Is a car needed in Chester, CT?

As of early 2026, 95% of users say car is needed

Is Chester, CT dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Does Chester, CT show holiday spirit?

As of early 2026, 93% of users say there's holiday spirit

Are yards well-kept in Chester, CT?

As of early 2026, 93% of users say yards are well-kept

Would people walk alone at night in Chester, CT?

As of early 2026, 84% of users say people would walk alone at night

Is parking easy in Chester, CT?

As of early 2026, 79% of users say parking is easy

Do residents of Chester, CT plan to stay at least 5 years?

As of early 2026, 78% of users say they plan to stay for at least 5 years

Is Chester, CT walkable to restaurants?

As of early 2026, 74% of users say it's walkable to restaurants

Is there wildlife in Chester, CT?

As of early 2026, 74% of users say there's wildlife

Is Chester, CT quiet?

As of early 2026, 69% of users say it's quiet

Are neighbors friendly in Chester, CT?

As of early 2026, 63% of users say neighbors are friendly

Does Chester, CT have sidewalks?

As of early 2026, 59% of users say there are sidewalks

Do kids play outside in Chester, CT?

As of early 2026, 52% of users say kids play outside

Are the streets well-lit in Chester, CT?

As of early 2026, 44% of users say streets are well-lit

Are there community events in Chester, CT?

As of early 2026, 37% of users say there are community events

Is Chester, CT walkable to grocery stores?

As of early 2026, 18% of users say it's walkable to grocery stores

FOR SALE

2.65 ACRES

288 Middlesex Avenue
Chester, CT 06412

4 Beds
5 Baths
4,926 sqft (on 2.65 acres)

$3,150,000

4 Beds

5 Baths

4,926 sqft

(on 2.65 acres)

Local Information

-- mins to

Commute Destination

Description

Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

Home Highlights

Parking

6 Car Garage

Outdoor

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$639

Listed

52 days ago

Home Details for 288 Middlesex Avenue

Interior Features
Interior Details Basement: Full,Storage Space,Interior Entry,Partially Finished,ConcreteNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Library, Living Room, Media Room, Office, Other
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Dimensions and Layout Living Area: 4926 Square Feet
Appliances & Utilities Utilities: Underground Utilities, Cable AvailableAppliances: Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Lower Level,Mud RoomMicrowaveWasher
Heating & Cooling Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls Window: Thermopane WindowsDoor: French Doors
View Has a ViewView: Water
Security Security: Security System

Exterior Features
Exterior Home Features Roof: AsphaltPatio / Porch: PatioExterior: Balcony, Awning(s), Rain Gutters, Stone Wall, Underground SprinklerFoundation: Concrete PerimeterNo Private Pool
Parking & Garage Number of Garage Spaces: 6Number of Covered Spaces: 6No CarportHas a GarageHas an Attached GarageParking Spaces: 6Parking: Attached,Detached,Garage Door Opener
Frontage WaterfrontWaterfront: Waterfront, River Front, Dock or MooringOn Waterfront
Water & Sewer Sewer: Septic Tank
Finished Area Finished Area (above surface): 4626 Square FeetFinished Area (below surface): 300 Square Feet

Days on Market
Days on Market: 52

Property Information
Year Built Year Built: 1800
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building Construction Materials: Shake Siding, CedarNot a New ConstructionDoes Not Include Home Warranty
Property Information Parcel Number: 941338

Price & Status
Price List Price: $3,150,000Price Per Sqft: $639
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Active

Media
See Virtual Tour

Location
Direction & Address City: Chester
School Information Elementary School: ChesterJr High / Middle School: WinthropHigh School: Valley

Agent Information
Listing Agent Listing ID: 24166793

Building
Building Area Building Area: 4926 Square Feet

Community
Community Features: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall

HOA
No HOA

Lot Information
Lot Area: 2.65 Acres

Energy
Energy Efficiency Features: Windows

Miscellaneous
BasementMls Number: 24166793Attic: Access Via HatchWater ViewWater View: WaterAttribution Contact: (860) 227-9071Above Grade Unfinished Area: 4626

Additional Information
LibraryMedical FacilitiesParkPublic Rec FacilitiesShopping/Mall

Last check for updates: about 22 hours ago

Listing courtesy of Nancy Mesham, (860) 227-9071

Coldwell Banker Realty, (860) 227-9071

Source: Smart MLS, MLS#24166793

Also Listed on Smart MLS.

Market trends in Chester

Last updated April 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Price History for 288 Middlesex Avenue

Date	Price	Event	Source
04/13/2026	$3,150,000	Listed For Sale	Smart MLS #24166793

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Property Tax and Assessment

Year	2025
Tax	$144
Assessment	$5,320

Home facts updated by county records

Comparable Sales for 288 Middlesex Avenue

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
136 Goose Hill Road, Chester, CT	0.42	Single-Family Home	$410,000	09/26/25	4	3	3,343
31 Parkers Point Road, Chester, CT	0.62	Single-Family Home	$3,100,000	06/10/25	3	3.5	4,727
226 Middlesex Avenue, Chester, CT	0.87	Single-Family Home	$695,000	05/15/26	4	2.5	2,029
47 Ferry Road, Chester, CT	1.34	Single-Family Home	$1,275,000	12/12/25	3	3	2,664
36 Kings Highway, Chester, CT	1.32	Single-Family Home	$469,900	12/18/25	4	2	1,516
96 Goose Hill Road, Chester, CT	0.69	Single-Family Home	$370,000	07/09/25	1	1	642
70 River Road, East Haddam, CT	1.33	Single-Family Home	$501,900	11/14/25	3	1.5	1,344

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
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19 Parkers Point Road,
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William Pitt Sotheby's Int'l
OFF MARKET
Est. $383,600
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261 Middlesex Avenue,
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William Pitt Sotheby's Int'l
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Re/Max Valley Shore

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 288 Middlesex Avenue.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
2y ago
"Local parades, community events and fairs and the friendliness of the neighborhoods. I am lucky to live here"
0
Flag
Jejoy924
Resident
5y ago
"Kindness and the feeling of community. Enjoy meeting new people and having new encounters. Kids in the neighborhood"
0
Flag
Lscd1959
Resident
7y ago
"Regular Sunday markets downtown. Great restaurants and shops. Very friendly staff. Walkable from my home"
1
Flag

LGBTQ Local Legal Protections

Nancy Mesham, Coldwell Banker Realty, (860) 227-9071

Agent Phone: (860) 227-9071

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.

288 Middlesex Avenue, Chester, CT 06412 is a 4 bedroom, 6 bathroom, 4,926 sqft single-family home built in 1800. This property is currently available for sale and was listed by Smart MLS on Apr 13, 2026. The MLS # for this home is MLS# 24166793.

288 Middlesex Avenue Chester, CT 06412

$3,150,000

$3,150,000

Local Information

Description

Home Highlights

Home Details for 288 Middlesex Avenue

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Media

Location

Agent Information

Building

Community

HOA

Lot Information

Energy

Miscellaneous

Additional Information

Market trends in Chester

Price History for 288 Middlesex Avenue

Similar Homes You May Like

New Listings near 288 Middlesex Avenue

Property Tax and Assessment

Comparable Sales for 288 Middlesex Avenue

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Chester

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

288 Middlesex Avenue
Chester, CT 06412