437 houses for sale in Kettletown

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

Welcome to 42 Berkshire Road, a charming 3-bedroom, 2 bath ranch! The upper level has a large bright living room with a window seat framed by bookcases and a cozy fireplace to warm your winter nights. There are 2 bedrooms, a full bath, kitchen and dining area with French doors leading to a patio. Heading down the spiral staircase to the lower level you are welcomed into a large living/family room. This level has a full bath, kitchenette, bedroom and a slider to the deck for relaxing, barbeques, or gazing at the stars. Perhaps a primary suite or guest lodging, lots of possibilities. The shed is large enough to store your outside furniture and gardening tools. Convenient to I-84. An Absolute must see! Highest and Best by Tuesday, 9/8/2026 at 5:00pm

Incredible custom built home sited on a serene 1.61-acre lot with views of an adjacent pond. At over 6000 SQ FT this prestigious home with 4 bedrooms and 2.5 baths, this house checks all the boxes and more! A sundrenched great room has ~14 ft ceilings, wood molding and double arched door leading to a huge 1200 sq ft deck. Stunning open floor plan kitchen with granite counters, wood cabinets and built-ins flows seamlessly to a dining area for easy entertaining. An arched doorway leads to a 22x 27 FT living room with ~14 ft ceilings, stone fireplace, oversized windows and two arched glass doors leading to the deck. There is a half bath, pantry closet, laundry room and a cozy den with fireplace. A library and a beautiful marble and tile entryway complete the 1st floor. The 2nd level features a two-room primary suite with a dressing room with a stone fireplace, large bedroom with vaulted ceilings, exposed wood beams and a huge 25x10 walk-in closet. An en-suite bath is just off the dressing

Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportuni

Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportuni

Welcome to 10 Pearl Street, a spacious and beautifully refreshed Colonial tucked into a desirable Newtown neighborhood just moments from the shops, restaurants and community charm of Sandy Hook Village. Fresh interior paint, new carpeting, updated lighting and new hardware create a bright, polished feel throughout. The main level offers an inviting two-story foyer, two private offices and a comfortable family room centered around a wood-burning fireplace. The kitchen features new appliances, a propane gas range, center island and pantry, with easy access to the deck for outdoor dining and entertaining. A refreshed powder room and laundry room complete the first floor. Upstairs, the spacious primary suite includes a walk-in closet and private bath with double sinks and a tiled shower. Three additional bedrooms, two with Elfa closet systems-share a generously sized hallway bathroom with double sinks. The finished lower level adds valuable flexibility with tile flooring, a freshly painted

Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive

Vacation at home and live your best life in this meticulously maintained, energy efficient waterfront cottage. Tucked away on a rustic private road on the scenic shores of Lake Zoar, this light filled home offers a rare opportunity to embrace a peaceful lakeside lifestyle as either a year round residence, or an enchanting weekend getaway. Imagine feeling a million miles away from the fast pace of the world while remaining just minutes away from local shopping, dining, and highway access - all while being less than 90 minutes away from Manhattan. Stepping inside, the open concept main level offers seamless indoor/outdoor living and exceptional craftsmanship with carefully curated features throughout the entire house. The home features designer inspired lighting throughout that uses only 10% of traditional energy consumption. In the cozy living room, fully wired for surround sound, enjoy energy independence with a high efficiency wood stove insert in your fully operational fireplace. Fre

Welcome to Old Field, one of Southbury's most sought-after communities! This beautifully maintained end-unit townhome offers the perfect blend of privacy, space, and convenience. Featuring 3 bedrooms, 3.5 bathrooms, and a desirable first-floor primary suite, this home is designed for comfortable everyday living and effortless entertaining. The spacious eat-in kitchen boasts granite countertops, a center island, and ample cabinetry, while the open-concept living and dining area is highlighted by a soaring cathedral ceiling, gas fireplace, elegant moldings, oversized windows, and French doors leading to a private terrace. With three distinct living areas spread throughout the home, there is plenty of flexibility for guests, a home office, hobby space, or multi-generational living. Enjoy the convenience of an attached two-car garage and the peaceful setting of this Nantucket-style community, consisting of just 51 homes nestled on nearly 27 picturesque acres. Residents enjoy access to exce

Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive

Welcome to 42 Berkshire Road, a charming 3-bedroom, 2 bath ranch! The upper level has a large bright living room with a window seat framed by bookcases and a cozy fireplace to warm your winter nights. There are 2 bedrooms, a full bath, kitchen and dining area with French doors leading to a patio. Heading down the spiral staircase to the lower level you are welcomed into a large living/family room. This level has a full bath, kitchenette, bedroom and a slider to the deck for relaxing, barbeques, or gazing at the stars. Perhaps a primary suite or guest lodging, lots of possibilities. The shed is large enough to store your outside furniture and gardening tools. Convenient to I-84. An Absolute must see! Highest and Best by Tuesday, 9/8/2026 at 5:00pm

COMPLETED AND READY TO MOVE IN! Luxury new construction set on a scenic 3.25-acre homesite. This 4BR, 3.5BA home offers 3,674 sq ft of beautifully finished living space including a walkout lower level. The exterior features board-and-batten siding and a covered front porch with composite decking. Inside, a bright open floor plan with hardwood floors throughout the main level includes a dedicated office, formal dining room, and a stunning kitchen with stone countertops, high-end stainless appliances including a double oven, a large island with sink, and a spacious walk-in pantry with custom shelving. The kitchen flows seamlessly into the family room with a gas fireplace and shiplap feature wall. A mudroom area just off the garage adds everyday convenience. Upstairs, the primary suite offers a walk-in closet and spa-like bath with double vanity, tiled shower, and heated marble floors. Three additional bedrooms provide generous space, including one with a large adjoining bonus room ideal

Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while the remaining units present an opportunity for renovation and value-add potential. The separate commercial building offers flexibility for a variety of business, office, or retail uses, creating multiple income opportunities on a single property. Properties offering this combination of residential and commercial space in such a prime Woodbury location rarely become available. Whether you're looking to expand your investment portfolio or reimagine a mixed-use property with significant upside, this is an opportunity not to be missed. Property is being sold as-is. Do not go on the property withou

Timeless Elegance and Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with p

Welcome home to this beautifully maintained Colonial-style Tudor, offering nearly 3,000 square feet of living space with 3 bedrooms and 3 full baths. Thoughtfully cared for by the same owners for the past 27 years, this inviting home offers a wonderful blend of comfort, character, and functionality for the whole family. The main level offers a spacious layout with formal living room and dining, updated kitchen, and beautifully updated bathroom, creating a comfortable setting for both everyday living and entertaining. The finished basement provides additional living space, complete with a gas fireplace and convenient walkout access to the backyard. Additional room downstairs offers flexibility for a home office, guest room, gym, playroom, or potential fourth bedroom. Set on 1.75 acres, the property boasts a spacious backyard with plenty of room for outdoor enjoyment, gardening, and recreation, while a private pond adds a peaceful, picturesque touch to the natural surroundings. The back

Perfectly perched among the rolling hills of Southbury, 132 Lurther Dr. offers the ideal combination of privacy without seclusion, along with more amenities and upgrades than typically found in this price range. This 4-bedroom, 3.5-bath ranch-style home delivers single-level living at its finest with a versatile, flowing floor plan perfect for entertaining, relaxing, working from home, and everyday living. The refreshed eat-in kitchen features abundant cabinet and counter space, stainless steel appliances, and plenty of room for the aspiring chef to create and gather. Spacious living and family rooms provide the perfect setting for hosting friends, watching the big game, or enjoying movie night. The primary suite is a true retreat with an updated spa-inspired bath and generous closet space, while three additional bedrooms are complemented by two updated full baths. Recent improvements include fresh interior paint, updated flooring throughout much of the home, a new front porch, bluesto

Welcome to 60 Old Field Road! This light-filled Contemporary Cape style home blends timeless charm with modern updates. Featuring hardwood and ceramic tile flooring, beautiful wood trim, solid wood doors, and fully renovated kitchen with granite countertops, recessed lighting, crown molding and ceiling fan. The upstairs bath offers both a Jacuzzi and separate shower. Whole house security system with 2 hard wired outside cameras. Situated on a private, tree-lined.46 ac lot with a fire pit, spacious deck with hot tub. Enjoy the convenience of a short walk to main street, also an ideal commuter location. An added plus there is just one owner of the home, he also built it! In keeping with efficiency the owners designed the home so that the ceiling fans work to circulate the air in the home (both upstairs and down stairs) Warm air when using wood stove and cool air when using the to built in a/c units. 74 Old Field lot also MLS# 24200531

Welcome to this spacious 3-bedroom, 2.5-bath townhouse end unit condo nestled in the heart of Sandy Hook. Offering a wonderful combination of comfort, privacy, and convenience, this home is an ideal opportunity for those looking to enjoy the charm of Sandy Hook with the ease of low-maintenance condo living. The thoughtfully designed layout features two spacious bedrooms on the upper level, each with its own private full bathroom, providing comfort and privacy for residents or guests. The third bedroom is located on the lower level, offering excellent flexibility as a guest bedroom, home office, den, or additional living space. The main living level provides a welcoming setting for everyday living and entertaining, with a comfortable living area, kitchen, dining space, and convenient half bath. The versatile floor plan offers plenty of room to make the home your own. Enjoy the convenience of being within walking distance of local shops, restaurants, cafes, and community amenities in the

New construction in 2021, this exceptional waterfront home blends modern design, comfortable living, and an unbeatable location. With 3 bedrooms, 3 full bathrooms, and 1 half bath, the layout is both spacious and functional. The heart of the home is the open floor plan, where a luxury kitchen flows seamlessly into the main living area beneath impressive, vaulted ceilings, creating a bright and welcoming space for everyday living and entertaining. The main-level primary bedroom suite offers the ease of one-floor living and features an en suite bathroom and walk-in closet. A dedicated office provides the perfect work-from-home setup or quiet retreat. The finished lower level expands the home's versatility with a huge rec room plus a separate gym or crafting room, giving you flexible space to fit your lifestyle. Enjoy outdoor living in every season from the covered deck and covered patio, both ideal for relaxing, dining, or hosting guests. Direct water access adds to the appeal, along wit

Amazing waterfront opportunity with breathtaking views of Zoar Lake and Kettletown State Park! Offered for the first time in nearly 40 years, this rare property combines an irreplaceable setting with exceptional craftsmanship. The interior showcases the work of a master finish carpenter, featuring custom trim, built-ins, and incredible closet space rarely found today. Because of the owner's health, the exterior has experienced deferred maintenance in recent years, creating an excellent opportunity for the next owner to restore and personalize this special home. Whether you're looking for a year-round residence, weekend retreat, or investment, the location and views are unmatched. Property is being sold AS IS. Don't miss this chance to own a piece of Zoar Lake waterfront that seldom becomes available

Timeless Elegance and Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with p

Incredible custom built home sited on a serene 1.61-acre lot with views of an adjacent pond. At over 6000 SQ FT this prestigious home with 4 bedrooms and 2.5 baths, this house checks all the boxes and more! A sundrenched great room has ~14 ft ceilings, wood molding and double arched door leading to a huge 1200 sq ft deck. Stunning open floor plan kitchen with granite counters, wood cabinets and built-ins flows seamlessly to a dining area for easy entertaining. An arched doorway leads to a 22x 27 FT living room with ~14 ft ceilings, stone fireplace, oversized windows and two arched glass doors leading to the deck. There is a half bath, pantry closet, laundry room and a cozy den with fireplace. A library and a beautiful marble and tile entryway complete the 1st floor. The 2nd level features a two-room primary suite with a dressing room with a stone fireplace, large bedroom with vaulted ceilings, exposed wood beams and a huge 25x10 walk-in closet. An en-suite bath is just off the dressing

Amazing waterfront opportunity with breathtaking views of Zoar Lake and Kettletown State Park! Offered for the first time in nearly 40 years, this rare property combines an irreplaceable setting with exceptional craftsmanship. The interior showcases the work of a master finish carpenter, featuring custom trim, built-ins, and incredible closet space rarely found today. Because of the owner's health, the exterior has experienced deferred maintenance in recent years, creating an excellent opportunity for the next owner to restore and personalize this special home. Whether you're looking for a year-round residence, weekend retreat, or investment, the location and views are unmatched. Property is being sold AS IS. Don't miss this chance to own a piece of Zoar Lake waterfront that seldom becomes available

Welcome to Old Field, one of Southbury's most sought-after communities! This beautifully maintained end-unit townhome offers the perfect blend of privacy, space, and convenience. Featuring 3 bedrooms, 3.5 bathrooms, and a desirable first-floor primary suite, this home is designed for comfortable everyday living and effortless entertaining. The spacious eat-in kitchen boasts granite countertops, a center island, and ample cabinetry, while the open-concept living and dining area is highlighted by a soaring cathedral ceiling, gas fireplace, elegant moldings, oversized windows, and French doors leading to a private terrace. With three distinct living areas spread throughout the home, there is plenty of flexibility for guests, a home office, hobby space, or multi-generational living. Enjoy the convenience of an attached two-car garage and the peaceful setting of this Nantucket-style community, consisting of just 51 homes nestled on nearly 27 picturesque acres. Residents enjoy access to exce

Welcome home to this beautifully maintained Colonial-style Tudor, offering nearly 3,000 square feet of living space with 3 bedrooms and 3 full baths. Thoughtfully cared for by the same owners for the past 27 years, this inviting home offers a wonderful blend of comfort, character, and functionality for the whole family. The main level offers a spacious layout with formal living room and dining, updated kitchen, and beautifully updated bathroom, creating a comfortable setting for both everyday living and entertaining. The finished basement provides additional living space, complete with a gas fireplace and convenient walkout access to the backyard. Additional room downstairs offers flexibility for a home office, guest room, gym, playroom, or potential fourth bedroom. Set on 1.75 acres, the property boasts a spacious backyard with plenty of room for outdoor enjoyment, gardening, and recreation, while a private pond adds a peaceful, picturesque touch to the natural surroundings. The back

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best

HIGHEST and BEST OFFER BY 5 PM WEDNESDAY 9/2/26* Beautifully maintained Raised Ranch nestled on a quiet cul-de-sac with plenty of privacy and the perfect, professionally landscaped, level yard for outdoor enjoyment. This pristine home is in a fantastic commuter location and just minutes away from parks, schools, shopping, restaurants and more. Just move in and relax because this home comes with many updates: a new roof, refrigerator, range/stove, family room wall to wall carpeting, new central air motor, newly stained hardwood flooring, complete interior painting w/beautiful crown molding, newer boiler and gutters. Also, peace of mind comes with a generator hookup in the garage and being close to the fire department and medical facilities. This desirable, 3 bedroom, 1 1/2 bath Raised Ranch has charm inside and out hosting central air for those hot summer days and the comfort of snuggling up around the living room gas fireplace. Windows and garage doors are double paned and insulated. E

New construction in 2021, this exceptional waterfront home blends modern design, comfortable living, and an unbeatable location. With 3 bedrooms, 3 full bathrooms, and 1 half bath, the layout is both spacious and functional. The heart of the home is the open floor plan, where a luxury kitchen flows seamlessly into the main living area beneath impressive, vaulted ceilings, creating a bright and welcoming space for everyday living and entertaining. The main-level primary bedroom suite offers the ease of one-floor living and features an en suite bathroom and walk-in closet. A dedicated office provides the perfect work-from-home setup or quiet retreat. The finished lower level expands the home's versatility with a huge rec room plus a separate gym or crafting room, giving you flexible space to fit your lifestyle. Enjoy outdoor living in every season from the covered deck and covered patio, both ideal for relaxing, dining, or hosting guests. Direct water access adds to the appeal, along wit

Privately tucked away in Monroe's desirable Stevenson area, 205 Cottage Street offers space, character and tremendous potential! This charming Cape is ready for updating and a new owner's personal vision. The spacious, flexible layout begins with an oversized living room with fireplace, perfect for cozy evenings or lively gatherings. French doors open to a versatile den or home office with deck access. The deck is also accessed from the kitchen for easy indoor-outdoor entertaining. The dining room features custom built-ins, while the kitchen offers a new tile floor and stainless steel appliances. A main-level bedroom and full bath provide convenient one-level living potential. Upstairs are two generously sized bedrooms with deep closets and a second full bath. The finished lower level offers a family room with fireplace accent, a separate bonus room ideal for a gym, office or guest space, plus laundry and abundant storage. Outside, enjoy an above-ground pool, established gardens and a

Exquisite 4-Bedroom Colonial on a Private Lot* Welcome to your dream home-a stunning 4-bedroom colonial nestled on an interior lot with a 3-car garage, offering both privacy and luxury. Professionally landscaped with elegant landscape lighting, security lighting, and motion detection, this home is a true gem. As you enter through the grand 2-story foyer adorned with a new chandelier, you'll be greeted by gleaming hardwood floors that flow throughout the main level. The formal dining room is a masterpiece, featuring a tray ceiling, crown molding, medallion, built-in speakers, and fixtures and mirrors from Drexel Heritage. The adjacent butler's pantry, complete with a wine rack and raised panel cabinetry, adds a touch of convenience and sophistication. The living room boasts hardwood floors, integrated speakers, 2-piece crown molding, and a stylish half bath with tile flooring. A dedicated office space, equipped with built-ins, a closet, and recessed lighting, provides the perfect enviro