252 Chestnut Hill Rd

Killingworth, CT 06419

$750,000
Last Sold Price
4
Beds
2,873 Sq. Ft.
$261 / Sq. Ft.
2,873
Sq. Ft.
$261
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 11/21/25
Closed 11/21/25
Welcome to 252 Chestnut Hill Road!

Description

Nestled on 2.6 acres along the scenic Hammonasset River, this custom-built 1988 home is a private retreat surrounded by nature and wildlife. With 4bd, 3.5ba, and 2,873 sqft. of space, this home is filled with natural light. Expansive picture windows flank the back of the house and showcase the STUNNING river views. Enjoy trout fishing right from your backyard, or simply relax in the beauty of the setting while making s'mores at the fire pit. The attractive kitchen with cherry cabinetry and 3 large...Nestled on 2.6 acres along the scenic Hammonasset River, this custom-built 1988 home is a private retreat surrounded by nature and wildlife. With 4bd, 3.5ba, and 2,873 sqft. of space, this home is filled with natural light. Expansive picture windows flank the back of the house and showcase the STUNNING river views. Enjoy trout fishing right from your backyard, or simply relax in the beauty of the setting while making s'mores at the fire pit. The attractive kitchen with cherry cabinetry and 3 large picture windows overlooks the property and provides some of the best inside views. The living room with an elegant, wood-burning fireplace, a primary suite, and the laundry room are also found on the 1st floor. Designed for multigenerational living, this flexible floor plan also includes a guest studio with its own entrance and full bath. Upstairs, you'll find 3 bedrooms and another full bath. This floor was formally used as an in-law space and features the largest of the 4 bedrooms that could easily be reimagined into an exceptional 2nd floor primary suite. The basement is highlighted by a Cedar closet and a finished room ideal as a gym or wine cellar. The beautiful post-and-beam construction, 3-car garage (with a 2nd floor loft!) will knock your socks off. This barn could house all your grown up toys! The seamless indoor-outdoor living at this unique property make it a rare opportunity for outdoor enthusiasts seeking both comfort and character. Not one to miss. Really special!
  1. Listed by Phoebe V Finch • William Pitt Sotheby's Int'l
    P: (617)-645-3907 C: (617)-645-3907 pschreiner@wpsir.com

Property Details for 252 Chestnut Hill Road

Basement Description
Full, Partially Finished
Direct Waterfront
Yes
Garages Number
3
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Detached Garage
Swimming Pool
No
LISTING CLOSED: 11/21/2025 12:00 AM

Property Details for 252 Chestnut Hill Road

StatusClosed
MLS #24125829
Days on Market5
Taxes$9,052 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1988
Lot Size2.60 AC / 113,256 SF
CountyMiddlesex County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch

Sold By William Pitt Sotheby's Int'l, Phoebe V Finch

Add your commute

Building Information for 252 Chestnut Hill Road

Stories-Year Built1988Building Size-Lot Size2.60 AC / 113,256 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$4,566 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,812

Property Taxes

$754

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 252 Chestnut Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 79 to Chestnut Hill. House on the right. Look for the barn.
  • Elementary School: Killingworth
  • High School: Haddam-Killingworth
  • Latitude: 41.327904
  • Longitude: -72.605578
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $9,052
Interior and Exterior Features
Exterior Features
  • Waterfront Description: River, Walk to Water, View, Access
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Freezer, Disposal, Washer, Dryer
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 1
  • Laundry Room Info: Main Level
  • Rooms Additional: Exercise Room, Laundry Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Corian Counters,Island,Hardwood Floor
  • Room Length: 27.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 24.0
Room 2
  • Room Entry Order: 2
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 27.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 19.0
Room 3
  • Room Entry Order: 3
  • Room Features: Balcony/Deck,Full Bath,Sliders,Walk-In Closet
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 4
  • Room Entry Order: 4
  • Room Features: Breakfast Bar,Built-Ins,Granite Counters,Wet Bar,Tub w/Shower,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Studio Apt
  • Room Width: 12.0
Room 5
  • Listing Key: 3E7A21F73C5359C4E0631A01100AED46
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 6
  • Room Entry Order: 6
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 7
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 8
  • Room Entry Order: 8
  • Room Features: Vinyl Floor
  • Room Length: 7.0
  • Room Level: Upper
  • Room Type: Other
  • Room Width: 9.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1988
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Separate Entry
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 2873
Lot Information
  • Lot Description: Lightly Wooded, Sloping Lot, Cleared, Professionally Landscaped
  • Parcel Number: 997780
  • Sq Ft Est Heated Above Grade: 2873.0
  • Sq Ft Total: 2873.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 252 Chestnut Hill Road

DateEvent & SourcePriceAppreciation
Nov 21, 2025

Closed (Public Record)

Public Record #1922180910

$750,000—
DateEvent & SourcePrice
11/21/2025

Closed (Public Record)

Public Record #1922180910

$750,000

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

Public Records for 252 Chestnut Hill Road

Taxable ValueLand$75,530Additions$269,710Total$345,240
Tax Record2024$9,052 ($754 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt2,873 SqFtAbove Grade Finished SqFt2,873 SqFtUnfinished Basement SqFt1,375 SqFtStories2Lot Size113,256 SqFtStyleSingle Family ResidenceYear Built1988Year Renovated2002ZoningR-2CountyLOWER CONNECTICUT RIVERAPNKILL M:35 B:43Fireplace TypeHas Fireplace

Schools near 252 Chestnut Hill Road

This home is within Regional School District 17.
Rating
School
Type
Grades
Distance
Haddam-Killingworth Intermediate School
Public - 4 to 5
Haddam-Killingworth Middle School
Public - 6 to 8
Haddam-Killingworth High School
Public - 9 to 12
Burr District Elementary School
Public - K to 3
Rating
School
Distance
Haddam-Killingworth Intermediate School
Public4 to 5

Haddam-Killingworth Middle School
Public6 to 8

Haddam-Killingworth High School
Public9 to 12

Burr District Elementary School
PublicK to 3

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.

Similar Homes

Nearby off-market homes

AddressSold priceBedsBathsSqftLot AC
249 Chestnut Hill Road, Killingworth, CT 06419
$205,000
4
1,824
2
253 Chestnut Hill Road, Killingworth, CT 06419
$360,000
4
2,180
2.1
Unk Chestnut Hill Road, Killingworth, CT 06419
$245,000
–
–
–
17.40
259 Chestnut Hill Road, Killingworth, CT 06419
–
4
2,080
2.2
237 Chestnut Hill Road, Killingworth, CT 06419
$391,000
3
1,852
2.3

Explore Nearby Homes

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 Pitt Sotheby's Int'l, Phoebe V Finch

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.