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$775,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24138386 MLS
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!

28 School St, Woodbury
$1,350,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24171849 MLS
Tucked behind mature trees and framed by classic stone walls, this remarkable Stonington property feels more like a private country estate than a traditional residence. Set on nearly three beautifully maintained acres, the grounds unfold with expansive lawns, established gardens, and peaceful outdoor spaces that create an immediate sense of calm and privacy. The setting tells a story of timeless New England charm and understated elegance. Inside the home is filled with natural light and thoughtfully designed living spaces. French doors open to an expansive bluestone patio designed for outdoor entertaining, quiet evenings under the stars, and effortless indoor outdoor living. The kitchen was designed for gathering, offering generous workspace, quality appliances, and views across the surrounding landscape. Throughout the home, historic architectural elements are balanced with tasteful modern updates, creating spaces that feel warm, refined, and inviting. Originally part of the historic Stone House estate, the residence carries a unique sense of heritage while offering the ease of contemporary living. The primary suite serves as a peaceful retreat with spa like finishes and carefully integrated original stone details. Every room feels connected to the beauty outside, whether overlooking the lawn, mature trees, or the property's idyllic natural surroundings. Located minutes from Mystic, fine dining, marinas, and the shoreline. 2 hours to NYC and Boston

1335 Pequot Trl, Stonington
$1,999,999
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24168304 MLS
Experience the character of the historic Northup-Scott House (c.1760), thoughtfully updated for today's lifestyle and set on four scenic acres. This well-maintained home offers a flexible floor plan with formal living and dining rooms, a spacious keeping room with original fireplace, a sun-filled family room with dramatic architectural window, private office, and first-floor guest suite. The renovated kitchen features a La Cornue range, 48 inch Pro Sub-Zero refrigerator/freezer, Wolfe double ovens, updated countertops, and opens seamlessly to the main living spaces. The second floor includes the primary suite, four additional bedrooms, three updated baths, and laundry room. A unique loft overlooks the impressive barn/great room, offering exceptional space for recreation, studio, gym, or entertaining. The owners put in $1M+ of improvements including newer roof, 75 thermopane windows, refinished hardwood floors, updated mechanicals, installed central air, interior and exterior painting, and renovated full bathrooms. Also purchased lot on Ridgefield border for $299K to allow seemless flow thru circular driveway. Outdoor amenities include pond, tennis court, expansive yard, gazebo and beautiful porch spaces ideal for relaxing or entertaining. A legal rental apartment provides added flexibility for guests, extended family, or supplemental income. A true Wilton gem.

1090 Ridgefield Rd, Wilton
$895,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172742 MLS
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.

253 Bacon Pond Rd, Woodbury
$3,500,000
7 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24169503 MLS
This stunning 1874 Federal house sits on a 3.93-acre lot and backs up to land-trust property. It was fully renovated and designed by Percy Steinhart, the design maven who created Stubbs & Wooton shoes. The estate contains a 6,641 square foot Main House, plus a wonderful Pool House and Carriage House. In the Main House, the spacious Entry Hall leads to the Living Room with a fireplace and a charming bay window. A large Library with a fireplace opens into a spacious Garden Room. The elegant Dining Room has a corner fireplace and double exposures. Adjacent is a gourmet Kitchen with a large island, high-end appliances, and a sizeable breakfast area with a spacious Cloak and Powder Room nearby. The front and back staircases lead to the second floor and a Primary Suite consisting of a large bedroom with a bay window and fireplace, and an elegant en-suite Bath. A second Bedroom with a fireplace is adjacent to the Primary. Two additional Bedrooms with en-suite Baths, and a Laundry Room, complete the second floor. On the third floor is a center gathering room plus two large Bedrooms and Baths. A large, unrenovated room has potential for use as an additional Bedroom, Gym, or Office. The Basement has a two-car garage with a Half Bath and generous storage rooms. The property is beautifully landscaped with a Croquet Lawn, a large pool, and Pool House with an outdoor fireplace for cooking, and a Greenhouse. The Main House and Pool House have updated HVAC systems with Central Air.

148 North St, Litchfield
$2,950,000
7 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24171893 MLS
Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and equestrian excellence. Spanning 27.3+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence/Inn, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The main house/inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 sqft heated indoor arena, which includes an owner's apartment and viewing area - and a professional grade outdoor ring. Enjoy all the area attractions including Tanglewood, the Mount, MASS MoCa and breathtaking hiking trails.

802 State Rd, Richmond
$874,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24165323 MLS
One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office, providing a dedicated work environment. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. As a gateway to the Litchfield Hills, the area provides access to a wider region known for its natural beauty and diverse attractions. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce.

339 Main St S, Woodbury
$1,495,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24067675 MLS
Rarely available. 1880 antique gem on 10 acres, with a first level primary bedroom and bath, situated on one of Bridgewater's most prestigious and quiet roads, offering a private setting. This residence masterfully blends historic character with an airy, open floor plan where the kitchen flows seamlessly into a spacious great room and a formal living room anchored by a classic fireplace. The interior living space consists of a main floor primary bedroom and bath, second level with 2 bedrooms and shared bath and a third level bedroom with it's own bath. The spaces transition beautifully to a 24 x 18 screened porch with slate flooring, opening onto a bluestone terrace. Perfect for entertaining, the terrace overlooks the pool and captures western exposures. The property is further enhanced by a two-story barn, providing ample space for storage or workshop. This is a unique opportunity to own a quintessential New England retreat in a premier location.

197 Skyline Ridge Rd, Bridgewater
$679,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24162576 MLS
Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a mahogany-floor kitchen. Plus a mudroom/laundry room leading to the back patio. A large barn provides ample storage, and the property includes a 1,250-gallon 4-bedroom septic tank installed in 2008, a fully fenced backyard, and a 24-foot-wide new asphalt driveway. Recent upgrades include a new barn roof and framing, new 200-amp electrical panel and some wiring in the main house, insulated exterior walls, remodeled shower and fireplace, new wainscoting in the upstairs hallway, new glass backsplash in the kitchen, and restored original wood floors upstairs. Enjoy relaxing on the front porch or rear stone patio and take advantage of nearby hiking trails, parks, and open space, with Southbury, Bridgewater, and Washington town centers just a short drive away. Confirmed appointment required for showings.

216 Baker Rd, Roxbury
$985,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24159885 MLS
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.

179 South St, Roxbury
$399,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24147691 MLS
Built in 1755, this interesting antique four-bedroom home offers classic country charm and the warmth of a place meant to be lived in and loved. Thoughtful and recent updates including new triple-pane windows, a Buderus boiler with four heating zones, and a French drain system in the basement, along with central air, provide comfort and peace of mind for everyday living. The home is ready to welcome its new owners, with space to settle in now and gradually add personal touches over time. A standout feature on the property is a 24' x 36' metal-sided three-bay garage with two overhead doors, a rear sliding door, full insulation, 220-volt service, and an 18' x 16' loft with steel stairs-ideal for car enthusiast, storage, hobbies, or a home workshop. Enjoy 1.32 acres of usable space surrounding the home for maybe a garden or play. Come take a look and see how this home can fit your lifestyle!

392 Boston Neck Rd, Suffield
$3,200,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24069608 MLS
Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a two-car detached garage, a sauna and spa room, Tabacco Barn & an expansive horse barn with fully operational paddocks complete with water and electricity. The artist's extraordinary vision brings the estate to life, creating a museum-quality residence that embodies elegance and sophistication. Rare materials and uncompromising attention to detail are evident throughout, including white oak hardwood floors sourced from MOMA, custom handmade mahogany windows fitted with imported wavy German glass, and advanced argon gas insulation. The chef's kitchen is thoughtfully designed with gnarled brass pulls, leathered limestone marble countertops, and a handmade, hand-painted tile backsplash. The retreat was constructed using Pennsylvania Lichen Stone, with stone walls and pillars carefully built to replicate the craftsmanship of centuries past. Bronze metal seamed-heated roofs, snow guards, and cupolas crown each structure, providing both durability and architectural distinction. The grounds are beautifully landscaped with rows of English dwarf boxwoods.

6 Hoyt Rd, Sherman
$5,000,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24148794 MLS
Originally built in the mid-1700s as a livestock farm, Deans Mill Farm has been beautifully restored & transformed into one of Ct's most charming destinations. Over 70 acres of pristine countryside in Stonington, property now operates as an event venue & 5-room bed & breakfast. It shares the grounds with Dragonfly Equestrian Center, stalls, Indoor/Outdoor riding ring, round pen, Multiple Buildings, wash stalls, trainer's apartment , hiking/horse trails & Dragonfly Disc Golf (NEW PRO SHOP)! Deans Mill Farm is ideal for weddings, parties, and special events. Guests may book individual rooms or reserve the entire property for privacy. The Farmhouse accommodates intimate indoor gatherings of up to 50 guests, while outdoor tented celebrations can host up to 250 guests with multiple picturesque backdrops. Whether you continue the existing business or make this amazing estate your home, the possibilities are endless. Picture the equestrian center as a unique indoor wedding venue, cocktail hour alongside the stalls, & private events where you live and entertain on-site. The equestrian center features a lovely living space above with a private deck-perfect for an owner, manager, or VIP guest. A small home serves as a full-time Airbnb or could house live-in help. The main estate functions as both an Airbnb and bridal suite. The beer garden hosts music every Thursday & Sunday, offering food, beer, and lively charm that adds to its income potential.

1189 Pequot Trl, Stonington
$699,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24139265 MLS
This authentic antique home is ideally located on one of Bethlehem's most desirable country roads, surrounded by other elegant historic properties. Meticulously maintained, it showcases true period charm with spacious rooms, high ceilings, original wide-board floors throughout, and a grand central chimney serving three fireplaces. The main level is perfect for both daily living and entertaining, featuring a large eat-in kitchen, a cozy wood-paneled study with built-in bookcases and fireplace, an inviting living room with fireplace, and a gracious formal dining room-all generously proportioned for comfortable gatherings. Upstairs you'll find three well-sized bedrooms, a full bathroom, a large walk-in attic over the kitchen that's already framed and ready to become a luxurious primary suite, plus a separate walk-up attic with plenty of headroom for additional finished space. The beautifully landscaped grounds include a sweeping level lawn, a fully approved extra building lot with its own private driveway, and a handsome post-and-beam barn offering ample room for vehicles, workshop space, and storage. Move right in and enjoy this classic beauty as-is, or take advantage of the rare opportunity to expand, add a guest house, or create a family compound.

114 Carmel Hill Rd N, Bethlehem
$825,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24130254 MLS
This reconstructed antique Colonial stands as an enduring example of 18th-century New England architecture. Reconstructed 50 years ago in its current setting in Lyme, this distinguished antique rests amid a rolling countryside of open meadow, sturdy hardwoods and bordered by the protected lands of Nehantic State Forest. Within its 3,400 square feet of living space are 2-3 bedrooms (town record says 2 bedrooms but there is a 1,000 gal. septic tank which would suit 3 bedrooms), two and a half baths, and an abundance of period detail. The Kitchen has been recently updated, while the baths are in need of renovation. Wide board floors, beamed ceilings, extensive moldings, and seven fireplaces showcase the craftsmanship of a bygone era, while 12 over 12 windows fill most rooms with natural light. Gracious formal rooms flow effortlessly into inviting gathering spaces, designed for comfortable living and easy entertaining. A finished walkout lower level provides flexible space-ideal for guests, office, or a private studio. Set off a quiet country road and surrounded by nature, the 'Gavitt House' offers timeless character, cherished privacy, and the rare opportunity to own a piece of New England's architectural heritage. Experience the rural charms of Lyme and the natural beauty of the Connecticut shoreline from this truly remarkable home.

55-2 Beaver Brook Rd, Lyme
$1,075,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24134097 MLS
Rare opportunity in Guilford! This home is currently used as a multifamily but can revert to a one family residence. Approximately 2400 sqft with the possibility of future expansion. Conveniently located close to Guilford's Historic Green, shops, restaurants, beaches and shoreline attractions.

51 Pearl St, Guilford
$7,400,000
7 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24129942 MLS
Reverie Farm is an exceptionally rare late 18th century stone and shingle estate, on more than one hundred acres, located in one of the highest and most private parts of Connecticut. Situated in the heart of Litchfield County, the property rises more than 1,200 feet in elevation across four distinct tax parcels, among which are several estate quality building sites. The setting is dreamlike in every season, and quintessentially New England. The 1799 Main house is an architectural marvel that achieves effortless balance between its Georgian-Federal, Dutch Colonial, and European elements. The effect is nothing short of entering a fairy tale, one that unfolds endlessly with each new detail that one discovers. An incredibly intimate home, the Main house at Reverie is nonetheless nearly 7,000 square feet and boasts seven bedrooms, five full and two half baths, several ancient fireplaces, and an historic "pub", reputed to be the oldest part of the house. There is a Gunite pool, privately situated among mature gardens, a tennis court, and a beguiling number of ancient trees around the property. Reverie has an overwhelming number of outbuildings including a guest house, separate dance studio with apartment, and an antique barn that was the studio of Abstract Expressionist painter Cleve Gray. Gray lived at the property with his wife Francine du Plessix, the noted journalist-novelist.

102 Melius Rd, Warren
$1,195,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24107477 MLS
There is a lot to enjoy here. A drive by of this property does not show the whole picture. This is an exceptional 3+ acre waterfront property on the Menunketesuck River. This package deal includes the well maintained Cerca 1745 Antique main home that is beautifully kept and appreciated, it shows beautifully. A fully equipped guest house is also included and has many options. A huge detached garage includes 4 bays, 3 drive-in bays and a workshop bay and is constructed with steel beam support and upper storage. There's also a two story "boat house" at the water's edge for a fun hang out by the water. The land dock platform is nice place for sitting by the river and throwing your rod and reel. A hardscape fire pit area overlooks the grounds to the river while you roast marshmallows. Access to Long Island Sound can be had right from your own back yard by small watercraft. Launch your Kayaks, paddleboards, tubes, and head to the L.I.S. Small trailered watercraft can be launched a minute away by car at the public small boat launch. The guest house on the property is perfect for in-laws, rental income, or home office space (purchaser to verify use). The beautiful Westbrook public beach is a few min drive away as well as marinas, restaurants, shopping, I-95 and RR nearby too. This property is located halfway between NYC and Boston.

448 Grove Beach Rd N, Westbrook
$675,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24127885 MLS
Toad Hall Offered for the first time in over forty-five years, Toad Hall is an utterly delightful 18th Century gem set on 11.6 acres in the heart of Cornwall Bridge, one of the most coveted areas in Litchfield County. This enchanting property features two barns, including a spacious main barn that has served as the studio of a renowned local artist. With its soaring space and rustic charm, it offers endless potential. Graceful stone walls meander through the property, surrounding the house and outbuildings, and weaving through the mature, thoughtfully landscaped gardens. The home itself is a true historic treasure, brimming with hand-hewn beams, original wood floors and classic moldings throughout. The entry foyer leads to a cozy living room on one side and a formal dining room currently used as a library with wood burning stove on the other. Upstairs you'll find four charming bedrooms and a full bath. The primary bedroom has sweeping views of the surrounding forest and mountains. The eat-in-kitchen opens to a delightful three season porch while a second porch at the back of the home overlooks a picturesque oasis. Extremely private, the property is bordered by large parcels of land providing unmatched tranquility and seclusion. Located in an area known for its natural beauty, farm to table dining, antiquing and shopping.

143 Whitcomb Hill Rd, Cornwall

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