660 Boulder Road, Cheshire, CT 06410
OFF MARKET

$914,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,843 sqft (on 4.01 acres)

660 Boulder Road, Cheshire, CT 06410

Est. Refi. Payment $6,422/mo*
Refinance Your Home
Currently Off Market - Sold Jun 16, 2023 for $850,000

Home Value

Trulia Estimate
$915K
Since last month
Increased$3K (+0.4%)
Since last year
Increased$15K (+1.6%)
Since last sale
Increased$65K (+7.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +147% in the last 10 years
MonthEstimated value
2026
August 2026$915K
August 2026$915K
July 2026$912K
June 2026$929K
May 2026$920K
April 2026$913K
March 2026$897K
February 2026$888K
January 2026$874K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
430 Cook Hill Road, Cheshire, CT
0.52
Single-Family Home
$780,000
09/12/25
3
3.5
4,059
896 Coleman Road, Cheshire, CT
0.45
Single-Family Home
$675,000
01/29/26
4
2.5
2,586
625 Tamarack Road, Cheshire, CT
0.82
Single-Family Home
$750,000
10/21/25
3
2
2,345
781 Cook Hill Road, Cheshire, CT
0.73
Single-Family Home
$550,000
01/13/26
3
2.5
2,593
1464 Tuttle Avenue, Wallingford, CT
0.75
Single-Family Home
$450,000
09/09/25
3
1.5
1,664
1500 Rhey Avenue, Wallingford, CT
0.69
Single-Family Home
$740,000
08/13/26
3
2.5
2,645
55 Pine Brook Court, Cheshire, CT
0.95
Single-Family Home
$725,000
10/15/25
3
3.5
3,663

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
35 Farmers Court, Cheshire, CT 06410
0.37
$1,418,400
4
3.5
3,260
Off Market
15 Philson Court, Cheshire, CT 06410
0.41
$268,000
-
-
-
Recently Sold
896 Coleman Road, Cheshire, CT 06410
0.45
$675,000
4
2.5
2,586
Recently Sold
968 Coleman Road, Cheshire, CT 06410
0.45
$629,000
5
2.5
1,995
Off Market
886 Coleman Road, Cheshire, CT 06410
0.46
$315,000
-
-
-
For Sale
957 Coleman Road, Cheshire, CT 06410
0.47
$490,700
3
1.5
1,312
Off Market
1435 Tuttle Avenue, Wallingford, CT 06492
0.53
$579,200
4
2.5
2,800
Off Market
28 Alison Avenue, Wallingford, CT 06492
0.53
$764,300
3
3
2,764
Off Market
430 Cook Hill Road, Cheshire, CT 06410
0.52
$811,800
3
3.5
4,059
Off Market
200 Cheshire Road, Wallingford, CT 06492
0.58
$803,000
3
2.5
2,906
Off Market
445 Wild Flower Place, Cheshire, CT 06410
0.55
$957,900
4
2.5
3,460
Off Market

Local Information

  • Map ViewExplore the area around 660 Boulder Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1756
4.01 acre lot
1,843 sqft
$496/sqft
Garage

About this House

Do you dream of stepping back in time but crave modern conveniences? This historic 1756 New England home nestled in on 4 acres delivers the best of both worlds. Enter & bask in sunlight through the newer Marvin windows. Step into the first floor “keeping room” & you may think you’ve stepped into Colonial times: Its open-hearth FP & bee-shaped brick oven welcome you as it did visitors of the past. Today, it’s a family room, where cool nights are warmed by a woodstove in the open hearth. A BR w/full bath and FP & office with built-ins add to the comfort of the first floor. Upstairs, a bath w/a clawfoot tub offers relaxation without compromising the historic aesthetic. Old-world charm meets modern-day function in the tastefully updated kitchen. With many features built or designed by CT artisans, it boasts an outdoor patio, wide-plank wood floors, custom Colonial era-looking FP, granite counters, expansive pantry & breakfast bar made from a salvaged birch slab from Choate Rosemary Hall. Cooks will love the Thermador gas convection oven, a new stainless steel Electrolux dishwasher & a refrigerator/freezer. Other modern amenities include Central air, propane furnace & cedar closet. The bucolic 4-acre setting includes six outbuildings. The Boulder Knoll Montessori School currently resides in the carriage house & can continue to run and generate income for a new homeowner, or the space may possibly be converted into a charming Air BnB space, in-law apartment, or home office. 2.09 acres adjacent lot (which should be subdividable) is included in sale. End of June closing date.
660 Boulder Road, Cheshire, CT 06410 is a 3 bedroom, 2 bathroom, 1,843 sqft single-family home built in 1756. It last sold for $850,000 on Jun 16, 2023 (3% below the $875,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $914,900, with a rent estimate of $3,551/month.
Last check for updates: about 9 hours ago
Listed by Stacey Deangelis, (203) 494-7068
Calcagni Real Estate, (203) 272-1821
Bought with: Anne T. Degregorio, (203) 415-0499, Press/Cuozzo Realtors, (203) 288-1900
Source: Smart MLS, MLS#170542782

Home Details for 660 Boulder Road

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Family Room, Kitchen, Living Room, Other, Study
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1843 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Refrigerator, Dishwasher, Water HeaterDishwasherLaundry: Lower Level,Mud RoomRefrigerator
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioOther Structures: Barn(s), Shed(s)Foundation: StoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 12Parking: Detached,Private,Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1843 Square Feet

Property Information

Year Built
Year Built: 1756
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2341822

Price & Status

Price
List Price: $875,000
Status Change & Dates
Off Market Date: Sat Feb 11 2023Possession Timing: End Of June 2023

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Cheshire
School Information
Elementary School: HighlandJr High / Middle School: DoddHigh School: Cheshire

Building

Building Area
Building Area: 1843 Square Feet

Community

Community Features: Golf

HOA

No HOA

Lot Information

Lot Area: 4.01 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 170542782Attic: StorageAbove Grade Unfinished Area: 1843

Additional Information

Golf

Price and Tax history

DateEventPrice
Jun 16, 2023
Source: Smart MLS #170542782
Sold
$850,000
Jun 16, 2023
Source: Smart MLS #170542782
Contingent
$875,000
Jan 15, 2023
Source: Smart MLS #170542782
Listed For Sale
$875,000
Dec 20, 2013
Source: N/A
Sold
$195,900
Jul 1, 2005
Source: N/A
Sold
$535,000

Market trends in Cheshire

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$522K
$55KMoM
Sale-to-List Price
102.5%
1.2%MoM
Price per sq ft
$266
$5MoM
Available listings
58
3MoM

Around this home

What Locals Say about Cheshire

At least 102 Trulia users voted on each feature.

  • 95 % Say car is needed

  • 94 % Say parking is easy

  • 85 % Say yards are well-kept

  • 85 % Say it's dog friendly

  • 84 % Say there's wildlife

  • 81 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 73 % Say people would walk alone at night

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say kids play outside

  • 62 % Say neighbors are friendly

  • 58 % Say there are sidewalks

  • 58 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 37 % Say there are community events

  • 35 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Beautiful respectful peaceful people and neighborhood grate community. Clean and organized and has such a great atmosphere and very family orientated "
    0
    Flag
  • Joshua Wendell
    "It’s easy to get to the highway. Though in some parts of town it can take time to get through and make your way towards where you’re going. "
    0
    Flag
  • Reneechoquette
    "Great for trick of treating, close to the rail trail for biking, walking, running, or walking the dog! "
    1
    Flag
  • Ctbondlynx
    "Yes dog friendly. Dog parks are near by. And plentiful. Many dogs in the Cheshire neighborhoods. Dogs"
    0
    Flag
  • Reneechoquette
    "Safe, quiet, friendly, and lots of kids in this neighborhood (great for trick or treating!) Thr elementary school and rail trail (for waking and biking) are all in walking distance. "
    0
    Flag
  • Hollie.barclay
    "Amazing school district and great for kids growing up. We drive a vehicle for all our needs and only use a bike for rec purposes. We have walked on a few occasions but not often. "
    1
    Flag
  • Reneechoquette
    "My commute is into Hartford and there is public transportation into the city. The drive otherwise is about 45 min. "
    0
    Flag
  • Taylor D.
    "Lights of hope, relay for life, town sports and community outreach programs. Fairs and festivals in the fall with small business promotion"
    0
    Flag
  • Russell P.
    "about half an hour, I don't work in town. traffic can get pretty bad going south on the highway. back roads offer a good alternative, drivers I. the area tend to be slow though. "
    0
    Flag
  • Sheena N.
    "Cheshire is a nice quiet town. Not too much to do, not many restaurants or shopping centers, but close enough to everything where you don’t really mind. "
    0
    Flag
  • Janemarques08
    "That there are plenty of walking trails and sufficient sidewalks to safely walk your dog, whether it’s early morning or late at night. Totally safe neighborhood. "
    2
    Flag
  • Sheena N.
    "Close to 84 and 691. Not too far from Merritt or 91. Route 10 can be congested at times, but mostly everything is easy to get to"
    0
    Flag
  • Stephanie B. P.
    "Dogs are usually seen walking on leashes. Most are friendly and owners greet each other allowing them to engage. "
    1
    Flag
  • Mary
    "On my neighborhood street almost everyone has well behaved dogs. The neighbors clean up after their dogs. The street is perfect walking dogs- less traffic and extra wide roads. "
    0
    Flag
  • Janemarques08
    "I’ve lived her for two years. I know most of my neighbors. I feel good knowing that my children attend top “A”rated schools and that we live in a safe neighborhood. "
    5
    Flag
  • Nelson_sheena
    "The school system in Cheshire is great. They have tons of fun family activities. The community seems safe as well. Kids ride bikes on the trails and always people are walking their dogs. "
    1
    Flag
  • Nelson_sheena
    "Route 10 can be a little crowded during rush hour, but its not bad. The roads are clear and cleaned. "
    0
    Flag
  • Sjhickok01
    "great safe place, lots of kids, lots of great wildlife. most people walk their dogs 2-3 times a day...almost everyone is friendly. Beautiful area due to all of the different trees and plants. Beautiful holiday lights and halloween is always a favorite. lots of festivals during the spring/summer season."
    0
    Flag
  • janemarques08
    "We have movie night with popcorn near my neighborhood. Lots of group support and activities for the children. "
    1
    Flag
  • Jcasner
    "Safe great schools, best fire department and good police department. Great parks overall one of the best towns in CT. "
    1
    Flag
  • Alyss L.
    "Lots of families with kids and a closed loop street. I also grew up here (1985+) and the town has barely changed. Love that I can raise my kids here now."
    2
    Flag
  • Sara c.
    "My neighborhood is amazing! It is very quiet and and neighbors are friendly. We have easy access to all major highways."
    1
    Flag
  • Nelson_sheena
    "Dogs are always walking all around the neighborhood. Dog friendly for sure. I see more pits and retrievers than any other dog breed"
    1
    Flag
  • Dorothy R.
    "I am retired so I don't have a commute. Family member does and has described it as usually uneventful."
    0
    Flag
  • Emily M. G.
    "Great neighborhood in a great town, I feel safe. I’ve lived and grew up here for 23 years and I would live in cheshire as an adult"
    2
    Flag
  • Nelson_sheena
    "Quiet, farm land, lots to do. Good restaurants and lots to do with the kids. Lots of shops, banks, pretty scenery"
    0
    Flag
  • Emily M. G.
    "It’s a small, nice, and safe neighborhood. I’ve lived in the same house my whole life. It’s right next to mixville, I love walking around my neighborhood, everyone’s very nice."
    0
    Flag
  • Nelson_sheena
    "Cheshire is a quiet well kept town. The condos I live in are quiet and everyone is respectful. Lots of wildlife too"
    0
    Flag
  • adsinsight
    "Live near by, wish I lived here! Great place to raise a family and enjoy life's simple pleasures. Community is very close.. "
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 660 Boulder Road

  • What is 660 Boulder Road estimated to be worth?
    Trulia's estimated value for 660 Boulder Road in Cheshire, CT is $914,900.
  • What is the price history for 660 Boulder Road?
    660 Boulder Road in Cheshire, CT last sold for $850,000 in June 2023.
  • Is Cheshire a buyer's or seller's market?
    Cheshire is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Cheshire?
    The median sale price in Cheshire is $522K. That is up $55K from the prior month.
  • Does 660 Boulder Road have air conditioning?
    Yes, 660 Boulder Road in Cheshire, CT has air conditioning.
  • Does 660 Boulder Road have laundry facilities?
    Yes, 660 Boulder Road in Cheshire, CT has laundry facilities.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Cheshire, CT

Explore by feature - Air Conditioning

12 rentals with air conditioning in Cheshire, CT

Explore by feature - Washer/dryer

13 rentals with a washer/dryer in Cheshire, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 660 Boulder Road

Skip to last item
Skip to first item

Homes for sale near 660 Boulder Road

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item