18 Chestnut Hill Road

Closed 8/22/25
Closed 8/22/25
Gallery Image 1
Last Sold Price
$593,000
4 beds2,636 sqft$225/sqft
18 Chestnut Hill Rd, Simsbury, CT 06092

Description

Welcome to 18 Chestnut Hill Road, where charm, updates, and outdoor beauty come together in a truly special West Simsbury setting. This 4-bedroom, 2.1-bath home offers 2,626 square feet of living space & thoughtful upgrades throughout. Step inside to a bright living room w/ brand-new picture windows (2024) and a double-sided wood-burning fireplace that flows into the dining area. The remodeled kitchen features natural gas cooking, stainless steel appliances, & a lovely eat-in area w/ sliders to the...Welcome to 18 Chestnut Hill Road, where charm, updates, and outdoor beauty come together in a truly special West Simsbury setting. This 4-bedroom, 2.1-bath home offers 2,626 square feet of living space & thoughtful upgrades throughout. Step inside to a bright living room w/ brand-new picture windows (2024) and a double-sided wood-burning fireplace that flows into the dining area. The remodeled kitchen features natural gas cooking, stainless steel appliances, & a lovely eat-in area w/ sliders to the beautiful composite deck (2019). The spacious primary suite includes a remodeled bath & large walk-in closet. Three additional bedrooms-two on the main level & one on the garden level--offer flexibility for any lifestyle. Relax and unwind in the family room anchored by a stunning oak gas fireplace (2021) and featuring a custom bar area. Just off the family room is a mudroom w/ direct walkout access to the fenced backyard area- ideal for letting pets out with ease. Outside, the setting is something special. The newer composite deck creates the ideal space for grilling, relaxing, and entertaining. The fenced area is beautifully landscaped with flowering gardens and fruit trees, a firepit, a peaceful koi pond, and a greenhouse ready for year-round growing. The yard connects directly to the Farmington River Trail, providing instant access to scenic paths for walking, jogging, or biking right from your backyard. Sought-after Mountain Farms neighborhood & Tootin' Hills school district.
LISTING CLOSED: 08/22/2025 12:00 AM

  1. Listed by Karen B Mendes • Berkshire Hathaway NE Prop.
    P: (860) 944-8585 C: (860) 944-8585 karenmendes@bhhsne.com
  2. Listed by Jennifer S Petron • Berkshire Hathaway NE Prop.
    P: (860) 658-1981 C: (860) 558-1880 jenandkaren@bhhsne.com

Property Details for 18 Chestnut Hill Road

Status
Closed
MLS #
24107050
Days on Market
5
Taxes
$8,888 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential
Year Built
1968
Lot Size
0.78 AC / 33,976 SF
County
Hartford County
Basement Description
Full
Direct Waterfront
No
Expected Active Date
07-12-2025
Garages Number
2
Neighborhood
West Simsbury
Style
Raised Ranch
Garage Parking Info
Attached Garage, Driveway
Swimming Pool
No
Expected On Market Date
07-12-2025

Recent comparable sales

Median sold price

$640,000

Avg days on market

5

Sale-to-list ratio

114.4%

Simsbury, CT

9 comparable properties found

$650,000 | 6 Stockade Road, Simsbury, CT 06092
1

$650,000

Sold 06/04/26

4
Bedrooms
2,708
Square Feet
1.41
Acres

6 Stockade Road, Simsbury, CT 06092

$590,000 | 39 Chestnut Hill Road, Simsbury, CT 06092
2

$590,000

Sold 06/27/25

4
Bedrooms
2,678
Square Feet
0.71
Acres

39 Chestnut Hill Road, Simsbury, CT 06092

$663,750 | 34 Rocklyn Drive, Simsbury, CT 06092
3

$663,750

Sold 03/31/26

4
Bedrooms
2,386
Square Feet
0.7
Acres

34 Rocklyn Drive, Simsbury, CT 06092

$676,000 | 37 Madison Lane, Simsbury, CT 06092
4

$676,000

Sold 06/25/26

4
Bedrooms
2,745
Square Feet
0.98
Acres

37 Madison Lane, Simsbury, CT 06092

$569,000 | 33 Chestnut Hill Road, Simsbury, CT 06092
5

$569,000

Sold 06/30/26

4
Bedrooms
2,300
Square Feet
0.77
Acres

33 Chestnut Hill Road, Simsbury, CT 06092

$515,000 | 5 Vining Drive, Simsbury, CT 06070
6

$515,000

Sold 10/15/25

4
Bedrooms
2,566
Square Feet
1.19
Acres

5 Vining Drive, Simsbury, CT 06070

$654,000 | 33 Lawton Drive, Simsbury, CT 06070
7

$654,000

Sold 05/23/25

4
Bedrooms
2,566
Square Feet
1.05
Acres

33 Lawton Drive, Simsbury, CT 06070

$630,000 | 299 Bushy Hill Road, Simsbury, CT 06070
8

$630,000

Sold 08/14/26

4
Bedrooms
2,325
Square Feet
0.92
Acres

299 Bushy Hill Road, Simsbury, CT 06070

9

$640,000

Sold 06/12/25

4
Bedrooms
2.5
Bathrooms
2,769
Square Feet
0.86
Acres

21 Park Road, Simsbury, CT 06070

Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Berkshire Hathaway NE Prop., Karen B Mendes; Berkshire Hathaway NE Prop., Jennifer S Petron

Sold By Lewis Real Estate Services, Amber Fischer

Add your commute

Building Information for 18 Chestnut Hill Road

Stories-Year Built1968Building Size-Lot Size0.78 AC / 33,976 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$3,755 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,014

Property Taxes

$741

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 18 Chestnut Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: West Mountain Rd to Chestnut Hill
  • Elementary School: Tootin' Hills
  • High School: Simsbury
  • Latitude: 41.846465
  • Longitude: -72.863993
  • Middle Jr High School: Henry James
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Playground/Tot Lot, Private School(s), Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 2
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $8,888
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Utilities, Shed, Fruit Trees, Wrap Around Deck, Gutters, Garden Area, Lighting
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Laundry Room Info: Lower Level
  • Laundry Room Location: Separate laundry area off family room
  • Rooms Additional: Mud Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Built-Ins,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Remodeled,Sliders
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 3
  • Room Entry Order: 3
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 4
  • Room Entry Order: 4
  • Room Features: Ceiling Fan,Full Bath,Walk-In Closet
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 5
  • Listing Key: 386A2E1E43B75457E063E201100A0909
  • Room Entry Order: 5
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Dry Bar,Gas Log Fireplace,Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Family Room
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Lower
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Driveway Type: Paved
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1968
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 804
  • Living Area SQFT Per Public Records: 1832
Lot Information
  • Lot Description: Lightly Wooded
  • Parcel Number: 700975
  • Sq Ft Est Heated Above Grade: 1832.0
  • Sq Ft Total: 2636.0
  • Zoning: R40OS
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: 50 Gallon Tank
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 18 Chestnut Hill Road

DateEvent & SourcePriceAppreciation
Aug 18, 2025

Closed (Public Record)

Public Record #1911643342

$593,000

+13.0% / yr

Nov 23, 2020

Closed (Public Record)

Public Record #685008568

$332,500

-0.1% / yr

May 23, 2005

Closed (Public Record)

Public Record #161000196

$340,000—
DateEvent & SourcePrice
08/18/2025

Closed (Public Record)

Public Record #1911643342

$593,000

+13.0% / yr

11/23/2020

Closed (Public Record)

Public Record #685008568

$332,500

-0.1% / yr

05/23/2005

Closed (Public Record)

Public Record #161000196

$340,000

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

Public Records for 18 Chestnut Hill Road

Taxable ValueLand$81,480Additions$178,710Total$260,190
Tax Record2025$8,888 ($741 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt1,832 SqFtAbove Grade Finished SqFt1,832 SqFtUnfinished Basement SqFt961 SqFtStories1Lot Size33,977 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1993ZoningR40OSCountyCAPITOLAPNSIMS M:B15 B:303 L:166

Schools near 18 Chestnut Hill Road

This home is within Simsbury School District.
Rating
School
Type
Grades
Distance
Tootin' Hills School
Public - K to 6
Henry James Memorial School
Public - 7 to 8
Simsbury High School
Public - 9 to 12
The Master's School
Private - PK to 12
Rating
School
Distance
Tootin' Hills School
PublicK to 6

Henry James Memorial School
Public7 to 8

Simsbury High School
Public9 to 12

The Master's School
PrivatePK 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.

Similar Homes

New listings in 06092

$584,000 | 4 Lenora Drive, Simsbury, CT 06092
1/40
Open: 8/23 10:00AM - 12:00PM

$584,000

4
Bedrooms
2,742
Square Feet
2.59
Acres

4 Lenora Drive, Simsbury, CT 06092

a view of house with backyard and sitting area
1/40

$999,900

5
Bedrooms
3,603
Square Feet
3.28
Acres

13 Woodchuck Hill Road, Simsbury, CT 06092

a front view of a house with a yard
1/33
Listed By Coldwell Banker Realty

$499,900

3
Bedrooms
2,352
Square Feet
4.36
Acres

112 Hedgehog Lane, Simsbury, CT 06092

$699,900 | 30 North Canton Road, Simsbury, CT 06092
1/40
Open: 8/22 11:00AM - 01:00PM

$699,900

4
Bedrooms
3,366
Square Feet
4
Acres

30 North Canton Road, Simsbury, CT 06092

$725,000 | 184 Westledge Road, Simsbury, CT 06092
1/20
Listed By Coldwell Banker RealtyUnder Contract - Continue To Show

$725,000

5
Bedrooms
4,627
Square Feet
7.7
Acres

184 Westledge Road, Simsbury, CT 06092

$600,000 | 7 Banbury Drive, Simsbury, CT 06092
1/40
Open: 8/23 11:00AM - 01:00PM

$600,000

4
Bedrooms
2,622
Square Feet
0.62
Acres

7 Banbury Drive, Simsbury, CT 06092

$599,000 | 369 West Mountain Road, Simsbury, CT 06092
1/33
Listed By Coldwell Banker RealtyUnder Contract - Continue To Show

$599,000

4
Bedrooms
3,267
Square Feet
1.37
Acres

369 West Mountain Road, Simsbury, CT 06092

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 18 Chestnut Hill Road, Simsbury, CT 06092
$593,000
4
2,636
33,976
4 Watch Hill Lane, West Simsbury, CT 06092
$427,000
4
2.5
2,024
36,590
6 Watch Hill Lane, West Simsbury, CT 06092
$217,500
3
2.5
1,838
36,155
8 Watch Hill Lane, Simsbury, CT 06092
$325,000
3
2,128
33,541
19 Chestnut Hill Road, Simsbury, CT 06092
$349,000
4
2,384
31,363
23 Chestnut Hill Road, Simsbury, CT 06092
$225,000
3
2,480
34,848

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 Berkshire Hathaway NE Prop., Karen B Mendes; Berkshire Hathaway NE Prop., Jennifer S Petron

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.