$2,995,000
4 Beds
5 Baths
4,926 sqft (on 0.37 acres)
288 Middlesex Avenue, Chester, CT 06412
Est. Mortgage $20,357/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1800
0.37 acre lot
$608/sqft
6 Car Garage
Local Information
- Map ViewExplore the area around 288 Middlesex Avenue.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge. Chester taxes $25,363 and Haddam taxes $758 for a total of $26,139
Last check for updates: about 18 hours ago
Listing courtesy of Nancy Mesham, (860) 227-9071
Coldwell Banker Realty, (860) 227-9071
Source: Smart MLS, MLS#24201816
Also Listed on Smart MLS.
Home Details for 288 Middlesex Avenue
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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 |
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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, Beach, Dock or MooringOn Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 4626 Square FeetFinished Area (below surface): 300 Square Feet |
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Days on Market: 16 |
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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 |
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Price List Price: $2,995,000Price Per Sqft: $608 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: Chester |
School Information Elementary School: ChesterJr High / Middle School: WinthropHigh School: Valley |
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Listing Agent Listing ID: 24201816 |
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Building Area Building Area: 4926 Square Feet |
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Community Features: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall |
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No HOA |
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Lot Area: 0.37 acres |
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Energy Efficiency Features: Windows |
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BasementMls Number: 24201816Attic: Access Via HatchWater ViewWater View: WaterAttribution Contact: (860) 227-9071Above Grade Unfinished Area: 4626 |
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LibraryMedical FacilitiesParkPublic Rec FacilitiesShopping/Mall |
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.
Market trends in Chester
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
4MoM
Home Value
Trulia Estimate
$2.79MSince last month
Decreased$174K (-5.9%)Since last year
Decreased$467K (-14.3%)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 +952% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $2.79M |
| August 2026 | $2.97M |
| June 2026 | $2.85M |
| May 2026 | $2.89M |
| April 2026 | $3.02M |
2025 | |
2023 | |
2022 | |
2021 | |
2020 | |
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 |
|---|---|---|---|---|---|---|---|
0.42 | Single-Family Home | $410,000 | 09/26/25 | 4 | 3 | 3,343 | |
0.69 | Single-Family Home | $515,000 | 07/27/26 | 3 | 3 | 2,971 | |
0.87 | Single-Family Home | $695,000 | 05/15/26 | 4 | 2.5 | 2,029 | |
1.04 | Single-Family Home | $470,000 | 06/12/26 | 3 | 1.5 | 1,092 | |
1.09 | Single-Family Home | $452,000 | 08/25/26 | 3 | 1.5 | 1,198 | |
1.09 | Single-Family Home | $400,000 | 10/15/25 | 2 | 2 | 2,209 |
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 |
|---|---|---|---|---|---|---|
0.04 | $1,193,400 | 3 | 3.5 | 2,800 | Off Market | |
0.42 | $394,600 | 3 | 1 | 1,248 | Off Market | |
0.42 | $983,500 | 4 | 3.5 | 2,755 | Off Market | |
0.43 | $436,800 | 2 | 1.5 | 1,160 | Off Market | |
0.46 | $1,062,000 | 4 | 2.5 | 2,680 | Off Market | |
0.60 | $461,000 | 3 | 1.5 | 1,560 | Off Market | |
0.60 | $1,192,400 | 4 | 3.5 | 4,862 | Off Market | |
0.62 | $3,364,000 | 3 | 3.5 | 4,727 | Off Market | |
0.62 | $366,500 | 2 | 1 | 1,032 | Off Market | |
0.63 | $976,300 | 4 | 3.5 | 4,361 | Off Market | |
0.69 | $400,200 | 1 | 1 | 642 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 26, 2026 Source: Smart MLS #24201816 | Listed For Sale | $2,995,000 |
Aug 23, 2026 Source: Smart MLS #24166793 | ListingRemoved | $3,150,000 |
Apr 13, 2026 Source: Smart MLS #24166793 | Listed For Sale | $3,150,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $144 | $5,320 |
Home facts updated by county records
LGBTQ Local Legal Protections
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.
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Frequently asked questions about 288 Middlesex Avenue
- What is the estimated monthly payment for 288 Middlesex Avenue?Based on a $2,995,000 list price with 20% down at today's rates, the estimated monthly payment for 288 Middlesex Avenue in Chester, CT is approximately $21,005 (about $16,188 principal & interest, $4,742 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- 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 homes for sale in Chester, CT.
- What are the closest schools to 288 Middlesex Avenue?The closest schools to 288 Middlesex Avenue in Chester, CT are Chester Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
- What is 288 Middlesex Avenue estimated to be worth?Trulia's estimated value for 288 Middlesex Avenue in Chester, CT is $2,793,700.
- Does 288 Middlesex Avenue have air conditioning?Yes, 288 Middlesex Avenue in Chester, CT has air conditioning.
- Does 288 Middlesex Avenue have laundry facilities?Yes, 288 Middlesex Avenue in Chester, CT has in-unit laundry.
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 Aug 26, 2026. The MLS # for this home is MLS# 24201816.