15

Cheshire, CT Homes for Sale with Acreage

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  • 15 Shire Ct, Cheshire, CT 06410
    15 Shire Ct, Cheshire, CT 06410
    15 Shire Ct, Cheshire, CT 06410
    /39

    $1,085,000

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,437 Sq Ft

    15 Shire Ct, Cheshire, CT 06410

    Sophisticated elegance defines this 4,437 sq ft architect-designed Contemporary Colonial, featuring a luxurious first-floor primary suite with a custom closet, walk-in limestone shower, and separate soaking tub. The chef will appreciate the beautifully designed kitchen with a stainless-steel six-burner Viking gas range, double ovens, and expansive thick granite counters with seating. A charming

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (475) 260-5765

    15 Shire Ct, Cheshire, CT 06410
  • 1 Mountaincrest Dr, Cheshire, CT 06410
    1 Mountaincrest Dr, Cheshire, CT 06410
    1 Mountaincrest Dr, Cheshire, CT 06410
    /40

    $1,175,000

    $50K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,718 Sq Ft

    1 Mountaincrest Dr, Cheshire, CT 06410

    Majestically situated on a gentle hill designed to capture sweeping views of horses mountains and the picturesque countryside. This impressive 4,701 sq ft contemporary colonial is located in the highly sought after South Cheshire neighborhood. A dramatic two-story marble foyer with a sweeping staircase welcomes you into elegant formal spaces, including a private office with glass French doors and

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (475) 244-8520

    1 Mountaincrest Dr, Cheshire, CT 06410
  • 936 S Meriden Rd, Cheshire, CT 06410
    936 S Meriden Rd, Cheshire, CT 06410
    936 S Meriden Rd, Cheshire, CT 06410
    /39

    $459,900

    Open Sun 12PM - 2PM Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    936 S Meriden Rd, Cheshire, CT 06410

    Welcome to 936 South Meriden Road - a classic Cheshire raised ranch that delivers the space, flexibility, and indoor-outdoor lifestyle today's buyers are looking for. The main level is made for living. A large family room anchors the space with a classic raised hearth fireplace, flowing seamlessly into a dining area with built-ins - perfect for everything from casual nights in to hosting a crowd.

    Agent Photo

    Carly Kirsch

    Lamacchia Realty

    (475) 255-3632

    936 S Meriden Rd, Cheshire, CT 06410
  • 50 River View Ct, Cheshire, CT 06410
    50 River View Ct, Cheshire, CT 06410
    50 River View Ct, Cheshire, CT 06410
    /34

    $898,000

    • 3 Beds
    • 2.5 Baths
    • 3,652 Sq Ft

    50 River View Ct, Cheshire, CT 06410

    This custom-built, one-owner home is nestled at the end of a quiet cul-de-sac in sought after Cheshire, Connecticut. Set on 2.2 acres of park like grounds, the home offers unmatched privacy and serene surroundings. Thoughtfully designed with meticulous craftsmanship, this home features three bedrooms, including a primary suite with a private exercise room with jacuzzi. The home also offers a two

    Lori Valimont Berkshire Hathaway NE Prop.

    50 River View Ct, Cheshire, CT 06410
  • 6 Waterside Way, Cheshire, CT 06410
    6 Waterside Way, Cheshire, CT 06410
    6 Waterside Way, Cheshire, CT 06410
    /8

    $299,900

    • Land
    • 1 Acre
    • $299,900 per Acre

    6 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-acre lot available to build your dream home. The location of the former Percival Estate home boasts vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your

    Anthony LaCava Berkshire Hathaway NE Prop.

    6 Waterside Way, Cheshire, CT 06410
  • 140 Willow St, Cheshire, CT 06410
    140 Willow St, Cheshire, CT 06410
    140 Willow St, Cheshire, CT 06410
    /29

    $469,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft

    140 Willow St, Cheshire, CT 06410

    Come see this rare 2 family find in the heart of Cheshire. Both units have been fully updated with new kitchens, granite countertops, stainless steel appliances, updated baths, plumbing, electrical, and HVAC. Schedule your showing today

    Michael Dziedzic Precision Realty LLC

    140 Willow St, Cheshire, CT 06410
  • 95 Higgins Rd, Cheshire, CT 06410
    95 Higgins Rd, Cheshire, CT 06410
    95 Higgins Rd, Cheshire, CT 06410
    /40

    $759,000

    Open Sun 12PM - 2PM Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,301 Sq Ft

    95 Higgins Rd, Cheshire, CT 06410

    Welcome to this beautifully maintained 5 bedroom, 3.5-bath Colonial, perfectly situated on 1.25 picturesque acres with its own private pond, creating a peaceful and private retreat right in your backyard. Designed with both comfort and entertaining in mind, this spacious home features an open-concept floor plan, soaring 9-foot ceilings, and gleaming hardwood floors throughout. The heart of the

    Shari DiDomenico Berkshire Hathaway NE Prop.

    95 Higgins Rd, Cheshire, CT 06410
  • 886 Coleman Rd, Cheshire, CT 06410
    886 Coleman Rd, Cheshire, CT 06410
    /2

    $360,000

    $15K PRICE DROP
    • Land
    • 1.85 Acres
    • $194,595 per Acre

    886 Coleman Rd, Cheshire, CT 06410

    886 Coleman Road is a 1.85 acre mostly level and gently wooded parcel with mature trees. It offers natural beauty abundant with wildlife. Located in the South end of Cheshire- it is known as Lot 3 of The Carol Ridge Subdivision. The spot offers a respite from the day- yet it is conveniently located within an easy commute from New Haven, Quinnipiac University and Yale. This makes it well suited

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    886 Coleman Rd, Cheshire, CT 06410
  • 15 Philson Ct, Cheshire, CT 06410
    15 Philson Ct, Cheshire, CT 06410
    /2

    $385,000

    $15K PRICE DROP
    • Land
    • 2 Acres
    • $192,500 per Acre

    15 Philson Ct, Cheshire, CT 06410

    15 Philson Court is a 2 acre lightly wooded parcel- also known as Lot 5 of The Carol Ridge Subdivision- which is a quiet established cul de sac in the south end of Cheshire. This lot is highlighted on this picture-it is to the left-large rectangle shaped. The location is ideal for those who value convenience and ease of commuting to New Haven, Yale, QU, and Tweed Airport for quick weekend jaunts.

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    15 Philson Ct, Cheshire, CT 06410
  • 1731 Marion Rd, Cheshire, CT 06410
    1731 Marion Rd, Cheshire, CT 06410
    1731 Marion Rd, Cheshire, CT 06410
    /26

    $849,900

    • 5 Beds
    • 3 Baths
    • 4,352 Sq Ft

    1731 Marion Rd, Cheshire, CT 06410

    Unique Multi-Home Property on Over 3 Private Acres! A rare opportunity to own two homes on one beautiful property in a peaceful, private setting. Property Highlights: Over 3 acres of land R-40 zoning - ideal for farming, gardening, horses, or hobby farm potential Quiet country setting surrounded by nature Endless possibilities for multi-generational living, rental income, or guest house Main

    Nancy Newman LPT Realty

    1731 Marion Rd, Cheshire, CT 06410
  • 735 Cook Hill Rd, Cheshire, CT 06410
    735 Cook Hill Rd, Cheshire, CT 06410
    735 Cook Hill Rd, Cheshire, CT 06410
    /35

    $729,900

    • 4 Beds
    • 2.5 Baths
    • 2,748 Sq Ft

    735 Cook Hill Rd, Cheshire, CT 06410

    LOCATION, LOCATION, LOCATION! This gorgeous home on Cook Hill Road sits set back from the road on a 2+ acer level lot. This open floor plan home is sure to please. Large kitchen featuring double ovens, cook top, plenty of counter space and multiple pantry's is a cook's dream. The kitchen is open to an ample casual dining area that overlooks the private level yard. Beyond the casual dining area

    Betsy Stellato LAER Realty Partners

    735 Cook Hill Rd, Cheshire, CT 06410
  • 1050 Jarvis St, Cheshire, CT 06410
    1050 Jarvis St, Cheshire, CT 06410
    1050 Jarvis St, Cheshire, CT 06410
    /33

    $685,000

    New Construction $104K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,506 Sq Ft

    1050 Jarvis St, Cheshire, CT 06410

    Brand-new construction completed on 12/12/2025 and currently receiving final finishing touches by the owner. This beautiful home offers 4 spacious bedrooms, 3 full bathrooms, and a 2-car garage with an additional 506 square feet of garage space. The Town has issued the Certificate of Occupancy (CO). Thoughtfully designed layout with modern finishes throughout. A rare opportunity to own a newly

    Carlos Ventura Ventura Group Realty LLC

    1050 Jarvis St, 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 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    /3

    $260,000

    $15K PRICE DROP
    • Land
    • 4.61 Acres
    • $56,399 per Acre

    0 Waterbury Rd Unit 24047391, 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

    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
  • 81 Mountain Rd, Prospect, CT 06712
    81 Mountain Rd, Prospect, CT 06712
    81 Mountain Rd, Prospect, CT 06712
    /23

    $349,900

    $25K PRICE DROP
    • Land
    • 2.18 Acres
    • $160,505 per Acre

    81 Mountain Rd, Prospect, CT 06712

    For the discriminating buyer seeking a private wooded retreat, this rare 2.18-acre parcel offers a truly special opportunity. Thoughtfully partially cleared, the land invites you to envision your custom dream home nestled among nature's beauty. Framed by gorgeous stone walls and offering serene views of a bucolic pond, this property is a nature lover's sanctuary. Located just steps from access to

    Philip Degennaro Coldwell Banker Realty

    81 Mountain Rd, Prospect, CT 06712
Connecticut New Haven County Cheshire

Homes for Sale with Acreage in Cheshire, CT

Home Prices in Cheshire, CT

The median home sale price in Cheshire, CT is $522,500, consistent with the median home sale price year-over-year. Homes in Cheshire sell in 54 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$522,500
Median Single Family Sale Price
$547,500
Median Townhouse Sale Price
$533,230
Median 2 Bedroom Sale Price
$325,000
Median 1 Bedroom Sale Price
$171,000
Average Price Per Sq Ft
$290
Number of Homes for Sale
22
Last 12 months Home Sales
314
Months of Supply
0.80
Median List Price
$499,999
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

In Cheshire, there are currently 15 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Cheshire, CT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Cheshire and discover the potential and freedom that comes with owning your own piece of property.

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