369 houses for sale in Boston, Redding town Fairfield County Connecticut

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This architecturally distinctive mid-century modern Deck House offers a rare lifestyle retreat on two serene acres in Lower Weston. Designed to embrace its surroundings, the home features signature walls of glass, warm wood ceilings, and an open-flow layout that creates a seamless connection between the indoors and the natural beauty outside. The main residence makes an unforgettable impression with expansive windows framing sweeping lawn views and stunning western sunsets. At the heart of the home, a renovated kitchen with a large island flows into the dining and living areas, anchored by two wood-burning fireplaces. With four bedrooms and 3 full baths, the layout provides exceptional flexibility, including a dedicated home office and additional flex space perfect for a fitness studio or creative retreat. The primary suite continues the aesthetic with oversized windows overlooking the private grounds. The property transforms into a private resort with an expansive wrap-around deck and

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular-truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen-all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private

NEWLY PRICED* Tucked behind classic wood rail fencing and stone walls, this charming, beautifully updated Colonial offers turn-key living with a right-sized footprint in a private Weston setting. Thoughtful improvements include renovated baths, new windows, a new roof, new kitchen appliances and numerous additional updates-allowing the next owner to simply move in and enjoy. The welcoming floor plan makes smart use of every space, with formal living and dining rooms and French doors opening to an expansive wraparound deck for easy indoor-outdoor living. A sun-filled family room with vaulted ceilings adds an airy gathering space, while the well-appointed kitchen and powder room complete the main level. Upstairs, the primary suite features a custom walk-in closet and en suite bath, with two additional bedrooms and a full hall bath. The finished walk-out lower level, with its own entrance, adds valuable flexibility for a home office, playroom, fitness space or guests. Set on.83 private ac

Old Redding charm meets elevated modern living at this exceptional gated Contemporary Colonial offering over 4,700 SF plus approximately 1,800 SF of finished walk-out lower level. Set behind stately iron gates and stone pillars, a private drive leads to a dramatic marble foyer and grand staircase. The custom Clark Construction kitchen, enhanced in 2023, features dual full-size Thermador ovens, Sub-Zero refrigerator, quartz countertops, expansive island, and butler's pantry with additional Sub-Zero, opening to a sun-filled great room w/stone fireplace and wall of windows overlooking private, level grounds. Seamless indoor-outdoor living extends to an expansive deck surrounded by mature landscaping and stone walls. The main level includes a flexible private office suite with multiple entrances, sitting area, bedroom, and full bath, ideal for guests or multigenerational living. Upstairs, the primary suite offers a sitting area, dual-sided fireplace, automated blackout shades, 2 walk-in cl

Beautifully professionally landscaped, level 2-acre lot on the peaceful end of Newtown Turnpike, this charming 3-bedroom, 2.5-bath. Cape combines classic character with modern living. The home has been meticulously maintained and upgraded, offering a perfect retreat in the heart of Redding. Step into the heart of the home: a brand-new custom kitchen featured in the recently added expansion. Designed with both style and functionality in mind, the kitchen boasts white shaker cabinets, quartz countertops, a spacious center island with built-in microwave and beverage fridge, and high-end stainless steel appliances, including a gas cooktop and double-door refrigerator. Two large gold pendant lights and recessed lighting highlight the vaulted ceilings, creating a bright and luxurious atmosphere ideal for cooking and entertaining

Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home features a flexible floor plan with generous living areas, a finished lower level, and a bright four-season room that provides additional year-round living space. The main level has the convenience of first-floor laundry along with an additional room and full bath, creating an ideal setup for guests, or a home office, while the finished lower level adds even more flexibility for a den or entertaining. Enjoy the best of Weston living with award-winning schools, and convenient access to major commuting routes. Here's your opportunity to create your dream home in one of Fairfield County's most desirable communities

Beautifully professionally landscaped, level 2-acre lot on the peaceful end of Newtown Turnpike, this charming 3-bedroom, 2.5-bath. Cape combines classic character with modern living. The home has been meticulously maintained and upgraded, offering a perfect retreat in the heart of Redding. Step into the heart of the home: a brand-new custom kitchen featured in the recently added expansion. Designed with both style and functionality in mind, the kitchen boasts white shaker cabinets, quartz countertops, a spacious center island with built-in microwave and beverage fridge, and high-end stainless steel appliances, including a gas cooktop and double-door refrigerator. Two large gold pendant lights and recessed lighting highlight the vaulted ceilings, creating a bright and luxurious atmosphere ideal for cooking and entertaining

Welcome to 29 Lonetown Road, a timeless 1915 Colonial, where historic character, thoughtful updates and an extraordinary setting come together. Set on 1.5 picturesque acres, this lovingly maintained home has been cherished by the same family for more than 36 years and is ready for its next chapter. Inside, original hardwood floors, built-ins and beautiful period details create warmth and character throughout. The main level offers a gracious living room anchored by a stone fireplace, a formal dining room, and a stunning four-season sunroom filled with natural light. The large kitchen blends vintage charm with a commercial-inspired feel, featuring a 6-burner Garland range, center island, generous prep space, pantry with French doors, and easy access to both the bluestone patio and rear deck for indoor-outdoor entertaining. A convenient powder room completes the first floor. Upstairs, the spacious primary suite offers a light-filled retreat with an oversized bath featuring skylights, lar

An extraordinary expression of timeless elegance and refined living, this stunning Nantucket-style residence is set amidst 2.33 acres of meticulously landscaped grounds and enhanced by a spectacular heated gunite pool and spa, beautifully integrated into the property's lush and private surroundings. A grand two-story marble foyer framed by stately columns opens directly into the living room with fireplace, creating a striking first impression and immediate sense of scale and sophistication. The dining room with French doors to the terrace overlooks the resort-inspired outdoor setting, while a richly appointed library with custom built-ins, fireplace, and terrace access provides an elegant retreat. Designed for both everyday living and grand-scale entertaining, the gourmet kitchen serves as the heart of the home, featuring double ovens, two dishwashers, updated appliances, a large center island with breakfast bar, and an expansive dining area. The kitchen flows seamlessly into the drama

Welcome to an incredible opportunity in the highly desirable town of Weston! Set back from Newtown Turnpike on a secluded, level 1.33 acre lot, this exceptionally well maintained 3 bedroom, 2 full bath ranch offers 1,332 square feet of comfortable single level living with hardwood floors throughout and a detached two car garage. Ideally located near the Saugatuck Reservoir, Merritt Parkway, and Devil's Den Nature Preserve, the property is ready for its next owner's vision. Thoughtful updates could transform the existing home into a beautiful retreat, while the generous lot may offer exciting possibilities for expansion, including a potential second story addition or new construction, subject to town approvals. Surrounded by impressive neighboring homes, the possibilities here are substantial. Whether you're looking to renovate, expand, build new, or simply create your dream home while enjoying convenient single level living, this Weston property offers a rare combination of location, p

Privately set back from the road on 2.94 wooded acres, this spacious Redding Colonial offers versatile living space, treetop views, and a layout designed for both everyday comfort and entertaining. The light-filled main level features an inviting family room with a gas fireplace, built-ins, and French doors opening to a private deck and backyard. At the heart of the home, the eat-in kitchen includes a center island, butler's pantry, and casual dining area, while separate formal living and dining rooms provide additional space for gatherings. Upstairs, the primary bedroom includes a walk-in closet and a freshly renovated en suite bathroom. Three additional bedrooms and an expansive recreation room offer flexible space for a home office, playroom, or a media room. The finished walkout lower level provides even more living space, with a full bathroom, ample storage, a workshop area, and a separate room well suited for an office, gym, or hobby space. A large backyard deck and pergola ideal

Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the original windows and hand-laid stone floors to the reclaimed shiplap walls and solid wood doors, every detail honors the home's 1959 roots with modern systems and design. A recent full-scale renovation touched virtually every system in the home - HVAC, tankless water heater, plumbing, electrical, kitchen, baths, flooring, and millwork -move in with confidence and none of the guesswork of an older home. The main level offers the open, connected layout today's buyers are searching for: a flowing family, living, and dining space anchored by three wood-burning fireplaces, a dedicated home office, and a bright four-season sunroom perfect for year-round enjoyment. The kitchen is a true showpiece, featuring marble countertops and a professional-grade appliance suite, ideal for both everyday living and entertaining. Upstairs,

Privately set back from the road on 2.94 wooded acres, this spacious Redding Colonial offers versatile living space, treetop views, and a layout designed for both everyday comfort and entertaining. The light-filled main level features an inviting family room with a gas fireplace, built-ins, and French doors opening to a private deck and backyard. At the heart of the home, the eat-in kitchen includes a center island, butler's pantry, and casual dining area, while separate formal living and dining rooms provide additional space for gatherings. Upstairs, the primary bedroom includes a walk-in closet and a freshly renovated en suite bathroom. Three additional bedrooms and an expansive recreation room offer flexible space for a home office, playroom, or a media room. The finished walkout lower level provides even more living space, with a full bathroom, ample storage, a workshop area, and a separate room well suited for an office, gym, or hobby space. A large backyard deck and pergola ideal

Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the original windows and hand-laid stone floors to the reclaimed shiplap walls and solid wood doors, every detail honors the home's 1959 roots with modern systems and design. A recent full-scale renovation touched virtually every system in the home - HVAC, tankless water heater, plumbing, electrical, kitchen, baths, flooring, and millwork -move in with confidence and none of the guesswork of an older home. The main level offers the open, connected layout today's buyers are searching for: a flowing family, living, and dining space anchored by three wood-burning fireplaces, a dedicated home office, and a bright four-season sunroom perfect for year-round enjoyment. The kitchen is a true showpiece, featuring marble countertops and a professional-grade appliance suite, ideal for both everyday living and entertaining. Upstairs,

Beautiful and serene, this special property has been lovingly maintained by the same family for the past 37 years. Set on 6.18 picturesque acres in a desirable neighborhood surrounded by other expansive properties, the 4 bedroom, 3.5 bath home offers privacy, space, and a wonderful sense of tranquility. Well maintained throughout, the home features thoughtful updates, including a roof that is just 3 years old. With generous living spaces, a beautiful natural setting, and plenty of room to enjoy the outdoors, this property presents a wonderful opportunity to create your own lasting memories in a truly special setting

Bring your creativity and vision to make this distinctive home your own. Ideally situated in lower Weston, just 1 mile from the award-winning Weston schools and minutes, this contemporary style home is set on 2.23 private acres with a heated pool. The flexible, open floor plan features dramatic walls of glass that bring the outdoors in and showcase the beautiful surroundings year-round. The home offers 4 bedrooms. a private office, and a finished walkout lower level with direct access to the pool-perfect for entertaining, recreation, or extended living

Revive a bygone era in this enchanting circa 1924 estate, idyllically sited on 2.30 extraordinary acres along the scenic Aspetuck River. A classic white picket fence welcomes you to the Main House, surrounded by mature specimen trees, lush gardens, and breathtaking river views. Rich in history and timeless character, the residence showcases original architectural details, gracious living spaces, exposed beams, and inviting fireplaces that evoke the romance of a simpler time. Nearly every room captures tranquil water views and spectacular sunrises, creating a seamless connection to the serene natural landscape. Designed for both relaxed everyday living and memorable entertaining, this distinctive home offers warmth, charm, and endless possibilities. A separate 550-square-foot, three-room Guest Cottage with a fireplace and attached garage provides exceptional flexibility for guests, a studio, home office, or future restoration. The outdoor setting is nothing short of extraordinary. Expan

First time on the market in over 60 years! Welcome to this lovingly maintained split-level home nestled on a level lot on a quiet cul-de-sac in the heart of Ridgefield. This home has a floor plan that offers both functionality and flexibility, with ease of everyday living in mind. The main level has an eat-in kitchen, living room and a bright and airy sunroom that provides the perfect place to relax year-round. Upstairs, you'll find three bedrooms, a half bath in the primary bedroom, and a full bath in the hall. Pull-down attic access from the hallway provides exceptional, easily accessible storage. The lower level offers a spacious family room with a cozy wood stove, a full bath, and direct access to the attached two-car garage. The basement includes a flex room, ideal for a home office, fitness area, hobby space, or additional storage, along with a dedicated laundry and pantry room with convenient access to the utility area. This home features an attached two-car garage, a spacious d

WOW! Gorgeous MID CENTURY MODERN nestled on over 300 feet of direct Saugatuck river frontage! Enter to sweeping views of the leafy bucolic scenes of nature through the walls of glass on both levels. Light and bright white kitchen opens to lovely deck for effortless entertaining. The inviting living room has a stunning floor to ceiling fireplace for cozy fall evenings. The primary bedroom suite is complete with a spa like bathroom, walk in closet, laundry and convenient office -ALL with RIVER VIEWS. The lower level is a comfortable relaxing family room, two bedrooms and full bath with direct access to the slate patio-with RIVER VIEWS. Thru a separate entrance in the back there is a newly finished sauna and shower. The cottage has endless possibilities. home office, work out space, separate lounge area. AND of course has gorgeous RIVER VIEWS! Pool permit has been approved; renderings attached just steps from the new sauna/shower. A pool would be a great addition 46 Valley Forge, a stunni

An extraordinary expression of timeless elegance and refined living, this stunning Nantucket-style residence is set amidst 2.33 acres of meticulously landscaped grounds and enhanced by a spectacular heated gunite pool and spa, beautifully integrated into the property's lush and private surroundings. A grand two-story marble foyer framed by stately columns opens directly into the living room with fireplace, creating a striking first impression and immediate sense of scale and sophistication. The dining room with French doors to the terrace overlooks the resort-inspired outdoor setting, while a richly appointed library with custom built-ins, fireplace, and terrace access provides an elegant retreat. Designed for both everyday living and grand-scale entertaining, the gourmet kitchen serves as the heart of the home, featuring double ovens, two dishwashers, updated appliances, a large center island with breakfast bar, and an expansive dining area. The kitchen flows seamlessly into the drama

Discover a truly special country retreat where warmth, character and timeless New England charm come together. Tucked away at the end of a long private drive, this inviting home offers a refreshing departure from the ordinary, with a thoughtfully designed floor plan that creates comfortable, flexible spaces for today's lifestyle. Sunlight streams in, enhancing the home's welcoming atmosphere and unique architectural character. Rich in authentic details-including reclaimed hand-hewn beams, 2 fireplaces, brick and hardwood floors, a country kitchen and a screened porch-the home offers five bedrooms and five full baths. The dramatic great room is the heart of the home-a relaxed, barn-inspired space with soaring cathedral ceilings and painted floors, made for gathering. Flowing easily to the kitchen, screened porch and pool, it's where entertaining feels effortless and traditions are made. The expansive rec room, with soaring vaulted ceilings, is ideal for a home gym, golf simulator, offic

Revive a bygone era in this enchanting circa 1924 estate, idyllically sited on 2.30 extraordinary acres along the scenic Aspetuck River. A classic white picket fence welcomes you to the Main House, surrounded by mature specimen trees, lush gardens, and breathtaking river views. Rich in history and timeless character, the residence showcases original architectural details, gracious living spaces, exposed beams, and inviting fireplaces that evoke the romance of a simpler time. Nearly every room captures tranquil water views and spectacular sunrises, creating a seamless connection to the serene natural landscape. Designed for both relaxed everyday living and memorable entertaining, this distinctive home offers warmth, charm, and endless possibilities. A separate 550-square-foot, three-room Guest Cottage with a fireplace and attached garage provides exceptional flexibility for guests, a studio, home office, or future restoration. The outdoor setting is nothing short of extraordinary. Expan

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every turn, including a coffered ceiling living room, a banquet sized dining room with a curved wall of windows, and an octagonal office. French doors create a natural flow to two stone patios and sweeping lawns. The gourmet kitchen, appointed with four Wolf ovens, dual Sub Zeros and dishwashers, and extensive custom cabinetry, is designed for both comfortable daily living and memorable entertaining. The serene primary suite offers a private sitting room, balcony, barrel-ceiling dressing room, and an inspiring octagonal bathroom, while additional en-suite bedrooms and a full in-law suite provide exce

Quintessential New England Colonial meets updated living at this gracious home. Set amid mature trees, stone walls and beautifully established gardens, this 4-bedroom, 3.5-bath home offers wonderfully proportioned rooms in a private, park-like setting - yet remains a commuter's dream. Inside, freshly painted rooms, refinished hardwood floors, and abundant natural light create a warm and inviting backdrop. The elevated open kitchen has new appliances: Wolf gas range, Sub-Zero refrigerator, double wall ovens, Bosch dishwasher, Zephyr hood. A fully renovated mudroom adds everyday functionality. The lower level has a playroom featuring 2 walls of windows, a renovated bathroom, study/gym room and access to the outside with in-law or au pair possibilities. For the car enthusiast, hobbyist or collector, the completely renovated garage is exceptional-finished with epoxy floors, insulated garage doors with Wi-Fi openers, heating and cooling via mini-splits on both levels, and three 50-amp EV ch

Perfectly positioned on a quiet in-town street with no through traffic, this classic 1948 Cape offers the rare combination of privacy, neighborhood charm, and exceptional walkability. Set on a beautifully landscaped half-acre, the home blends timeless character with thoughtful updates, including refinished hardwood floors and a freshly painted exterior. Sun-filled living spaces feature detailed moldings, a fireplace, window-lined sunroom, home office, custom mudroom, and an updated kitchen with custom cabinetry, soapstone countertops, stainless appliances, and center island. Upstairs, the spacious primary suite includes an updated marble bath. The finished lower level with full bath and separate entrance is ideal for recreation, guests, gym, or in-law/au pair use. A large deck overlooks the expansive yard, while a roof replaced approximately five years ago, updated baths, and abundant storage complete the offering. What truly sets this home apart is its coveted walk-to-town location. E

Move right in and enjoy easy living just minutes from Main Street and all that Ridgefield has to offer! This light and bright two-level home offers 2 bedrooms plus a first-floor den and 2.5 baths, along with fresh paint and new flooring throughout the entire unit. The open-concept living and dining areas offer an easy flow for everyday living and entertaining, with sliders from the living room leading to a beautiful Trex deck. The first-floor den provides flexible space for a home office, guest room, or sitting area. Abundant storage throughout makes organization easy. The primary suite features brand-new hardwood floors, a large window, and two generously sized closets, while the primary bath offers a convenient walk-in shower. The second spacious bedroom is sunny and bright, with hardwood floors and a large closet. A full hall bath with a tub and shower provides additional convenience. In-unit laundry. Residents of Casagmo enjoy access to an in-ground pool, tennis courts, and basketb

The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous maintenance, and thoughtful updates throughout. Offering more than 4,100 square feet of living space, this distinguished 12 room residence features 5 bedrooms, 4 updated full baths, and an updated half bath. Details include the original historic front door, exposed beams, paned windows, hardwood floors, five fireplaces (one gas fireplace in the family room and four wood-burning fireplaces), and abundant natural light throughout. Designed for both elegant entertaining and comfortable everyday living, the home offers gracious living and dining spaces with exceptional versatility, including a private entra

A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. Albeit, the renovation of the property's antique 1,100 SF, 2 BR continually-rented cottage may be the financial coup for 42% marginal tax bracket (Fed+CT) buyers who assume a 6.25%, 80% ($2,080,000 of 2.6M asking) 30 yr. fixed mortgage. The rent, presently $30,000/yr and tax advantaged deductions will contribute funds that amortize $915,000 of the 2.080M. Accordingly, the effective purchase price could be $1,685,000. High-quality finishes aside, consider the setting: brook-fed pond for large-mouth-bass anglers and visiting egrets; stunning fall foliage surrounding the pond; 450 ft. long, bleached-stone, maple tree-lined driveway to the main house; just a 2-minute drive to the Weston Town Center and K-12 school campus; 150 SF of veggie-intensive raised beds along with wild blackberries, and Concord grapes where you mean