9

Cheshire, CT Homes for Sale under $300,000

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  • Lot 13 Waterbury Rd, Cheshire, CT 06410
    Lot 13 Waterbury Rd, Cheshire, CT 06410
    Lot 13 Waterbury Rd, Cheshire, CT 06410
    /3

    $239,900

    • Land
    • 4.61 Acres
    • $52,039 per Acre

    Lot 13 Waterbury Rd, Cheshire, CT 06410

    4.61-Acre Lot on Waterbury Road, Cheshire. Discover the perfect blend of privacy and convenience with this stunning 4.61-acre lot located on Waterbury Road. This treed and rolling lot features a small stream in one corner, offering a serene and picturesque setting. Currently a single lot, it may be subdividable, providing potential for future development. Ideal for those seeking privacy and a

    Mark Foreman Press/Cuozzo Realtors

    Lot 13 Waterbury Rd, Cheshire, CT 06410
  • 459 E Mitchell Ave Unit 459, Cheshire, CT 06410
    459 E Mitchell Ave Unit 459, Cheshire, CT 06410
    459 E Mitchell Ave Unit 459, Cheshire, CT 06410
    /26

    $160,000

    Coming Soon
    • 1 Bed
    • 1 Bath
    • 872 Sq Ft

    459 E Mitchell Ave Unit 459, Cheshire, CT 06410

    Welcome to easy, one-level living in Cheshire Hillside Village, a desirable 62+ active adult community. The standout feature of this inviting one-bedroom condo is its large, open floor plan with generously sized rooms and a beautiful vaulted ceiling in the living room, creating a spacious, airy setting that is ideal for entertaining and everyday living. Located on the upper level, this

    Melissa Mesite Coldwell Banker Realty

    459 E Mitchell Ave Unit 459, Cheshire, CT 06410
  • 502 Oak Ave Unit 17, Cheshire, CT 06410
    502 Oak Ave Unit 17, Cheshire, CT 06410
    502 Oak Ave Unit 17, Cheshire, CT 06410
    /26

    $199,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    502 Oak Ave Unit 17, Cheshire, CT 06410

    Stylish, beautifully renovated and filled with natural light, this end-unit condominium is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. Beautiful, move in condition! The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops, self-closing cabinets with lighting and

    Dorothy Karska-Piech Calcagni Real Estate

    502 Oak Ave Unit 17, Cheshire, CT 06410
  • 414 Robin Ct, Cheshire, CT 06410
    414 Robin Ct, Cheshire, CT 06410
    414 Robin Ct, Cheshire, CT 06410
    /25

    $229,995

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,122 Sq Ft

    414 Robin Ct, Cheshire, CT 06410

    Welcome to this beautifully maintained townhouse in the highly desirable Deepwood community of Cheshire. Offering privacy and tranquility in a wonderful neighborhood setting, this home is perfect for those seeking low-maintenance living with the benefits of true ownership. Step inside to find bright, welcoming living spaces that are clean and move-in ready. The functional layout provides

    Josh Arkenbout Coldwell Banker Realty

    414 Robin Ct, Cheshire, CT 06410
  • 1116 Wallingford Rd, Cheshire, CT 06410
    1116 Wallingford Rd, Cheshire, CT 06410
    /2

    $229,000

    • Land
    • 1.84 Acres
    • $124,457 per Acre

    1116 Wallingford Rd, Cheshire, CT 06410

    Your blank canvas - with a head start A rare opportunity to build the home you've been picturing on a 1.84-acre lot in Cheshire. The existing structure will be removed prior to closing - or within 60 days of closing at the latest - leaving you a cleared, ready-to-build site with the foundation remaining in place. That foundation is the difference-maker. Pouring a new foundation is one of the most

    George Daniolos eRealty Advisors, Inc.

    1116 Wallingford Rd, Cheshire, CT 06410
  • 1708 Byam Rd, Cheshire, CT 06410
    1708 Byam Rd, Cheshire, CT 06410
    1708 Byam Rd, Cheshire, CT 06410
    /28

    $265,000

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    1708 Byam Rd, Cheshire, CT 06410

    Welcome to 1708 Byam Road. Fully renovated down to the studs in 2105 this home is the perfect condo alternative. This one floor one bedroom ranch, featuring full kitchen wth stainless steel appliances and updated cabinetry and countertop is waiting for you to call it home. Recent updates in 2025 include a new updated shower stall and tankless hot water heating system. With detached garage with

    Anthony LaCava Berkshire Hathaway NE Prop.

    1708 Byam Rd, Cheshire, CT 06410
  • 5 Waterside Way, Cheshire, CT 06410
    5 Waterside Way, Cheshire, CT 06410
    5 Waterside Way, Cheshire, CT 06410
    /8

    $299,900

    • Land
    • 1.3 Acres
    • $230,692 per Acre

    5 Waterside Way, Cheshire, CT 06410

    Unique opportunity to own Waterfrontage in Cheshire. This one of a kind planned unit development, sitting on the pristine Lake Percival with an exquisite waterfall is offering a 1.32 acre lot available to build your dream home. Boasting vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your vision today, or contractor consultations

    Anthony LaCava Berkshire Hathaway NE Prop.

    5 Waterside Way, Cheshire, CT 06410
  • 0 Main St S Unit 24155068, Cheshire, CT 06410
    0 Main St S Unit 24155068, Cheshire, CT 06410
    0 Main St S Unit 24155068, Cheshire, CT 06410
    /19

    $49,995

    $25K PRICE DROP
    • Land
    • 27,007 Sq Ft
    • $80,637 per Acre

    0 Main St S Unit 24155068, Cheshire, CT 06410

    Prime corner lot opportunity in desirable South Cheshire! This 0.62-acre parcel boasts approximately 243 feet of frontage on South Main Street (Route 10) and 138 feet on Fenn Road, offering excellent visibility and dual-road access in a serene residential area. Zoned for single-family residential use with great build potential-imagine your dream home nestled near open space, and convenient

    Josh Arkenbout Coldwell Banker Realty

    0 Main St S Unit 24155068, Cheshire, CT 06410
  • 443 E Mitchell Ave, Cheshire, CT 06410
    443 E Mitchell Ave, Cheshire, CT 06410
    443 E Mitchell Ave, Cheshire, CT 06410
    /25

    $199,900

    Open Sat 11:30AM - 1PM
    • 1 Bed
    • 1 Bath
    • 853 Sq Ft

    443 E Mitchell Ave, Cheshire, CT 06410

    This beautifully renovated condo features a versatile flex/bonus room and is located in a desirable 62+ community nestled within the town of Cheshire. The bright and inviting first floor unit has been completely updated from top to bottom, featuring brand new appliances, crown molding, modern fixtures, new flooring, paint, a custom feature wall, and a fully refreshed kitchen and bathroom. The

    Elizabeth Sabo Coldwell Banker Realty

    443 E Mitchell Ave, Cheshire, CT 06410
Connecticut New Haven County

Real Estate & Homes in Cheshire, CT under $300,000

Home Prices in Cheshire, CT

The median home sale price in Cheshire, CT is $533,800, up 2% year-over-year. Homes in Cheshire sell in 55 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$533,800
Median Single Family Sale Price
$560,000
Median Townhouse Sale Price
$530,000
Median 2 Bedroom Sale Price
$344,000
Median 1 Bedroom Sale Price
$187,450
Average Price Per Sq Ft
$294
Number of Homes for Sale
36
Last 12 months Home Sales
337
Months of Supply
1.30
Median List Price
$529,900
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
2%
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