Refine Search
Sort by
388 Sharon Dr, Cheshire
$419,900
3 Beds ⋅ 2 Baths ⋅ 24210609 MLS
Charming three bedroom ranch offering spacious living and a convenient location close to shopping, dining, schools and amenities. The large open kitchen features a generous dining area perfect for everyday meals and entertaining. Enjoy the inviting first floor family room with a cozy fireplace, creating a warm and comfortable gathering space. The primary bedroom includes it's own primary bath for added comfort and convenience. Beautiful hardwood floors run throughout much of the home adding character and appeal. An Unfinished lower level provides potential to nearly double the living space, offering endless possibilities for future expansion. Situated on a level lot, the property also features a lovely deck, ideal for relaxing.

388 Sharon Dr, Cheshire

980 Notch Rd, Cheshire
$434,900
3 Beds ⋅ 2 Baths ⋅ 24210481 MLS
Welcome to this beautifully maintained 3-bedroom, 2-full-bath raised ranch tucked away on a quiet cul-de-sac, conveniently located near Mixville Recreation Area, Route 84, and area restaurants. The main level features HW floors throughout, recessed lighting, and a spacious living room with built-ins, ceiling fan, wood shutters, and a wall-mounted A/C unit replaced in 2026. The living room flows seamlessly into the dining area, where a slider leads to the deck overlooking the private backyard. The inviting eat-in kitchen features hardwood floors, stainless steel appliances, range hood, and ample cabinetry. The primary bedroom offers HW floors, recessed lighting, and ceiling fan, with convenient access to the Jack-and-Jill full bath. Two additional bedrooms feature hardwood floors, with one offering a ceiling fan. A pull-down attic provides additional storage. The finished lower level adds valuable living space with a comfortable family room featuring recessed lighting, beautiful exposed beams, stucco-style walls and ceiling, and built-in cabinetry. A slider leads to the area beneath the deck and private backyard. The lower level also includes a second full bath with a unique stone-accented shower and a dedicated laundry closet. Most windows were replaced approximately 5-8 years ago, and the roof is approximately one year old. Public water and sewer. A wonderful opportunity to enjoy comfortable living, great outdoor space, and a convenient location! Sold in AS IS condition.

980 Notch Rd, Cheshire

190 Remus Rd, Cheshire
$525,000
4 Beds ⋅ 2 Baths ⋅ 24207733 MLS
A great opportunity to own this 4 Bedroom, 2 Bath Ranch in South Cheshire with a versatile open floor plan and one level living! A welcoming first impression can be felt as you enter the light and bright living room and continues into the Dining Area and Eat-in Kitchen with electric cooktop, built-in oven, pantry and stainless appliances. Conveniently off the Kitchen is the laundry/mud room with an entrance to the driveway for ease in carrying in groceries! A Family Room, with large picture window looking out to the yard, is the perfect spot for relaxing at the end of the day. A four season Sun Room, equipped with heat and A/C and statement skylight, provides access to the deck and yard making this the ideal spot for entertaining! Separate from the other bedrooms is the Primary Bedroom with attached full bath with walk-in shower. The additional 3 bedrooms and full Bath are located just down the hall. A walk up attic is positioned for future ease of expansion to the home. Full, unfished walk-out basement leads to a large shed area and the spacious, level back yard. Solar panels, central air, new roof, freshly painted throughout, updated baths, gutter guards, newer windows. Convenient to shopping, restaurants and highways. Don't miss your chance to make this spacious Ranch Style home your own!

190 Remus Rd, 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

233 Forest Ln, Cheshire
$319,900
3 Beds ⋅ 2 Baths ⋅ 24208227 MLS
There's a lot to work with at 233 Forest Lane wether you're an investor or future owner occupant. This three-bedroom, one-and-a-half-bath ranch offers a practical single-level layout, hardwood floors, and the kind of footprint that gives its next owner plenty of options. The home has been well lived in and is ready for someone with a fresh vision to make it their own. Downstairs, the basement provides even more opportunity, with space that could potentially be finished into an additional living area, home office, gym, or playroom. Outside, a sizeable yard gives you room to spread out, while the carport adds everyday convenience. There's public sewer available in the street for those who may want that option in the future. Whether you update a little at a time or have bigger plans from day one, there's real potential here to create something that feels entirely your own.

233 Forest Ln, Cheshire

122 Green Hill Ln, Cheshire
$439,900
3 Beds ⋅ 2 Baths ⋅ 24208667 MLS
Welcome to 122 Green Hill Lane, a beautifully updated 3-bedroom, 1.5-bath ranch offering 1,572 square feet of comfortable living space in desirable South Cheshire. Step inside to gleaming new hardwood floors throughout and an updated kitchen featuring stainless steel appliances. The spacious family room is a standout, with vaulted ceilings, a ceiling fan, and an impressive wood-burning stone fireplace. Step outside to the private rear deck, perfect for relaxing or entertaining. Additional features include thermopane replacement windows, ceiling fans in all three bedrooms, a covered front porch, and a one-car underneath garage. The expansive 1,056-square-foot unfinished basement offers tremendous potential for additional finished living space, potentially bringing the home to approximately 2,500 square feet. Situated on .42 acres with convenient access to Quinnipiac University, Sleeping Giant State Park, Yale University, shopping, dining, and major commuting routes. Move-in ready with room to grow!

122 Green Hill Ln, Cheshire

58 Old Towne Road Unit 58, Cheshire
$429,900
3 Beds ⋅ 3 Baths ⋅ 24207116 MLS ⋅ Old Towne BLDG.
Welcome to 58 Old Towne Rd. This rare 3 bedroom 3 bath unit is located in the highly sought after Old Towne Condos. It is an end unit in what some say is the best location in the complex. It sits adjacent to a wooded area with views of nature all around. There is ample parking directly in front of the unit along with its one car attached garage. The home has a first floor bedroom with bath. The kitchen has been remodeled and there is plenty of room in the eat in kitchen/dining room space. The living room has a wood burning fireplace and an elevated deck located off the rear for those comfortable nights. The upper level has two large bedrooms with a bath, giving this unit tons of space. The lower level has both a partial finished area as well as an unfinished area with laundry hook up and plenty of storage. There is also a walk out slider from the lower level giving you the ability to enjoy the wooded lot and quiet outdoor space. If that's not enough, there is a community pool. The complex is next to a local favorite coffee house, and is close to Rt 10 giving you access to the center of Cheshire. This well established complex is near all amenities and only a few miles from the new Shopping plazas just built in the wonderful town of Cheshire. Home of award winning schools, and a regular as one of the best places to live in Connecticut.

58 Old Towne Road Unit 58, Cheshire

80 Contour Dr, Cheshire
$449,900
3 Beds ⋅ 2 Baths ⋅ 24207039 MLS
Welcome to this beautifully maintained, freshly painted, move-in-ready home offering the perfect blend of one-level living, modern style, and convenience. This property features 3 bedrooms and 2 full bathrooms, highlighted by an open and inviting floor plan with gleaming hardwood floors throughout. Enjoy a beautifully updated kitchen (2016) featuring a functional breakfast bar that flows seamlessly into the main living spaces. For ultimate daily convenience, one of the main-level full bathrooms features a dedicated laundry setup. The attached oversized garage also offers excellent extra storage space. Step outside to your private, fully fenced backyard-the perfect secure space for outdoor entertaining, gardening, or pets Experience true peace of mind with extensive mechanical and structural upgrades completed in 2016, including a newer roof, durable siding, a high-efficiency HVAC system, updated plumbing, and a brand-new 200-amp electrical service panel. The home is connected to public water and public sewer. Ideally situated just minutes away from Cheshire's vibrant town center, premier parks, schools, local shopping, and a fantastic dining scene. This turnkey property is ready for its next owner. Please reach out directly to the owner for more information.

80 Contour Dr, Cheshire

98 Merwin Cir, Cheshire
$599,900
4 Beds ⋅ 3 Baths ⋅ 24205796 MLS
Enjoy spacious ranch living and beautiful outdoor surroundings at 98 Merwin Circle in South Cheshire! A welcoming front porch, lovely gardens, and professionally landscaped grounds create an inviting setting for this home, offering 1,848 square feet on the main level plus approximately 900 square feet of finished living space in the walkout lower level. The generous living room features a fireplace and slider to the large deck, while the large eat-in kitchen provides plenty of room for everyday meals and gatherings. Three main-floor bedrooms include a primary bedroom with its own full bath and two additional bedrooms served by a second full bath. Downstairs, the finished lower level offers a family room with a second fireplace, a large bedroom or office with exterior windows, and an additional full bath. Laundry is also in the finished lower level. An exceptionally spacious deck provides room for outdoor dining, entertaining, and relaxing while enjoying the gardens. Awnings shade the home's south-facing windows, and a two-car attached garage adds everyday convenience. Features include central air (2021) three-zone oil-fired baseboard heat (2008), Well water with a water softener, and City sewer. Windows, vinyl siding, and the roof were replaced in 2006, Comfortable main-floor living, flexible additional space, and beautiful grounds make this South Cheshire home a wonderful place to call your own!

98 Merwin Cir, 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

374 Moss Farms Rd, Cheshire
$384,900
3 Beds ⋅ 1 Baths ⋅ 24206787 MLS
Welcome to 374 Moss Farms Rd! This adorable ranch-style home is ready to begin its next chapter. Nestled in a desirable neighborhood on over an acre of land, this charming 3-bedroom, 1-bath home offers the perfect blend of character, comfort, and opportunity. Step inside to find a cozy living room featuring a fireplace and hardwood flooring, creating a warm and inviting space to relax and gather. One of the home's true highlights is the spacious 408-square-foot four-season porch-a wonderful spot to enjoy your morning coffee. The home also offers plenty of basement storage, providing room for all your seasonal items and more. Outside, enjoy the newer paver patio, perfect for entertaining or enjoying quiet evenings, along with a 2-car detached garage offering excellent parking and additional storage or workshop potential. Major updates offer added peace of mind, with the roof, furnace, and oil tank all less than 15 years old. With its generous lot, desirable location, cozy features, and plenty of potential to make it your own, this is an opportunity you won't want to miss. Located near Cheshires newly built schools. Easy access to shopping, library and local amenities. Subject to Probate Court Approval., Sold As-Is

374 Moss Farms Rd, Cheshire

401 Juniper Ln, Cheshire
$499,900
3 Beds ⋅ 2 Baths ⋅ 24206266 MLS
PRICE REDUCTION - Exceptional Value in Cheshire! Move right in and enjoy this completely refreshed ranch offering comfortable one-level living in a sought-after neighborhood setting. Recently reduced and ready for its next owner, this turnkey home combines modern updates with major improvements already completed. The interior features engineered hardwood flooring throughout the main living areas, creating a clean, modern feel. At the heart of the home is a fully remodeled kitchen with new cabinetry, countertops, stainless steel appliances and updated finishes. The kitchen opens to the dining and living areas, creating an easy flow for everyday living and entertaining, The spacious living room is warm and inviting with a wood-burning fireplace and abundant natural light. The dining area provides plenty of room for gatherings and convenient access to the rear patio and private yard.The bedroom wing includes three well-proportioned bedrooms, including a primary suite with its own private full bath, plus an additional remodeled full hall bath. A two-car garage, separate enclosed storage area and generous closet space provide excellent additional storage. Outside, the landscaped property offers attractive curb appeal and a private setting with plenty of space to relax, entertain or create your own backyard retreat. Newer major systems and exterior improvements, including the roof, siding, windows, heating and central air, provide added peace of mind. Conveniently located near park

401 Juniper Ln, Cheshire

110 Green Hill Ln, Cheshire
$429,900
5 Beds ⋅ 2 Baths ⋅ 24206251 MLS
Welcome to this spacious 5-bedroom Cape located in the desirable south end of Cheshire! Situated in the brand-new Norton School District, this home offers a convenient location within walking distance of the Farmington Canal Heritage Trail and close to parks, shopping, and the community pool. The main-level bathroom has been recently updated, while the full basement provides laundry, abundant storage, and utility space. The boiler and water heater were updated in 2020. Laminate flooring runs throughout the home over the original hardwood floors on first floor only, offering a practical and versatile living space. With two driveways, there is plenty of off-street parking for residents and guests. A great opportunity to own a well-located home with generous bedroom space and easy access to many of Cheshire's amenities.

110 Green Hill Ln, Cheshire

950 Peck Ln, Cheshire
$459,900
3 Beds ⋅ 1 Baths ⋅ 24199844 MLS
Move In ready! Home Sweet Home! Look No Further! Tired of hearing the same old thing? 950 Peck Lane is so amazing, you will stop your search here! Come see for yourself what this 3 bedroom 1 1/2 bath ranch style home offers and watch your wish list dwindle to nothing. Outstanding features include beautiful hardwood floors throughout, updated kitchen and baths, a 1 car attached garage, central air. Outside welcomes you to a deck and gorgeous, level backyard with direct access to Farmington Canal Rail Trail where morning walks or bike rides start or end your day. Siding, Septic Tank, Driveway, Roof, Well Water Tank have all been replaced since 2013. Whole house generator and security system are additional features a new homeowner will inherit. See complete list of upgrades with dates in attachments. This home is 100% ready for a new homeowner to enjoy for years to come.

950 Peck Ln, Cheshire

125 Wallingford Rd, Cheshire
$425,000
3 Beds ⋅ 2 Baths ⋅ 24205907 MLS
Welcome home to 125 Wallingford Road in Cheshire, CT! Loaded with curb appeal, this sweet home welcomes you with a wonderful wrap-around porch and fenced-in back yard. Built in 1900 and extensively renovated in 2009, this charming 3-bed, 2-bath home beautifully blends modern updates with the character of its era. Inside, natural light fills the main level, where red oak hardwood floors run throughout. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances, including a new fridge, and a butcher-block-topped island with seating, perfect for casual meals or working from home. Two dining areas offer flexibility for everyday living and entertaining. A convenient entry by the back door keeps things organized, while an office off the kitchen provides a dedicated workspace. There is a main level, beautifully updated full bath with tub/shower combination. Upstairs are three comfortable bedrooms with hardwood floors and another updated full bath. Major improvements include a new septic tank in 2022, a new roof and a solar installation in 2023. A new washer and dryer are in the basement where you will find plenty of storage; more storage is in the shed in the backyard.Centrally located within walking distance of downtown coffee shops, the library, Town Hall and Cheshire Academy, plus a short drive to The Shops at Stone Bridge and convenient access to the Farmington Canal Heritage Trail...Charm, updates and location make this home one not to miss!

125 Wallingford Rd, Cheshire

72 Willow St, Cheshire
$484,900
4 Beds ⋅ 2 Baths ⋅ 24203699 MLS
Amazing quality and custom workmanship throughout this colonial featuring Kitchen with coffered ceiling, Kraft-Maid hickory kitchen cabinets, granite counters, copper backsplash, tongue and groove ceilings & recessed lighting! Vaulted wood ceiling in family room with cultured stone propane fireplace & ceiling fan. Dining room has crown molding and open to kitchen. Formal living room with built in "reading nook" under stairs. First floor full bath has shower, built in radiator/towel warmer, with wood ceiling. First floor bedroom/den. 2nd floor has 3 very generous bedrooms, one with custom builtins & walk-in closet. The full bath with tub on 2nd floor features a tongue and grove ceiling. New oil tank and hot water heater. Close to Linear Trail and Ball & Socket Arts Place. 5-circuit generator hook-up.

72 Willow St, Cheshire

1338 Avon Blvd, Cheshire
$439,900
3 Beds ⋅ 2 Baths ⋅ 24199826 MLS
Welcome home to 1338 Avon Boulevard, a beautifully updated Cape Cod tucked on a private, tree-lined 0.4-acre lot in sought-after Cheshire. This 3-bedroom, 2-bath retreat blends classic New England charm with thoughtful modern upgrades throughout. Step inside to an open, light-filled living and dining area with gleaming hardwood floors and a statement chandelier, flowing into a chef-inspired kitchen featuring rich blue cabinetry, butcher block countertops, hexagon tile backsplash, and stainless steel appliances. The main level also offers a serene bedroom retreat with a spa-inspired bath: skylights flood the vaulted ceiling with natural light over a dual-vanity counter, matte black fixtures, a glass-enclosed multi-jet shower, and a freestanding soaking tub surrounded by lush greenery. Outside, enjoy your own private oasis. Mature trees and landscaping frame a stone patio built for entertaining, complete with a cozy fire pit seating area. The attached garage adds everyday convenience, while central air and forced-air heat keep you comfortable year-round. Set on a quiet, tree-lined street with easy access to shopping, dining, and commuter routes, this move-in-ready home won't last. Schedule your private showing today!

1338 Avon Blvd, Cheshire

225 Timber Ln, Cheshire
$529,900
2 Beds ⋅ 3 Baths ⋅ 24203640 MLS
Tucked well back from the road on 4.13 beautiful acres, this inviting Raised Ranch offers a peaceful, private setting surrounded by nature and lovely garden areas. The home features 1,234 sq. ft. on the main level plus an additional 576 sq. ft. of beautifully finished living space in the walk-out lower level. The light and bright main level features a beautifully updated kitchen with white cabinetry and center island, open to the dining area with sliders leading to a spacious deck with awning-the perfect spot to relax and enjoy the serene surroundings. A sun-filled living room, two bedrooms and two full baths complete this level. The generously sized primary bedroom features its own private full bath. The finished walk-out lower level offers additional flexible living space with built-ins, a half bath and laundry area-ideal for a family room, home office, gym or guest space. Set back among the woods with plenty of privacy and beautiful natural surroundings, this special property is a wonderful retreat for nature lovers while still offering the convenience of Cheshire living. Come see the beauty of what the town of Cheshire offers with its open space, Roaring Brook Falls, The Farmington Canal Heritage Trail, Parks & Outdoor Recreation. Offering several retail districts that feature a variety of shops and restaurants including Whole Foods, Starbucks, Barnes & Noble. Seller to find suitable housing.

225 Timber Ln, 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

445 Lincoln Dr, Cheshire
$455,000
3 Beds ⋅ 1 Baths ⋅ 24203408 MLS
Welcome to 445 Lincoln Drive in Cheshire! This beautifully remodeled home offers the perfect blend of modern updates and comfortable living. Step inside to discover a bright, inviting interior featuring a renovated kitchen with stylish finishes, an updated bathroom, and thoughtful improvements throughout. The finished lower level provides valuable additional living space-perfect for a family room, home office, gym, playroom, or guest area. Whether you're entertaining friends or enjoying a quiet evening at home, this move-in-ready property offers the flexibility and comfort today's buyers are looking for. Conveniently located near shopping, restaurants, parks, and major commuter routes, this is a wonderful opportunity to enjoy all that Cheshire has to offer.

445 Lincoln Dr, Cheshire

137 Harrison Rd, Cheshire
$449,900
3 Beds ⋅ 2 Baths ⋅ 24202606 MLS
Settle right into this thoughtfully maintained Cheshire Farmhouse Cape, where classic character, smart updates, and an unexpectedly flexible layout come together on a beautiful .81-acre lot. Hardwood floors and abundant natural light carry through the main level, highlighted by a fireplaced living room, dining area, and updated kitchen with stainless appliances, generous cabinetry, and breakfast-bar seating. A first-floor bedroom, full bath, and dedicated home office with closet create valuable flexibility for guests, work-from-home needs, or single-level living. Upstairs boasts two spacious bedrooms and a second full bath. Outside, the newer wraparound front porch adds standout curb appeal, while the expansive level yard, stone patio, garage, and shed offer room to entertain, garden, play, or simply enjoy the setting. Major updates include a new roof plus new boiler, water heater, and oil tank. Enjoy all that Cheshire has to offer, including award-winning schools, the new Whole Foods Market, Route 10 shopping and restaurants, the Farmington Canal Heritage Trail, Sleeping Giant State Park, and convenient access to I-691, I-84, and the Merritt Parkway.

137 Harrison Rd, 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

1251 S Main St, Cheshire
$575,000
4 Beds ⋅ 3 Baths ⋅ 24201800 MLS
Exceptional in-law potential with over 3,300 sq ft of finished interior space! Expansive and versatile home offering an ideal setup for extended living, along with numerous updates and amenities. Main level features a sun-filled living room with HW floors and large picture window, dining room with HW flooring and decorative chair rail. Very spacious eat-in kitchen features HW floors, island with cooktop, newer refrigerator and dishwasher, double oven, skylight, garden and Palladian-style window, recessed lighting, wine rack, and direct access to the deck. Primary bedroom offers hardwood flooring, a generous size closet, and private bath, plus two additional upper-level bedrooms. The sizeable lower level provides incredible flexibility with French doors leading to a sunroom/game room, pellet stove, skylights, bonus room with walk-in closet, den with brick wood-burning fireplace, bedroom, full bath, and laundry (newer washer + dryer). The separate in-law-style living area features a full kitchen, tile flooring, pellet stove, full bath, and convenient access to the two-car garage. Exterior highlights include a large, level lot, partially fenced backyard, patio, newer roof, gutters, and garage doors. Additional features include 200-amp electrical service, two pellet stoves, public water + public sewer. A unique opportunity offering space, flexibility, and exceptional potential for multigenerational living! Convenient to the new Norton Blue Ribbon School, shopping + restaurants.

1251 S Main St, 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. Hardwood flooring is throughout this condo. 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. Welcome home!!!

443 E Mitchell Ave Unit 443, Cheshire

25 Stacy Ct, Cheshire
$499,900
3 Beds ⋅ 2 Baths ⋅ 24198101 MLS
***Seller is asking for highest and best Due 12 pm on Tuesday August 18th. *** Welcome to 25 Stacy Court, a well-maintained raised ranch set on 0.92 acres in a desirable Cheshire cul-de-sac. Offered by the original owners after 55 years, this 1,905-square-foot home features three bedrooms, one full and one half baths, hardwood floors throughout the main level and plenty of indoor and outdoor living space. The living room has vaulted ceilings, a wood-burning fireplace and opens to the dining room, where a newer slider leads to the Trex deck. Three bedrooms and one full bath offering a tub, double-sink vanity and granite countertop complete the main level. Downstairs, the carpeted family room features a second wood-burning fireplace, along with a half bath, laundry area and access to the attached two-car with newer doors. Enjoy summer days around the in-ground vinyl pool with concrete surround and pool house. Additional features include a whole-house fan, gutter guards, paver side walk, and nicely landscaped yard. Valuable updates include the driveway in 2023, roof in 2014, pool liner and filter in 2016, chimney repairs and new chimney cap in 2024, boiler servicing in 2025 and a brand-new septic system in 2026. Private well, oil-fired baseboard heat and wooden shake siding. Convenient to Cheshire amenities and the new Barnum Elementary School. A wonderful opportunity to personalize a cherished one-owner home! Owner to find suitable housing.

25 Stacy Ct, Cheshire

722 Allen Ave, Cheshire
$599,000
3 Beds ⋅ 2 Baths ⋅ 24191300 MLS
***PRICE REDUCTION*** Need serious garage space? This property features a brand-new commercial-sized detached garage that's ideal for collectors, mechanics, contractors, landscapers, hobbyists, or anyone looking for exceptional storage or workspace. Welcome to 722 Allen Avenue, Cheshire! This beautifully updated 3-bedroom, 2-bath ranch is set on a level 1-acre lot with public water and public sewer and offers the perfect blend of comfort, flexibility, and exceptional space. The open floor plan features a spacious living room with hardwood floors and a fireplace, a dining room with hardwood flooring, and an updated kitchen that flows seamlessly into the main living areas. The primary suite offers a cathedral ceiling, private full bath, and convenient first-floor laundry. Two additional bedrooms and a full hall bath complete the home. Additional features include a family room with access to the attached 2-car garage, a walk-up attic, and an oversized screened-in porch overlooking the private backyard. The true standout feature is the brand-new commercial-sized detached garage with electric. With updated kitchen and baths, hardwood floors, one-level living, an oversized detached garage, and a desirable Cheshire location, this unique property offers endless possibilities - must-see!

722 Allen Ave, Cheshire

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.