18

Cheshire, CT Homes for Sale with Acreage

Section Image Section Image
  • /2

    $919,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    1800 Blackberry Place, Cheshire, CT 06410

    Build your own expanded Cape Cod (or bring your own plans) on Blackberry Woods, Cheshire's newest development. 4 bedroom, 2.5 bathroom Maple model with a primary bedroom on the main floor. Oversized family room with fireplace opens to a custom kitchen with island. Formal dining room for get togethers and events. The 1st floor hosts the primary suite with large walk in closet and tile shower, and

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 445-2914

    1800 Blackberry Place, Cheshire, CT 06410
  • /3

    $1,060,000 New Construction

    • 4 Beds
    • 3 Baths
    • 3,029 Sq Ft

    1500 Blackberry Place, Cheshire, CT 06410

    Welcome to Blackberry Woods, Cheshire's newest development. Consider The Willow, with its 3,029 sqft of Living Space on just over 1.36 Acres of Land. Fabulous Floor Plan includes an impressive 2 Story Foyer, First-Floor Full Bath, Large Kitchen Pantry, and Private Office on the Main Level. The Master Suite will "WOW" You with a Walk-In Closet, Double Vanities, Water Closet, and a Luxurious

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 427-0372

    1500 Blackberry Place, Cheshire, CT 06410
  • /6

    $869,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,459 Sq Ft

    Lot 30 Blackberry Place, Cheshire, CT 06410

    Blackberry Woods presents the gracious Charter Oak model which provides 2,459 sqft of thoughtful living space with 4 Bedrooms and 2 1/2 Baths. Desirable features of this plan include a spacious foyer entry with coat closet, mudroom off the garage entry w/ half bath and laundry, an open floor plan including a custom kitchen, dinette & family room, gas log fireplace, kitchen pantry, and sliders to

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 793-6459

    Lot 30 Blackberry Place, Cheshire, CT 06410
  • /37

    $1,099,000

    • 5 Beds
    • 5.5 Baths
    • 5,081 Sq Ft

    435 Maple Ave, Cheshire, CT 06410

    Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

    Amy LaMaster The Bella Group, LLC

    435 Maple Ave, Cheshire, CT 06410
  • /2

    $1,959,900

    • 5 Beds
    • 4.5 Baths
    • 7,762 Sq Ft

    764 Bethany Mountain Rd, Cheshire, CT 06410

    Inspiring country home. Inground pool, tennis court and equestrian features.

    Joel Matson Coldwell Banker Realty

    764 Bethany Mountain Rd, 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
  • /2

    $360,000

    • 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
  • /2

    $385,000

    • 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. 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. The Town of Cheshire has many offerings: Nearby shopping and restaurants

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

    15 Philson Ct, Cheshire, CT 06410
  • /39

    $524,900

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft

    1324 Notch Rd, Cheshire, CT 06410

    Welcome to this charming 4-bedroom, 2-bath home set on a picturesque 2-acre lot offering exceptional privacy and space to enjoy the outdoors. Tucked back from the road, this property features a large, sun-filled family room with a fireplace (for decorative purposes only), an inviting eat-in kitchen, and a convenient first-floor laundry area. The expansive yard is perfect for gardening, play, or

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    1324 Notch Rd, Cheshire, CT 06410
  • /26

    $849,900

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

    1731 Marion Rd, Cheshire, CT 06410

    Welcome to this exceptional estate set deep off the road on 3.3 private, beautifully wooded acres in Cheshire, Connecticut. The main residence offers over 4,000 sq. ft. of living space, combining comfort, elegance, and versatility for today's lifestyle. Inside, you'll find five generous bedrooms, multiple living and entertaining areas, and a warm, inviting fireplace on the main level. The fully

    Nancy Newman LPT Realty

    1731 Marion Rd, Cheshire, CT 06410
  • /9

    $789,000 New Construction

    • 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
  • /36

    $649,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,498 Sq Ft

    34 Nathan Hale Ct, Cheshire, CT 06410

    Welcome to this expansive Colonial nestled on almost 2 secluded acres in one of Cheshire's sought-after neighborhoods. Presenting 4 bedrooms (potential for a 5th) each with its own walk-in closet, this home provides exceptional space and flexibility. Step into the grand foyer, highlighted by a beautiful chandelier and a newer window that fills the entry with natural light. The main level offers a

    Stephanie Plaza Lamacchia Realty

    34 Nathan Hale Ct, Cheshire, CT 06410
  • /8

    $190,000

    • Land
    • 1.84 Acres
    • $103,261 per Acre

    1116 Wallingford Rd, Cheshire, CT 06410

    Here's your opportunity to own a rare 1.8 acre lot in Cheshire. The existing home will be dismantled, leaving a clear, build-ready site for your dream home or investment property. Septic system will need to be replaced.

    Christopher John Mentley New Haus Group LLC

    1116 Wallingford Rd, Cheshire, CT 06410
  • /40

    $849,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,815 Sq Ft

    1412 Marion Ave, Cheshire, CT 06410

    HOUSE IS FRAMED AND READY FOR BUYER CHOICES! GREAT NEW CONSTRUCTION READY FOR QUICK DELIVERY FOR NEW OWNERS!! Amazing open layout on this modern colonial. This home is perfect for entertaining with a huge kit island open to a spacious Family Room. The floor plan is versatile with 4 bedrooms on the second floor and an optional 5th bedroom/office on the main level. Perfect for a work from home

    Roy Evjen Evjen Agency

    1412 Marion Ave, Cheshire, CT 06410
  • /30

    $1,299,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,775 Sq Ft

    1481 Marion Rd, Cheshire, CT 06410

    Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in the main living areas, and a custom-designed kitchen that seamlessly

    Abby Breau New England Prestige Realty

    1481 Marion Rd, Cheshire, CT 06410
  • /3

    $260,000

    • 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
  • /23

    $374,900

    • Land
    • 2.18 Acres
    • $171,972 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
  • /3

    $375,000

    • Land
    • 1.81 Acres
    • $207,182 per Acre

    1032 Meriden-Waterbury Turnpike, Southington, CT 06479

    Level lot with asphalt parking area ready for your new business idea, with the New local mall nearby you will have plenty of customers. The property actually just over the line into Southington. This is a great opportunity for a niche business. Previous approval was for a drive through type business. Just over a mile from rte 84 exit 28, rte 10 is 1/2 mile

    Mark Giumarra North Point Properties

    1032 Meriden-Waterbury Turnpike, Southington, CT 06479

Home Trends in Cheshire, CT

Housing Trends

Median Sale Price
$525,000
Median Single Family Sale Price
$550,000
Median Townhouse Sale Price
$533,230
Median 2 Bedroom Sale Price
$199,000
Median 1 Bedroom Sale Price
$166,000
Average Price Per Sq Ft
$287
Number of Homes for Sale
23
Last 12 months Home Sales
325
Months of Supply
0.80
Median List Price
$509,950
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
7%
How to Buy a Home How to Finance a Home How to Sell a Home