luxury properties for sale New Milford, United States

Nestled in the serene cul-de-sac of prestigious Hubbell Mountain Farm North, 3 Partridge Trail in Sherman, CT, offers a luxurious and carefree lifestyle in a custom Colonial home. Set on 9.24 acres of level land adorned with colorful trees and charming stone walls, this property provides a tranquil retreat with picturesque country views. The open floor plan of this 4-bedroom, 2.5-bathroom residence exudes modern elegance and vintage charm, featuring gleaming hardwood floors, French doors, and antique finishes. A spacious living room, private home office, and powder room complete the main level, while a spindle staircase leads to the primary sanctuary upstairs, offering a walk-in closet and a luxurious marble bath with Edwardian-style console sinks, The heart of the home is the gourmet kitchen, complete with a center cherry top island, sun-drenched window seat, and stainless steel high- end appliances. It flows seamlessly into the elegant dining and family room area, highlighted by a custom, dual-sided smooth stone wood burning fireplace. and a soaking tub. Additional guest bedrooms with generous closet space and a shared full bath provide comfort and style, with a convenient laundry room rounding out the upper level. The full walk-out lower level offers potential for additional living space and storage, complemented by a 3-car garage and a Generac generator for added convenience.

Beautifully sited on nearly eight private acres with spectacular views, this turn-key Sherman estate encompasses an amenity-filled main residence, renovated guest house, spring-fed pond, classic stone walls, and exquisite English gardens. Offering luxurious resort-style living in one of Sherman's most captivating settings, the home welcomes you with a marble foyer leading to a dramatic double-height living room, where a wall of glass frames the breathtaking vistas. There are two luxurious primary suites - one on each level - with the main-level BR featuring a fireplace and French doors opening to the expansive deck. The top-of-the-line eat-in kitchen features custom cherry cabinetry, a sun-filled dining area, adjoining butler's pantry, and formal dining room. Upstairs are the second ensuite primary bedroom, two additional bedrooms, a den, full bath, and flexible space/artist's studio. The walk-out lower level is an exceptional space, with custom millwork, marble floors, an antique English bar, gas fireplace, sauna, and gym. Pocket doors reveal a spectacular in-home spa featuring a 24' x 14' heated Gunite spa pool, radiant heated floors, a Desert Aire climate-control system, and walls of glass overlooking the mountains and gardens. Outside, stone pathways meander through beautifully landscaped English gardens to the spring-fed pond and guest house, while classic stone walls and a circular driveway connect the main residence, guest house, and attached and detached garages. Despite its remarkable privacy, this beautiful estate is just minutes from Metro-North rail service and less than ninety minutes from New York City. Extensive recent improvements include a new roof, a newly paved circular driveway with restored stone walls, generator, beautifully updated bathrooms, custom built-ins, a steam room, a new four-person sauna, fresh interior and exterior paint, a fully renovated guest house, and thoughtfully redesigned Zen and English gardens. See attached list of features and capital improvements.

A classic Colonial set on a quiet cul-de-sac, this beautifully maintained home offers an exceptional combination of refined living spaces, thoughtful updates, and inviting indoor-outdoor living. A welcoming front porch leads to a bright, open interior featuring hardwood floors, oversized windows, formal living and dining rooms, and elegant architectural details including custom mouldings, wainscoting, a tray ceiling, and French doors. At the heart of the home, the well-appointed kitchen showcases custom cabinetry, granite countertops, stainless steel appliances, a large center island, and a sun-filled dining area with sliders opening to an elevated deck overlooking the patio and private backyard. Just beyond, the vaulted family room with a brick fireplace flows seamlessly into a spacious four-season sunroom and charming screened porch, creating the perfect setting for both everyday living and entertaining. A private office, laundry room, powder room, and full bath complete the main level, offering added flexibility for guests or multi-generational living. Upstairs, the primary suite features a walk-in closet and a beautifully renovated bath with a double vanity and glass-enclosed tiled shower. Three additional bedrooms include a private en-suite, while two share a Jack-and-Jill bath. The finished lower level expands the home's appeal with a recreation room, full bath, and dedicated media room complete with projector and screen for an immersive entertainment experience.

Nestled on a private, beautifully landscaped lot in the Barkwood Falls community, this charming four-bedroom, two full and one-half bath Colonial offers the perfect blend of comfort, style, and lake community living. The inviting main level features a spacious eat-in kitchen with granite countertops and tile flooring, a formal dining room, a cozy family room with a fireplace, and a sun-filled sunroom with pellet stove and vaulted ceilings that brings the outdoors in. Upstairs, you'll find a spacious primary suite along with three additional bedrooms, providing plenty of room for family and guests. Outside, the grounds have been lovingly cultivated using many native species, creating a spectacular perennial display of color and texture throughout the seasons. Just steps from your door, enjoy Barkwood Falls' private sandy beach, picnic area, playground, and boat launch. Dock slips are available by waitlist for just $25 per foot, while kayak or canoe storage is only $175 per space annually. The low annual association dues of just $200 makes it easy to enjoy all the amenities this wonderful lake community has to offer. Conveniently located close to shopping, downtown, and major highways, this exceptional home offers the perfect balance of privacy, convenience, and year-round recreation.

Instantly inviting this pristine circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with beautiful Antique wide board wood floors and it really celebrates the natural light in every room and enjoys woodland and meadow views with peeks at gardens right outside the windows. The Living room is open to both the formal dining room with a gas fireplace and the recently updated the kitchen. Two stone patios one in the front of the house and another in the rear of the house create private places to relax or entertain or just soak up the lovely scenery at different times of day. The primary bedroom is a quiet private suite at the back of the house There is a small bedroom also used as an office. There is a mudroom with laundry. The property features a very detailed designed horse barn that stuns in it beauty yet is also completely functional for a very happy horse or used as an art studio, office, guest quarters. The stall is built with I.P.E wood and the wash stall features hand painted Moroccan tiles. Antique brass fixtures. The potential use of this building is endless! The 2 car detached garage is a quick walk from the house and is actually pretty with Belgian Block floor so

Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

Candlewood Lake Waterfront — Experience refined lakefront living within the Candlewood Shores community, where a private dock and a natural connection to the water set the tone for this light-filled residence. Designed for both relaxation and entertaining, the home offers multiple levels of thoughtfully arranged living space and a seamless transition between indoors and out. The main level presents an open-concept design with cohesive tile flooring throughout the living, dining, and kitchen areas, creating a clean, airy aesthetic. A main-level bedroom and full bath provide versatility for guests or flexible living arrangements. Upstairs, the primary suite serves as a serene retreat, featuring soaring ceilings, sweeping lake views, and an expansive sitting area or office. The lower level extends the home's lifestyle appeal with a bonus room, wet bar, and direct walk-out access to the patio and waterfront—ideal for effortless summer gatherings. Notable recent improvements include major system and exterior updates, offering ease of ownership.

Welcome to this beautifully maintained 4-bedroom home in a wonderful Brookfield location. A charming front porch greets you before stepping inside, where you will find a formal dining room and a private home office just off the entryway. The heart of the home is the spacious eat-in kitchen, complete with crisp white cabinetry, quartz countertops, a large center island, and a pantry. It flows effortlessly into the family room—anchored by a cozy gas-log fireplace—and offers sliding glass doors right out to the deck. Hardwood floors shine throughout the main living spaces, and a freshly painted interior makes the home feel incredibly bright and move-in ready. For everyday convenience, the main level also includes a laundry room, a powder room, and easy access to the two-car garage. Upstairs, the primary suite is a true retreat featuring a walk-in closet and a luxurious en-suite bath with a separate shower and jetted tub. Three additional spacious bedrooms share a full hall bath. Looking to expand? The unfinished lower level provides endless potential for a recreation room, studio, or home gym. Enjoy outdoor living on the back deck overlooking the yard, all while being just minutes from Candlewood Lake, shopping, dining, Route 7, and I-84. (Approx. 75 miles to NYC!)

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

Stone Bridge: The Ultimate Classic Country Estate - PERFECTION AND READY TO MOVE IN! Embodying the pinnacle of refined country living, Stone Bridge is a magnificent stone and shingle estate with Elevator to all floors and Geothermal Heating, that seamlessly marries timeless architectural grandeur with state-of-the-art modern amenities. Situated on over 24.9 private, bucolic acres in Washington, Connecticut's highly desirable Nettleton Hollow area, this masterfully crafted property offers an unparalleled sanctuary of elegance and privacy. Constructed by the HOBI Award-winning Corbo Associates, the residence spans more than 7,000 square feet of sophisticated living space, complemented by an additionally finished 3,100 square feet on the lower level. A seamless indoor-outdoor flow defines the main living areas, which open gracefully onto sprawling terraces and a covered patio complete with an outdoor fireplace. The manicured grounds serve as a private resort, featuring mature plantings, artisanal stonework, a full irrigation system, and a pristine, heated gunite pool. Inside, soaring ceilings and expansive walls of glass flood every room with natural light while bringing the breathtaking countryside views indoors. The estate features five luxurious bedroom suites, including the rare flexibility of both first- and second-floor primary retreats. An elevator effortlessly ensures absolute accessibility throughout the home. An entertainer's paradise, the estate boasts seven fireplaces, an elegant library, home theater, a game room, gym and a spectacular 1,500-bottle wine cellar with a dedicated tasting room. Culinary enthusiasts will appreciate the top-of-the-line main kitchen, which serves as the heart of the home, alongside a full butler's kitchen designed for seamless event hosting. Built to the highest standards of construction and energy efficiency, the home features sound-dampened walls, a comprehensive security system, an integrated generator, and central vacuum. Future-proof technology is woven throughout the property, utilizing a cutting-edge geothermal heating and cooling system and Cat 6 audio wiring for premium sound, data, and internet connectivity. The estate is approached via a long, meandering driveway that overlooks a nearby pond, leading to a three-car garage connected via a stately porte-cochere to a second garage. Stone Bridge is more than a residence; it is an extraordinary country lifestyle.

This classic center-hall Colonial combines a well-designed floor plan with a highly convenient neighborhood setting. Boasting approximately 1,800 square feet, four bedrooms, and two-and-a-half bathrooms, the home offers a comfortable scale where every room serves a distinct purpose. It features central air conditioning and hardwood floors throughout both levels. The main level includes a spacious living room and a dining room that opens seamlessly into the kitchen, creating a natural flow between spaces. Just beyond the kitchen lies a charming family room—a flexible area ideally suited for a den, home office, playroom, or casual relaxation. Upstairs, the primary bedroom includes a private en-suite bathroom, while three additional bedrooms share a full hall bathroom. A full, unfinished basement provides excellent storage and offers potential for future expansion. Outside, the level yard provides ample room to enjoy the outdoors while maintaining a comfortable sense of privacy from neighboring homes. Best of all is the location: an established, walkable neighborhood where homes feel connected without being crowded, placing everyday conveniences just minutes away. Ultimately, this traditional Colonial offers a practical layout, inviting outdoor spaces, and a location that makes daily life effortless.

Ideally situated on a quiet cul-de-sac of similar fine homes, this beautifully renovated four-bedroom Colonial offers an exceptional location just minutes from the Brookfield town line and the Candlewood Lake Lattins Cove Boat Launch, providing easy access to lake activities, shopping, dining, and commuting routes. Convenient to I-84, this home combines a peaceful neighborhood setting with everyday accessibility. Inside, the home blends classic Colonial design with extensive modern updates, including a brand-new roof (June 2025). The main level features new porcelain tile flooring in the entry, an upgraded kitchen with high-end appliances, and a newly renovated powder room appointed with premium Kohler fixtures, a Milano vanity, and an electric mirror. Fresh crown molding enhances the living and dining rooms, while a striking new chandelier welcomes guests in the foyer. Recessed lighting brightens the family and living areas, and hardwood floors extend throughout all bedrooms. The walk-out finished basement provides additional living space with fresh paint and quality laminate flooring. Outdoors, the oversized saltwater pool serves as the focal point for entertaining and relaxation, complete with an automatic cover and attractive new stone wall surround. A stone walkway from the street adds to the home's curb appeal. Additional features include a spacious attic, two-car garage, wiring for an interlock generator, and numerous thoughtful upgrades throughout. Owner/Agent.

Elegance, scale, and solitude define this exceptional home. Set behind a sweeping circular drive accented with custom pavers, this sprawling 4-bedroom, 3.5-bath residence seamlessly pairs refined craftsmanship with a resort-inspired outdoor sanctuary. Step into the center-hall foyer, flanked by formal living and dining rooms that showcase beautiful wide-plank hardwood floors and picturesque seasonal views. The heart of the home is the spectacular Great Room, highlighted by vaulted ceilings, exposed beams, a majestic center fireplace, and direct deck access for effortless indoor-outdoor entertaining. The expansive kitchen offers granite countertops, generous cabinetry& tile flooring with convenient access to the laundry room and garage. Just off the kitchen, a charming breakfast room set within a sunlit turret awaits, complete with an electric fireplace, vaulted ceilings, and its own deck entrance. The luxury main-level Primary Suite serves as a private retreat, offering a walk-in closet and a spa-like en-suite bath with an oversized glass shower, Bain Ultra Spa tub. Step from the bedroom onto a private deck with immediate access down to the gardens, patio, and pool. Upstairs, the balcony leads to a quiet reading space, leading to generously sized bedrooms with ample storage and dedicated baths-including a Jack-and-Jill layout-all enjoying lovely views. Outside, the grounds offer custom Gunite pool and spa, gazebo, private decks and patio. This beloved home is exceptional

This exquisitely appointed Colonial estate has the WOW factor! At its heart lies an opulant living room, where soaring cathedral ceilings meet a wall of grand windows, inviting the outdoors in, while a bespoke fireplace serves as a luminous anchor of comfort. The expansive, double height windows provide dramatic light to the open plan living/ dining/ kitchen. Miele and Bosch appliances are featured in the Chef's kitchen with a breakfast nook and a formal dining room adjoining. Transition effortlessly to the private, elevated deck; a serene sanctuary designed for seamless indoor-outdoor entertaining amidst tranquil vistas. Exceptional versatility defines the residence, featuring a main level Bedroom-ideal as a guest suite or private study; complete with an adjacent full bath. Retreat to the primary suite, a masterwork of design boasting vaulted ceilings, a statement chandelier and a cozy fireplace. This private haven further indulges with a dedicated seating area, an intimate balcony for morning coffee, full bath with double vanities, soaking tub, large stall shower AND an enormous dressing room. The two additional bedrooms are generously appointed with the convenience of walk-in closets and a Jack-n-Jill full Bath. The sun-drenched walk-out lower level is reimagined as the ultimate wellness retreat, featuring picture windows that frame the landscape. This multifaceted space offers a dedicated gym, spacious sauna and full Bath with rainfall shower for a true spa experience. Adjoining space could be used as a TV room, office/workspace, music studio or craft room. Perfectly situated on 3+ acres of manicured, private grounds with specimen plantings and trees, this residence offers an unparalleled blend of privacy, sanctuary, sophistication and refined living. Located only a few mins from the vibrant town of Kent with its cafes, restaurants, shops and art galleries. The Appalachian Trail, Lake Waramaug, Housatonic River for fishing, Kent Waterfalls are all only minutes away. Easy access to NYC and Metro North Trains! Floorplans available.

A welcoming front porch is the perfect 'rocking chair' spot...to take a breath of fresh air and gaze out over the serene, protected pasture stretching across the road. With freshly painted spaces, this classic farmhouse seamlessly blends New England charm with modern comfort, offering incredible value in the heart of Kent. Inside, newly refinished hardwood floors gleam under natural light, welcoming you into an expansive open-concept living space where kitchen, dining, and cozy moments flow naturally together around a magnificent fieldstone fireplace. The adjacent formal dining room and living room offer additional entertaining spaces. The story of relaxation continues upstairs in the impressive primary suite, defined by a vaulted ceiling which creates a bright, airy sanctuary. Here, you'll find a spacious walk-in closet and an en-suite bath designed for unwinding, complete with a soothing Jacuzzi tub and separate stall shower. Two guest bedrooms and a full bath complete this level. Down below, a finished lower level with glowing light and elegant French doors offers flexible space for a home office, media room or guest lounge that leads right out to the yard. Equipped with a high-ceilinged, attached two-car garage offering plenty of extra storage or workshop potential, the property's true magic extends far beyond its walls. With thirty acres of open space directly abutting the rear of the property, you'll enjoy total privacy and endless natural views all just minutes from Kent's vibrant village center, local dining, art galleries, skiing at Mohawk Mountain, scenic hiking trails, and the Housatonic River. Experience the best of Litchfield County living, less than 2 hours from Manhattan!

Escape to this mountaintop retreat with sweeping, unobstructed views located off one of the most desirable scenic roads in the Litchfield Hills. Set in complete privacy, this four-bedroom home offers a perfect blend of comfort and sophistication with an open-concept layout designed for both relaxation and entertaining. The chef's kitchen, featuring a central island, flows seamlessly into a cozy reading nook with fireplace, a screened porch, and a dining area that opens to an expansive deck overlooking the breathtaking vistas. The spacious living room, anchored by a striking fieldstone fireplace, also connects to the deck and includes a charming home office. Upstairs, the primary suite offers a private balcony, spa-like bath with soaking tub, and walk-in closet. An additional ensuite bedroom, two more bedrooms with a shared full bath, and convenient laundry complete the upper level. The walkout lower level provides versatile living space, currently used as a media room and gym, and includes a full bath. Located just minutes from the shops and restaurants of Kent's vibrant village center-and only two hours from New York City-this property is the ultimate country retreat.

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep. While honoring its historic character, the home has also benefited from over $300,000 in thoughtful improvements that enhance comfort and preservation without compromising authenticity. Notable upgrades include the installation of central air conditioning for modern year-round comfort and elegant copper gutters that complement the home's historic architecture while providing lasting durability. These investments ensure the property is as functional as it is beautiful, blending 18th-century craftsmanship with the conveniences expected today. Beyond the historical significance, this home offers genuine livability with four full bathrooms, one half bath, and spacious rooms designed for both elegant entertaining and comfortable everyday living. The residential zoning ensures a peaceful setting that honors the home's timeless nature. The location is equally enchanting. Situated near Hollow Park in Woodbury - a town Reader's Digest once described as simply charming - you'll enjoy walkable access to local restaurants, unique shops, and the vibrant heart of this beloved New England community. Opportunities to own a property of this caliber, significance, and authenticity come along once in a lifetime. Don't let this extraordinary piece of American history pass you by. Schedule your private showing today.

Timeless Elegance & 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 potential for expansion. A private patio, stunning formal garden with pagoda and mature trees offer the perfect setting for outdoor enjoyment. A recently renovated barn includes new structural beans and flooring. This lovely home offers in town conveniences like walking to restaurants, shops and local parades while set off of Main Street. Enjoy the beautiful historic architecture with the peace of mind that comes from a property that has been meticulously cared for inside and out.

Experience the perfect blend of sophisticated design and rural tranquility in Lakeside. This beautifully remodeled cottage has been reimagined with a distinct modern flair, offering a turnkey escape that balances contemporary finishes with the peaceful soul of Morris. This recent renovation has been executed with an eye for style, making it an ideal sanctuary for those seeking a chic weekend retreat from the city or a charming permanent residence. Set on a sprawling 3.68-acre lot, the property offers a rare level of privacy and serves as a true blank canvas for your future lifestyle. The interior radiates a bright, airy energy, featuring contemporary lines and thoughtful details that honor the home's original character. Outside, the vast grounds invite you to explore, garden, or simply soak in the quietude of Litchfield County. The location is a dream for outdoor enthusiasts and foodies alike. You are just moments away from the shimmering waters of Bantam Lake for summer recreation and the expansive trail systems of White Memorial Conservation Center for year-round hiking and exploring. When it's time to head into town, the iconic Litchfield Green is a short drive away, offering world-class restaurants, artisanal shops, and gourmet food markets. Whether you are looking for a minimalist haven or a stylish home base to enjoy the best of Northwest Connecticut, 72 Hickory Hill Road is a masterclass in modern country living.

Charming Country Cottage in the Heart of Kent Tucked away on a peaceful private road just a short walk from the vibrant village of Kent. This charming country cottage offers the perfect blend of privacy, convenience, and classic New England character. Surrounded by picturesque meadows and mountain views and located near the scenic Housatonic River, this home provides a tranquil setting while remaining close to everything Kent has to offer. A spacious deck welcomes you into a bright, open-concept main level featuring generous living and dining areas, ideal for entertaining or relaxing. Upstairs you'll find a large primary bedroom and two additional bedrooms, all served by a full bathroom. Whether you're searching for a full-time residence, a weekend getaway, or an investment property, this home offers endless possibilities to make it your own. Major improvements provide peace of mind, including a year old roof, new windows, well, and septic system. Enjoy the convenience of walking to Kent's charming shops, restaurants, Kent Center School, and the renowned Kent School. Metro-North train service to New York City is just minutes away making this an ideal country retreat with easy access to the city. Don't miss this opportunity to own a home in one of Litchfield County's most sought-after communities.

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to create a true family compound. Two additional buildable parcels are available from the same family. MLS 1037478 and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request. The exterior is as enchanting as the interior, offering a large heritage red brick patio that provides the perfect vantage point to overlook the acreage, which gently slopes down to a babbling brook at the property's edge. The outbuilding includes a charming potter's shed equipped with electricity, ideal for gardening, while the barn with original hand-hewn beams, lower-level stalls, and running water is ready for equestrian use or a premier hobby space. Bacon Pond House isn't just a home; it's a piece of history, updated for the way you live today. A 90-minute drive from the bustle of NYC, this property is moments away from the quaint shops, parks, and eateries of historic Woodbury.