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Chester, CT Homes for Sale with Garage

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  • /40

    $2,200,000

    • 4 Beds
    • 3.5 Baths
    • 3,957 Sq Ft

    47 E Kings Hwy, Chester, CT 06412

    A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American

    Agent Photo

    Al Chiarito

    Chiarito Real Estate LLC

    47 E Kings Hwy, Chester, CT 06412
  • /40

    $900,000

    Open Sat 11AM - 12:30PM $95K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,343 Sq Ft

    136 Goose Hill Rd, Chester, CT 06412

    Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and

    Chris Torrez RE/MAX One

    136 Goose Hill Rd, Chester, CT 06412
  • /24

    $495,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    42 Straits Rd, Chester, CT 06412

    Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths,

    Stephanie Stone William Raveis/First Town RE

    42 Straits Rd, Chester, CT 06412
  • /37

    $2,100,000

    • 11 Beds
    • 12 Baths
    • 8,500 Sq Ft

    59 Maple St, Chester, CT 06412

    A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

    Connor Wenchell VC Property Group, LLC

    59 Maple St, Chester, CT 06412
  • /38

    $3,150,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    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

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412
  • /24

    $385,000

    Open Sat 10AM - 12PM Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,454 Sq Ft

    25 Goose Hill Rd, Chester, CT 06412

    Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers

    Janet Mashia William Pitt Sotheby's Int'l

    25 Goose Hill Rd, Chester, CT 06412
  • /5

    $799,900

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    88 Winthrop Rd, Chester, CT 06412

    Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs you'll find 3 additional bedrooms with 2 full baths. The bright, open living room features soaring ceiling and a second floor balcony overlooking the main living space, creating an airy feel. Large south facing

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • /39

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,560 Sq Ft

    38 Main St, Deep River, CT 06417

    Nestled in the charming town of Deep River, between the villages of Essex and Chester, this beautiful Colonial offers the perfect blend of classic character and modern updates. Featuring 4 bedrooms, 2 full baths and 2 half baths, this spacious home is designed for comfortable living and entertaining. Enter through the welcoming foyer, where the dining room sits to the left, while French doors

    Sue Bowes RE/MAX on the Bay

    38 Main St, Deep River, CT 06417

Home Price Trends

Median Sale Price
$613,000
Median Single Family Sale Price
$610,000
Median 2 Bedroom Sale Price
$550,000
Median 1 Bedroom Sale Price
$274,900
Average Price Per Sq Ft
$343
Number of Homes for Sale
9
Last 12 months Home Sales
38
Months of Supply
2.80
Median List Price
$645,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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