248 Middlesex Avenue, Chester, CT 06412
OFF MARKET

$1,192,400

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 4,862 sqft (on 5.07 acres)

248 Middlesex Avenue, Chester, CT 06412

Est. Refi. Payment $8,271/mo*
Refinance Your Home
Currently Off Market - Sold Jun 20, 2024 for $1,025,000

Home Value

Trulia Estimate
$1.19M
Since last month
Increased$1K (+0.1%)
Since last year
Increased$98K (+8.9%)
Since last sale
Increased$171K (+16.7%)
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 +52% in the last 10 years
MonthEstimated value
2026
August 2026$1.2M
August 2026$1.19M
July 2026$1.19M
June 2026$1.22M
May 2026$1.22M
April 2026$1.2M
March 2026$1.19M
February 2026$1.15M
January 2026$1.14M
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
12 Meadow Lane, Chester, CT
0.09
Single-Family Home
$515,000
07/27/26
3
3
2,971
226 Middlesex Avenue, Chester, CT
0.27
Single-Family Home
$695,000
05/15/26
4
2.5
2,029
136 Goose Hill Road, Chester, CT
0.29
Single-Family Home
$410,000
09/26/25
4
3
3,343
47 Ferry Road, Chester, CT
0.74
Single-Family Home
$1,275,000
12/12/25
3
3
2,664
36 Kings Highway, Chester, CT
0.76
Single-Family Home
$469,900
12/18/25
4
2
1,516
19 Castle View Drive, Chester, CT
0.43
Single-Family Home
$470,000
06/12/26
3
1.5
1,092
1 Ferry Road, Chester, CT
1.03
Single-Family Home
$635,000
04/30/26
3
3
2,752
7 Old Depot Road, Chester, CT
1.61
Single-Family Home
$975,000
11/17/25
4
2.5
3,149
1 Kirtland Avenue, Chester, CT
0.50
Single-Family Home
$452,000
08/25/26
3
1.5
1,198

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
3 Meadow Lane, Chester, CT 06412
0.07
$366,500
2
1
1,032
Off Market
12 Meadow Lane, Chester, CT 06412
0.09
$515,000
3
3
2,971
Recently Sold
19 Denlar Drive, Chester, CT 06412
0.15
$1,350,000
2
2
5,886
For Sale
261 Middlesex Avenue, Chester, CT 06412
0.23
$394,600
3
1
1,248
Off Market
31 Parkers Point Road, Chester, CT 06412
0.21
$3,364,000
3
3.5
4,727
Off Market
96 Goose Hill Road, Chester, CT 06412
0.30
$400,200
1
1
642
Off Market
226 Middlesex Avenue, Chester, CT 06412
0.27
$695,000
4
2.5
2,029
Recently Sold
49 Parkers Point Road, Chester, CT 06412
0.32
$2,875,200
6
4.5
3,968
Off Market
6 Castle View Drive, Chester, CT 06412
0.41
$465,000
3
1.5
2,031
For Sale
19 Castle View Drive, Chester, CT 06412
0.43
$470,000
3
1.5
1,092
Recently Sold
14 Castle View Drive, Chester, CT 06412
0.44
$378,200
3
1
1,533
Off Market

Local Information

  • Map ViewExplore the area around 248 Middlesex Avenue.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2007
5.07 acre lot
4,862 sqft
$245/sqft
2 Car Garage

About this House

Welcome to this magnificent colonial-style residence nestled in the picturesque town of Chester, CT, a haven for boating enthusiasts and those who appreciate the serene beauty of the Connecticut River. This expansive home is a perfect blend of classic charm and modern luxury, offering an exceptional living experience. As you step inside, you are greeted by an elegant foyer that sets the tone for the rest of the home. The heart of this residence is undoubtedly the chef's kitchen, a culinary dream featuring top-of-the-line appliances, oversized island and tons of natural sunlight. Whether hosting celebrations or intimate gatherings, the kitchen flows seamlessly into the formal dining area and living spaces, making entertaining a breeze. The home boasts generous living areas with plenty of natural light, accentuating the rich hardwood floors that run throughout. The traditional colonial layout includes spacious bedrooms, providing a private and tranquil retreat for family and guests. The finished basement is a bonus flex space. Outside enjoy the patio and hot tub. The proximity to the Connecticut River is a boater's dream, with easy access to marinas and waterways for endless aquatic adventures. This home is not just a residence but a lifestyle offering comfort, elegance, and the perfect setting for creating lasting memories. Experience the best of living in Chester and their amazing downtown filled with restaurants and shops.
248 Middlesex Avenue, Chester, CT 06412 is a 4 bedroom, 4 bathroom, 4,862 sqft single-family home built in 2007. It last sold for $1,025,000 on Jun 20, 2024 (2% below the $1,050,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,192,400, with a rent estimate of $7,678/month.
Last check for updates: about 11 hours ago
Listed by Tammy J. Tinnerello, (860) 867-6120
William Pitt Sotheby's Int'l, (860) 434-2400
Bought with: Kyle S. Hinding, (860) 857-4219, Coldwell Banker Realty
Co-Buyer's Agent: Peg Mitchel, (860) 391-1701, Coldwell Banker Realty
Source: Smart MLS, MLS#24016366

Home Details for 248 Middlesex Avenue

Interior Features

Interior Details
Basement: Full,Storage Space,Interior Entry,Partially Finished,ConcreteNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Great Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4862 Square Feet
Appliances & Utilities
Utilities: Underground UtilitiesAppliances: Gas Cooktop, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water Heater, Tankless Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hydro Air,Zoned,PropaneHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ZonedHas HeatingHeating Fuel: Hydro Air
Fireplace & Spa
Number of Fireplaces: 1Spa: HeatedHas a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioOther Structures: Shed(s)Exterior: Awning(s)Foundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Paved,Driveway,Garage Door Opener,Shared Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4862 Square Feet

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 941647

Price & Status

Price
List Price: $1,050,000
Status Change & Dates
Off Market Date: Thu May 23 2024Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: ChesterCommunity: Parker's Point
School Information
Elementary School: ChesterHigh School: Region 4

Building

Building Area
Building Area: 4862 Square Feet

Community

Community Features: Golf, Medical Facilities

HOA

No HOA

Lot Information

Lot Area: 5.07 Acres

Miscellaneous

BasementMls Number: 24016366Attic: Storage, Floored, Walk-upAbove Grade Unfinished Area: 4862

Additional Information

GolfMedical Facilities

Price and Tax history

DateEventPrice
Jun 20, 2024
Source: Smart MLS #24016366
Sold
$1,025,000
Jun 7, 2024
Source: Smart MLS #24016366
Pending
$1,050,000
May 17, 2024
Source: Smart MLS #24016366
Listed For Sale
$1,050,000
Dec 29, 2023
Source: Smart MLS #170606345
ListingRemoved
Oct 27, 2023
Source: Smart MLS #170606345
Listed For Sale
$1,195,000

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

Around this home

What Locals Say about Chester

At least 14 Trulia users voted on each feature.

  • 95 % Say car is needed

  • 94 % Say it's dog friendly

  • 93 % Say there's holiday spirit

  • 93 % Say yards are well-kept

  • 84 % Say people would walk alone at night

  • 79 % Say parking is easy

  • 78 % Say they plan to stay for at least 5 years

  • 74 % Say it's walkable to restaurants

  • 74 % Say there's wildlife

  • 69 % Say it's quiet

  • 63 % Say neighbors are friendly

  • 59 % Say there are sidewalks

  • 52 % Say kids play outside

  • 44 % Say streets are well-lit

  • 37 % Say there are community events

  • 18 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Jcollier82816
    "Local parades, community events and fairs and the friendliness of the neighborhoods. I am lucky to live here"
    0
    Flag
  • Jejoy924
    "Kindness and the feeling of community. Enjoy meeting new people and having new encounters. Kids in the neighborhood"
    0
    Flag
  • Lscd1959
    "Regular Sunday markets downtown. Great restaurants and shops. Very friendly staff. Walkable from my home"
    1
    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 248 Middlesex Avenue

  • What is 248 Middlesex Avenue estimated to be worth?
    Trulia's estimated value for 248 Middlesex Avenue in Chester, CT is $1,192,400.
  • What is the price history for 248 Middlesex Avenue?
    248 Middlesex Avenue in Chester, CT last sold for $1,025,000 in June 2024.
  • Is Chester a buyer's or seller's market?
    Chester is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chester?
    Residents describe Chester, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Chester, CT.
  • Does 248 Middlesex Avenue have air conditioning?
    Yes, 248 Middlesex Avenue in Chester, CT has air conditioning.
  • Does 248 Middlesex Avenue have laundry facilities?
    Yes, 248 Middlesex Avenue in Chester, CT has in-unit laundry.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 248 Middlesex Avenue

Skip to last item
Skip to first item

Homes for sale near 248 Middlesex Avenue

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