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Cheshire, CT Homes for Sale with Acreage

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  • /40

    $929,000

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    776 Bethany Mountain Rd, Cheshire, CT 06410

    Welcome to 776 Bethany Mountain Road - an enchanting private estate where timeless charm meets modern family living. Set on nearly 4 wooded acres in Cheshire, this 4-bedroom, 3,300+ sq ft Dutch Colonial offers the perfect blend of comfort, beauty, and fun. Create unforgettable memories hosting gatherings by the heated saltwater pool, cooking in your outdoor pizza oven, or growing fresh produce

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (203) 990-1268

    776 Bethany Mountain Rd, Cheshire, CT 06410
  • /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
  • /2

    $699,900 New Construction

    • 3 Beds
    • 3 Baths
    • 1,908 Sq Ft

    1600RR S Main St, Cheshire, CT 06410

    To be built. Modern Raised Ranch with plenty of room for all. Wonderful layout with endless possibilities. 3 large bedrooms and 3 full bathrooms, including one on the lower level allowing for easy accommodation of guests. Set on more than 2 acres. Open floor plan on the main level with sliders and lots of natural light. Finished basement area with sliders and a full bathroom offers flexible use

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 439-5995

    1600RR S Main St, Cheshire, CT 06410
  • /3

    $950,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,821 Sq Ft

    1600 S Main St Unit BFraser Model, Cheshire, CT 06410

    Wonderful opportunity to build in the south end of Cheshire. Consider The Frasier model with 2,821 sqft of living space , w/ 4 Bedrooms and 2 1/2 Baths. This both elegant and practical model features a spacious Foyer with double coat closets, Mudroom and Half Bath off garage entry, open floor plan between the Family Room, Dinette & Kitchen, Gas Log Fireplace, Kitchen Pantry, and a backyard Patio

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 445-1113

    1600 S Main St Unit BFraser Model, Cheshire, CT 06410
  • /4

    $859,000 New Construction

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

    1600 S Main St Unit Model A (Charter Oak, Cheshire, CT 06410

    Wonderful opportunity to build in the south end of Cheshire. The custom built gracious Charter Oak model provides 2,459 sq ft 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

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 806-9529

    1600 S Main St Unit Model A (Charter Oak, Cheshire, CT 06410
  • /21

    $799,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    1600 S Main St, Cheshire, CT 06410

    Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal. One level living at its finest, with 9ft ceilings throughout, custom kitchen w/granite countertops and center island, hardwood flooring in the main living areas, gas fireplace in the family room and a mudroom with half bath and laundry. Large Primary bedroom with bathroom en-suite, and walk-in closet. 2 guest

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 251-8839

    1600 S Main St, 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
  • /2

    $899,000 New Construction

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

    1600 S Main St, Cheshire, CT 06410

    Build your own expanded Cape Cod inn the South End of Cheshire. Large lot of 2.96 acres. Convenient to Quinnipiac, Yale and New Haven. 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

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 885-1679

    1600 S Main St, Cheshire, CT 06410
  • /37

    $1,250,000

    • 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
  • /40

    $1,149,000

    • 4 Beds
    • 4.5 Baths
    • 4,791 Sq Ft

    1 Mountaincrest Dr, Cheshire, CT 06410

    Outstanding Mountaincrest custom colonial, a beautiful & spacious home designed for comfortable living & elegant entertaining. A dramatic two-story foyer sets the tone, leading to a private home office with built-in bookshelves. The expansive living room has a wood fireplace. The banquet-sized dining room features a bay of windows that fills the space with natural light.The heart of the home is

    Susan Santoro William Pitt Sotheby's Int'l

    1 Mountaincrest Dr, Cheshire, CT 06410
  • /26

    $999,999

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

    1731 Marion Rd, Cheshire, CT 06410

    The Newman Compound! You are going to love this sprawling ranch that includes two houses! The guest house is fully rented. This home is truly spectacular. The floor plan is open & huge. The main house has 4+ bedrooms. Full finished lower level features large family room accented by a wood stove, office, additional bedrooms & a full bathroom. Beautiful stream on boundary. Both houses 1731 & 1735

    Nancy Newman LPT Realty

    1731 Marion Rd, Cheshire, CT 06410
  • /25

    $1,150,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,832 Sq Ft

    23 Melrose Dr, Cheshire, CT 06410

    23 Melrose Dr is nearly complete and ready for you to move in and call it HOME! This is a beautifully designed classic New England Cape Farmhouse-where timeless tradition meets thoughtful modern upgrades. This home boasts classic curb appeal with its inviting front porch, classic New England shaker style siding and stylish black exterior windows. Step inside to discover a light-filled interior

    Dori Degennaro William Raveis Real Estate

    23 Melrose Dr, Cheshire, CT 06410
  • /30

    $1,299,000 New Construction

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

    1481 Marion Rd, Cheshire, CT 06410

    Inquire about special builder incentives available until June 30th! 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

    Abby Breau New England Prestige Realty

    1481 Marion Rd, Cheshire, CT 06410
  • /5

    $1,299,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,011 Sq Ft

    15 Melrose Dr Unit Lot 4, Cheshire, CT 06410

    Presenting 15 Melrose Drive! This beautiful, To Be Built, new construction home is the layout that you have been waiting for! At 4,011 square feet this house plan is the perfect size for any family. A very spacious home with 9 ft ceilings on the main level, and a beautiful cathedral ceiling in the Family Room that perfectly highlights the decorative propane fireplace. A very functional mudroom

    Dori Degennaro William Raveis Real Estate

    15 Melrose Dr Unit Lot 4, Cheshire, CT 06410
  • /40

    $639,000 Open Sun 11AM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 1,910 Sq Ft

    5 Smith Place, Cheshire, CT 06410

    Welcome to this beautifully maintained 4-bedroom Colonial nestled on a peaceful cul-de-sac. Set on a generous lot with a large, private backyard - perfect for outdoor entertaining and play - this home offers space, comfort and style. Step inside to find a thoughtfully renovated kitchen featuring modern finishes, updated appliances, and ample cabinet space. The main level boasts a traditional

    James Bulger Calcagni Real Estate

    5 Smith Place, Cheshire, CT 06410
  • /40

    $649,999

    • 4 Beds
    • 2.5 Baths
    • 2,758 Sq Ft

    40 Nathan Hale Ct, Cheshire, CT 06410

    Welcome to this beautifully maintained 4-bedroom Colonial, perfectly nestled on over 3 acres in a serene cul-de-sac setting. A dramatic two-story foyer sets the tone for a home that blends comfort, style, and thoughtful design. The warm, inviting living room with custom built-ins connects seamlessly to the family room via a stunning two-sided wood-burning fireplace-ideal for entertaining or

    Brette Stern Calcagni Real Estate

    40 Nathan Hale Ct, Cheshire, CT 06410
  • /30

    $875,000

    • 3 Beds
    • 3.5 Baths
    • 3,663 Sq Ft

    55 Pine Brook Ct, Cheshire, CT 06410

    You will love this address in the south end of Cheshire. Located at the end of sought after cul de sac this Tudor revival home boasts 4 bedrooms and 3.5 bathrooms. Custom kitchen offers modern finishes with stainless steel appliances and island. The Den is warm and inviting with its stone fireplace as the centerpiece. Impressive Great room/ formal dining room combo with cathedral ceilings and

    Brian Botti Botti Realty

    55 Pine Brook Ct, Cheshire, CT 06410
  • /3

    $275,000

    • Land
    • 4.61 Acres
    • $59,653 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
  • /7

    $335,000

    • Land
    • 1.00 Acre
    • $335,000 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
  • /4

    $335,000

    • Land
    • 1.32 Acres
    • $253,788 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
  • /40

    $2,200,000

    • 5 Beds
    • 4.5 Baths
    • 3,174 Sq Ft

    630 Cook Hill Rd, Cheshire, CT 06410

    Welcome to your own piece of heaven on Earth! This Cape Cod gem boasts not just a home but a lifestyle surrounded by 8.5 acres of sprawling land, perfect for your own little homestead. Inside you will find a Chef's Dream, an expansive eat-in kitchen that's the heart of the home that includes a colossal 10x5 island for gatherings, an additional prep island for culinary adventures, and a wet bar

    Kelsey Oddo Kelsey & Co. Real Estate

    630 Cook Hill Rd, Cheshire, CT 06410
  • /2

    $1,759,900

    • 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
  • /2

    $169,900

    • Land
    • 1.22 Acres
    • $139,262 per Acre

    0 Moss Farms Rd, Cheshire, CT 06410

    Approved and cleared .93+/- acre rear building lot located behind 916 Moss Farms Rd, Cheshire. Maps available upon request. Please do not walk property without a scheduled appointment. Contact for additional information. Subject to easements and approval stipulations.

    Jorge Zea Blue Lighthouse Realty, Inc

    0 Moss Farms Rd, Cheshire, CT 06410
  • /13

    $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
  • /40

    $625,000

    • 4 Beds
    • 3 Baths
    • 1,938 Sq Ft

    258 New Cheshire Rd, Wallingford, CT 06492

    There's no place like home! This exceptionally maintained 4 bedroom, 3 bath Cape style home boasts quality and comfort & features gleaming hardwood floors, C-Air and tons of natural sun light! This great location with amazing curb appeal & a peaceful country setting, borders the Wallingford/Cheshire line with easy access to everything! The open kitchen layout with a peninsula, eating area & main

    Linda Conchado Century 21 AllPoints Realty

    258 New Cheshire Rd, Wallingford, CT 06492
  • /3

    $399,000

    • Land
    • 1.81 Acres
    • $220,442 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
$571,000
Median Townhouse Sale Price
$570,028
Median 2 Bedroom Sale Price
$245,000
Median 1 Bedroom Sale Price
$189,900
Average Price Per Sq Ft
$279
Number of Homes for Sale
48
Last 12 months Home Sales
325
Months of Supply
1.80
Median List Price
$525,000
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
10%
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