

Public Record #91099327

$785,000—
Jun 22, 2000

Closed (Public Record)

Public Record #91099326

$250,000

+36.9% / yr

DateEvent & SourcePrice
04/08/2026

Closed (Public Record)

Public Record #1936245766

$1,325,000

+2.1% / yr

06/22/2000

Closed (Public Record)

Public Record #91099327

$785,000
06/22/2000

Closed (Public Record)

Public Record #91099326

$250,000

+36.9% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

381 Chestnut Hill Road

Beds

4

Baths

4.5

Total Finished SqFt

3,438 SqFt

Above Grade Finished SqFt

3,438 SqFt

Unfinished Basement SqFt

1,253 SqFt

Stories

2

Schools near 381 Chestnut Hill Road

This home is within Norwalk School District.
Rating
School
Type
Grades
Distance
Cranbury Elementary School
Public - PK to 5
West Rocks Middle School
Public - 6 to 8
Norwalk High School
Public - 9 to 12
P-Tech Norwalk
Public - 9 to 12
Rating
School
Distance
Cranbury Elementary School
PublicPK to 5

West Rocks Middle School
Public6 to 8

Norwalk High School
Public9 to 12

P-Tech Norwalk
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Michelle Genovesi

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.