Cheshire Real Estate

Welcome to Cheshire, Connecticut – a picturesque town nestled in the heart of New Haven County. Known for its charming neighborhoods, rich history, and vibrant community spirit, Cheshire offers a unique blend of suburban tranquility and easy access to urban amenities.

With a population of just over 29,000 residents, Cheshire prides itself on its strong sense of community and family-friendly atmosphere. The town is renowned for its excellent school system, making it an ideal place for families seeking a nurturing environment for their children. The local parks, such as the expansive Cheshire Park and the scenic Bartlem Park, provide ample opportunities for outdoor activities, from hiking and biking to picnicking and playing sports.

Cheshire’s historical roots run deep, with many well-preserved buildings and landmarks that tell the story of its past. Strolling through the town center, you’ll find a delightful mix of quaint shops, cafes, and restaurants, each offering a taste of local flavor. The annual Cheshire Fall Festival and other community events foster a sense of belonging, bringing residents together to celebrate their town’s unique character.

Conveniently located near major highways, Cheshire offers easy access to nearby cities like New Haven and Hartford, making it a perfect choice for commuters. Whether you’re drawn to its scenic landscapes, vibrant community life, or top-notch schools, Cheshire is a hidden gem waiting to be explored. Discover the charm of Cheshire – where small-town warmth meets modern convenience!

Newest Listings in Cheshire

$849,900

4 Beds ⋅ 3 Baths ⋅ 24194347 MLS

Stately home set on just under 2 acres in a beautiful country setting. Built from the foundation up in 2006, this home offers soaring ceilings, flowing rooms and space for everyone! The welcoming foyer leads to the dining room highlighted by a fireplace with pellet stove insert, and the living room beyond - both with hardwood floors. A balcony from the upper level looks down on the kitchen with high ceilings, dramatic chefs vent, beautiful granite countertops and new refrigerator. Also included on the main level is an office, a bedroom that can be utilized as a den, and a laundry room that leads to the huge three car garage. Upstairs you'll find three large bedrooms with new LVP flooring, including the primary suite with walk-in closet and spa bath with whirlpool tub. Another office, another full bath and a bright reading nook complete the upper level. The lower level is semi-finished (no heat) to offer more room to spread out. Numerous updates include a brand new roof (2026), new driveway (2025), new well tank, newer washer and dryer, and an electric car charger in the garage. Welcome Home!

662 Coleman Rd, Cheshire

$650,000

4 Beds ⋅ 3 Baths ⋅ 24192046 MLS

Nestled in one of Cheshire's most sought-after neighborhoods, 46 Dundee Drive puts you just steps from Barnum School, a rare convenience for growing families. From the moment you arrive, it's clear this home has been meticulously refreshed from top to bottom: fresh paint throughout, brand-new carpet on the staircase and entire second floor (except two bedrooms), and a fully renovated basement featuring sleek new LVT flooring, ready to flex as a playroom, home office, or media retreat. The kitchen shines with all-new appliances, making meal prep feel like a pleasure, not a chore. Peace of mind comes standard with a new roof installed in 2024, so the big-ticket items are already behind you. Whether you're right-sizing, starting out, or simply ready for something turnkey, this home checks every box. Priced to move and positioned for a quick close. Schedule your private showing today.

46 Dundee Dr, Cheshire

$475,000

3 Beds ⋅ 2 Baths ⋅ 24187815 MLS

This expansive Cape Cod is filled with charm, character, and plenty of space to make your own. The spacious eat-in kitchen offers abundant storage and cooking space, along with flexible room for a dining table, breakfast bar, or both. Step outside to the large Trex deck, where you can enjoy your morning coffee while overlooking the private, peaceful wooded yard. A charming screened porch provides another relaxing spot to read, unwind, or simply enjoy the sounds of nature. The main level includes a generously sized front-to-back living room with a propane fireplace, as well as a spacious dining room that could also serve as a home office, playroom, or additional sitting area. Upstairs, you'll find three bedrooms and a full bath. The finished lower level offers an inviting family or recreation room, along with an additional flexible space ready to suit your needs. Outside, the property includes a hot tub, two storage sheds, and plenty of yard space for entertaining, gardening, or future expansion. This special home offers comfort, versatility, and wonderful indoor and outdoor living spaces.

479 Blacks Rd, Cheshire

$209,900

2 Beds ⋅ 1 Baths ⋅ 24193724 MLS ⋅ Birchwood BLDG.

Beautifully renovated and filled with natural light, this first-floor condo is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops and stainless steel appliances. The beautifully remodeled bathroom features modern tile, a contemporary vanity, and a glass-enclosed shower. Additional amenities include a large private storage unit and shared laundry in the basement. The HOA fee covers water, heat, hot water, management, grounds and road maintenance - offering truly exceptional value. With no current special assessments and strong association reserves, this home provides peace of mind and affordability. Enjoy a prime Cheshire location with access to Farmington Canal Trail, just minutes from excellent restaurants and charming cafes. New Stonebridge shopping center features Whole Foods, Barnes & Noble, TJ Maxx, J.Crew and other popular retailers. This is a wonderful opportunity to own a move-in ready home and enjoy easy, low-maintenance living in one of Connecticut's most desirable towns with very good school system.

502 Oak Ave Unit 17, Cheshire

$769,900

3 Beds ⋅ 4 Baths ⋅ 24193469 MLS ⋅ The Reserve At Stonebridge Crossing BLDG.

Step into low-maintenance luxury at The Reserve at Stonebridge Crossing, where this immaculate 2024 Carriage Home offers the appeal of new construction without the wait. This home provides nearly 3,000 square feet of beautifully designed and flexible living space. The open-concept main level features engineered hardwood flooring, a welcoming foyer with double-stacked crown molding, soaring vaulted great room, and an upgraded kitchen with a contrasting stained island and Frigidaire Professional appliances, including an induction range. The first-floor primary suite offers a tray ceiling, two closets, a double vanity, floor to ceiling tiled walk-in shower, and private laundry hookups. Upstairs are two additional bedrooms, a full bath, a dedicated study ideal for remote work, an open loft perfect for a reading retreat or television area, and a second laundry area with utility sink. The finished 525 sq ft lower level includes another full bathroom and can be adapted as a recreation room, media room, guest suite or comfortable private space for extended family. Enjoy a composite deck, attached garage, electronic blinds, and true lock-and-leave living with landscaping, irrigation, snow removal and ground maintenance included. Residents enjoy a pavilion with gas grills, tables, fire pit and a walking loop that connects to a trail leading to The Shops at Stone Bridge Crossing. Easy access to highways for commuting. This carriage home offers value and lifestyle that makes living easy.

48 Soderman Way Unit 48, Cheshire

$800,000

6 Baths ⋅ 24192426 MLS

Rare Opportunity to Acquire a 5-Unit Commercial Portfolio! Five separate commercial condominium units are available in Curtis Homestead Village, a well-maintained professional complex in Cheshire's C-3 General Business Zone. Each unit may be purchased individually, although the Seller prefers to sell all five together. Unit 2 consists of 3 floors includes an executive office with private full bath. There is another full bath, 4 additional 1/2 baths, a kitchen, numerous private offices, and professional gym in the lower walk-out level, which also features loading dock access. The post-and-beam design offers exposed timber construction, impressive ceiling heights, and a mix of hardwood and carpeted flooring. Each self-contained unit includes a private entrance, kitchenette, restroom(s), and a flexible layout suitable for a variety of office, medical, retail, and service uses. Additional features include ample on-site parking, convenient access to Route 10 and major highways, and association-provided exterior maintenance and snow removal. Units may be purchased furnished or delivered empty. Unit 7 is leased through March 2027, with no renewal option. Units for sale include 1, 2, 3, 6 & 7, see related ML# 24192424, 24192428, 24192430 and 24192431.

908 S Meriden Rd Unit 2, Cheshire

$350,000

1 Baths ⋅ 24192430 MLS

Rare Opportunity to Acquire a 5-Unit Commercial Portfolio! Five separate commercial condominium units are available in Curtis Homestead Village, a well-maintained professional complex in Cheshire's C-3 General Business Zone. Each unit may be purchased individually, although the Seller prefers to sell all five together. Unit 6 can be accessed through an enclosed shared lobby and features a large, covered patio. There is a full kitchen and 1/2 bath. The post-and-beam design offers exposed timber construction, impressive ceiling heights, and a mix of hardwood and carpeted flooring. Each self-contained unit includes a private entrance, kitchenette, restroom(s), and a flexible layout suitable for a variety of office, medical, retail, and service uses. Additional features include ample on-site parking, convenient access to Route 10 and major highways, and association-provided exterior maintenance and snow removal. Units may be purchased furnished or delivered empty. Unit 7 is leased through March 2027, with no renewal option. Units for sale include 1, 2, 3, 6 & 7, see related ML# 24192424, 24192426, 24192428, and 24192431.

908 S Meriden Rd Unit 6, Cheshire

$135,000

1 Baths ⋅ 24192424 MLS

Rare Opportunity to Acquire a 5-Unit Commercial Portfolio! Five separate commercial condominium units are available in Curtis Homestead Village, a well-maintained professional complex in Cheshire's C-3 General Business Zone. Each unit may be purchased individually, although the Seller prefers to sell all five together. Unit 1 features open space with kitchenette and 1/2 bath. The post-and-beam design offers exposed timber construction, impressive ceiling heights, and a mix of hardwood and carpeted flooring. Each self-contained unit includes a private entrance, kitchenette, restroom(s), and a flexible layout suitable for a variety of office, medical, retail, and service uses. Additional features include ample on-site parking, convenient access to Route 10 and major highways, and association-provided exterior maintenance and snow removal. Units may be purchased furnished or delivered empty. Units for sale include 1, 2, 3, 6 & 7, see related ML# 24192426, 24192428, 24192430 and 24192431.

908 S Meriden Rd Unit 1, Cheshire

$125,000

1 Baths ⋅ 24192428 MLS

Rare Opportunity to Acquire a 5-Unit Commercial Portfolio! Five separate commercial condominium units are available in Curtis Homestead Village, a well-maintained professional complex in Cheshire's C-3 General Business Zone. Each unit may be purchased individually, although the Seller prefers to sell all five together. Unit 3 is the smallest of available units and features a covered front walkway with easy access to lower parking lot. The post-and-beam design offers exposed timber construction, impressive ceiling heights, and a mix of hardwood and carpeted flooring. Each self-contained unit includes a private entrance, kitchenette, restroom(s), and a flexible layout suitable for a variety of office, medical, retail, and service uses. Additional features include ample on-site parking, convenient access to Route 10 and major highways, and association-provided exterior maintenance and snow removal. Units may be purchased furnished or delivered empty. Unit 7 is leased through March 2027, with no renewal option. Units for sale include 1, 2, 3, 6 & 7, see related ML# 24192424, 24192426, 24192430 and 24192431.

908 S Meriden Rd Unit 3, Cheshire

$130,000

3 Baths ⋅ 24192431 MLS

Rare Opportunity to Acquire a 5-Unit Commercial Portfolio! Five separate commercial condominium units are available in Curtis Homestead Village, a well-maintained professional complex in Cheshire's C-3 General Business Zone. Each unit may be purchased individually, although the Seller prefers to sell all five together. Unit 7 features a stately executive office with private full bath, 2 additional 1/2 baths, and eat-in kitchen. This unit is leased through March 2027, with no renewal option. The post-and-beam design offers exposed timber construction, impressive ceiling heights, and a mix of hardwood and carpeted flooring. Each self-contained unit includes a private entrance, kitchenette, restroom(s), and a flexible layout suitable for a variety of office, medical, retail, and service uses. Additional features include ample on-site parking, convenient access to Route 10 and major highways, and association-provided exterior maintenance and snow removal. Units may be purchased furnished or delivered empty. Units for sale include 1, 2, 3, 6 & 7, see related ML# 24192424, 24192426, 24192428, and 24192430.

908 S Meriden Rd Unit 7, Cheshire

$229,000

24193230 MLS

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 expensive and time-consuming early phases of any new build. Here, that groundwork is already done, which can meaningfully cut cost and shave weeks off your construction timeline. Bring your own plans and builder, or design around the existing footprint. Why this lot Foundation already in place - a substantial cost and schedule advantage over a raw lot Building to be removed - the site will be cleared, so you start with a clean slate above grade Private well and septic - no dependency on municipal water/sewer hookups R-80 zoning - single-family residential 1.84 acres of space to design around

1116 Wallingford Rd, Cheshire

$349,900

3 Beds ⋅ 3 Baths ⋅ 24192035 MLS ⋅ Currier Woods BLDG.

One of the many advantages of purchasing a home in Currier Woods is its location directly across the street from the brand-new Norton Elementary School. This beautifully designed, state-of-the-art K"6 school is a convenient neighborhood amenity within feet of the community. Currier Woods offers the benefits of modern living in a desirable location with easy access to local schools, parks, shopping and other everyday conveniences.

54 Currier Pl Unit 54, Cheshire

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