454 houses for sale in Berkshire, Newtown town Fairfield County Connecticut

A rare opportunity to own a piece of Southbury history while enjoying a home that lives comfortably for today. The Aaron Bronson House is a beautifully maintained 18th-century Cape set on 2.6 private acres, where character, natural light and a thoughtful floor plan come together. The home flows naturally from room to room, with large windows offering plenty of light and beautiful views of the gardens and backyard. The home features a spacious eat-in kitchen with a wood-burning fireplace, exposed hand-hewn beams and antique windows. Four formal rooms each feature a fireplace, while wideboard floors and original details add warmth throughout. A modern addition provides a main-level living option with cathedral ceilings, skylights, two walk-in closets, a home office and a wall of French doors overlooking the backyard. A stone terrace extends the living space outdoors. Upstairs, another bedroom suite and additional bedroom share a well-appointed full bath. Outside, enjoy established garden

75' of direct waterfront on Lake Zoar in Sandy Hook's Shady Rest community, with your own private dock and boat launch. Here, the lake becomes part of everyday life, whether you're boating, kayaking, or simply enjoying the view and level backyard. A screened porch, oversized deck and patio give you three distinct places to relax, dine and entertain outdoors. Inside, the oversized kitchen is a true standout, featuring a large center island with two electric Thermador cooktops, a double wall oven, generous cabinetry and counter space, and a wall of windows overlooking the water and backyard. There's plenty of room for cooking, gathering and entertaining, all with the lake as the backdrop. The main level also includes a flexible living space that can work as an office, den, playroom or whatever makes sense for the way you live. Downstairs, a garage/storage area with an exterior garage door provides convenient access to your water toys, outdoor equipment and everything that comes with lake

Nestled on 4 secluded acres in the Sandy Hook section of Newtown, this unique property offers the perfect blend of privacy, character, and natural beauty. The private drive leads to your own peaceful retreat tucked away from the road. Originally built in 1941 as a hunting lodge, the home has been thoughtfully expanded while preserving its rustic charm. At the heart of the home is the impressive great room, featuring a soaring ceiling and a stunning 17.5-foot fieldstone fireplace. The main level offers a semi-open floor plan where the great room, dining room, flexible living space, and kitchen flow seamlessly together. The kitchen also includes a cozy breakfast nook, a half bath, and new stainless steel appliances. The main level features two bedrooms connected by a Jack-and-Jill bathroom. Upstairs, you'll find two additional bedrooms and a full bath. The spacious primary suite boasts vaulted ceilings, a ceiling fan, and custom-built closets. Beautiful wood floors run throughout the hom

Welcome to 4 Founders Way, a meticulously maintained 4-bedroom, 2.5-bath Colonial in one of Monroe Center's most desirable neighborhoods. Set on a beautiful level 1.08-acre lot, this home offers the perfect blend of timeless charm, modern updates, and an ideal location. 2026 updates include a beautifully renovated kitchen with new cabinetry, quartz countertops, and all new appliances, including the washer and dryer, refinished hardwood floors throughout, new hardwood flooring in the family room, upstairs hallway, and three bedrooms, new ductwork, and fresh interior paint, including all trim. The bright, open main level offers seamless flow between the kitchen and spacious family room with a cozy fireplace. Upstairs, the primary suite provides a private retreat with a walk-in closet and en suite bath. The finished lower level features two flexible rooms ideal for a home office, gym, or recreation space. Enjoy outdoor living on the expansive wraparound deck overlooking the level backyard

Welcome to this beautifully updated, turn-key Colonial nestled in Monroe's highly desirable Great Oak Farm neighborhood. Packed with high-value upgrades and freshly painted throughout, this pristine property offers the perfect blend of modern comfort and classic charm. The main level boasts a completely updated kitchen, a tastefully renovated half bath, and an inviting living space anchored by a cozy wood-burning fireplace. Unwind in the sun-drenched sunroom or head down to the expansive, finished walk-out basement, which features brand-new carpeting and generous extra storage space. Structural and mechanical integrity shine with a two-year-old roof, seven new Andersen windows, a new skylight, and a full-house generator for total peace of mind. Outside, the fully fenced-in backyard provides a private oasis for outdoor enjoyment and relaxation. Enjoy all the local features of Great Oak Farm like summer movie nights and holiday parties, walks to local Rails to Trails hiking and biking as

This is the one you've been waiting for! Step into this stunning 4,000+ square foot Colonial built in 2021, filled with abundant natural light and gleaming hardwood floors. The expansive main floor features an open floorplan with soaring ceilings, a generous dining area and a living area anchored by a gas fireplace. The gorgeous kitchen has a bright breakfast nook that opens to the backyard and patio through elegant French doors. There is a formal sitting room off the front foyer that could be utilized as a quiet study or home office. There is also a main-floor bedroom and full bath that add flexibility for guests or multigenerational living. Upstairs you'll find four additional bedrooms, including a luxurious primary suite with a spa-like bath-large tile shower, freestanding tub, double sink vanity, and a spacious walk-in closet. An additional full bathroom and a dedicated laundry room complete the second level for everyday ease. The lower level delivers over 1,000 square feet of fini

WELCOME HOME to this exquisite Horse Property at the end of a private cul-de-sac, up a tree-lined driveway with no neighbors in sight. This 1,584 sqft Raised Ranch offers 3 Bedrooms, 2 Bathrooms, and an OPEN FLOOR PLAN with a Living Room bay window, Dining Room, and Kitchen with center island and Stainless Steel appliances. Hardwood floors throughout and a brand new back deck (May 2026) make this home perfect for entertaining and enjoying the changing seasons. Down the hall you'll find a Full Bathroom, Primary Bedroom with double closets, and two additional Bedrooms. The finished lower level features a Family Room with a brand new wood stove (July 2026), Laundry Room, Half Bath, and access to the two-car garage. Set on 1.87 grassy, level acres of complete privacy, with room to build the farm you've always wanted. The 3-stall barn, purchased from the Barn Yard in December 2019, features Dutch doors, kick board-lined stalls, electricity, 2 farm-approved fans, rubber matting, and a Centau

Nestled in a prime Newtown Borough location, this spacious home offers the convenience of public sewer, town water, and natural gas while being just moments from shopping, dining, parks, and all the charm of the Borough. The heart of the home is the oversized kitchen featuring cherry cabinetry, honed granite countertops, a gas cooktop, an extra-large sink, and abundant workspace for cooking and entertaining. Beautiful hardwood floors flow throughout both the main and upper levels. (Hardwood under carpet in bedrooms.) Designed for comfortable everyday living and entertaining, the home boasts oversized rooms throughout, including a formal living room, formal dining room, inviting family room with fireplace, and a bonus recreation room on the main level. A large first-floor office with extensive built-ins provides the perfect work-from-home space. One of the home's standout features is the impressive 300-square-foot three-season sunroom with vaulted ceiling and walls of windows, creating

Welcome to 296 Lakemere Drive! Tucked away near the waters of Lake Zoar in desirable Southbury, this home offers a seamless blend of classic charm, expansive living spaces, and exceptional entertaining features. Hardwood floors extend throughout the entire main level. Step into the welcoming entry foyer; to the left sits an inviting living room, while to the right, a formal dining room comfortably accommodates extra seating. A quaint home office provides a quiet work-from-home sanctuary just before reaching the open eat-in kitchen, which boasts expansive floor space, abundant cabinetry, and a sunlit breakfast nook. Designed for hosting, a wet bar sits conveniently off the kitchen, leading straight into the warm family room featuring custom built-in bookshelves, a cozy fireplace, and sliding glass doors that open out to the back deck. Upstairs, all three bedrooms are generously sized. The primary suite serves as an impressive private retreat complete with a ceiling fan, walk-in closet,

Welcome to Monroe, Connecticut, as you ascend the paved, picturesque treed and private paved driveway, you will observe stone walls and additional parking. Upon reaching the front of the house via the paver walkway, you will notice the recently updated front porch, ideal for morning coffee and relaxation. As you enter the home, you will find the formal dining room to your left and the Den/Office to your right. As you traverse the hallway, you will discover the sliders leading to the rear patio and the spacious island in the newly renovated kitchen. The kitchen underwent a comprehensive update and remodel in 2021, incorporating ample storage and counter space, making it a true chef's kitchen. The great room, situated adjacent to the kitchen and dining room, boasts high vaulted ceilings adorned with beams and a corner fireplace with a propane insert, complemented by abundant natural light, creating an inviting atmosphere for entertaining. The upper level comprises three bedrooms, a hall-

Charming Ranch Living in the Heart of Newtown. This inviting 1,408 square-foot ranch sits on a sunny, level corner lot and offers the relaxed lifestyle so many are searching for. Step inside to cathedral ceilings that create an open, airy feel throughout the living space. A warm fireplace anchors the home, perfect for cozy evenings or quiet mornings with coffee. The single-story layout means no stairs to climb, just comfortable, practical living designed for everyday ease. Outside, the level lot gives you plenty of space to garden, play, or simply enjoy the outdoors. Dickinson Park is just a short stroll away, ideal for morning walks, weekend picnics, or letting off some energy close to home. Newtown living with neighborhood amenities right at your doorstep

Timeless character meets exceptional modern living in this beautifully updated 1950s Cape, ideally located in the heart of the Borough of Newtown. Just a short walk to restaurants, shops, parks and community events, this home offers the perfect combination of charm, convenience and thoughtful updates. Rich hardwood floors, classic Craftsman-style woodwork, custom millwork and inviting living spaces create warmth throughout. The stunning remodeled kitchen is the centerpiece of the home, featuring a dramatic vaulted ceiling, custom cabinetry and backsplash, quartz countertops, a center island, farmhouse sink, designer lighting and premium stainless steel appliances. The spacious dining room is perfect for entertaining, while the beautifully renovated second-floor primary bath showcases timeless finishes and quality craftsmanship. Practical features include a large laundry room with custom floor tiles, an oversized mudroom, secondary pantry-storage area and a dedicated workshop. Outside,

Tucked beneath a canopy of mature trees along the gentle waters of Lee Brook, this thoughtfully updated retreat offers an intentional way of living-where mornings begin with coffee on the deck to the sound of a babbling brook and weekends are spent kayaking, fishing, or exploring the interconnected waterways of Lake Zoar, Lake Lillinonah, the Pomperaug and Housatonic Rivers. Whether you're searching for a peaceful weekend escape, a low-maintenance full-time residence, an inspiring artist's retreat, or a smart investment opportunity, this home embraces the beauty of living simply. Inside, it has been designed to feel warm, bright, and functional, with skylights that fill the space with natural light, updated luxury vinyl flooring, a cottage-style kitchen, and a recently renovated bathroom. Outside, a cozy detached shed offers flexibility as a workshop, creative office or studio. The wraparound deck, concrete patio, and stone walls become an extension of your living space, immersed in th

Tucked beneath a canopy of mature trees along the gentle waters of Lee Brook, this thoughtfully updated retreat offers an intentional way of living-where mornings begin with coffee on the deck to the sound of a babbling brook and weekends are spent kayaking, fishing, or exploring the interconnected waterways of Lake Zoar, Lake Lillinonah, the Pomperaug and Housatonic Rivers. Whether you're searching for a peaceful weekend escape, a low-maintenance full-time residence, an inspiring artist's retreat, or a smart investment opportunity, this home embraces the beauty of living simply. Inside, it has been designed to feel warm, bright, and functional, with skylights that fill the space with natural light, updated luxury vinyl flooring, a cottage-style kitchen, and a recently renovated bathroom. Outside, a cozy detached shed offers flexibility as a workshop, creative office or studio. The wraparound deck, concrete patio, and stone walls become an extension of your living space, immersed in th

A rare opportunity to acquire a five-unit multifamily investment property in the heart of Newtown, Connecticut. Ideally situated just minutes from the town center, this income-producing asset offers investors the perfect combination of strong rental demand, long-term appreciation potential, and the charm of one of Fairfield County's most desirable communities. Featuring five residential units with excellent income potential, this property presents an exceptional opportunity for seasoned investors, those looking to expand their portfolio, or owner-occupants seeking to offset their mortgage with rental income. The property's attractive setting, ample parking, and convenient location make it highly desirable to tenants seeking easy access to local shopping, restaurants, parks, schools, and major commuting routes. Whether your strategy is long-term buy-and-hold, value-add improvements, or generating reliable monthly cash flow, this multifamily property offers outstanding flexibility and in

Discover a refreshing new lifestyle within the Traditions of Southbury community. This particular home offers a private, fenced-in backyard, providing a secluded outdoor space. Fencing can enhance privacy and exercise for your dog. Inside, an open and bright floor plan creates an inviting atmosphere. The family room, featuring nine-foot ceilings, contributes to a sense of spaciousness and allows for increased natural light. A gas fireplace in the family room offers warmth and ambiance. Sliders lead from the family room to the private backyard, seamlessly connecting indoor and outdoor living areas and enhancing natural light and ventilation. The finished lower level presents versatile options, perfect for a workout room, home office, or an additional playroom. This adaptable space can cater to various needs, adding significant functional living area to the home. Traditions of Southbury is an amenity-rich community. Residents can enjoy amenities such as a clubhouse, fitness center, Tot L

Multiple offers - highest and best due Monday 8 PM*. Welcome home to this 3-bedroom, 2-bath ranch set on a desirable corner lot with a private in-ground pool-perfect for summer entertaining! Hardwood floors run throughout the home, except in the kitchen and bathrooms. The updated kitchen features granite countertops, stainless steel appliances, and a casual dining area and opens directly to a comfortable family room with sliding doors leading to the expansive rear deck overlooking the pool and backyard. The spacious formal living room is filled with natural light from a beautiful bow window and features a classic wood-burning fireplace, while the formal dining room offers the perfect setting for holidays and gatherings and conveniently connects to both the foyer and kitchen. The primary suite is privately situated at the end of the hallway and includes its own full bath. Two additional bedrooms and a beautifully updated hall bath complete the main level. The full unfinished basement pr

Enjoy a wonderful Life style at Traditions! This home offers numerous upgrades and a desirable floor plan. The open kitchen features a center island, newer stainless steel appliances, crown molding, and a neutral backsplash. Adjacent is a pantry for additional storage. The two-story family room boasts a gas fireplace, built-in cabinetry, hardwood floors, and an open feel. Formal living and dining rooms include custom crown molding, with the dining room also showcasing custom wainscoting. A first-floor office provides a pleasant view of the wooded backyard. Upstairs, the primary bedroom is spacious with his/her closets, a trey ceiling, and a newly remodeled, state-of-the-art primary bathroom. This luxurious en-suite features a doorless shower, dual sinks with marble counters, and elegant new lighting. Three additional spacious bedrooms and a reading nook or study area complete the second floor. The finished lower level expands living space with a full bath, a separate room with French d

Welcome to White Hills! Set on 1.36 private acres in one of Shelton's most desirable neighborhoods, this expansive Colonial offers over 3,884 square feet of living space with a versatile layout ideal for multigenerational living, extended family, or guests. Featuring 5 bedrooms and 5 bathrooms, including 3 full and 2 half baths, this home provides an impressive combination of space, privacy, and flexibility. A standout feature is the spacious in-law suite, complete with a large private bedroom, full bath, and half bath, creating a comfortable and separate living space while still being connected to the main home. The main residence offers 4 additional generously sized bedrooms and 2.5 baths. At the heart of the home is an oversized eat-in kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a generous pantry. The expansive family room is highlighted by dramatic vaulted ceilings and a wood-burning fireplace, creating a warm and inviting gathering sp

Welcome to 211 Cooper Hill Road, a magnificent 4-5 bedroom colonial set on 1.43 beautifully landscaped acres in one of Southbury's most coveted cul-de-sac neighborhoods. Freshly painted and better than ever, this home now offers an outdoor living experience to match its refined interior, anchored by a heated saltwater inground pool, hot tub, and a private pool house with its own half bath. Step inside to a welcoming two-story foyer with custom millwork leading to an updated eat-in granite kitchen with stainless appliances, tiled backsplash, large island, custom cabinetry, second sink, and pantry. The adjoining family room features a cathedral ceiling, dual skylights, and a cozy gas fireplace. A private office with French doors, formal dining room, and living room, all with hardwood floors, complete the first level. Upstairs, an interior balcony leads to a luxurious primary suite with walk-in closet, double sink vanity, and soaking jetted tub. Three to four additional bedrooms, includin

Welcome to White Hills! Set on 1.36 private acres in one of Shelton's most desirable neighborhoods, this expansive Colonial offers over 3,884 square feet of living space with a versatile layout ideal for multigenerational living, extended family, or guests. Featuring 5 bedrooms and 5 bathrooms, including 3 full and 2 half baths, this home provides an impressive combination of space, privacy, and flexibility. A standout feature is the spacious in-law suite, complete with a large private bedroom, full bath, and half bath, creating a comfortable and separate living space while still being connected to the main home. The main residence offers 4 additional generously sized bedrooms and 2.5 baths. At the heart of the home is an oversized eat-in kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a generous pantry. The expansive family room is highlighted by dramatic vaulted ceilings and a wood-burning fireplace, creating a warm and inviting gathering sp

Set in the desirable White Hills area of Shelton, this beautifully maintained 2,516-square-foot Colonial offers generous living spaces, thoughtful updates, and a beautiful setting on a professionally landscaped 0.69-acre lot. The main level features a spacious formal living room and dining room, a bright eat-in kitchen with abundant cabinetry, ample counter space, and stainless-steel appliances including two ovens making meal preparation and entertaining a breeze. An oversized family room with vaulted ceilings and a gas fireplace that creates a warm and inviting gathering space. A convenient powder room with first-floor laundry hookups completes the main level. Upstairs, the spacious primary suite offers a walk-in closet, private full bath, and adjoining bonus room ideal for a home office, exercise room, nursery, or sitting area. Two additional generously sized bedrooms and a large full bath provide plenty of space for family and guests. The partially finished lower level offers additi

Down a quiet stretch of Boggs Hill, framed by open land and historic stone walls, this 5-bedroom, 3,200+ sq ft country retreat is a rare blend of privacy, space, and view. A grand two-story foyer opens into a light-filled living and dining room, flowing easily into an eat-in kitchen overlooking the yard and a cozy family room with access to the stone patio. A sun porch wrapped in windows on nearly every side makes for the perfect morning-coffee or golden-hour spot. The main level offers a peaceful primary suite plus a second bedroom or office with oversized windows, ideal for one-level living, guests, or remote work. Upstairs, three generously sized bedrooms share a full bath, joined by a secret bonus space (playroom, studio, storage - your call) and an unfinished attic with soaring ceilings, ready to become whatever you need next. Hardwood floors in most of the house, central air, and stone walls throughout give this home timeless country character. And the setting doesn't stop at the

Ever dreamed of living in an exceptional home with the feel of a private estate' Your search ends here! Nestled in one of the area's most sought-after neighborhoods, this stunning 5,700 sq. ft. residence offers 5 spacious bedrooms and room for everyone to live, work, and entertain in style. The beautifully updated chef's kitchen features premium appliances, a breakfast bar, separate dining area with a wine chiller and beer taps, plus French doors leading to a private patio with a fire pit-perfect for relaxing or gathering with friends. Rich hardwood floors flow throughout the home, connecting elegant living spaces including a library with fireplace, formal dining room, gracious living room with fireplace, cathedral-ceiling family room with a fireplace and wood stove insert, and a bright home office ideal for today's lifestyle. Upstairs, you'll find the generous bedrooms and three full baths, including a luxurious primary suite with a walk-in closet, private bath, and its own fireplace.

Ever dreamed of living in an exceptional home with the feel of a private estate' Your search ends here! Nestled in one of the area's most sought-after neighborhoods, this stunning 5,700 sq. ft. residence offers 5 spacious bedrooms and room for everyone to live, work, and entertain in style. The beautifully updated chef's kitchen features premium appliances, a breakfast bar, separate dining area with a wine chiller and beer taps, plus French doors leading to a private patio with a fire pit-perfect for relaxing or gathering with friends. Rich hardwood floors flow throughout the home, connecting elegant living spaces including a library with fireplace, formal dining room, gracious living room with fireplace, cathedral-ceiling family room with a fireplace and wood stove insert, and a bright home office ideal for today's lifestyle. Upstairs, you'll find the generous bedrooms and three full baths, including a luxurious primary suite with a walk-in closet, private bath, and its own fireplace.

Set on a picturesque 11-acre parcel featuring expansive lawns, a tranquil pond, and beautiful hiking trails, 437 George's Hill presents a rare opportunity for multi-generational living, investment income, or a private compound. With 3 separate structures, the main residence is a charming Cape-style home offering 3+ bedrooms and 2 full baths, with a garage under and additional space ready for expansion. The main level showcases an open-concept layout where the kitchen, dining, and living areas flow seamlessly together. A bright sunroom just off the living room provides the perfect space for a home office, studio, fitness room or playroom. The primary bedroom and a beautifully updated full bath complete the first floor. Upstairs, you'll find two additional bedrooms, another full bath, and a large space ready for your vision. Behind the main home sits The Cottage, a fully renovated, thoughtfully designed building featuring two separate apartments; A 2-bedroom, 1-bath unit on the ground le

Outstanding Opportunity to live close to Newtown's historic Town Center! This sparkling split level on a flat as a pancake lot is just one turn away from Newtown's Iconic Flagpole! This home offers 4 bedrooms, 2 full baths, Central AC, a lovely, walkable neighborhood, and town water and sewer! You'll love living close to shopping and services, as well as the outstanding array of restaurants which has made Newtown a Foodie destination! You'll also be close to schools, grocery stores, multiple coffee spots and bakeries, while still having easy access to major commuter routes such as I-84, Rte. 25, and Rte. 34. In addition, you'll be close beautiful Dickenson Park, and two popular golf courses! Yes, the Good Life awaits! Call TODAY because it may not be here tomorrow!

A Strategic 6,500 Gross SF Single-Level Estate for the Entrepreneur, the Patriarch, and the Equestrian. If you are looking for a standard 3-bedroom ranch on a suburban cul-de-sac, stop please reading now. THIS IS MORE. Bethel 3492 sf House, 3-5 Bedrooms, Huge 2 story Garage, 2 Barns, Giant yard, Horse Property, Paddock, Dreamy Porch, Inlaw Suite. 1900 SF partial finished Basement. Close to shopping dining, commuting. This property is ideal for: *CONTRACTORS - Oversized detached garage with storage for tools, vehicles, and equipment. Bonus space above the garage is ready to finish as a caretaker's apartment or office. *MULTI-GENERATIONAL LIVING - Includes a finished in-law apartment with private entrance, offering separation and flexibility for extended family or guests. *EQUESTRIAN/HOBBY FARMING - Features two barns and a fenced paddock, perfect for a horse, ponies, goats, or other animals. Set back from the road for privacy, the home is clean and functional, with land and infrastructu

EXCEPTIONAL VALUE BELOW JANUARY 2026 APPRAISAL OF $503,000. Experience the privacy of country living with convenient access to the city and coast. This beautifully renovated Newtown home is 75-90 minutes from Manhattan, convenient to Metro-North stations in Bethel and Brewster, and 40 minutes from Milford beaches and Connecticut's shoreline. Set on 1.5 acres surrounded by mature trees, experience wooded privacy, scenic sunrises and seasonal distant views. Inside, the brand new stylish kitchen with custom two-toned cabinetry, granite countertops, oversized island and stainless-steel appliances adjoins a formal dining room with a vaulted ceiling, skylight and modern gold chandelier. The fully remodeled bathroom features marble tile and warm brass fixtures. Two bedrooms plus an additional room with closet, currently furnished and used as a THIRD BEDROOM, make the home live larger than expected. Outside, enjoy a spacious deck, above-ground pool, fire-pit patio, expansive lawn and detached

Rare opportunity to own one of Oxford's finest two-family homes! Custom built by the original owners, this unique property was thoughtfully designed to give each residence its own private entrance, full basement, and attached garage while providing comfortable, independent living. The main home features a welcoming sitting room, private office, guest powder room, formal dining room with pocket and french doors, along with a spacious kitchen centered around an impressive 3' x 9' island. The kitchen opens to a great room with a fireplace, French doors leading to a beautiful outdoor entertaining area. Upstairs, you'll find a convenient laundry room with a utility sink, built-in ironing board, and access to a walk-in attic. The spacious primary suite includes a walk-in closet and a beautifully appointed bath. Three additional bedrooms and a full bathroom complete the second floor. The attached second residence offers an open-concept layout with two bedrooms, a full bathroom, in-unit washer