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25 Stonegate Cir, Cheshire
$500,000
4 Beds ⋅ 2 Baths ⋅ 24163807 MLS
A rare opportunity to own the Reverend John Hull House at Stonegate, a 55+ community in Cheshire. This home was originally built in 1764 but was gutted and restored for today's living in 2005, still keeping all it's historic charm and features such as original wide plank flooring, exposed hand-hewn beams and 4 fireplaces (3 functioning w gas). The spacious Living Room w large gas FP creates a warm and inviting atmosphere. The updated Kitchen is equipped w granite counters, gas FP, island w seating and stainless appliances (newer dishwasher, gas range, microwave). The Dining Room is the perfect place for enjoying meals w an impressive stone FP (non functioning) for ambiance. Also on the main level of the home are the Primary Bedroom w attached full Bath and gas FP for added comfort and an additional Bedroom also w an attached full bath and WI closet. The second level of the home is an enchanting space w a mural leading up the staircase to two additional Bedrooms. The first Bedroom has WW carpet, paneling and a WI closet. The second spacious Bedroom has wide board flooring, ample storage space, built-ins and cozy window seats w beautiful windows. Well cared for home-new gas furnace & AC installed 4 y/o, hot water heater 2020, whole house generator, roof 2019, new Radon system, alarm system, new smoke & CO detectors, 2 car attached garage. Great location close to shopping and restaurants. Enjoy maintenance free condominium living in this prestigious active adult community.

25 Stonegate Cir, Cheshire

1486 Highland Ave Unit STE 7A, Cheshire
$500,000
2 Baths ⋅ 24151227 MLS ⋅ Highland Industrial Center BLDG.
Position your business for growth with this highly versatile 4,347 SF Class A office condominium. There is 3,155 SF of office space with 1,192 SF of warehouse space, complemented by an additional 1,113 SF of mezzanine, offering an ideal balance of premium office space and functional warehouse/storage. Located in Highland Industrial Park on the north end of Route 10, this centrally positioned Connecticut property delivers exceptional regional access and efficiency for a wide range of business uses. The office space was fully renovated in 2017, creating a true Class A environment, including: Updated kitchen, new HVAC system, carpeting and interior finishes. The layout is well suited for businesses looking to start, expand, or relocate, featuring 8-9 private offices and conference room(s), two bathrooms, mezzanine storage and ground level loading dock access-ideal for companies requiring light industrial, distribution or storage capabilities alongside professional administrative space. With immediate access to I-84 and Route 691 and convenient connectivity to I-91, the property allows for efficient travel throughout Connecticut and beyond, making it an excellent choice for companies serving multiple markets and managing logistics.

1486 Highland Ave Unit STE 7A, Cheshire

1124 Pamela Ln, Cheshire
$495,000
3 Beds ⋅ 3 Baths ⋅ 24200371 MLS
Beautifully updated, move-in-ready ranch tucked away on a quiet cul-de-sac in desirable Cheshire! Offering 3 bedrooms and 2.5 bathrooms, this home combines modern updates and comfortable single-level living in a perfect location. Refinished hardwood floors lead to a spacious living room with a cozy fireplace and an inviting dining room with direct access to the oversized deck. The updated kitchen showcases white shaker soft-close cabinetry, quartz countertops, a tiled backsplash, and brand-new stainless steel appliances. Down the hall, you'll find two generously sized bedrooms and a full bathroom, along with a private primary suite featuring double closets and its own beautifully updated full bathroom. The fully finished lower level provides even more living space, featuring luxury vinyl flooring, a large open area ideal for a family room, a half bathroom with modern finishes, and a versatile bonus room that could serve as a 4th bedroom, home office, gym, or guest space. The lower level also offers abundant storage and convenient walkout access to the backyard. Outside, enjoy the privacy of the backyard from the oversized deck-perfect for entertaining, relaxing, or enjoying your morning coffee. With modern finishes throughout, ample storage, flexible living space, and a peaceful cul-de-sac setting, this home truly has it all. Move-in ready and waiting for its next owner-schedule your showing today!

1124 Pamela Ln, Cheshire

1090 Notch Rd, Cheshire
$490,000
3 Beds ⋅ 2 Baths ⋅ 24184249 MLS
HIGHEST AND BEST BY SUNDAY 5PM. The home is located on the cul-de-sac side of Notch Rd, sitting in an established neighborhood. The house is on a flat lot with plenty of yard space and continues to a wooded area in the back yard. Plenty of sunlight comes through the thermo pane windows.The house boast hardwood floors on the main level and tile flooring in the great room located in the basement. Each bedroom is spacious and the primary has an attached full bath. A second full bath is on the main level adjacent to the other bedrooms with easy access to the living area. The large living room has a working wood stove to keep the house cozy on those chilly winter days. A dining room adjoins the living room and kitchen. The dining room has a slider to the rear deck. The kitchen boast an island and plenty of cabinets. a ceiling fan keeps the kitchen cool as well. A partially finished basement with a fireplace creates much added space for an extra room. It also has a large closet. A mechanical room is off the lower level room with a recently serviced boiler and brand new oil tank. The other room off the lower room hosts the laundry and a workshop area and storage space. 200 amp service is another upgrade as is the brand new roof. A large garage has plenty of room for vehicles as well as storage. This house brings great value for its features and its price. The sellers prefer an AS-IS sal

1090 Notch Rd, Cheshire

424 Cedar Ln, Cheshire
$485,000
4 Beds ⋅ 3 Baths ⋅ 24183374 MLS
Present owner has done many updates during the time they lived here. New roof (2025), New furnace(2026), New AC Compressor(2023), New Flooring (2021), New Propane tanks(2023), Upgraded baths(2021), New granite in kitchen(2022). Still time for new buyer to make it your own with cosmetics to your liking! Step outside into your own private resort, designed entirely around warm-weather enjoyment. The main event is a sparkling inground pool complete with a pool slide, ready for sunny afternoons and lively weekend gatherings. You can host barbecues on the raised Trex deck overlooking the water or stroll along the charming brick walkways. Rain or shine, the party keeps going in the massive 400-square-foot 3-season porch that wraps around the rear of the home, creating the perfect spot for shaded lounging, outdoor dining, or a poolside cocktail lounge. Inside, the floor plan flows naturally from everyday living to hosting a crowd. Guests are greeted by a large, welcoming living room anchored by a cozy double-sided fireplace that sets a warm tone the moment you step through the front door. The eat-in kitchen leads seamlessly into the den, making it easy to prep food while staying connected to the action, and connects directly to a separate laundry room and convenient half-bath positioned perfectly for quick access from the pool area. With four spacious bedrooms and 2.5 baths, including a private primary suite, there is plenty of room for family and overnight guests alike.

424 Cedar Ln, Cheshire

39 Green Hill Ln, Cheshire
$484,000
3 Beds ⋅ 2 Baths ⋅ 24171596 MLS
Welcome home to this beautifully updated 3-bedroom ranch in the highly desirable town of Cheshire. This move-in ready property combines modern comfort with classic charm in a peaceful neighborhood setting. Step inside to find a bright, open layout featuring gleaming hardwood floors, an updated eat-in kitchen with sleek countertops and stainless-steel appliances, and a spacious living room perfect for entertaining or relaxing. Each bedroom offers generous closet space and natural light, while the updated bathroom features tasteful finishes for a clean, contemporary feel. The finished lower level adds valuable living space - ideal for a family room, home office, or fitness area. Outside, the meticulously landscaped yard provides plenty of room for outdoor gatherings, gardening, or simply enjoying your surroundings. You'll also love the oversized shed, and the overall sense of privacy and pride of ownership throughout. A true turn-key home in one of Cheshire's most sought-after neighborhoods - combining small-town charm, top-rated schools, and easy access to local shops, parks, and highways.

39 Green Hill Ln, Cheshire

34 Pehr Ln, Cheshire
$480,000
3 Beds ⋅ 2 Baths ⋅ 24183210 MLS
Move-in ready ranch set on a private .80-acre cul-de-sac lot in Cheshire. This 3-bedroom, 2-bath home offers hardwood floors, central air, city water and sewer, and mature, low-maintenance landscaping - all for effortless everyday living. With nearly 1,500 square feet of finished interior space, another 500 of outdoor patio and deck, and thoughtful storage and built-ins throughout, this home lives larger than it looks. The living room features exposed beams and a fireplace with wood-burning insert, creating a warm and inviting gathering space. The updated kitchen has stainless steel appliances, abundant cabinetry, and easy access to outdoor living areas. The main bedroom offers a walk-in closet with custom-built storage. Two bedrooms and a full bath are located on the main level, while the finished lower level provides flexibility for a third bedroom, family room, office, or guest suite - complete with second full bath and laundry room.The fully fenced-in backyard is designed for entertaining and relaxing, featuring a spacious deck, brick patio, hot tub, and mature landscaping with room to garden, play, or simply enjoy the privacy. Surrounded by thoughtfully landscaped grounds, the outdoor space feels like a private retreat while remaining close to everyday conveniences. Updates: roof ('17), water heater ('23), wood-burning insert and liner ('23), hot tub ('21), and energy audit ('23). Minutes from schools, parks, shopping, restaurants, Cheshire town center, and I-84.

34 Pehr Ln, Cheshire

328 Patton Dr, Cheshire
$478,000
3 Beds ⋅ 2 Baths ⋅ 24183905 MLS
Nestled on a quiet no-through street, this exceptional custom-built Cape offers 3 bedrooms, 1.5 baths, and timeless craftsmanship throughout. Rich architectural details set this home apart, including wide-plank hardwood floors, hand-hewn ceiling beams, a striking floor-to-ceiling brick fireplace, custom built-ins, Dutch door, elegant wainscoting, and spacious walk-in closets. Large windows throughout the home invite an abundance of natural light, creating a warm and welcoming atmosphere. Updated mechanicals, including the furnace, hot water heater and central air conditioning, provide modern comfort and peace of mind. Step outside to a private backyard retreat surrounded by mature landscaping, established gardens, and beautiful natural surroundings. Enjoy exceptional privacy while taking in the sights and sounds of local wildlife from the thoughtfully placed birdhouses. Relax and unwind under your naturally shaded pergola. The expansive grounds offer plenty of room for a future pool, with electrical service already in place. A versatile outbuilding provides endless possibilities for a home office, studio, workshop, fitness area, hobby space, or additional storage. Offering a rare combination of character, privacy, and flexibility, this one-of-a-kind property presents an outstanding opportunity to enjoy peaceful living while still being convenient to everyday amenities. A truly special home ready for its next chapter.

328 Patton Dr, Cheshire

479 Blacks Rd, 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

840 Westside Rd, Cheshire
$475,000
3 Beds ⋅ 1 Baths ⋅ 24163158 MLS
Inquire immediately-ask your agent to secure this one before it's gone. Welcome to 840 Westside Road in Cheshire, a beautifully updated and meticulously cared-for home set on a prime lot in one of the area's more desirable neighborhoods. From the moment you arrive, you'll notice the curb appeal and thoughtful landscaping. Inside, the home features a stylish NEW kitchen opening seamlessly to the dining area and family room that brings in great natural light. The bathroom has been tastefully updated with contemporary finishes, and the layout offers a comfortable flow for everyday living and entertaining. Step outside to your own manicured backyard retreat with a private patio and plenty of room for gatherings. Whether you're sipping morning coffee or hosting friends on a summer night, this yard delivers. The home has been lovingly maintained with updates throughout, offering a turnkey opportunity in a location that's close to everything: parks, schools, shops, and more. The seller is ready for their next chapter. Don't miss your chance to turn this turnkey property into your forever home-opportunities like this don't come around often!

840 Westside Rd, Cheshire

1185 Highview Ter, Cheshire
$470,000
3 Beds ⋅ 3 Baths ⋅ 24195608 MLS
Come see this versatile split level home offering 3 bedrooms, 2.5 baths, an oversized 2 car garage, and a finished walkout lower level with endless possibilities. The flexible layout makes it ideal for a potential in law setup, home office, recreation room, or guest space. The lower level features laminate flooring, a half bath with laundry, and sliders to the backyard. The main level offers an updated kitchen with granite countertops and a door leading to the deck, perfect for entertaining. The separate living and dining rooms feature beautiful hardwood floors. Upstairs you'll find a spacious primary bedroom with a full bath, two additional generously sized bedrooms, all with hardwood floors, and an updated full guest bath. Additional features include central air, ceiling fans, two attic storage areas, newer driveway (2025), well pump and tank (2025), vinyl siding, newer windows (2010), roof (approx 10 yrs old) and furnace (2010). Enjoy everything Cheshire has to offer, including Roaring Brook Falls, the Farmington Canal Heritage Trail, parks, and open space and Blue Ribbon Schools. Conveniently located near The Shops at Stone Bridge, Whole Foods, Costco, Starbucks, restaurants, and major highways including I-691 and I-84 for an easy commute. This home offers space, flexibility, and a fantastic location. Property being sold "as it."

1185 Highview Ter, Cheshire

80 Contour Dr, Cheshire
$469,500
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

20 Watch Hill Rd, Cheshire
$466,000
4 Beds ⋅ 3 Baths ⋅ 24178385 MLS
Much-loved home for over 40 years. But it's time to move on. This 4 bedroom 2.5 bath colonial is located in a neighborhood of more expensive homes. Kitchen includes a stainless steel gas range with double ovens, Stainless refrigerator and wood top island. The bright sunroom entered from the kitchen and family room is heated by passive solar. The bedrooms are spacious with hardwood flooring. The home has been priced, taking into consideration any deferred updating that is needed, while you live in the home. Except for the bow windows in front, the windows have been replaced. When the home was built the builder installed a sump hole for potential future pump if ever needed. It has never been needed. The fireplace in the family room was never used. The central air compressor is older but works. There is also a whole house attic fan and attic storage in both the house and above the garage. At one time the owner was going to move the guest bath and laundry to a planned addition by using the right side garage bay. The 2nd bay was completed on the left hand side but the interior addition was not completed. The concrete flooring in the garage where disturbed, was not re-done. The lot is a beautiful level acre of land. Seller prefers an 'as is' purchase. This is not a distressed property.ALL OFFERS MUST BE RECEIVED BY 5 pm. Saturday, May 30, 2026

20 Watch Hill Rd, Cheshire

7 Bayberry Rd, Cheshire
$462,000
3 Beds ⋅ 2 Baths ⋅ 24163085 MLS
**MULTIPLE OFFERS - HIGHEST & BEST BY TUES 4/7 @ 10AM** Welcome to this well-maintained 3-bedroom, 1.5-bath home set on a level lot surrounded by mature trees in desirable Cheshire. Inside, you'll find hardwood floors throughout and freshly painted interiors that create a bright, move-in ready feel. The main living spaces offer a comfortable flow, while the partially finished basement provides additional flexible space for a home office, playroom, or gym, along with a cedar closet for added storage. Enjoy outdoor living on the deck overlooking the flat backyard, ideal for relaxing or entertaining. The property features an under house garage with a 200amp electrical service including generator hookup. Additional features include central air and a hardwired security system for year-round comfort and peace of mind. Convenient access to restaurants, stores and schools. The perfect blend of comfort, convenience & value. Come see what makes this house feel like home!

7 Bayberry Rd, Cheshire

1244 Long Hill Rd, Cheshire
$457,000
3 Beds ⋅ 2 Baths ⋅ 24162959 MLS
Welcome to 1244 Long Hill Road, where comfort, style, and functionality come together seamlessly. This charming 3-bedroom residence offers an inviting, floor plan complemented by thoughtful updates throughout. Step inside to a spacious living and dining area, perfect for both entertaining and everyday living. The kitchen features updated appliances and sleek granite countertops, providing a modern and functional space for cooking and gathering. The fully renovated main level bathroom adds a fresh, contemporary touch. The lower level offers additional heated space with endless potential, ideal for future finishing, a home office or recreation area, along with extra storage and a convenient half bathroom. Enjoy the warmer months on the Trex deck overlooking a private, beautifully landscaped yard lined with perennial plantings. Additional highlights include an attached one car garage, low maintenance vinyl siding, and updated doors and windows. Ideally located near shopping, dining, and just minutes from Route 10, I-84, and the Merritt Parkway. Don't miss your opportunity. Schedule your private showing today!

1244 Long Hill Rd, Cheshire

1757 Musso View Ave, Cheshire
$455,000
4 Beds ⋅ 4 Baths ⋅ 24181266 MLS
Searching for a 4-bed home in Cheshire, CT, with flexible living space and room for extended family? This versatile 4-bedroom, 3.5-bath home offers 1,928 square feet of living space on a .46-acre lot. It features a legal in-law apartment with its own private entrance and separate driveway, making it ideal for multigenerational living, guests, or added privacy. (The in-law apartment contains 1 bed and bathroom out of the total count.) The home combines classic charm with practical updates, including a 1yr old heating system. public sewer and a private well. The finished basement contains an additional 700 sq ft of space with its own entrance from the garage. Outside, beautifully gardens create a peaceful setting, the spacious lot provides room for entertaining, gardening, recreation, or simply enjoying the outdoors. The separate driveway for the legal in-law apartment adds a rare level of functionality and flexibility.Located in desirable Cheshire, this home is close to schools, parks, shopping, dining, and major commuter routes. Whether you're seeking space for a private guest suite, or a home office, this property offers comfort, convenience, and value in a sought-after location. Schedule your private showing today.

1757 Musso View Ave, Cheshire

54 Hemlock Rdg, Cheshire
$451,000
3 Beds ⋅ 2 Baths ⋅ 24182408 MLS
Great opportunity to experience the Cheshire lifestyle! I am an older three bedroom home with 1.5 baths and a two car garage on quiet cul-de-sac minutes from town center, schools, shopping, cultural events, restaurants, walking trails and more. I was built in 1955 and comfortably housed the same family since my initial construction. I am now waiting for new owners with a vision and creative mine to make me new and vibrant again! Over the years I've become a bit cluttered and dated but if you know value when you see it then I'm the home for you. I have lots of potential and most would describe me as a Diamond In The Ruff located in a great area ready to become a precious gem again!! I'm mechanically sound, a newer roof, sprinkler system. exterior has been recently painted. There is hardwood floors under my carpet.. I have a tired in-ground pool which was once the center of fun and entertainment. It is structurally sound but bottom needs sand resurfacing and new liner. Small areas of my brick walkway in rear and patio area are in process of being reset. If you see what I see, you'll love me, buy me and live happily ever after. I'm being offered at a very inviting price and I am anxious to meet my new owners. My neighbors are great and I'm in a great location close to the Canal Trail. Just waiting for my new owner(s) to make me feel refreshed, bright and a happy place again filled with laughter and love!! Stop by to see me! ***HIGHEST AND BEST - MONDAY June 15th 6 p.m*

54 Hemlock Rdg, Cheshire

960 Peck Ln, Cheshire
$451,000
3 Beds ⋅ 2 Baths ⋅ 24167821 MLS
Nestled in the charming town of Cheshire, this well maintained ranch-style home offers the perfect blend of comfort, character and convenience. The one level design features 3 bedrooms and 2 full baths with additional flexible space in the lower level. Step inside and feel at home immediately as the natural light beams throughout the updated kitchen that is open to a Great Room and overlooks a beautiful backyard. The inviting living room is highlighted by elegant arched doorways, a built in bookcase and cozy gas fireplace insert. The finished walk out lower level provides additional living space for a home office and rec room or in law potential with direct access to the backyard. Outside you will find a parklike setting complete with a charming gazebo and patio. A standout feature is the property's direct access to the scenic Farmington Canal Trail offering endless opportunities for walking, biking and enjoying nature . Did I mention the roof on the house , gazebo and shed were replaced in 2022? Additional information can be found in the attachments.

960 Peck Ln, Cheshire

137 Harrison Rd, Cheshire
$450,000
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

44 Roslyn Dr, Cheshire
$450,000
3 Beds ⋅ 2 Baths ⋅ 24186652 MLS
First time offered in 70 years! Impeccable pride of ownership shines throughout this spacious, well-maintained three-bedroom ranch. The main level living features a large, sun-filled living room that flows seamlessly into a gracious dining room. The eat-in kitchen boasts sliders leading to a newly installed composite deck-perfect for entertaining while overlooking the private backyard. The primary bedroom includes an en-suite full bath with a walk-in shower, complemented by two additional generously sized bedrooms and a central hall bath. Classic hardwood floors are preserved under the carpeting in the two rear bedrooms and hallway (and potentially the primary bedroom!).Downstairs, expand your living space in the finished recreation room complete with a dry bar, a fabulous workshop, and convenient access to the laundry area and one-car garage. Location is everything! You are just minutes away from local shopping and the scenic Farmington Canal Trail system. This home is being sold AS-IS, offering an incredible opportunity to bring your own personal touches to a rock-solid property. Newer Hot Water Heater and Roof was replaced in 2019!

44 Roslyn Dr, Cheshire

39 Winslow Rd, Cheshire
$450,000
3 Beds ⋅ 2 Baths ⋅ 24168914 MLS
Welcome to 39 Winslow Rd in Cheshire-a beautifully updated Cape set in one of the town's most desirable locations. This 3-bedroom, 2 full bath home blends charm, functionality, and modern updates in all the right ways. Step inside to a spacious foyer that doubles as a cozy sitting area, complete with a built-in coffee bar-perfect for starting or ending your day. The fully renovated kitchen features stainless steel appliances, ample cabinetry, and generous counter space, flowing seamlessly into a formal dining room with refinished hardwood floors. Across the way, the sun-filled living room showcases a stunning bay window that floods the space with natural light. The main level also offers a versatile bedroom and a beautifully remodeled full bath-ideal for guests or a private home office. Upstairs, you'll find two additional bedrooms along with a large family room anchored by a wood stove, creating the perfect setting for cozy winter nights. An additional office space in the rear adds even more flexibility. Outside, enjoy a professionally landscaped front yard bursting with seasonal color, while the backyard offers a peaceful natural setting overlooking a stream. Additional highlights include a partially finished basement, updated roof, vinyl siding, thermopane windows, and ceiling fans in every bedroom. Truly move-in ready-just unpack and enjoy.

39 Winslow Rd, Cheshire

38 Mountain Rd, Cheshire
$449,900
4 Beds ⋅ 2 Baths ⋅ 24161844 MLS
Nicely maintained 4-bedroom, 2 full bath split-level home offering 1,488 sq. ft. of living space plus an additional 216 sq. ft. in the finished lower level with walk-out access. This home features hardwood flooring and a bright, inviting living room with a large bow window and a cozy brick-faced raised hearth fireplace with wood-burning insert. The spacious kitchen offers white cabinetry, stainless steel appliances and a convenient breakfast bar, opening to a dining room with access to a covered three-season porch-perfect for relaxing or entertaining. The upper level includes four bedrooms and two full baths, including a primary bedroom with en suite bath, along with two large hall closets providing excellent storage. The finished lower level offers flexible living space ideal for a family room, playroom, home office, or gym, with direct access to the two-car garage and laundry area. Additional highlights include a newer roof (2024) and a versatile layout that suits today's lifestyle. A wonderful opportunity to own a move-in ready home with great space inside and out! Come see the beauty of what the town of Cheshire offers with it's 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. Easy commuting with I-91, I-84, I-691, and Rt 15 (The Merritt Parkway) 30 minutes to New Haven and Hartford. Seller to find suitable housing.

38 Mountain Rd, Cheshire

936 S Meriden Rd, Cheshire
$447,000
4 Beds ⋅ 3 Baths ⋅ 24174221 MLS
Welcome to 936 South Meriden Road - a classic Cheshire raised ranch that delivers the space, flexibility, and indoor-outdoor lifestyle today's buyers are looking for. The main level is made for living. A large family room anchors the space with a classic raised hearth fireplace, flowing seamlessly into a dining area with built-ins - perfect for everything from casual nights in to hosting a crowd. The bright kitchen leads out to a two-tiered deck overlooking just over an acre of private yard. Mornings with coffee out here? Yes, please. The upper level offers a primary ensuite bedroom plus two additional bedrooms and a full bath - giving everyone their own space to decompress. The lower level is where this home really sets itself apart. Whether you need a multi-generational setup, a guest suite, or a dedicated home office - the versatility delivers with a fourth bedroom, half bath, kitchen area, living room, and a flex room perfect for a home office or den. Laundry, a workshop, and storage round it all out - with an attached two-car garage. Four bedrooms, two and a half baths, over an acre of privacy, and room to grow in every direction - and when you're ready to venture out, everything Cheshire has to offer is right at your fingertips. Restaurants, shopping, and local favorites are just minutes away, with charming farm stands just up the street. 936 South Meriden Road is the one you've been waiting for.

936 S Meriden Rd, Cheshire

39 Fernwood Ln, Cheshire
$445,000
3 Beds ⋅ 2 Baths ⋅ 24163245 MLS
**Best and final requested by Wednesday, May 20 at 8pm.** Nestled on a quiet cul-de-sac in desirable South Cheshire, 39 Fernwood Lane offers exceptional privacy and seclusion on over 2 acres of picturesque property. Surrounded by mature trees and a natural landscape, the expansive yard creates a peaceful retreat with endless possibilities for outdoor living, entertaining, gardening, recreation, or simply enjoying the beauty and tranquility of your own private setting. This charming ranch-style home features 3 bedrooms, 2 full baths, and approximately 1,610 sq ft of comfortable living space with hardwood floors, a spacious living room with a fireplace, and an inviting eat-in kitchen. The unfinished basement offers additional flexibility for a gym, or recreational room or storage. A detached 2-car garage, deck, and expansive outdoor setting complete the package. Enjoy the tranquility of a secluded setting while still being conveniently close to local schools, shopping, dining, and commuter routes. Whether you're looking for a serene escape, room to expand, or the perfect property to enjoy nature and privacy this unique property delivers endless possibilities in one of Cheshires most sought after locations. Recent upgrades include new deck and porch railings (2026), a fireplace chimney rebuff (2025), and energy efficient windows and doors.

39 Fernwood Ln, Cheshire

767 Ives Row, Cheshire
$445,000
3 Beds ⋅ 2 Baths ⋅ 24165723 MLS
HIGHEST AND BEST 4/12 7PM Welcome to this beautifully maintained 3-bedroom, 1.5-bath ranch nestled in one of Cheshire's most desirable neighborhoods-where comfort, functionality, and location come together effortlessly. From the moment you arrive, you'll appreciate the inviting curb appeal and pride of ownership throughout. Step inside to discover gleaming hardwood floors, with additional hardwood hidden beneath select carpeted areas-offering the opportunity to further enhance the home's natural beauty. The sun-filled living room features a stunning bay window that fills the space with natural light, along with a convenient coat closet. It flows seamlessly into the dining area, complete with a charming built-in hutch. Sliding glass doors lead to a spacious deck overlooking a private, level backyard-ideal for entertaining, relaxing, or enjoying peaceful outdoor moments. The adjacent kitchen offers ample space for cooking and meal preparation, abundant cabinetry, and a pantry for extra storage, along with direct access to the attached two-car garage.The main level includes three comfortable bedrooms, including a primary suite with a walk-in closet and a private half bath. A full bathroom serves the additional bedrooms, providing a practical and well-designed layout. The lower level adds valuable living space with a partially finished area-perfect for a recreation room, home office, or gym-along with a dedicated laundry room and exceptional stora

767 Ives Row, Cheshire

611 Ives Row, Cheshire
$441,500
3 Beds ⋅ 2 Baths ⋅ 24168897 MLS
Act Fast... This Rare Gem Won't Last! Tucked away in the peaceful and highly sought-after section of Cheshire, this home located at the end of the cule-de-sac and offers the perfect blend of serenity and convenience, just minutes from the vibrant town center and all local amenities. This home offers Solar to reduce your electric costs and is your chance to own a property with incredible potential! Whether you're downsizing, right-sizing, or just starting out, this home is the perfect canvas waiting for your vision. Bursting with character and nestled in a lovely neighborhood, it's the ideal place to create your dream space. The motivated seller is ready and has priced this home to sell quickly. Don't wait... opportunities like this are rare. Contact your agent and schedule a showing today! This property is sold as-is where-is.

611 Ives Row, Cheshire

261 Winthrop Dr, Cheshire
$440,000
3 Beds ⋅ 2 Baths ⋅ 24161568 MLS
Beautifully maintained and fully updated 3-bedroom, 2 full bath ranch located in Cheshire. This move-in ready home features laminate flooring throughout the main level, with cathedral ceilings and an open-concept layout that allows for abundance of natural light. The eat-in kitchen is equipped with quartz countertops, stainless steel appliances, and a center island that provides additional prep space and seating-ideal for entertaining. A slider off the kitchen leads to a private, spacious backyard. The inviting family room showcases a cozy stone fireplace, creating a warm and welcoming atmosphere. The primary bedroom includes a private full bath, while two additional bedrooms offer flexibility, with one ideal for a nursery or home office. Laundry is conveniently located on the main level. The lower level offers great potential for future finishing to suit your needs .It is partially sheet rocked and heated. Additional updates include a new roof (2024), most windows have been replaced, with the exception of the living room picture window. Come see and make this your home. City water, City sewer.

261 Winthrop Dr, Cheshire

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