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$565,000
3 Beds 3 Baths 24140877 MLS
Welcome to this beautifully maintained home. The house features hardwood floors throughout along with well finished rooms with oak trim and molding. The entire interior has been freshly painted. The living space on the first floor is bright with a fireplace and the kitchen has tile floors, and an additional fireplace and room for an island or kitchen table. The first floor has a bedroom suite with sitting room and private bathroom. The second bedroom on the first floor features lots of closet space. Upstairs is a primary bedroom suite with a private bathroom and bonus room with vaulted ceilings and skylights. There is a large vaulted attached 2 car garage with a propane heater. Outside the house has nice curb appeal and a flat backyard with a shed and large deck with new decking. The house is move in ready to enjoy.

975 Wolf Hill Rd, Cheshire

$565,000
4 Beds 2 Baths 170624319 MLS
This home is a WOW!!! Immediately take in the open floor upon entering this ranch style sunny & spacious home. Not only a large living room with a fireplace and a big picture window, but also a huge family room with incredible light and 2 doors that lead onto a relaxing oversized patio, gardens and fenced yard. Just off the family room is the beautifully remodeled kitchen. The kitchen is a cooks dream with the abundance of white cabinets, large island, granite counters and a WALK IN pantry! There is a separate large dining area as well. Just down the hall are 4 great size bedrooms and 2 NEW fabulous remodeled baths. As if that is not enough…the lower level has a brand new incredible bonus room with tons of storage. The gorgeous yard is private and fenced in. Tons of upgrades including 50 year roof (2019) water heater(2023), repointed & relined chimney. Central air and a very low solar lease that will allow you to pay almost zero to an electric company. Garage & so much more! Seller can close soon but needs to remain in the home till July 1st. ALL OFFERS DUE BY 11 AM ON MONDAY 3-11-24

140 Chipman Dr, Cheshire

$565,000
4 Beds 3 Baths 24014311 MLS
MULTIPLE OFFERS, PLS SUBMIT HIGHEST & BEST OFFER BY 5/5/24, 9:00 PM Welcome to your New Home! Nestled in a quiet, no drive-through area on 1.81 acres of scenic woodlands in Cheshire, CT, this colonial home, built in 1987, features four generously sized bedrooms and three full baths. The main level begins w/ an entrance foyer and an eat-in kitchen, both adorned w/ durable ceramic tiles. The kitchen is well-appointed w/ dark cherry cabinets, granite countertops, stainless steel appliances, a peninsula, and an enormous eat-in area, making it perfect for family gatherings and entertaining. Adjacent is a formal living rm with a full-sized brick chimney & wood stove that adds charm and warmth to family and social gatherings. This level also includes a spacious dining rm and a family rm, both w/ oak hardwood flooring, as well as a separate laundry room. A cozy three-season room opens to a deck overlooking a mostly flat backyard framed by mature evergreens & a subtle slope, ideal for outdoor enjoyment & activities. The upper level houses the oversized primary bedroom suite, complete w/ 2 closets & an en-suite bath, plus three additional large bedrooms, all carpeted for comfort, & another full bathroom. A new flat driveway leads to a 2-car garage, which features a loft for additional storage & provides easy access to the home. The home also features a sizable basement, approximately 1200 sqft, which offers extra space for various needs and the potential for you to add your finishing

46 Belridge Rd, Cheshire

$560,000
4 Beds 3 Baths 24174238 MLS
Charming colonial located in a sought-after neighborhood in Cheshire. This 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and functionality. The eat-in kitchen features stainless steel appliances and flows into an inviting dining room that opens to the living room, with hardwood floors in both rooms creating a warm and welcoming atmosphere. Just off the kitchen is a spacious family room with a cozy wood stove and access to a wooden deck overlooking a beautiful private backyard with plenty of room for outdoor entertaining, gardening, or relaxing. Upstairs, you'll find four generously sized bedrooms and two full bathrooms, along with a whole house fan. The hall bath features an updated tub, while the remodeled primary bath includes a tiled stall shower. The full basement offers an abundance of storage and the opportunity to create additional living space in the future. Additional features include central air, gutter guards, city water, city sewer, and a portable generator connection located in the garage for added convenience and peace of mind. Conveniently located near schools, parks, shopping, and commuter routes, and the Farmington Linear Trail. This home is ready to welcome its next owners.

375 Sycamore Ln, Cheshire

$560,000
4 Beds 3 Baths 24152619 MLS
Classic Colonial * 0.92-acre private lot * 4 BR, 2.1 BA * 1,696 sf * Quartz kitchen * Hardwood floors throughout * Fireplace family room * French doors to patio * Roof 2022 * Thermopane windows * Electric baseboard heat * Split system * 2-car garage Set on a peaceful 0.92-acre setting in the Town of Cheshire, 346 Village Drive offers classic New England style with thoughtful updates. The remodeled kitchen features quartz countertops and opens to the inviting family room with a fireplace and French doors that lead to a spacious patio for easy indoor outdoor living. A formal dining room, expansive living room, and a convenient half bath complete the main level. Upstairs you will find four generously sized bedrooms and two full baths, including a remodeled primary bath, plus ceiling fans in the bedrooms. Recent improvements include a 2022 roof, 2021 hot water heater, freshly painted exterior in 2025, and thermopane windows throughout except the bay window. The home is served by well water and septic, offers electric baseboard heat on the first and second floors plus a first-floor split system that provides heating and air conditioning in the living room and dining room. Additional highlights include an attached two-car garage. Outside, enjoy the large patio and level backyard with established perennial gardens while appreciating the home's serene, private feel.

346 Village Dr, Cheshire

$560,000
3 Beds 3 Baths 24115230 MLS
Location-Peace and Tranquility is offered with this beautiful well maintained home located in a quiet neighborhood at the end of a cul de sac with over 1 acre of land. The kitchen has granite countertops with stainless steel appliances and freshly painted oak cabinets with new hardware. It also has luxury wide plank vinyl flooring leading to a sitting area with a large whitewashed fireplace off the kitchen. With the laundry room also located on the main level with a half bath leading to a large living room with lots of natural light and gorgeous Hardwood floors that have been refinished throughout the entire house. The extra large master bedroom has 3 closets and a full bathroom. The 2 additional bedrooms are spacious with their own large closets. This home offers a brand new roof, brand new septic tank and newer windows. The freshly stained deck overlooks the private wooded back lot. The 2 car oversized garage has freshly painted walls, ceilings and an epoxy painted finished floor. The front yard features a nice lawn and beautiful landscaping. The large unfinished basement has lots of shelving space for storage with a natural gas furnace and water heater for efficient heating. This home is waiting for the perfect family to enjoy all it has to offer! You Must See this gem!

50 Wintergreen Ln, Cheshire

$560,000
4 Beds 3 Baths 24109365 MLS
Situated at the end of a quiet cul-de-sac, in one of Cheshire's desired locations, this meticulously maintained 4-bedroom, 2 1/2 bath, center hall Colonial offers space, comfort, & beauty inside & out. Set on a private lot w/ professionally landscaped grounds & full yard irrigation, the home features stunning HW floors throughout & 4 ductless split systems for personalized climate control, plus ceiling fans in nearly every room. Spacious front to back living room w/ wood-burning brick fireplace & pocket door closure is perfect for entertaining, while the formal dining room features classic chair rail moldings. Large eat-in kitchen boasts a greenhouse window, pantry, & a pass-through to the family room with built-ins & a fireplace featuring a Fuego Fireplace insert. Updated guest bathroom showcases granite countertops & elegant tilework. Back door foyer provides enclosed laundry as well as additional closet & storage space. Step out to the inviting 3-season sun porch for morning coffee, or relax on the fieldstone patio overlooking the tranquil & private backyard. The primary bedroom on the 2nd floor includes a full bath & double closets, with 3 additional well-sized bedrooms & spacious main bath. Finished lower level adds versatile living space & a 2nd laundry hookup & utility sink. Interior recently painted. Steel beam construction, full-house generator, 4-zone heating, & hard-wired full home alarm system complete this exceptional offering. Recently appraised at $588,000!

198 N Timber Ln, Cheshire

$560,000
4 Beds 3 Baths 170583891 MLS
Well maintained Colonial tucked away on a quiet cul-de-sac in sought after, south Cheshire neighborhood. Spacious home offering 8 rooms, 4 bedrooms & 2 car garage. The main level has a large living room, formal dining room, fully applianced kitchen, 1/2 bath w/ pantry, family room w/ fireplace and sliders to beautiful screened-in porch. 2nd floor has a primary bedroom suite w/ full bath & walk-in closet, 3 more nice size bedrooms and 2nd full bath. Central A/C and hardwood floors throughout. Many recent updates, architectural roof (2020), furnace (2013), oil tank (2021), windows (2009), remodeled baths & more! Gorgeous 3/4 acre, level lot, lightly wooded w/ plenty of privacy providing a quiet and serene setting. Convenient location, close to linear trail, shopping, restaurants, schools, less than 20 mins to downtown New Haven & Yale hospital. Great commuter location, within minutes of highways & less than 2 hours from NYC!

20 Arrowleaf Ct, Cheshire

$560,000
6 Beds 2 Baths 170625513 MLS
Expansive and updated 6 Bedroom, 2 Bath Cape with open floor plan! This is the home you've been waiting for! Enter through an inviting foyer and proceed to the generous open floor plan living space. The updated Kitchen offers ample counter space and white cabinetry, a large island with seating, granite counters, glass tiled backsplash, stainless appliances and new dishwasher and smart fridge. You will find the Living Room and Dining Area to be a comfortable and cozy space to relax with a wood burning fireplace with insert and access to the large backyard patio. The main level also features 3 Bedrooms and an updated full Bath. Continue to the upper level of the home where you will find a spacious Primary Bedroom Suite with 4 large closets and access to the updated Jack and Jill Bath. Two additional Bedrooms and a laundry area complete the upper level of the home along with an unfinished 37x21 9' ceiling space for all your storage needs. This home is light and bright throughout with beautiful windows. Hardwood flooring in all rooms with the main level of the home having radiant heat flooring. Firepit and Playscape in backyard. 2 car garage and driveway with a huge turn-around. Home is wired for a generator. This home is a must see!

405 Blacks Rd, Cheshire

$558,695
2 Beds 3 Baths 24052077 MLS The Reserve At Stonebridge Crossing BLDG.
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. Experience the joy of owning a new townhome offering 2 bedrooms, 2 1/2 baths, a tandem garage, and more. This 1,850-square-foot townhome is scheduled for construction and ready for move-in Summer 2025. Enjoy a hassle-free move-in with no exterior upkeep required. The HOA includes affordable monthly fees covering mail services, garbage collection, landscaping, lawn care, leaf removal, and snow removal during winter. Step into a welcoming foyer leading to an open floor plan. Entertain guests while preparing meals in the kitchen, featuring a spacious island with ample room and a granite top. The kitchen extends to a deck for outdoor leisure. Benefit from a study area ideal for remote work or a cozy living room to unwind. Upstairs, revel in privacy with a primary bedroom and bath showcasing a large closet. A second bedroom, full bath, and discreet laundry area are conveniently situated upstairs. Townhomes do offer structural options. This maintenance-free community will have a pavilion, fire pit, walking loop, and trails. Our Zero Energy Ready homes boast combustion-free water heating and space conditioning, rapid hot water delivery through an on-demand recirculation loop, induction cooking, and spray foam insulation.

115 Shea Cir Unit 115, Cheshire

$558,000
3 Beds 2 Baths 24083855 MLS
Tucked away on a peaceful dead-end street right in the center of Cheshire, 32 Bennett Avenue blends charm, space, and smart updates-all in one spot. With over 1,850 square feet, this 3-bedroom, 2-bath colonial has room to grow and plenty of features to love. Step inside and you'll find a bright, welcoming first floor that's made for everyday comfort. The large, updated kitchen is a standout, featuring granite countertops, a center island, stainless steel appliances, and plenty of room to gather. Just off the kitchen, sliders lead you to a low-maintenance Trex deck that steps down to a custom paver patio, fire pit area, and an open yard-perfect for relaxing or entertaining. Also on the main level: a full bathroom, an office or flex room, a formal dining room, and a cozy living room with a classic wood-burning fireplace. Hardwood floors run throughout the entire home, continuing upstairs where you'll find three comfortable bedrooms, another updated full bath, and a second office or study space. The basement has plenty of room for storage, mechanicals, and includes washer/dryer hookups. And if you're looking for even more storage or workspace, you'll love the oversized detached two-car garage-with a full walk-up second level, there's no shortage of options. Additional highlights include central air, natural gas furnace (2010), city water and sewer, Roof (2010) and hot water heater (2025) **Highest and Best due by Monday April 7th at 7 PM

32 Bennett Ave, Cheshire

$557,000
4 Beds 3 Baths 24110282 MLS
Don't miss this gorgeous 4-bedroom, 2.5-bath colonial set on a pristine, beautifully landscaped lot. Hardwood floors flow throughout the home, adding timeless charm. The bright and sunny living room features a welcoming wood-burning fireplace and a large bay window. Enjoy meals in the elegant dining room with bay window and classic moldings. The expansive kitchen offers granite countertops, tile flooring, ceiling fan, under-cabinet lighting, and a convenient desk area-perfect for a computer setup. A cozy family room includes built-ins, a ceiling fan, and a slider to the Trex deck, ideal for relaxing or entertaining. A guest bath is conveniently located off the kitchen. Upstairs, the freshly painted upper level includes an attic fan for comfort, a spacious primary suite with a full bath and large closet, plus three more perfectly sized bedrooms-one with built-ins. The main bath features marble countertop, double sink and updated fixtures. Outside, enjoy a private backyard retreat with lush gardens, a solar-heated above-ground pool, an outdoor shower, and utility shed. Added bonuses include a 2022 roof, 2013 furnace and oil water heater, tilt-in windows for easy cleaning, generator hookup, and a 7-camera security system. This home offers the perfect blend of comfort, space, and modern amenities-schedule your showing today!

622 Wiese Rd, Cheshire

$555,000
3 Beds 2 Baths 24136138 MLS
Completely remodeled and move-in ready! This stunning Cheshire home offers 3 bedrooms, 2 full baths (including a primary en suite), an open kitchen/dining area with new cabs, quartz countertops, island, and stainless steel appliances. Enjoy a partially finished basement with family room and laundry (new washer/dryer included). Bright lightly stained hardwood floors throughout. Oversized 2 car garage with room for your handy projects. Recent updates include a new roof, energy efficient windows, garage door, siding, central air, driveway, paver patio, walkway, stone steps, and a freshly landscaped lawn. Conveniently located near markets, restaurants, shopping, the Farmington Canal Trail, and excellent Cheshire schools - nothing to do but move right in!

160 Willow St, Cheshire

$552,565
2 Beds 3 Baths 24100425 MLS The Reserve At Stonebridge Crossing BLDG.
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious interior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers endless restaurants nearby, as well as myriad shopping options & easy commuting routes. Our Zero Energy Ready homes boast combustion-free water heating and space conditioning, rapid hot water delivery through an on-demand recirculation loop, induction cooking, and spray foam insulation. Our Indoor airPLUS certification ensures that your home maintains exceptional indoor air quality. The photos, renderings and floorplans represent the model home and are for marketing purposes only. Photos may show features at additional cost. The included features supersede all artistic renderings and photos. All specifications are subject to change without notice.

130 Shea Cir Unit 130, Cheshire

$552,500
3 Beds 3 Baths 24163501 MLS
Open Saturday 4-4-26 12-2pm Desirable Cheshire neighborhood. Step into this inviting 3bedroom, 2.5bath home and feel the possibilities open up. The moment you walk in, you're greeted by a bright open floor plan that's perfect for everyday living and effortless entertaining. Updated kitchen and bathrooms. The primary bedroom offers comfort and convenience with its own full ensuite bath. Head outside and you'll find a spacious backyard featuring both a deck and patio-ideal for summer gatherings, quiet mornings, or anything in between. Need even more space? The large 800 square foot finished basement delivers a fantastic hosting area complete with a half bath and a full bar. Wood stove for heat. New oil tank and gutters. It's ready for game nights, celebrations, or your own personal retreat. Love the outdoors? Simply walk across the street to enjoy the scenic Cheshire Park Trails. Plus, you're just minutes from major highways 691, 91, and 84, and close to the new Stonebridge Commons along with plenty of shopping and dining options. This is the kind of home you walk into and instantly know-it's the one!

107 Country Club Rd, Cheshire

$550,060
3 Beds 3 Baths 24001773 MLS The Reserve At Stonebridge Crossing BLDG.
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious townhome in a desirable location. This maintenance-free community will have a pavilion, fire pit, walking loop, and trails. A convenient location offers endless restaurants nearby, as well as myriad shopping options & easy commuting routes. Our Zero Energy Ready homes boast combustion-free water heating and space conditioning, rapid hot water delivery through an on-demand recirculation loop, induction cooking, and spray foam insulation. Our Indoor airPLUS certification ensures that your home maintains exceptional indoor air quality. The photos, renderings and floorplans represent the model home and are for marketing purposes only. Photos may show features at additional cost. The included features supersede all artistic renderings and photos. All specifications are subject to change without notice.

104 Shea Cir Unit 104, Cheshire

$550,000
4 Beds 2 Baths 24174035 MLS
*Highest and best offers due by Tuesday, 5/19 at 5 PM* Welcome to 649 Maple Ave in desirable Cheshire! Set on nearly half an acre, this beautifully remodeled 4-bedroom, 2-bath Cape Cod offers a rare combination of charm, flexibility, and functionality. Inside, you'll find heirloom hardwood flooring, a beautifully updated kitchen with quartz countertops, pull-outs, and thoughtful storage, plus a versatile layout designed for modern living. The oversized first floor primary ensuite offers abundant his & hers closet space, while the main level features an additional bedroom, additional bath, laundry/mudroom combo, & bonus room ideal for an office, den, or playroom. Step outside and enjoy your own private retreat with a Trex deck and stunning pergola setup perfect for entertaining, dining, or relaxing, overlooking a fully fenced backyard with generous lawn space, garden areas, and room for kids, pets, or future outdoor enjoyment for everyone. A truly standout feature is the oversized detached 2-car garage with huge loft,detached office/workspace with own entrance; ideal for contractors, business owners, hobbyists, or flexible living needs. Massive parking accommodates multiple vehicles, trailers, equipment, RVs, or campers! Major updates include roof (~10 years), gas conversion with furnace + central air (~2018), water heater (2020), electrical updates (2026), and generator hookup. A truly unique opportunity in one of Connecticut's most sought-after communities!

649 Maple Ave, Cheshire

$550,000
4 Beds 2 Baths 24146203 MLS
Welcome to 1023 King Road-far from a cookie-cutter colonial. This charming 1950s-built home sits on over three-quarters of an acre in the desirable south end of Cheshire. Elevated above the roadway, the property offers privacy, space, and curb appeal, along with a detached two-car garage. A stairway leads to the main residence and a covered front porch, while multiple entrances-including front, side, and sliding doors-create easy indoor-outdoor living. The expansive yard features beautiful gardens and a fenced, in-ground swimming pool, perfect for relaxing or entertaining. Entering through the side door, you're welcomed into a cozy breezeway that opens into the family room. This inviting space features a propane fireplace, a wet bar, and an exposed wooden beam that highlights the home's unique character. The family room flows seamlessly into the open kitchen and a small office area. The kitchen offers a casual seating area, breakfast bar, granite countertops, newer appliances, and a slider leading to the rear stone patio. Just off the kitchen are the laundry room and a conveniently located bathroom. The living room features hardwood floors, a wood-burning fireplace insert, and another slider that opens to the patio and garden area, enhancing the home's warm and welcoming feel. Upstairs, you'll find four spacious bedrooms and a full bathroom. The upper level features new carpeting throughout, with one bedroom offering durable laminate flooring.

1023 King Rd, Cheshire

$550,000
4 Beds 3 Baths 24143042 MLS
Welcome to this large and spacious Colonial set on a beautiful one-acre lot in one of Cheshire's most desirable residential communities. This well-cared-for home offers exceptional space with 4 bedrooms plus a dedicated office, perfect for today's work-from-home needs. The main level features a welcoming living room with a wood-burning fireplace, a comfortable family room with its own wood-burning fireplace, and an eat-in kitchen overlooking the private grounds. Additional highlights include central air, a 2-car garage under, and generous room sizes throughout. Cheshire is known for its top-rated schools, New England charm, and strong community appeal. Residents enjoy the scenic Farmington Canal Linear Trail, nearby parks, farms, and local amenities, as well as close proximity to The Farms Country Club and golf. Commuters will appreciate the easy access to Route 15, I-691, and I-84. A wonderful opportunity to own a spacious home in a town celebrated for its quality of life.

501 Radmere Rd, Cheshire

$550,000
3 Beds 3 Baths 24134904 MLS
Welcome to 781 Cook Hill Road, where classic charm meets modern updates on a private, nearly 2-acre level lot. This inviting Cape features a convenient breezeway and mudroom; an oversized two-car garage; a large eat-in kitchen with elegant cabinetry - complete with a built-in coffee station and wine bar; and three generously sized bedrooms, including a primary suite with a beautifully bright arched window and a half bath. Delight in cozy evenings by the wood-burning fireplace in the living room, or gather around the gas fireplace in the family/dining room, enjoying the large bay window. You'll find hardwood floors and exquisite woodwork throughout, adding warmth and character to every room. Appreciate central air and the large Trex deck off the back - perfect for entertaining, grilling, or simply enjoying the serene views of the expansive, lightly wooded property, finished with a front-facing white picket fence. The tiled space on the lower level with glass sliders to the backyard provides an added space for a play/recreation room or a personal gym. Whether you're looking for a peaceful retreat or a place to host family and friends, this home checks all the boxes. Recent updates include new electrical wiring, a newer well pressure tank, and a new interior channel drainage system on the lower level. Great schools, parks and farms, don't miss this rare opportunity to own a move-in-ready home on a large, scenic lot in a desirable location!

781 Cook Hill Rd, Cheshire

$550,000
2 Beds 2 Baths 24069756 MLS
Classic, architecturally expanded Cape with unrivaled elegance and detail. Set on a private, fully fenced half acre featuring amazing brick patios, landscaping, gardens and abundance of lighting for perfect outdoor entertaining.Kitchen with Viking propane range, Zephyr Hood, Bosch combo convection oven/micro, Miele dishwasher, Sub Zero Refrigerator. Carrera marble counters with OG edging. Extensive, exquisite lighting. Arched entries from kitchen and dining. Dining room features wall of custom cabinetry for display and storage. Travertine shelf will stay. Living room distinctive features include a granite wet bar with Sub Zero refrigerator and freezer drawers and Miele dishwasher. Wall of bookcases and storage. French door with sidelights to large patio. Several awnings (elec. & manual) along with magnificent mature trees and gardens to enjoy the pristine manicured property. Relax in the cozy library with built in bookcases/storage. 1st fl bath w custom designed granite vanity & tub. Primary bedroom offers wall of closets, cathedral ceiling and window seat (w/storage). 2nd bedroom has generous closet space and is connected to studio/office w/ slider to balcony, skylights, and bookcases. Tasteful & elegant limestone & tile full bath w/ whirlpool tub. Too many custom and creative details to list. House must be seen to appreciate the thoughtful details, design and lifestyle this property affords. Lower level with cedar closet, additional closets and laundry.

376 Peck Ln, Cheshire

$550,000
3 Beds 2 Baths 24030855 MLS
Welcome to this charming 3-bedroom Cape cod style house with 2 full baths nestled in the heart of Cheshire. The inviting living room features a stunning bay window that allows plenty of natural light, creating a warm and welcoming atmosphere with stone wood burning Fireplace. The dining room has a sidebar which is great for entertainment. The kitchen area is generous size and opens to eat in area which looks out to the family room. Off the family room is a delightful sunroom which overlooks a level private backyard. This is perfect for enjoying some time alone or entertaining guests. Upstairs 2 bedrooms and a full bath. The Primary bedroom has great closet space and a separate room currently used as walk in closet. The lower level includes a playroom, workshop, wine closet, and unfinished space. There are hardwood floors throughout this home. Great location in a sought-after neighborhood, walk to Ball & Socket Arts Center, the Farmington Canal Heritage Trail. City Water, City Sewer, Roof (2021) Boiler (2022) 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. Easy Commuting with I-84, I-91,691 and The Merritt Parkway- 32 Minutes to New Haven and Hartford. 2 1/2 Hours to Boston or NYC.

478 Westland Ave, Cheshire

$550,000
3 Beds 2 Baths 24099254 MLS
Charming Center Hall Colonial on Quiet Dead End St in Cheshire- 3 bedrooms 1.5 baths, 2,239 SqFt. Welcome to this well- loved, center-hall Colonial ideally located just minutes from Cheshire's charming town center, walking paths and only 20 minutes from downtown New Haven. Nestled on a peaceful dead end street, this 2239 square-foot home offers timeless character and thoughtful updates throughout. The main level features beautiful hardwood floors, a formal dining room, a cozy breakfast area off the kitchen, and a convenient half bath. The spacious living room opens to a family room which has sliders to an oversized deck-perfect for entertaining or enjoying the serene backyard. Upstairs you'll find three generously size bedrooms and a stunningly remodeled full bath featuring a soaking tub and separate shower. The walk up third-floor attic offers flexible space for a playroom, office, or potential fourth bedroom. Set on tranquil, private grounds in a prime location, this charming home is the perfect blend of comfort, style, and convenience. Don't miss out on this amazing property!!

85 Ridgeview Pl, Cheshire

$550,000
4 Beds 3 Baths 24087887 MLS
Welcome to this charming Colonial nestled on a flat half-acre lot in the heart of Cheshire. Inside, you'll find beautiful hardwood floors throughout, four generously sized bedrooms, two and a half baths, and a fully applianced eat-in kitchen, plus classic formal dining and living rooms perfect for entertaining. Just off the family room is a new deck that overlooks a large private backyard complete with 2 storage sheds; an ideal space for relaxing or hosting summer gatherings. The full basement offers an abundance of storage and the opportunity to create even more living space in the future. The roof and driveway have been recently replaced, and the home has been freshly painted. This home is super convenient to local parks, schools, and even nearby orchards for those perfect fall weekends. While in need of some updating, this property offers great bones and a perfect layout, space and flow for today's modern living needs. Don't miss your chance to personalize and create the home you've been envisioning. This is an estate sale- no disclosures. Being sold in "as-is" condition.

614 Wiese Rd, Cheshire

$550,000
4 Beds 3 Baths 24120827 MLS
Make yourself at home in this updated and expanded 4 Bedroom, 3 Bath Ranch style home! Enjoy the spacious Living Room with brick fireplace and large window to let in plenty of natural light. The Dining Room has a slider leading to the screened and tiled porch, a perfect place to spend your summer evenings! An inviting eat-in Kitchen is equipped with ample cabinetry and counter space, a built-in oven, electric cooktop, white cabinetry and granite counters. Double sliders lead to an over-sized Trex deck for ease in outdoor entertaining. Three Bedrooms, one with an attached full Bath, and a full hall Bath complete the main level of the home. An expansive Primary Bedroom Suite is located on the upper level of the home with wall to wall carpet, vaulted ceiling and office space. An attached primary Bath boasts double vanity, walk-in shower, tub and vaulted ceiling. The full, unfinished basement has potential to be finished for additional living space. There is hardwood flooring throughout the main level of the home. Central air, city water and sewers, 2 car attached garage. Nicely landscaped level, treed lot. Convenient to Highways, shopping and restaurants. Don't miss your chance to see this lovely and spacious Ranch home!

168 Pleasant Dr, Cheshire

$550,000
3 Beds 2 Baths 24112658 MLS
This thoughtfully remodeled three-bedroom, two-bath ranch is move-in ready and waiting for its new owner! Enjoy a stunning new kitchen, modern updated bathrooms, and hardwood floors throughout. Every detail has been carefully considered-from the refreshed screened porch to the practical partially finished basement. The spacious primary suite offers privacy and comfort, while the screened porch extends your living space and invites you to relax in style. Step outside to a welcoming patio, perfect for entertaining or unwinding at the end of the day. Additional highlights include a two-car garage, plenty of storage, and charming curb appeal. Don't miss this turn-key home that blends modern updates with classic comfort! *Agent related to owner

29 Bates Dr, Cheshire

$550,000
3 Beds 3 Baths 24056538 MLS
Due to Multiple offers received, HIGHEST AND BEST DUE BY 8 PM SUNDAY NIGHT, ALL offers will be reviewed Monday. Stunningly Remodeled 3-Bedroom Home in South Cheshire! Welcome to your dream home, all you have left to do is pack your bags! This completely remodeled gem is located on a cul-de-sac road in the South end of Cheshire, offering easy access to highways for commuters. Step inside to discover a bright and airy space, freshly painted in modern tones that complement the new hardwood floors throughout. The kitchen features gleaming quartz countertops, contemporary fixtures and all-new cabinetry. Perfect for both everyday living and entertaining with the open concept. This home boasts three bedrooms and 2 and 1/2 beautifully remodeled bathrooms, each boasting modern high-quality finishes and fixtures. Every detail has been thoughtfully considered in this renovation, ensuring a turnkey experience for the new owners. Built with quality construction, this home has not only aesthetic appeal but also lasting durability with superior craftsmanship and attention to detail. Additional features include a convenient 2-car garage and a newly paved driveway providing storage and plenty of parking. This home is truly move-in ready, offering a blend of luxury and convenience that is hard to find. Don't miss the opportunity to own this exceptional property!

20 Brentwood Dr, Cheshire

$547,560
2 Beds 3 Baths 24111375 MLS The Reserve At Stonebridge Crossing BLDG.
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers endless restaurants nearby, as well as myriad shopping options & easy commuting routes. Our Zero Energy Ready homes boast combustion-free water heating and space conditioning, rapid hot water delivery through an on-demand recirculation loop, induction cooking, and spray foam insulation. Our Indoor airPLUS certification ensures that your home maintains exceptional indoor air quality. The photos, renderings and floorplans represent the model home and are for marketing purposes only. Photos may show features at additional cost. The included features supersede all artistic renderings and photos. All specifications are subject to change without notice.

135 Shea Cir Unit 135, Cheshire

$547,500
5 Beds 4 Baths 24111929 MLS
Expansive Cape on a quiet neighborhood street in the south end of Cheshire. Welcome to 1681 Orchard Hill Road - a beautifully expanded Cape Cod-style home nestled on a landscaped .45 acre lot. This exceptional property blends classic charm with modern updates offering the perfect balance of comfort, space, and privacy. Inside, the home features an updated kitchen with SS appliances, granite countertops plus a breakfast nook ideal for everyday living. Off the kitchen is a Remodeled Sunroom with vaulted ceilings, French doors, and new windows that flood the space with natural light overlooking the upper deck. A spacious living room with a cozy wood burning stove opens to the dining room and hallway leading to 2 bedrooms and a full bath. Off the Sunroom are French doors that lead to a potential in-law suite with a bedroom, walk in closet, full bath, eat-in-kitchen space and a separate entrance! Upstairs you will find the primary bedroom with a jack-in-jill bath, storage closets and another bedroom. Family room, half bath and laundry are located in the lower level with access to the garages. With 5 bedrooms, 3.5 bathrooms and 3 garages, this home provides ample space for family and guests. Relax, Entertain and BBQ on the large upper deck offering views of the private backyard. Updates Include: New Hot Water Heater. Roof on left side of home 1.5 yrs old. Roof on right side 5 yrs old. Majority of windows have been replaced. Septic system updated in 1998 with addition of 5th bedroom

1681 Orchard Hill Rd, Cheshire

$547,000
3 Beds 2 Baths 24159847 MLS
OFFER DEADLINE WEDNESDAY 5/27 12:00 NOON 200 Chipman Drive is the home that Cheshire buyers wait for! A move-in ready gem, it offers the ease of one-floor living without sacrificing space or style. With over 3,100 square feet of usable space, a warrantied basement, solar efficiency, updated windows, and set on a one acre lot nestled at the end of a quiet, sought-after prime cul-de-sac location; it is a property that truly has it all. This is not your standard ranch; it is an expansive, meticulously upgraded sanctuary offering nearly 2,000 square feet of main-level elegance and a newly improved lower level that doubles the home's utility. The home provides a rare sense of privacy and space while remaining minutes from the heart of Cheshire's vibrant community. Some highlights include: Vaulted Beamed Ceiling, refinished hardwood floors, upgraded windows, 2 fireplaces, updated kitchen, Life-proof laminate flooring, fresh paint throughout, 2-car garage, outdoor deck, solar panel efficiency, newer Peerless boiler, CT basement warrantied system, .03 mile from Cheshire high school and Bartlem park's pool and trails. Properties in this neighborhood rarely come to market - don't miss this opportunity!

200 Chipman Dr, Cheshire

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