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$624,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24119748 MLS
Built by Dr. Elisha Sill, this 1800 clapboard, central-hall Georgian style home, boasts a mid-to-late 19th century English barn and a brick carriage house listed on the National Register of Historic Places. Rich in character and architectural detail, this spacious ten room residence boasts over $300,000 in upgrades and offers four bedrooms, two full and one half baths. A grand central hall welcomes you inside and sets the tone for the home's classic elegance. The remodeled kitchen features original wide board flooring, stainless steel appliances, and an expansive pantry, blending modern convenience with historic appeal. The formal dining room and inviting living room showcase beautiful and original wide board flooring and are the perfect area for entertaining. The second level offers four generously sized bedrooms with wide board flooring and two full baths. Set on approximately four picturesque acres, the property includes a carriage house, barn, and abundant space for gardens, outdoor recreation, or hobby farming. A rare opportunity to own a piece of Windsor history while enjoying the convenience of living near the center of town. There is tremendous value in the fresh interior paint (2026), fresh exterior paint and new garage doors (2025), new roof on the home (2024), new roof on the barn (2023), furnace and hot water heater (2023), central air (2023), remodeled kitchen (2015), and two story attached garage with studio (2010). Come on let's take a look inside

209 Palisado Ave, Windsor
$825,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204013 MLS
This beautiful old Colonial home was built on one of the first four parcels of land when Brooklyn was first settled. The historic character is seen throughout the home but with many modern amenities. Five Bedrooms, 2.5 Baths, 2 Fireplaces, 2 Woodstoves, Hot air heat, Newer Windows and beautiful old wood flooring. The attached heated workshop is state of the art and offers many uses. There is a very cool walkup attic, and several outbuildings. The land consists of 21.6 Acres of land with open fields, woodlands and frontage on Blackwell's brook. This lovely setting is off the main road for peace and quiet. The amount of frontage has potential for subdivision and is eligible for a free split.

26 Beecher Rd, Brooklyn
$3,395,000
7 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24202586 MLS
Cove Lawn - Historic Italianate Estate with Water Views & Guest House. Walk to Stonington Borough. Experience the charm of village living just moments from Historic Stonington Borough at Cove Lawn, a magnificent c.1860 Italianate estate steeped in local history and timeless elegance. Ideally located just a short stroll to the Borough's deep-water marinas, boutique shopping, seaside cafes, and fine restaurants, this extraordinary property offers the rare combination of estate privacy with walkable coastal village convenience. Set on 3.19 beautifully landscaped acres, the property features a stately 7-Bedroom, 5-Full and 2-Half Bath main residence, an attached au pair apartment, a sparkling inground pool, a charming 2-Bedroom, 1 1/2-Bath guest house, and an impressive three-bay garage/barn of approximately 2,000 sq. ft. The elegant 7,060 sq. ft. main residence has been carefully restored and thoughtfully modernized while preserving its historic architectural character. Inside, graceful 10+ foot ceilings, original hardwood floors, numerous marble fireplaces and exquisite period moldings create a sense of grandeur throughout. Many rooms capture lovely water views, bringing the beauty of the nearby harbor into everyday living. The 1,098 sq. ft. 2 Bedroom guest house provides ideal accommodations for extended family, guests, or caretakers, while the expansive grounds offer privacy and serenity rarely found so close to the village center.

259 N Main St, Stonington
$789,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204166 MLS
Surrounded by rolling farmland and open meadows, 16 Rhynus Road offers a peaceful country setting in beautiful Sharon, Connecticut. Set on 1.07 acres, the 3-bedroom, 3-bath main home offers 2,595 sqft, an in-ground pool and a separate cottage with dedicated parking. Hardwood floors run throughout, including antique hardwood floors in the original portion of the home. A large bay window fills the living room with natural light. The updated eat-in kitchen opens to the dining room and a spacious screened-in porch-an inviting extension of the living space overlooking the side yard. The family room features exposed beams and a wall of glass doors opening to the updated deck and pool area, while the primary suite has a private deck with stair access to the pool. Upstairs, the current laundry room offers flexible space for a home office or other use if laundry is relocated, and a floored, insulated attic provides generous storage. The renovated 475 sqft detached studio cottage, currently rented for the academic year, features a kitchen, full bath and open living/sleeping space. Updates include the cottage renovation, newly graveled driveway, kitchen upgrades, split heating/cooling, replacement windows and sliding doors, decks, front porch and electrical improvements. A new septic system serving the main house and cottage will be installed prior to closing. Enjoy a peaceful Northwest Connecticut lifestyle with nearby hiking, lakes, outdoor recreation, arts and culture.

16 Rhynus Rd, Sharon
$1,250,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24200143 MLS
Welcome to 39 Wilcox Road, a meticulously maintained Stonington sanctuary offering coastal elegance and exceptional craftsmanship. Configured as a 3-bedroom home, it is currently utilized as a spacious 2-bedroom residence. In very close proximity to the upper Quiambaug Cove area, this home sits just steps from the Knox Preserve-26.8 acres of beautiful protected land featuring stone foundations, open fields, notable migrating birds, and serene kayaking access.The heart of the home features a gourmet chef's kitchen equipped with top-tier appliances, including a Wolf gas range, Thermador double wall ovens, and a KitchenAid refrigerator set against custom cabinetry and expansive prep space. Designed for year-round enjoyment, the main floor boasts a dedicated home office and a sun-drenched enclosed front porch where you can unwind while taking in serene water views.Step through to the spectacular sunroom-complete with radiant heated floors-that opens directly to a private backyard oasis featuring a sparkling in-ground pool, lush garden areas, and sweeping coastal vistas. Additional highlights include a convenient central vacuum system and an oversized two-car garage with a fully equipped attached workshop. A rare coastal retreat combining luxury, comfort, and unmatched pride of ownership.

39 Wilcox Rd, Stonington
$3,850,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24191176 MLS
Rock House Farm, c.1765. One of Wilton's most treasured historic estates, this extraordinary former dairy farm blends nearly three centuries of history with the comforts of modern living. Originally built by Reuben Olmstead in 1765, expanded in the 1800s, and thoughtfully renovated and enlarged in 1997, the estate has been beautifully preserved for generations. Set on six spectacular acres bordered by 14 acres of permanently protected open space, the property offers exceptional privacy and breathtaking pastoral views. The gracious main residence spans over 6,000 square feet with five bedrooms, five full and one half baths, and seven fireplaces. A charming two-bedroom, two-bath guest cottage with full kitchen, laundry and three fireplaces evokes the charm of the English countryside. Completing the estate is a magnificent four-story red dairy barn, a rare architectural treasure and lasting reminder of the property's rich agricultural heritage. Ancient stone walls, rolling lawns, specimen trees and timeless beauty create one of Fairfield County's most remarkable country estates.

430 Nod Hill Rd, Wilton
$1,999,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24203160 MLS
A Frazier Peters masterpiece awaits its next steward on a private two-acre sanctuary in New Canaan. Enchanting stone steps lead the way to this magical home, where a great room with a soaring cathedral ceiling and large wood burning fireplace anchors the residence - flanked on one side by effortless entertaining spaces including a gourmet kitchen, formal dining room, and wet bar, as well as the private primary suite, and on the other by three additional bedrooms, a dedicated office, and two full baths. A sunroom bathes the home in natural light, offering a serene retreat to take in the lush, private grounds. Full of timeless character, architectural provenance, and enduring construction quality, this rare offering is ripe for re-imagination by someone ready to put their own stamp on something truly special.

Gravel Island Road, New Canaan
$2,595,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24201998 MLS
The Yellow House is a warm and gracious country retreat set amid an extraordinary natural landscape at the gateway to the Berkshires. Just minutes from the charming villages of Salisbury, Lakeville, Norfolk, Sheffield and Great Barrington, the property offers easy access to the exceptional cultural, culinary, and recreational offerings of the Massachusetts-Connecticut border. Set against a backdrop of rolling hills, open meadows, gardens, and mature trees, the property was designed to embrace its spectacular surroundings. Light-filled interiors are relaxed and inviting, with expansive views. The grounds offer an exceptional country lifestyle, with an organic vegetable garden, apple orchard, and acres of meadow enclosed by a mowed walking loop. Whether enjoying a morning walk, an afternoon in the garden, or the changing beauty of the seasons, the land is as much a part of the experience as the house itself. Inside, a central kitchen serves as the heart of the home, connecting a thoughtfully arranged collection of spaces including a formal dining rm, living rm, media rm, breakfast rm, and sunroom. The floor plan offers both elegance and flexibility, with wonderful spaces for entertaining as well as comfortable living. The home is officially 5 bedrms, but has flexibility for use as 8 or more bedrms, providing generous accommodations for family and guests. Recent improvements include a new furnace, wood-shingle roof, new gym in the barn, and new hardwood floors on 3rd floor.

547 Under Mountain Rd, Salisbury
$995,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24200800 MLS
Multiple offers received. Highest and best by 5:00pm, Tuesday September 1st. Set on 5.47 private acres with access from both North Salem Road and Old Sib Road, this remarkable 1928 residence presents a rare opportunity to reimagine an estate rich in history, character and extraordinary potential. Tucked at the top of a long approach, the 10-room, 3-bedroom, 3.5-bath home is a true time capsule, retaining architectural details that speak to its nearly century-old past, including original Hope steel windows, textured stucco, period millwork and beautifully proportioned rooms. The home unfolds with an understated European sensibility, offering a series of distinctive spaces including gracious living and dining rooms. An expansive, light-filled sunroom was added in 1960. Original details and unexpected architectural moments offer a foundation for thoughtful restoration while leaving room to make it your own. The property itself is equally compelling. A four-stall barn with tack room and attached shed, riding ring and paddock reflect its longtime equestrian use and offer possibilities for horses, hobby farming or the creation of a private country compound. A detached guest house/garage provides additional space ready to be completely reimagined. Property may offer subdivision potential, subject to buyer due diligence and all applicable municipal and regulatory approvals. A rare opportunity for the buyer with vision to bring this distinctive property into its next chapter

799 N Salem Rd, Ridgefield
$699,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199460 MLS
Welcome to an "Antique Gem" in Oxford, Connecticut. Step into a beautifully preserved piece of Connecticut history. Set on 1.6 private acres in Oxford, CT, this exceptional 1769 Vintage Home has remained in the same family for generations, and offers a rare combination of authentic period character, thoughtful restoration, and comfortable modern living. The current owner has invested more than $195,000 in improvements and restoration, carefully preserving the home's historic integrity, while updating it for today's lifestyle. Original wide-board Chestnut Floors, exposed Post & Beam construction, and period details throughout, give this home a warmth and character that simply cannot be replicated. This unique home offers 2123 square feet, four bedrooms & two full baths, and features a flexible & inviting floor plan. The main level includes a beautifully updated Kitchen with Bay Window, formal Dining Room with a Fireplace, Living Room with a Fireplace, Family Room, and a first floor Bedroom currently used as an Artists Studio. A charming Full Bath features a clawfoot tub with shower and a large pedestal sink. A small room adjoining the Dining Room provides an ideal space for a home office, while the renovated Screened In Porch, with an artistic flair, offers a distinctive and relaxing place to enjoy the surrounding landscape. Just off the Kitchen, a large walk-up Attic, with heat and electricity, presents an exciting opportunity for additional finished living space.

136 Chestnut Tree Hill Rd, Oxford
$749,900
7 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24198629 MLS
Step back in time while enjoying the comforts of today in this exceptional Antique Colonial, built in 1830 and proudly situated on historic Thompson Hill. From the moment you arrive, the home makes a lasting impression with its welcoming wrap-around front porch, tastefully landscaped grounds, and classic circular driveway. The property also features a sizeable barn, offering abundant storage and endless possibilities. There is even an original "privy"! Inside, the 5-bedroom main residence offers generous closet space, 2 full baths, a thoughtfully designed updated kitchen, both formal and informal dining spaces, and beautifully updated bathrooms.A convenient first-floor laundry adds to the functionality of this spacious home, while the property's original character provides the warmth and charm that only an antique Colonial can offer. A standout feature is the spacious two-story in-law apartment, complete with a private entrance and rear deck. With 2 bedrooms and 1 1/2 baths, this versatile space is perfect for extended family, guests, a home office, or other living arrangements. The property has been thoughtfully improved with updated mechanical systems and a brand-new septic system, providing modern peace of mind while maintaining the home's historic character. This home is ideally located just minutes from the Massachusetts and Rhode Island state lines and major commuter routes allowing quick and easy access to the Arts, Dining, Shopping, Medical facilities and Airports

362 Thompson Rd, Thompson
$429,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24197488 MLS
Looking for more space without sacrificing character? This 4-bedroom, 2-bath Victorian-style Colonial offers over 2,400 square feet, a finished third floor, detached 2-car garage and the timeless details that make older homes special. Step inside from the inviting covered front porch to hardwood floors, original moldings, high ceilings and abundant natural light. The spacious eat-in kitchen features newer stainless steel appliances and recessed lighting, while the farmhouse-style dining room and oversized living room provide plenty of room to gather and entertain. The finished third floor creates valuable bonus space for a home office, playroom, guest area or additional living space. Outside, enjoy a landscaped yard, newer paver patio and partially fenced backyard. Central air, public water and sewer, plus convenient second-floor laundry add everyday functionality. Convenient to Route 8, Route 67, shopping, dining and local amenities. A distinctive Seymour home offering the space, character and flexibility to make it your own.

32 Union St, Seymour
$1,795,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24196189 MLS
Historic elegance meets modern luxury in this extraordinary residence located on one of the most desirable roads in Litchfield County. Positioned just an hour and fifteen minutes from New York City, this property offers quintessential Bridgewater charm paired with stunning sunsets and breathtaking views of the Litchfield Hills. The home is a brilliant architectural achievement that masterfully incorporates the historic 1829 Mallet District Schoolhouse into a seamlessly expanded 2006 Williamsburg-style new build. Set on a coveted, level one-acre lot framed by iconic New England stone walls, the freshly painted estate unfolds across sweeping, park-like lawns that are perfectly sized for large gatherings or sports games, yet easily manageable as a lock-and-leave retreat for busy families. Inside, period craftsmanship shines alongside sophisticated contemporary finishes, highlighted by bespoke millwork, seven-inch wide oak floors, and five magnificent wood-burning fireplaces. The main level is designed for both grand entertaining and intimate living, offering formal living and dining rooms that are each anchored by striking brick fireplaces. These spaces flow effortlessly into a sunlit, paneled family room warmed by a rustic fieldstone fireplace. At the heart of the home sits a chef-grade kitchen outfitted with an eleven-foot center island, a classic farmhouse sink, premium high-end appliances, and a bright

397 Christian St, Bridgewater
$619,900
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24197024 MLS
Set on over 7 private acres, this beautifully restored 1700 historic property offers a rare blend of New England character and modern updates. The current owner has thoughtfully cleared much of the land, revealing a gently flowing brook and historic dam while maintaining the privacy and serenity. A newly built oversized deck creates the perfect place to relax or entertain while overlooking the landscape. From your kitchen window, enjoy views of the gently flowing brook through every New England season. The expansive yard is a blank canvas for gardens, outdoor living spaces, or simply enjoying the quiet beauty of nature. Inside, you'll find wide plank floors, exposed beams, five fireplaces, mini splits for heating and cooling, with propane as primary heating fuel source, brand new kitchen, appliances and many more updates. This home has timeless character throughout yet seamlessly blended with thoughtful renovations and modern amenities. The finished lower level provides exceptional flexibility for multi-generational living and is already plumbed for a future kitchen, offering the potential for a legal in-law apartment with the proper approvals. Rich in history, thoughtfully renovated, and truly one of a kind, this is a property you'll want to experience in person.

291 Cossaduck Hill Rd, North Stonington
$749,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196454 MLS
Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield
$959,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188039 MLS
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.

11 Pleasant St, Woodbury
$995,000
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24194248 MLS
The Fenner-Matthewson Mansion-an extraordinary piece of Connecticut history. Built circa 1855 for prominent mill owner Arnold Fenner, this magnificent Italian Villa is a distinguished contributing property within the National Register-listed Central Village Historic District. Nearly 6,000 SF of timeless grandeur offers 12 rooms, 6 bedrooms and 4.5 baths, with soaring 12' ceilings and exquisite period detail throughout. A grand foyer and sweeping staircase make an unforgettable first impression, complemented by 2 additional staircases, original black walnut doors and millwork, red pine floors, mercury glass doorknobs and beautiful built-ins. An incredible 9 working fireplaces, many with distinctive Italian marble surrounds, grace the home-including fireplaces in the updated kitchen and primary suite. The kitchen blends historic character with modern function, featuring a Sub-Zero refrigerator, pantry and butler's pantry. The primary suite offers a private full bath with soaking tub and fireplace. Recent improvements include a new roof and new central air. Set on 2.65 acres with an inviting front porch, stone courtyard and charming stucco outbuilding. More than a home-this is architecture, history and legacy, awaiting its next steward.

40 Main St, Plainfield
$799,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193491 MLS
56 expansive ACRES of pristine Connecticut COUNTRYSIDE with quiet rural atmosphere. Space for HUNTING wildlife viewing and trails. Recreational Haven, Homestead with enough room for FARMING and timber. ENORMOUS 2400 square-foot GARAGE/WORKSHOP with 12 x 12 doors HEATED with two zones, office with a full bathroom and additional bathroom and its OWN Septic! DETACHED two car garage with (two NEW doors) next to a ONE of a KIND almost 3000 square-foot Country home with BEAUTIFUL CRAFTMANSHIP throughout with CUSTOM STONE fireplace in the large living room with a second FIREPLACE in the dining/custom kitchen (new oven and microwave) area for entertaining with an ambience and 1/2 bath laundry area. Upper level has primary bedroom suite and three additional bedrooms with two full bathrooms. 2 brand NEW mini splits $15,000, two NEW wood stoves and piping $14,000, two NEW well pumps $10,000, NEW spray foam and attic $18,000, 10 NEW windows, two NEW front doors and exterior doors $20,000. Peace of mind with a brand NEW GENERAC generator 24,000 Watts $12,000, newer heating system and updated electrical panels NEW $10,000 kennel for the animals. CAMERAS and AUDIO and OCCUPIED-DO NOT GO ON PROPERTY without LISTING AGENT-THANKYOU

233 Fire Tower Rd, Pomfret
$1,076,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193014 MLS
Rare Bethlehem Offering - 1740s Antique + Commercial-Ready Barn on 2 Acres Welcome to a rare offering in the heart of Bethlehem, CT, sited at the town's famous blinking light with easy proximity to Washington, Litchfield & Woodbury. Dating to the 1740s, this sensitively preserved 4-bedroom antique is rich with period charm - 5 fireplaces, including a 12' hearth housing a beehive oven, historic detailing, a walk-up attic, and a basement with soaring 9' ceilings that homes a Viessmann Furnace and hot water heater. Thoughtful updates throughout make it a warm, move-in-ready home. The real story here is the barn: a striking 3,000 SF structure originally restored for a commercial dine in bakery, with the significant investment already behind it - new roof, doors meeting fire & code, 4-phase electrical, roughed plumbing & HVAC, and poured concrete floors. Reimagine it as an event space, artisan workshop, wellness retreat, or second residence - the foundation is already in place. A picturesque pond adds ambiance, ideal for commercial use or connecting the structures for potential multi-generational living. A charming milk house offers even more flexible space - guest quarters, studio, gym, or workshop. Grounds feature ornamental Japanese & red maples, flowering pear, cherry, birch & magnolia, plus a newly graded and re-graveled driveway (2023) and 75 feet of town-maintained sidewalk! A rare chance to own a piece of Bethlehem's history - the work is already done.

18 East St, Bethlehem
$1,495,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189157 MLS
The Seely House is a rare opportunity to become the next steward of one of New Canaan's enduring historic treasures. This remarkable residence traces its origins to the years surrounding the American Revolution and stands as a tangible link to the town's earliest beginnings. Rich in character and architectural authenticity, the home showcases the craftmanship and charm that can only be achieved through centuries of careful preservation. Historic details blend seamlessly with modern comforts, creating a warm and inviting living experience that honors the home's heritage while accommodating today's lifestyle. Set along picturesque Old Stamford Rd., the property enjoys an enviable location just moments from downtown New Canaan's acclaimed restaurants, boutiques, parks, train station and schools. Here, homeowners can enjoy the rare combination of historic significance and walk-to-town/schools convenience. More than a residence, The Seely House is a legacy property offering timeless character, irreplaceable authenticity, and the chance to write the next chapter in a story that has endured for generations.

68 Old Stamford Rd, New Canaan
$650,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192511 MLS
A rare opportunity to own TWO single-family adjacent homes in the heart of East Hampton! Rich in history and thoughtfully updated, the main residence at 124 Main Street beautifully blends timeless architectural character with the comfort and convenience of modern living. Historic details, classic craftsmanship, and tasteful updates create a home that is both elegant and inviting. A first-floor bedroom and full bath provide the option for a desirable primary bedroom suite or flexible living arrangement to accommodate a variety of lifestyles. Situated toward the rear of the property, 126 Main Street is a second single-family residence offering exceptional versatility. While it could benefit from some updating, it presents endless possibilities as an in-law home, income-producing rental, private guest house, home office, studio, or space for entertaining family and friends. Whether you're looking for multi-generational living, rental income, or simply the flexibility of owning two homes on one parcel, this unique property offers endless potential in a desirable location close to East Hampton's charming downtown, Lake Pocotopaug, restaurants, shopping, and local amenities. A truly one-of-a-kind opportunity!

126 Main St, East Hampton
$559,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191342 MLS
When you pull up to this home you will be struck by a setting has all of the ambiance that it had when it was built in 1835. Gorgeous country setting. Home on 2.34 acres including large field area. Large one story shed. Incredibly unique two-story barn. This home has clearly been loved and updated through the years. Gorgeous sunny kitchen that extensive cabinetry, island and a cute breakfast nook. Large dining room open to the living room with hardwood flooring and a fireplace. 1st floor den with built-ins. 1st floor laundry room between the kitchen and garages. Large very updated bathroom. 2nd floor has three bedrooms and a half bath. Such a unique setting In today's world is truly a special opportunity.

2865 South St, Coventry
$1,200,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24187090 MLS
Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated. Level agricultural acreage stretches across the property, bordered by old farm stonewalls. Outstanding potential-whether your vision is a hobby or gentleman's farm, livestock, or equipment storage. Ideal for multi-generational living for those seeking shared but private living. Investors seeking income producing property, entrepreneurial minded, and creatives looking for a home office, in-home gym with full bath, and studio space. The property has two separate septic systems and utilities offering true independence. Farmhouse style home is enchanting with 3-bedrooms. Dual staircases with private access to the primary ensuite bedroom complete with sliding glass doors opening to a private balcony overlooking the serene pastoral landscape. Wide floorboards throughout the main and upper floors. Two enclosed front porches, open covered back patio, solarium, provide additional spaces for hobbies and respite.

1209 Durham Rd, Madison
$1,195,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24179647 MLS
Steeped in history and radiating timeless elegance, this 1870 Victorian masterpiece stands as one of Kent's most grand and storied residences. Boasting a striking architectural facade, this magnificent home welcomes you into its grand entrance, featuring soaring ceilings and beautiful woodwork that flows throughout the entire property. Throughout its rich past, this versatile estate has been cherished both as a luxurious private residence and as a welcoming bed and breakfast. Today, it stands ready for its next chapter, offering multiple rooms across the premises and an incredible canvas for the next owner to bring their own vision and elevate it to its next level of brilliance. Location is everything. Situated right in the heart of the vibrant Kent Village center, this property offers unmatched walkability. Step outside your door and immerse yourself in the town's renowned culture-just a short stroll to world-class art galleries, gourmet restaurants, boutique shopping, local museums, and premier antiquing. Whether you envision a spectacular, expansive private compound, a boutique hospitality venture, or an elegant live-work space, the possibilities here are as vast as the home's rich history. Don't miss the rare opportunity to own a true piece of Kent heritage and define its next great era. Schedule your private showing today.

67 N Main St, Kent
$625,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24186602 MLS
Steeped in New England history and perfectly positioned directly across from Shenipsit Lake, this extraordinary farmhouse traces its origins to the 1700s before being thoughtfully expanded in the 1840s during the Civil War era. Inside, you'll discover wide pine floors, hand-hewn exposed beams, three fireplaces, and beautifully preserved architectural details that capture the craftsmanship of centuries past. Thoughtful updates provide modern comfort without sacrificing authenticity, including central air, replacement windows, updated siding, a 60-year roof, generator hookup, new well pump, and numerous additional improvements completed by the current owners as they meticulously restored the home from the windows and sheetrock to the mechanical systems. Offering the flexibility of up to four bedrooms, the home also features a private in-law suite, providing an ideal layout for multigenerational living, guests, or extended family. Step outside to experience over 6.5 picturesque acres, where a beautifully rebuilt historic barn, fenced in-ground pool, mature landscaping, and open grounds create endless opportunities for horses, hobby farming, gardening, recreation, or simply enjoying the peaceful Connecticut countryside. The property also offers potential for future subdivision (buyer to perform due diligence), making it as appealing for its possibilities as it is for its beauty. Conveniently located just minutes from the University of Connecticut. A MUST SEE

352 Shenipsit Lake Rd, Tolland
$1,055,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182878 MLS
Welcome to 8 Meeting House Road, a secluded and serene retreat. This special property was the former Reverend John Marsh parsonage circa 1818. It has been privately owned for the last 41 years by the same family and is now ready for a new steward. This gracious historic home features a light-filled eat-in kitchen, a fabulous enclosed sunporch overlooking verdant views of the property, and multiple fireplaces. There are several multifunctional rooms including a library with built-in bookcases, a music room, and a generously sized great room with beamed cathedral ceilings. There are also five spacious bedrooms and 2.5 updated bathrooms. The property is set on over four acres with stone walls running throughout, and outbuildings, including a carriage house that has plenty of space for a workshop, a studio, or an office. Behind the carriage house you'll find a natural in-ground gunite pool in a lush private setting. This is a rare opportunity to own an intact historic property with this kind of heritage in the Connecticut River Valley.

8 Meeting House Rd, Haddam
$850,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS
Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury
$12,000,000
4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24183764 MLS
A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a local treasure for generations. The improvements require significant modernization and renovation, presenting an ideal opportunity for someone seeking to preserve and enhance a historic property. Whether envisioned as a private estate, hospitality-related use, office, wellness concept, or other permitted use, the property offers exceptional potential for those with a vision for restoration and stewardship. Ideally situated on Boston Post Road with convenient access to Interstate 95, Route 9, shoreline beaches, marinas, shopping, and restaurants, the property benefits from excellent visibility and accessibility within one of Connecticut's most desirable shoreline communities. This offering is subject to the property's historic designation and must be purchased together with the adjoining Bushnell Farm land parcel (MLS #24183765). The combined offering presents a truly unique opportunity to preserve, restore, and shape the future of one of the Connecticut shoreline's most recognizable historic properties.

1445 Boston Post Rd, Old Saybrook
$2,995,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24163576 MLS
Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury
$1,199,999
9 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24179935 MLS
Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access.

209 Main St, Deep River

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