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644 S Brooksvale Rd, Cheshire
$1,630,000
5 Beds ⋅ 5 Baths ⋅ 24207257 MLS
Nestled on 2.26 beautifully landscaped acres and set well back from the road, this exceptional contemporary Colonial offers a rare blend of privacy, elegance, craftsmanship, and resort-style living. With more than 6,300 square feet of above-grade living space and views of Cheshire Land Trust property, the home enjoys a peaceful natural setting while delivering an extraordinary collection of indoor and outdoor amenities. Natural light fills the home from every angle, beginning in the dramatic two-story foyer, where soaring floor-to-ceiling windows, a striking brick accent walls, elegant chandelier, and pellet stove create a grand first impression. The expansive first level features radiant floor heating and remarkable flexibility, offering a spacious family room, private office, full bath, and an impressive 43' x 15' room with endless possibilities. Walkout access leads to a covered deck and the private grounds beyond, making this level ideal for entertaining, a fitness studio, guest accommodations, an in-law suite, or multi-generational living. Upstairs, the main living spaces are both sophisticated and inviting. The gourmet kitchen showcases rich custom cherry cabinetry, granite countertops, custom stainless steel appliances, a center island, and a sun-drenched breakfast area overlooking the surrounding landscape. Formal living and dining rooms provide elegant entertaining spaces, while the vaulted Great Room with pellet stove serves as a warm and welcoming gathering place.

644 S Brooksvale Rd, Cheshire

16 Mountaincrest Dr, Cheshire
$1,590,000
5 Beds ⋅ 5 Baths ⋅ 24207532 MLS
Perched high above the landscape of South Cheshire, this extraordinary custom-built Colonial is a residence of uncommon beauty, privacy, and scale. Set against the natural backdrop of Bethany Mountain and surrounded by meticulously maintained, park-like grounds, this exceptional 4/5-bedroom home captures magnificent views, abundant sunshine, and a remarkable sense of tranquility. From the moment you arrive, there is an unmistakable feeling that this is something special. Thoughtfully designed and impeccably cared for, the home combines the timeless elegance of classic Colonial architecture with the openness and amenities expected of today's finest residences. Inside, soaring ceilings, gleaming hardwood floors, and an inviting open floor plan create an effortless connection between the home's gracious living spaces. At its center is a beautifully appointed gourmet kitchen, equally impressive as a gathering place for family and friends or as the culinary heart of sophisticated entertaining. The main level continues with an elegant formal living room, formal dining room, private library, laundry room, and oversized three-car garage, providing an exceptional balance of formal spaces, everyday comfort, and practical convenience.

16 Mountaincrest Dr, Cheshire

1 Mountaincrest Dr, Cheshire
$1,375,000
4 Beds ⋅ 5 Baths ⋅ 24206472 MLS
A timeless, flexible floor plan with all the newest upgrades. Majestically situated on a gentle hill in a South Cheshire neighborhood, this home is designed to capture the country setting.The impressive 4,000+ sqft contemporary colonial is move-in ready. The cook's delight kitchen features stainless steel appliances, a Sub-Zero refrigerator, a 5-burner gas stove with vented hood,Two full size microwaves, Fisher Paykel drawer dishwasher and an expansive granite island w/seating for 5 & opening into the spacious living room with gas fireplace, wet bar and built-in sound system. The familyroom has french doors opening on to an expansive deck & screened gazebo. The private main floor study comes complete with custom built-ins, hardwood floors and glass french doors, this extra first floor room can serve as a multipurpose area as well. A large mudroom with built-ins and a separate laundry room add everyday function. All-new stunning baths and hardwood floors throughout add polish. Upstairs, your private primary retreat awaits, a cozy sitting nook plus spacious marble bath with soaking tub, glass shower, oversized vanity & expansive separate closets. There is a princess bedroom with private marble bath. As well as, a Jack-n-Jill layout bedrooms and bath. Flexible living space on the walk-out lower level ideal for recreation,media, guestroom, gym or just to relax in nature with a wonderful outdoor hot tub. In addition to the 3 car garage there is an EV hook-up!

1 Mountaincrest Dr, Cheshire

885 S Brooksvale Rd, Cheshire
$1,279,000
5 Beds ⋅ 5 Baths ⋅ 24202325 MLS
Discover this truly exceptional custom Colonial home, distinguished by its thoughtful design, custom millwork, architectural details, and masterful craftsmanship both inside and out, situated on a desirable 2.37 acres corner lot in one of South Cheshire's most sought-after areas. Custom wrought iron gates welcome you into this warm, inviting home, flooded with natural light from the abundant large windows, skylights, and French doors. The heart of the home is the beautifully remodeled kitchen, with its expansive center island offering both exceptional functionality and a wonderful gathering space. The kitchen flows into the spacious family room which provides easy access to the covered porch, allowing effortless, comfortable daily living and entertaining. The first-floor primary bedroom provides convenience and privacy, while three large bedrooms upstairs offer generous space for all. Enjoy year-round sunshine in both the four-season terrace room and the separate sunroom, which bring the outdoors in. A versatile finished space with a full bath above the garage offers possibilities for home offices, a studio, a recreation room, and more. The exceptional outdoor setting offers a resort-like experience; the covered rear porch featuring a raised cedar ceiling, skylights, and terracotta tile, provides an inviting gathering space. Follow the path through the gardens to the heated in-ground Gunite swimming pool and hot tub, creating your own retreat for relaxation and entertaining!

885 S Brooksvale Rd, Cheshire

140 Willow, Cheshire
$899,900
4 Beds ⋅ 3 Baths ⋅ 24157332 MLS
Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly connect the kitchen, dining, and living areas-ideal for both everyday living and entertaining. The spacious primary suite will feature a private en-suite bath and generous closet space. With ample room for customization, buyers will have the opportunity to personalize finishes and selections to truly make this home their own. Enjoy the serenity of a tucked away setting while still being close to everything this sought after area has to offer. Don't miss the chance to create your perfect home from the ground up! Agent/owner

140 Willow, Cheshire

6 Mt Sanford Rd, Cheshire
$850,000
4 Beds ⋅ 4 Baths ⋅ 24164583 MLS
A rare opportunity, back on the market! Don't miss this brand new farmhouse style contemporary Colonial in south Cheshire. A picturesque country setting close to shopping & easy highway access. Private backyard, protected from any future development. Ready for late October occupancy. This stunning home blends modern elegance with exceptional craftsmanship throughout. Soaring 9-ft ceilings, 1.5" thick engineered HW floors set the tone on the main level, anchored by a gas fireplace with slate surround & wood mantle. The gourmet kitchen features granite countertops, stainless steel appliances and a chimney-style hood perfect for everyday living & entertaining. Step outside to a private patio off the kitchen or a lovely farmer's porch ideal for relaxing. A office/mudroom completes the main floor. Upstairs a luxurious primary suite is joined by two additional bedrooms, which share a Jack-n-Jill bathroom, plus a private en-suite guest bathroom. A second floor laundry adds extra convenience. Potential additional space in basement, that could be easily finished for additional cost, with or without a bathroom. Offered again due to no fault of the sellers- previous buyers were unable to secure financing. An incredible value for brand new construction - schedule your showing today!

6 Mt Sanford Rd, Cheshire

256 Beacon Hill Dr, Cheshire
$839,900
4 Beds ⋅ 3 Baths ⋅ 24214742 MLS
This stunning home feels brand new, with extensive updates and impeccable attention to detail. Newly refinished HW floors, fresh paint including ceilings, newer roof and siding, and beautifully remodeled kitchen and baths make this home move-in ready. The custom kitchen features new cabinetry, quartzite countertops, stainless steel appliances, a center island, built-in desk area, spacious dining space, skylights that bring in morning sun, and one of the home's three fireplaces. The dining space of the kitchen showcases a vaulted cedar-lined ceiling, more skylights, and a beautiful copper fireplace. Just off the kitchen, the family room has a dramatic vaulted ceiling, palladium windows, built-in bookshelves, and another fireplace. The inviting living room offers a decorative fireplace, custom built-in bookcases, and French doors leading to a sun-filled all-season room with a propane stove. A convenient 1st floor laundry room adds everyday practicality. Upstairs, you'll find 4 updated bedrooms, including a spacious primary suite with a remodeled bath, along with a fully renovated guest bathroom. Outdoor living is equally impressive, featuring an expansive brick patio overlooking a lush lawn and established perennial gardens, creating the perfect setting for relaxing, entertaining, and enjoying the seasons. Located in Cheshire's desirable Beacon Hill neighborhood, this exceptional home offers timeless charm with modern updates in one of the town's most sought-after settings!

256 Beacon Hill Dr, Cheshire

400 Beacon Hill Dr, Cheshire
$824,900
5 Beds ⋅ 4 Baths ⋅ 24176902 MLS
Timeless Center Hall French Colonial featuring 5 Bedrooms and 3.5 Baths, gracefully set within a quiet neighborhood. This charming residence showcases exceptional curb appeal, highlighted by beautifully crafted stone walls and professionally designed landscaping that draw the eye to its stately brick facade and custom, functional shutters. Just beyond the inviting entryway, you'll find a light-filled Living Room featuring a wood-burning fireplace, crown molding and gleaming hardwood floors. The adjoining Dining Room is perfect for gatherings, complete with built-in cabinetry and a slider that opens to an expansive backyard deck, ideal for entertaining. At the heart of the home is a thoughtfully designed custom Kitchen-truly a chef's dream-featuring a Bertazzoni gas range, abundant quartz countertops, rich cherry cabinetry and elegant Italian tile flooring. An informal dining area and cozy sitting space create a warm, inviting atmosphere for everyday living. A private first-floor office, complete with built-in bookshelves and generous windows, provides an ideal setting for a home workspace. The spacious Primary Suite, conveniently located on the main level, offers ample closet space and a full en-suite Bath with a walk-in shower and water closet. An additional full bath, beautifully updated with marble finishes, completes the main level. Upstairs, you'll find four generously sized Bedrooms, along with a well-appointed Hall Bath featuring marble accents and double sinks.

400 Beacon Hill Dr, Cheshire

662 Coleman Rd, Cheshire
$775,000
4 Beds ⋅ 3 Baths ⋅ 24211310 MLS
Beautiful home set on almost 2 acres in a beautiful country setting, yet only 1.5 miles from the town center! Built from the foundation up in 2006, this home offers a brand new roof, new septic tank, 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 1250 plastic septic tank being installed (2026), new driveway (2025), newer well tank, newer washer and dryer, and an electric car charger in the garage. Welcome Home!

662 Coleman Rd, Cheshire

368 Charles Dr, Cheshire
$749,000
4 Beds ⋅ 3 Baths ⋅ 24208525 MLS
Welcome to this completely remodeled home w/ a private In-law apartment in a highly desirable Cheshire neighborhood! Set on a spacious 1-acre lot, this truly move-in-ready property has been extensively renovated from top to bottom. The main living level features 3 BR & 2 full BA, offering comfortable & inviting living spaces throughout. The newly renovated kitchen is the heart of the home, featuring brand-new appliances, perfect for everyday living & entertaining. All new flooring throughout! Step outside through the DR onto the new deck, the perfect setting for family gatherings. The professionally landscaped, level yard is enhanced by a charming stone wall, an irrigation system, & a brand-new patio. Brand-New Handicap-Accessible in-law apt, a wonderful addition to this home offers its own private entrance & is thoughtfully designed for comfortable, accessible living. The spacious layout includes BR, full BA, living room, beautiful eat-in kitchen & washer dryer hookups. This private suite offers convenience, & endless possibilities. The extensive list of improvements includes a new roof, new windows, multiple new split-units heating & cooling system, new hot water heater, brand-new septic system, & solar panels. This is a rare opportunity to own a meticulously renovated Cheshire home with an in-law apartment that is set on a picturesque acre of land in a sought-after location. Simply unpack, settle in, and enjoy everything this extraordinary property has to offer!

368 Charles Dr, Cheshire

21 Berkshire Ct, Cheshire
$725,000
4 Beds ⋅ 3 Baths ⋅ 24210753 MLS
Welcome to 21 Berkshire Court, a beautifully updated 4-bedroom, 2.5-bath Colonial offering 2,373 square feet of living space plus approximately 500 additional square feet in the beautifully finished lower level. Set on a manicured .59-acre lot, this impressive home features thoughtfully designed renovations, wonderful living spaces, and exceptional curb appeal. The heart of the home is the gorgeous expanded kitchen featuring a breakfast bar, abundant cabinetry, and custom built-ins, all opening seamlessly to the inviting family room with additional custom built-ins and French doors leading to the large deck. Just off the kitchen is a highly functional laundry area with additional cabinetry and a convenient coffee bar, along with access to the half bath and attached two-car garage. A formal dining room, spacious living room, and beautiful entryway complete the main level, which features hardwood flooring throughout. Upstairs, the primary suite offers a walk-in closet and beautifully appointed full bath with double sinks and a walk-in shower. Three additional bedrooms and a second full bath complete the upper level. The beautifully finished lower-level rec room is perfect for entertaining, a home gym, playroom, media room, or home office, while still offering plenty of storage. Outside, enjoy the beautifully manicured yard and large deck overlooking the private backyard. Conveniently located close to the center of town with easy access to parks, restaurants & shopping!!

21 Berkshire Ct, Cheshire

295 Towpath Ln, Cheshire
$725,000
4 Beds ⋅ 3 Baths ⋅ 24208080 MLS
This desirable home offers large spacious living spaces to accommodate many living needs. Love a family room with a fireplace? This room also has built in shelves. Always wanted a kitchen with glass door cabinets to display your beautiful treasured glassware? This kitchen has that and a lot of workspace, counter space for your kitchen machines, as well as a nice dining area overlooking a bright window to the outdoors. A very large formal living room that maybe you want to use as a home office. All hardwood flooring on first floor offers a warm environment and easy maintenance. A sunporch off the back of the house is a treasure. Hang out here and head out to the built in pool- perfect for large gatherings all summer. The second floor bedrooms boast nice ceiling fans and good size rooms that can fit the bill for your personal needs. Guest rooms, home office, art room, playrooms.. the opportunities are endless. The lower level offers even more space... gym anyone? and storage areas too. The home is nicely updated with a classic style and appeal. The rear yard in addition to the in ground pool has a fenced in yard that appeals to many for their furry friends and more. Irrigation system. You will want to call this "home".

295 Towpath Ln, Cheshire

35 Brookside Pl, Cheshire
$675,000
4 Beds ⋅ 3 Baths ⋅ 24215798 MLS
Welcome to 35 Brookside Place, a spacious and inviting four-bedroom Colonial offering comfortable living, thoughtful updates, and exceptional spaces for entertaining. Set on a beautifully landscaped property in Cheshire, this home combines classic New England charm with the features today's buyers appreciate. Step inside to discover a versatile floor plan with generous living areas, hardwood flooring, and abundant natural light. The welcoming living room features a beautiful bay window, while a separate den with a fireplace provides a cozy place to relax. The updated eat-in kitchen is the heart of the home. Sliding glass doors lead to one of the property's most distinctive features-a spectacular sunroom with soaring curved wood framing and expansive glass walls and ceiling. Filled with natural light and overlooking the backyard, this wonderful space is perfect for morning coffee, entertaining, or simply enjoying the changing seasons. Upstairs, four generously sized bedrooms provide comfortable accommodations, including a spacious primary bedroom with ample closet space and ensuite bathroom. Another full bathroom completes the second level, while a convenient half bath and laundry area are located on the main floor. The finished lower level adds additional square feet of flexible recreation space.

35 Brookside Pl, Cheshire

385 Sir Walter Dr, Cheshire
$649,900
3 Beds ⋅ 3 Baths ⋅ 24211153 MLS
Welcome to this immaculate Colonial nestled in a desirable neighborhood on a level, one-acre lot! This move-in-ready, 3-bedroom, 2.5-bath home offers numerous updates and exceptional living spaces with so much flexibility. The spacious and bright front to back living room features crown molding and fireplace while the formal dining room showcases classic shadow box trim. The custom renovated kitchen features abundant cabinetry, quartz countertops, tile backsplash, newer appliances, and a breakfast bar overlooking the family room which offers built-ins and a window seat. The spectacular sun drenched Great Room boasts a soaring ceiling punctuated with exposed beams, walls of windows, and a stone fireplace with pellet-stove insert that can heat the entire first floor. Upstairs, the expanded primary bedroom includes a fully updated bath and two custom California closets. Additional updates include a new roof, updated windows, and more! This home features fully paid-off solar panels that generate approximately 114% of the home's annual electricity usage, resulting in no electric bills over the past year, making electric heating even more desirable and are under warranty through 2048! Outside, enjoy the level yard with professional landscaping and newer composite deck-perfect for relaxing or entertaining. A wonderful blend of character, comfort, updates, energy efficiency and no electric bills, this home will check all the boxes!

385 Sir Walter Dr, Cheshire

70 Heritage Dr, Cheshire
$649,900
3 Beds ⋅ 3 Baths ⋅ 24208189 MLS
Welcome to 70 Heritage Drive, a beautifully maintained 3-bedroom, 2.5-bath home offering 2,080 sq. ft. of living space plus an additional 525 sq. ft. in the finished lower level. Set on .35 acres with wonderful curb appeal, this inviting home offers a spacious and versatile floor plan. The welcoming entry leads to a beautiful kitchen featuring granite countertops, stainless steel appliances, and an eat-in area with sliders to a large deck with awning-perfect for outdoor dining and entertaining. A formal dining room with bay window and formal living room, currently used as a home office, provide additional flexible living space. At the back of the home, the expanded family room is a standout, featuring a gas fireplace and a wall of windows that fills the room with natural light. A half bath completes the main level. Upstairs, the spacious primary bedroom features a beautifully updated private bath. Two additional bedrooms and a second full bath complete the upper level. The finished lower level adds approximately 525 sq. ft. of additional living space with a rec room, plus a laundry area and additional storage. Outside, enjoy the large deck, patio, irrigation system, and nicely maintained yard. Additional features include a 2-car garage, city water and sewer, a new roof (2026), Central Air on 2nd floor and a ductless split in Living Room & Family Room. Conveniently located just a short walk from in-town activities, this home combines space, comfort, and a great location

70 Heritage Dr, Cheshire

1100 Coleman Rd, Cheshire
$649,000
4 Beds ⋅ 3 Baths ⋅ 24205288 MLS
OWNER MOTIVATED! Great Opportunity. Beautiful setting. Come see! Welcome to 1100 Coleman Rd, a charming, timeless Colonial nestled on a peaceful, private 1.85-acre lot in the heart of Cheshire, CT. Built in 1957, this home combines classic architectural craftsmanship with 2,280 square feet of functional living space, highlighted by beautiful hardwood floors throughout. The main level features a formal living room anchored by a fireplace with a custom-built mantel, traditional dentil crown molding, built-in bookcases, and convenient wood storage. Host large gatherings in the formal dining room, or relax in the eat-in kitchen and family room combination, which features two beautiful bay windows, a main-floor powder room, and direct access to an expansive deck that spans nearly the entire back of the home. This massive outdoor living space flows effortlessly into a park-like backyard, creating an ideal setting for seamless indoor-outdoor entertaining, gardening, or quiet relaxation. The second floor hosts 4 spacious bedrooms and 2 full bathrooms, offering plenty of room for family, guests, or a dedicated home office. The lower level maximizes every square foot, starting with a convenient underhouse side-load garage that opens into a finished, generous laundry room. Down the hall past the utility room, you will find a versatile finished bonus room with its own cozy fireplace-perfect for a playroom, media room, or art studio.

1100 Coleman Rd, Cheshire

256 Nob Hill Rd, Cheshire
$599,900
3 Beds ⋅ 3 Baths ⋅ 24213120 MLS
Welcome to this spacious 2,280 sq ft Ranch in the desirable Nob Hill area! This inviting home offers steel beam construction, C/A, two-zone heating and beautiful views. The kitchen features granite countertops, tile floors, a breakfast bar, cooktop, stainless steel appliances and opens to the family room with HW floors and gas fireplace with an impressive brick wall. Enjoy the scenic views from the screened-in porch! The dining room features HW floors and wainscoting. The spacious living room offers a gas fireplace, built-ins, recessed lighting, and a large picture window overlooking the backyard, with potential for a home office. The primary bedroom boasts HW floors and an impressive 14 x 6 walk-in closet with shelving and recessed lighting. The primary bath features double-sink vanity with marble top. Two additional bedrooms feature HW floors. The updated main bath has double sinks. Additional highlights include a tiled foyer, large closet, mudroom with washer + dryer, updated half bath, and large pantry. The expansive walk-out lower level features a wood-burning fireplace and wet bar, perfect for recreation. Enjoy the fenced backyard and patios. Other features include: replacement windows, whole-house fan and pull-down attic. Updates include roof and chimney (2025), refrigerator and dishwasher (2024), washer and dryer (2023), and garage door and back entry door (2019). Public water and sewer in the street. A wonderful opportunity in a sought-after location!

256 Nob Hill Rd, Cheshire

531 Blacks Rd, Cheshire
$599,000
3 Beds ⋅ 4 Baths ⋅ 24209218 MLS
Welcome to 531 Blacks Road, a spacious and distinctive split-level home set on a beautiful, level 1.93 acre property. A broad front lawn creates a generous set back from the street, while the park-like backyard provides an exceptional amount of usable outdoor space. From the covered front porch, double-entry doors welcome you into a dramatic, light-filled two-story foyer with soaring windows and an open staircase, an impressive introduction to the home's multi-level layout. Hardwood floors and abundant windows enhance the main living areas and bedrooms. The kitchen, with side door access, features abundant cabinetry, Corian countertops, and a generously proportioned dining area with plenty of room for everyday dining and entertaining. The adjoining living room is anchored by a full-wall brick fireplace, while two sets of glass doors open to the screened porch and frame views of the grounds. Upstairs are three bedrooms, including a primary with a private full bath, along with a versatile flex room ideal for a den, home office or hobby space. The walkout lower-level family room includes a half bath and access to the backyard and two-car garage. Recent improvements include a new roof and new gutters. Cheshire is known for its well-regarded public schools, extensive walking trails, parks, and wide selection of shopping and dining destinations, including The Shops at Stone Bridge. This home offers easy access to recreation, everyday amenities, and major commuter routes.

531 Blacks Rd, Cheshire

178 Harrison Rd, Cheshire
$589,900
3 Beds ⋅ 2 Baths ⋅ 24213428 MLS
CHARMING CHESHIRE CAPE ON A NEAR-ACRE LOT - welcome to 178 Harrison Road, a well-loved three-bedroom, two-bath Cape Cod set on 0.97 lightly-wooded acres in a quiet, tree-lined neighborhood. The kitchen features granite counters, stainless appliances and timeless brick accents, flowing seamlessly to a sun-filled eat-in dining area with vaulted ceiling and walls of windows framing peaceful views of the private backyard. Multiple distinct living spaces give you room to spread out: a formal living room with tile-surround fireplace, a cozy family room with pellet stove, and a formal dining room with built-in cabinets. Hardwood flooring throughout the first-floor living areas. Three generous bedrooms including a main-floor primary, two full baths, and 2,054 square feet above grade, plus a built-out finished lower level ideal as a home gym, playroom, or office. Major capital improvements already addressed: 2024 ROOF, 2025 OWNED solar panels (no lease/loan to transfer), 2021 HVAC/Central Air, 2023 chimney liner, and underground irrigation. Oversized 2-car under-house garage offers abundant storage. Step outside to a versatile outdoor retreat with zones for every season - generous back deck, flagstone patio at the front entrance, dedicated children's play area with playscape, and plush lawn framed by stacked stone retaining walls and mature landscaping. Short distance to Cheshire schools, parks, and shopping. DONT MISS OUT!

178 Harrison Rd, Cheshire

42 Eastgate Dr, Cheshire
$579,900
4 Beds ⋅ 3 Baths ⋅ 24207101 MLS
Welcome to 42 Eastgate Drive, a spacious and well-cared-for 4 bedroom, 2-1/2 bath Colonial located in a desirable Cheshire neighborhood, just moments from Highland Elementary School. Offering 2,042 square feet of living space, this inviting home features a welcoming foyer, comfortable living room, formal dining room and a warm family room with fireplace and sliders leading to the screened porch. The eat-in kitchen features beautiful custom cherry cabinetry, granite countertops, a tile backsplash, hardwood flooring and generous pantry storage. Upstairs, the primary bedroom includes an updated private bath, while three additional bedrooms and a full hall bath provide plenty of space for family, guests or a home office. Hardwood flooring adds warmth and character throughout much of the home. The partially finished lower level offers additional flexible living space, a workshop, laundry and ample storage. Enjoy the screened porch overlooking a level backyard with established landscaping, colorful perennials and visiting birds throughout the seasons. Additional features include an attached two-car garage, vinyl siding, city water, city sewer, oil heat. Conveniently located near schools, shopping, restaurants and major highways. Come experience all that Cheshire offers, including the Farmington Canal Heritage Trail, Roaring Brook Falls, beautiful parks and open spaces, along with Whole Foods, Starbucks, Barnes & Noble and local shops and restaurants.

42 Eastgate Dr, Cheshire

450 Cardinal Ln, Cheshire
$579,900
4 Beds ⋅ 3 Baths ⋅ 24213826 MLS
Welcome to 450 Cardinal Lane! This well-maintained 4-bedroom, 2.5-bath Colonial offers 2,042 square feet of living space on a beautifully landscaped .46-acre lot in Cheshire. The spacious first floor features a large living room, formal dining room, and a beautifully remodeled kitchen with white cabinetry, stainless steel appliances, and a comfortable eat-in area. Just off the kitchen is the inviting family room with a fireplace, access to the attached two-car garage, and direct access to the backyard. You'll also appreciate the convenience of an updated half bath on the main level. Upstairs, you'll find a generously sized primary bedroom with direct access to the full hall bathroom, along with three additional bedrooms. Hardwood flooring throughout adds warmth and character to the home. The partially finished lower level offers plenty of storage space, laundry area and a second full bathroom that has not been used in many years. Step outside to enjoy the beautiful, oversized patio overlooking the private, nicely manicured backyard, perfect for outdoor entertaining, dining, or simply relaxing. Additional highlights include a two-car attached garage with new door openers, replacement windows (2017), a brand-new roof (2026), and a newer oil tank (2020). Conveniently located near Cheshire's shopping, restaurants, parks, and recreational amenities, this lovely home offers a wonderful combination of space, comfort, and location. Don't miss this opportunity to make it your own!

450 Cardinal Ln, 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

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

120 Hilltop Rd, Cheshire
$519,900
3 Beds ⋅ 2 Baths ⋅ 24215666 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath Ranch located in a quiet neighborhood in Cheshire's desirable south end! This inviting home offers a bright, open floor plan featuring hardwood floors, crown molding, and a spacious living and dining area. The updated kitchen boasts white cabinetry, granite countertops, and stainless steel appliances, while the comfortable family room features a cozy fireplace. The primary bedroom includes a beautifully updated ensuite bath. Additional highlights include custom closet built-ins and custom window shades throughout the home. A partially finished lower level provides flexible space for a home office, gym, or recreation room, along with laundry and access to the 2-car garage. Enjoy outdoor entertaining on the deck overlooking the level backyard. Conveniently located near schools, parks, shopping, restaurants, and major highways. Move-in ready and a must-see!

120 Hilltop Rd, Cheshire

268 Eastgate Dr, Cheshire
$499,999
3 Beds ⋅ 3 Baths ⋅ 24213257 MLS
Come and see this terrific home in an ideal central Cheshire location in a sidewalked neighborhood next to Highland Elementary. Enter this terrific home and be welcomed by gorgeous hardwood floors, an updated modern kitchen with doorway to large 16x20 rear deck, dining room and living room with fireplace. The primary bedroom has a half bath, 2 additional bedrooms and a full bathroom complete the 1st floor. The lower level features a light and bright recreation room with walk out to the back yard, a full bathroom with shower and laundry, an office/flex use room, and utility/storage area. The rear yard features a 13.5x21 covered paver patio for enjoying your summer afternoons in the shade. Home is wired for a generator (included), 200 amp upgraded electrical, central air conditioning, new garage door opener, and much more.

268 Eastgate Dr, 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

190 Remus Rd, Cheshire
$469,900
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

68 Pleasant Dr, Cheshire
$469,000
4 Beds ⋅ 3 Baths ⋅ 24214579 MLS
Welcome to 68 Pleasant Drive, where a potential in-law suite with its own private entrance offers flexibility for extended family or guests. Hardwood floors, a spacious floor plan, and a convenient Cheshire location create a wonderful place to call home. Sidewalks line the road, adding to the appeal of this walkable setting close to shopping and local restaurants. The large backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing in privacy. Enjoy space, versatility, and everyday convenience in an established neighborhood. Showings begin tomorrow! NOTE: the square footage reflected in the MLS is based on town assessor records. SELLER BELIEVES it may not accurately represent the home's actual living space. The property offers additional living area beyond what is recorded. Buyers and their agents are encouraged to independently verify total square footage.

68 Pleasant Dr, Cheshire

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