Cheshire Condos for Sale

Cheshire Condos for Sale

Welcome to Cheshire, Connecticut—a picturesque town nestled in New Haven County, where charming suburban living meets a vibrant community spirit. Known for its scenic landscapes and friendly atmosphere, Cheshire offers residents a delightful blend of tranquility and accessibility. With its rich history dating back to the 17th century, this town boasts a unique character that resonates through its well-preserved architecture and lush parks.

Cheshire is renowned for its excellent school system, making it an ideal place for families seeking quality education for their children. The town is also home to a variety of recreational activities, including hiking trails, sports facilities, and community events that bring neighbors together. With convenient access to major highways and public transportation, commuting to nearby cities like New Haven and Hartford is a breeze, allowing residents to enjoy the best of both worlds.

If you’re considering making Cheshire your home, you’ll be delighted to discover an array of stunning condos for sale. These modern residences combine comfort and style, offering open floor plans, contemporary finishes, and amenities that cater to today’s lifestyle. Whether you’re a first-time buyer or looking to downsize, the condos in Cheshire provide a low-maintenance option without sacrificing quality or space. Imagine sipping your morning coffee on a private balcony or enjoying the community pool—a perfect way to unwind after a busy day.

Explore the charm and convenience of Cheshire, CT, and find your dream condo today. Embrace a lifestyle where community and comfort come together, making every day feel like a retreat.

Newest Cheshire Condos for Sale

12 Southwick Court Unit 12, Cheshire
$350,000
2 Beds ⋅ 2 Baths ⋅ 24216609 MLS ⋅ Southwick At Cheshire BLDG.
Southwick at Cheshire is offering unit 12 in this sought after 55+ community. This cottage style condo offers 2 bed, 2 bath and in unit washer and dryer. The living space is the ideal open layout to downsize to without feeling like you've compromised lifestyle. Vaulted ceilings, architectural columns and a beautiful staircase leading to a large upper level loft add an extra special touch to this floorplan. This unit comes with a 1 car detached garage. We welcome you in to see for yourself what your next chapter can look like in this centrally located town of Cheshire where restaurants, shopping and highway access will ultimately check all the boxes on your wish list.

12 Southwick Court Unit 12, Cheshire
747 W Main St Unit H, Cheshire
$349,900
2 Beds ⋅ 2 Baths ⋅ 24217287 MLS ⋅ Hidden Pond BLDG.
Welcome to Hidden Pond, a highly desirable, secluded condominium community in Cheshire set on 17 acres! This fully renovated townhouse-style home features 2 bedrooms, 1 full bath, and 1 half bath. Truly move in ready, the home offers a spacious layout featuring an open living and dining area, a finished basement with additional storage space, and vaulted ceilings on the upper level. The kitchen flows seamlessly into the main living space, creating a welcoming setting for everyday living and entertaining. Upstairs, both bedrooms feature vaulted ceilings and walk-in closets. The finished lower level provides additional living space with a fireplace and walk-out access. Enjoy outdoor relaxation on either of the two brand-new decks overlooking Cheshire's protected wetlands. Additional highlights include a heat pump, air conditioning, an attached garage, and a dedicated driveway. Conveniently located on West Main Street, with easy access to the Farmington Canal, local shopping, dining, parks, and commuter routes. Experience comfortable townhouse living in Cheshire!

747 W Main St Unit H, Cheshire
27 Soderman Way Unit 27, Cheshire
$771,900
3 Beds ⋅ 3 Baths ⋅ 24216806 MLS ⋅ The Reserve At Stonebridge Crossing BLDG.
FINAL NEW CONSTRUCTION OPPORTUNITY AT THE RESERVE AT STONEBRIDGE CROSSING! Ready for immediate occupancy, this beautifully appointed carriage home offers the last opportunity to become an original homeowner in this sought-after Cheshire community. Featuring nearly 3,000 square feet of finished living space, this thoughtfully designed home combines luxury finishes, architectural appeal, and the convenience of low-maintenance living. A dramatic two-story great room with soaring ceilings and abundant natural light anchors the open-concept main level, complemented by engineered hardwood flooring and a beautifully upgraded Pro Kitchen featuring ceiling-height cabinetry, granite countertops, a 36-inch JennAir induction range, farmhouse sink, and vented hood. The first-floor primary suite offers a spacious walk-in closet, spa-inspired bath with oversized tiled shower, and convenient main-level laundry. Upstairs, an open loft overlooks the great room and connects two additional bedrooms, a full bath, and a private home office. The finished lower level adds approximately 525 square feet of flexible recreation space and a plumbing rough for future bathroom. Built to EG Home's Zero Energy Ready standards, this home has solar panels, high-efficiency heating and cooling, advanced insulation, and enhanced indoor air filtration. Enjoy community amenities including walking trails, a pavilion, and fire pit, with convenient access to every day living.

27 Soderman Way Unit 27, Cheshire
72 Quarry Village Rd Unit 72, Cheshire
$425,000
2 Beds ⋅ 3 Baths ⋅ 24214748 MLS ⋅ Quarry Village BLDG.
Step inside this stunning, fully updated end-unit condo, offering an exceptional blend of style, comfort, and modern finishes throughout! The impressive living room features soaring vaulted ceilings, a skylight that fills the space with natural light, and a beautiful wood-burning fireplace with a honed granite hearth and surround. French doors lead directly to a spacious deck overlooking the backyard, perfect for relaxing or entertaining. The fully renovated kitchen is a showstopper, featuring custom cabinetry, a center island, and gorgeous quartz countertops, flowing seamlessly into the spacious dining area. Luxury vinyl flooring extends throughout the main level, creating a warm and cohesive feel. The beautifully appointed bathrooms feature custom Birch vanities, quartz countertops, and elegant brass fixtures. Upstairs, you'll find a spacious primary bedroom with a walk-in closet, abundant natural light, and a stunning private bathroom featuring a custom vanity and oversized walk-in shower with marble surround and glass doors. The additional full bathroom is equally impressive, offering a luxurious soaking tub with marble surround and porcelain tile flooring. Luxury vinyl flooring continues throughout the second level. The large unfinished basement provides plenty of storage space and features an existing basement water management system. Additional highlights include a newer furnace, central air conditioning, and hot water heater.

72 Quarry Village Rd Unit 72, Cheshire
420 Robin Ct Unit 420, Cheshire
$230,000
2 Beds ⋅ 3 Baths ⋅ 24214604 MLS ⋅ Deepwood BLDG.
Enjoy the convenience of townhouse living with the space and comfort of home in Cheshire's Deepwood community. This two-bedroom condo offers 1 full and 2 half baths, hardwood floors, crown molding, and a kitchen with granite countertops. Spacious living and dining areas welcome you on the main level, while upstairs features two generously sized bedrooms with hardwood floors, an updated full bath, and convenient laundry. The finished, heated lower level adds approx. 257 sq. ft. of living space with a family room, half bath, and separate unfinished storage area. Step outside and enjoy access to backyard open space, a welcome feature that adds to the home-like setting. Improvements include a new roof (October 2026), & anticipated paving. Air-conditioning units and two assigned parking spaces add everyday convenience. Access to Farmington CanalHeritage Trail, and nearby shopping, restaurants, and commuter routes including I-691 and I-84.

420 Robin Ct Unit 420, Cheshire
83 Quarry Village Rd Unit 83, Cheshire
$335,000
2 Beds ⋅ 2 Baths ⋅ 24205596 MLS ⋅ Quarry Village BLDG.
This unit is located in the highly desirable Quarry Village complex, a quiet and exceptionally maintained residential community. Enjoy the proximity to the center of Cheshire, numerous parks and playgrounds, the Cheshire Community Pool, orchards, the Farmington Canal Heritage Trail, as well as extensive dining and shopping options. It is approximately 30 minutes to Hartford or New Haven. Your main level includes your living room with bay window and a gas fireplace, the kitchen with esthetically pleasing appliances and half bath. The double doors of the light-filled dining room lead to an updated Trex deck. The 2nd floor has two bedrooms with ample walk-in closet space, a full bath, as well as a bonus room that can be a third bedroom or home office. The basement is partially finished with a workshop room and extra humidity-controlled storage. The unit has an attached garage and driveway parking. Ample visitor and guest parking is available throughout the complex. Recent condo updates include: 2026 new roof depicted in aerial photos, new a/c compressor and fan (2026), updated Trex deck and new dishwasher (2025). The amenities & services covered by the low monthly Homeowners Assoc. include ground maintenance, snow removal, trash collection, and public water fee.

83 Quarry Village Rd Unit 83, Cheshire
2 Saxon Woods Ct, Cheshire
$497,700
3 Beds ⋅ 2 Baths ⋅ 24207223 MLS ⋅ Copper Hill BLDG.
DESIRABLE COPPER HILL STAND-A-LONE RANCH CONDO in Cheshire on a Cul-de-sac Setting !!! BRING your vision to life at 2 Saxon Woods Court. This home offers great bones and a flexible layout, ready for your personal touch. With some updating, this home presents a wonderful opportunity to create the home of your dreams in a peaceful, private setting. This spacious standalone condo is tucked away on a quiet cul-de-sac in Copper Hill community. Offering 2459 square feet of living space, three bedrooms, two full baths and an open floorplan, that's ideal for both everyday living and entertaining. The finished lower level adds valuable bonus space, complete with a cozy fireplace and bar area-perfect for game nights, gathering or a relaxing retreat. REMEMBER there is no age restriction, making this home a perfect fit for buyers of all ages.

2 Saxon Woods Ct, Cheshire
502 Oak Ave Unit 17, Cheshire
$199,000
2 Beds ⋅ 1 Baths ⋅ 24203224 MLS ⋅ Birchwood BLDG.
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 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 - 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 truly beautiful home and enjoy easy, no-maintenance living in one of Connecticut's most desirable towns with very good school system.

502 Oak Ave Unit 17, Cheshire
459 E Mitchell Ave Unit 459, Cheshire
$160,000
1 Beds ⋅ 1 Baths ⋅ 24202177 MLS ⋅ Cheshire Hillside Village BLDG.
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 sought-after style unit has no neighbors above, allowing for added privacy and helping create the wonderful sense of openness and natural brightness throughout. Despite being an upper-level unit, there are no stairs to enter the building, thanks to the convenient layout of the complex. Brand-new flooring throughout, fresh paint, in-unit washer and dryer and a slider that leads from the living room to the private deck with convenient exterior storage add to the appeal. The monthly HOA fee includes heat and hot water, offering added convenience and helping make monthly expenses more predictable. Ideally located in the center of Cheshire, near the Stop & Shop plaza, with easy access to I-84, I-91, and Route 691, and just a quick ride down Route 10 to the new shops at Stonebridge Crossing. Nearby recreational facilities are also easily accessible, making this a wonderful opportunity for comfortable, convenient, and low-maintenance living in the heart of Cheshire.

459 E Mitchell Ave Unit 459, Cheshire
443 E Mitchell Ave Unit 443, Cheshire
$199,900
1 Beds ⋅ 1 Baths ⋅ 24201442 MLS ⋅ Cheshire Hillside Village BLDG.
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 stainless-steel appliances, tiled backsplash, crown molding, modern fixtures, new flooring, paint, a custom feature wall, and a fully refreshed kitchen and bathroom.The primary bedroom includes a well-designed closet system offering ample storage. The spacious flex room offers endless possibilities perfect for a home office, guest space, hobby room, or second bedroom. Your new sliders open to a back patio where you can relax with your morning coffee and watch the birds. The HOA includes heat and hot water, making this a truly affordable, and complete turnkey living within the town of Cheshire. There is easy parking and mailbox access. Just pack your suitcases and enjoy comfortable, low maintenance living in this well-kept community designed for active adults. SEE AGENT to AGENT REMARKS!!!Welcome home!!!

443 E Mitchell Ave Unit 443, Cheshire
418 Greens Loop, Cheshire
$324,900
2 Beds ⋅ 2 Baths ⋅ 24200337 MLS ⋅ Country Village BLDG.
Location! Location! Location! Easiest in and out from the Country Club Rd entrance (Fairway Dr), just a few feet from the mail, pool, clubhouse, and basketball courts-wooded rear yard. Beautifully updated, featuring new hardwood floors and carpet. Refreshed kitchen cabinets with quartz counters and new appliances. All new bathrooms! Freshly painted throughout. Great location close to orchards, shopping, and "The Shops at Stone Bridge." Plenty of fun can be found nearby, including the Linear Trail and the Farmington Canal Heritage Trail, Bartlem Recreation Area, and Cheshire Park. Also for rent, see MLS#24213124

418 Greens Loop, Cheshire
48 Soderman Way Unit 48, Cheshire
$759,900
3 Beds ⋅ 4 Baths ⋅ 24193469 MLS ⋅ The Reserve At Stonebridge Crossing BLDG.
Modern Style, Flexible Space & Low-Maintenance Living! Built in 2024, this beautifully appointed carriage home at The Reserve at Stonebridge Crossing offers a beautiful home with finished living space across three levels - room to live, work, and entertain. The welcoming foyer opens to a vaulted great room and an impressive kitchen featuring upgraded cabinetry, a contrasting stained island, and Frigidaire Professional appliances. Engineered hardwood flooring adds warmth throughout the main and upper levels. The main-level primary suite offers a tray ceiling, two spacious closets, and a private bath with double vanity and floor-to-ceiling tiled walk-in shower, plus convenient laundry hookups. Upstairs, two additional bedrooms, a full bath, dedicated study, open loft, and second laundry area provide exceptional flexibility. The finished lower level adds 525 square feet and a full bath, perfect for a media room, gym, guest space, or recreation area. Enjoy morning coffee or evening relaxation on the outside deck, with electronic blinds on the main level and an attached garage adding everyday convenience. Leave the landscaping, irrigation, snow removal, and grounds maintenance to the community. A pavilion with gas grills, tables, and fire pit, plus a neighborhood walking loop, makes it easy to enjoy the outdoors. With quick highway access to shopping, dining, and more, this home delivers modern comfort without the upkeep. Come see how easy living can be.

48 Soderman Way Unit 48, Cheshire
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