249 Cheshire Rd, Prospect, CT 06712
OFF MARKET

$327,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,784 sqft (on 1 acre)

249 Cheshire Rd, Prospect, CT 06712

Est. Refi. Payment $2,354/mo*
Refinance Your Home
Currently Off Market - Sold Mar 5, 2025 for $310,000

Home Value

Trulia Estimate
$327K
Since last month
Increased$3K (+0.9%)
Since last year
Increased$8K (+2.6%)
Since last sale
Increased$18K (+5.8%)
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 +48% in the last 10 years
MonthEstimated value
2026
August 2026$328K
August 2026$328K
July 2026$325K
June 2026$324K
May 2026$322K
April 2026$320K
March 2026$323K
February 2026$323K
January 2026$325K
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
16 Plank Road, Prospect, CT
0.13
Single-Family Home
$365,000
02/12/26
3
2
2,385
7 Rolling Ridge Court, Prospect, CT
0.11
Single-Family Home
$553,000
05/01/26
4
2.5
2,266
38 Tress Rd, Prospect, CT
0.42
Single-Family Home
$380,000
09/12/25
3
2
1,134
2 Mixville Road, Prospect, CT
0.09
Single-Family Home
$390,000
08/10/26
3
1.5
1,008
205 Mountain Road, Cheshire, CT
0.74
Single-Family Home
$417,000
07/21/26
3
1.5
1,796
10 Laurel Lane, Prospect, CT
0.72
Single-Family Home
$530,000
07/14/26
3
2
1,880
261 Winthrop Drive, Cheshire, CT
0.53
Single-Family Home
$440,000
05/27/26
3
2
1,152
1124 Pamela Lane, Cheshire, CT
0.55
Single-Family Home
$200,000
06/09/26
3
2.5
1,955
19 Heath Court, Cheshire, CT
0.55
Single-Family Home
$430,000
01/05/26
4
3
2,100
248 Mountain Road, Cheshire, CT
0.79
Single-Family Home
$416,100
11/14/25
3
2
1,955

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
7 Rolling Ridge Court, Prospect, CT 06712
0.11
$553,000
4
2.5
2,266
Recently Sold
2 Mixville Road, Prospect, CT 06712
0.09
$390,000
3
1.5
1,008
Recently Sold
5 Mixville Road, Prospect, CT 06712
0.09
$542,700
4
2
2,652
Off Market
8 Plank Road, Prospect, CT 06712
0.10
$489,900
3
1.5
1,296
For Sale
16 Plank Road, Prospect, CT 06712
0.13
$365,000
3
2
2,385
Recently Sold
223 Cheshire Road, Prospect, CT 06712
0.22
$552,300
3
2
2,465
Off Market
1224 Prospect Road, Cheshire, CT 06410
0.25
$399,200
2
2
1,374
Off Market
7 Mixville Road, Prospect, CT 06712
0.30
$507,300
3
2.5
1,521
Off Market
1161 Tucker Road, Cheshire, CT 06410
0.34
$494,900
4
3
2,123
Off Market
11 Boardman, Prospect, CT 06712
0.32
$637,200
4
2.5
2,650
Off Market
9 Boardman Drive, Prospect, CT 06712
0.33
$652,200
4
1.5
2,830
Off Market
166 Mixville Road, Cheshire, CT 06410
0.39
$709,800
4
2.5
2,764
Off Market

Local Information

  • Map ViewExplore the area around 249 Cheshire Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1846
1 acre lot
1,784 sqft
$183/sqft

About this House

Charming 1800's cape with 1.6 acres in a park-like setting. Very large landscaped corner lot. Great for an outdoor party with plenty of parking. Home features 3 bedrooms and 2 full bathrooms with newer replacement windows, roof and vinyl siding. Master bedroom with full bath on first floor. Kitchen is current and first floor has an open concept. Newer natural gas furnace and hot water heater and you can save on your electricity bill with the solar panels installed in 2014. For that handyman, there is an oversized shed/barn with electricity. The home is move in ready.
249 Cheshire Rd, Prospect, CT 06712 is a 3 bedroom, 2 bathroom, 1,784 sqft single-family home built in 1846. It last sold for $310,000 on Mar 5, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $327,300, with a rent estimate of $2,894/month.

Home Details for 249 Cheshire Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, Gas, SolarHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylPatioPorch

Property Information

Year Built
Year Built: 1846Year Updated: 1983
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 3

Lot Information

Lot Area: 1 acre

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Mar 5, 2025
Source: N/A
Sold
$310,000
Sep 22, 2019
Source: Agent Provided
ListingRemoved
$245,000
Aug 21, 2019
Source: Agent Provided
PriceChange
$245,000
Price decreased by 2%
Jul 30, 2019
Source: Agent Provided
PriceChange
$251,000
Price decreased by 3%
Jul 2, 2019
Source: Agent Provided
PriceChange
$257,900
Price decreased by 2%

Market trends in Prospect

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
4MoM

Around this home

What Locals Say about Prospect

At least 52 Trulia users voted on each feature.

  • 89 % Say parking is easy

  • 89 % Say car is needed

  • 88 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 73 % Say there's wildlife

  • 68 % Say it's quiet

  • 60 % Say neighbors are friendly

  • 59 % Say it's dog friendly

  • 54 % Say they plan to stay for at least 5 years

  • 50 % Say kids play outside

  • 46 % Say people would walk alone at night

  • 29 % Say there are community events

  • 27 % Say it's walkable to grocery stores

  • 25 % Say there are sidewalks

  • 19 % Say it's walkable to restaurants

  • 18 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Mary Mcgrath
    "I have a dog and most neighbors have animals. Very pet friendly neighborhood and friendly neighbors when you go out "
    0
    Flag
  • Tracy Graves
    "It’s private and well maintained. Peaceful and a lot of community involvement of keeping your neighborhood clean."
    0
    Flag
  • Jlee093074
    "There’s plenty of room to run and walk your dog. Sidewalks are an issue in some areas, but overall a great area to have a dog."
    0
    Flag
  • Monica F.
    "Great neighborhood to live in. Everyone in the town knows each other one way or another, most kids grow up with the same friends/classmates their entire school career. Neighbors are super friendly and the town is very safe with no crime. "
    0
    Flag
  • Monica F.
    "Dog owners would love that there is a regular park right in town, and that (in being so close to cheshire) it is right near a fenced dog park. Most small streets are safe for walking dogs, but its not recommended on main roads."
    0
    Flag
  • CM
    "Relatively easy to get on route 84 and route 8 and it’s convenient spot in the valley makes it easy to get to any store you would need to go to within around 30 minutes "
    0
    Flag
  • Joanne
    "It’s quiet and people are friendly. Everything is close and convenient. Neighborhood is safe and is dog friendly."
    1
    Flag
  • Lauren P.
    "I’ve lived in prospect for 22 years. It’s quiet, there are great schools, and everyone knows each other. It’s a wonderful community!"
    0
    Flag
  • Jan
    "I’ve lived in the area for 10 years. It’s a great place to raise a family. Love the small town not too many with a small town feel. It’s refreshing yet still populated enough to keep your privacy."
    0
    Flag
  • Tj L.
    "great town lots of parks and fun things to do just moved here and me and my family love it already everyone in the town is friendly "
    0
    Flag
  • Kellyajxn
    "Love the small town charm & local small businesses, although my favorite part about prospect is the amazing school system!"
    1
    Flag
  • Jennifer c.
    "The homes are close enough to be able to regularly see & converse w/ your neighbors, but also spaced out enough to have privacy when ya need/want it. Everyone’s willing to lend a helping hand or keep an eye out for things out of the ordinary. A great community."
    1
    Flag
  • Aeromotivedist
    "We live in the most cohesive and careing neighborhood anywhere. People reach out to help and nobody is left out. what a dream to be a part of such a group."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 249 Cheshire Rd

  • What is 249 Cheshire Rd estimated to be worth?
    Trulia's estimated value for 249 Cheshire Rd in Prospect, CT is $327,300.
  • What is the price history for 249 Cheshire Rd?
    249 Cheshire Rd in Prospect, CT last sold for $310,000 in March 2025.
  • Is Prospect a buyer's or seller's market?
    Prospect is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Prospect?
    Residents describe Prospect, CT as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Prospect, CT.
  • Does 249 Cheshire Rd have laundry facilities?
    Yes, 249 Cheshire Rd in Prospect, CT has in-unit laundry.
  • How big is the lot at 249 Cheshire Rd?
    The lot at 249 Cheshire Rd in Prospect, CT is about 1 acre.

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