luxury real estate for sale Chester, United States

Charm, character, original features and details and the amazing farm porch. This classic antique farmhouse, perched on a knoll set back off the street with mature landscaping and privacy, yet just a short distance to restaurants, library, grocery store and pharmacy. Three bedrooms, 1.5 baths, second floor laundry room, large unfinished basement and a walk-up attic. Many seller improvements including, roof, generator switch, and electrical panel upgraded. All you need to do is unpack.

Selden Farm, a landmark 1690s property steeped in history and set in a picturesque corner of Lyme, is once again available for new stewardship. Upheld by only three families since 1695 when it sat on over 6,000 acres, it presents a rare opportunity to own a beautiful country Antique home now set on 9 pastoral acres abutting conservation land with sweeping views of Selden Cove and the CT. River. At its heart is a gracious and authentic 5-bedroom Colonial which exudes history, charm and character. House features include a tavern room, wide board floors, original paneling & moldings, 6 fireplaces and an abundance of windows which invite lovely views and light into each room. Adjacent to the home is a 3-bay garage with self-sufficient guest accommodation for visiting family and friends. Dotted throughout the property are a renovated barn used as a studio/office/ gym, several outbuildings, a greenhouse and sunny open meadow for animals or farming. Two privately situated guest houses (one needing renovation) are ideally suited for in-law, caretaker, or income purposes. Relax by the large saltwater pool with patio and full-service cabana or play tennis on the all-weather court. The land is open, tranquil, and beautifully sited, offering long views, privacy, and a deep sense of place. Rarely does a property combine this level of authenticity, acreage, outbuildings, and river-valley setting in Lyme. Ideal for buyers seeking history, creative space or a generational retreat.

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.

Set along one of Essex's most coveted stretches of River Road, this exceptional waterfront estate offers a rare blend of understated elegance, privacy, and Connecticut River waterfront. Privately sited on nearly three acres, the property enjoys a serene, tucked-away feel while remaining just minutes from the heart of Essex Village. Custom-built and thoughtfully designed by its original owner, the residence spans over 4,600 square feet of beautifully scaled living space. Sun-filled interiors, expansive rooms, and a seamless layout create an inviting atmosphere ideal for both sophisticated entertaining and relaxed everyday living. Outdoors, the estate unfolds into a true retreat - complete with a substantial pool house, in-ground pool, and multiple areas for gathering and unwinding. Rarely does a property combine size, setting, and location so effortlessly. This is a distinguished offering in one of the Connecticut shoreline's most desirable enclaves.

After a year of rehabilitation, this beautiful & spacious colonial home has been thoughtfully & tastefully completely remodeled & enhanced! Located in the heart of Lyme just a short distance from the historic ferry, Gillette's Castle & Fox Hopyard Country Club, this home boasts a very modern feel with an open & airy floor plan. All aspects have been brilliantly brought to life inside & out! The exterior thrives with the pavered walk-ways & patio to the bluestone entry porches, added attached 3 bay garage & newly paved circular driveway. The interior main level features an open & flowing floorplan from the gourmet kitchen featuring white swirled Quartz counters, banks of white cabinetry, Thor gourmet stainless appliances to a formal dining room & living room with dual sided floor to ceiling wood burning fireplace. All tied together with new gleaming hardwood floors & recessed lighting. The upper level sleeping quarter is smartly setup with a well appointed primary suite, 4 additional & spacious bedrooms as well as 2 full baths beyond the primary. This level is also tied together with new hardwood & recessed lighting. There's also a 3rd level loft ideal as guest space or remote office. The lower level provides ample finished family room space. As mentioned, this home has been completely renewed & enhancements include new vinyl siding, architectural asphalt shingle roof, heating & cooling with on-demand hot water, Thermopane windows, interior & exterior doors & much, much more!

Elevated on a dramatic rise above the Connecticut River, this captivating property, aptly named River Knoll, showcases one of the most breathtaking private settings on the river. The historic home has been featured in multiple publications such as Veranda and CTC&G for its exceptional beauty. Stunning landscape design frames every vista from the river's edge to the meticulously tended grounds that flow effortlessly into the natural surroundings. At the heart of the property is an 18th-century Cape, artfully expanded with architectural additions that honor the home's original character while delivering modern luxury. Step inside to discover the soul of the home: original hand-hewn beams, rich paneled walls, and wide-plank flooring that whisper stories of centuries past. Yet, every room has been thoughtfully enhanced with upscale improvements that marry history with today's lifestyle demands. The chef's kitchen, complete with a butler's pantry, is designed for serious cooking and effortless entertaining. Updated bathrooms throughout reflect refined taste and functionality. The primary suite is a private sanctuary with extraordinary river views that unfold in quiet splendor.

Located on coveted River Road in picturesque Essex, this charming ranch-style home offers the perfect balance of privacy and convenience, set on 2 beautiful acres just minutes from Essex Village. Boasting over 1,900 square feet of living space, this 3-bedroom, 3 full bathroom home features an open floor plan filled with natural light and designed for comfortable everyday living and entertaining. The inviting living area is centered around a fireplace, while the expansive finished basement provides exceptional additional living space, ideal for a family room, home office, gym, or guest accommodations. Step outside to enjoy the outdoor patio and peaceful surroundings. Additional highlights include a two-car garage and a highly sought-after location along one of Essex's most scenic roads.

Perched above the CT River with breathtaking panoramic views and unforgettable sunsets from every room, this extraordinary waterfront compound is the definition of luxury coastal living. Set on one of the most sought-after private lanes & completely fenced for privacy and security, the property is designed for both grand entertaining and relaxed everyday comfort. It includes a spectacular main residence, a beautifully appointed guest house, an impressive post-and-beam barn, multiple outbuildings, and deep-water dock with two boat lifts. From the moment you arrive, the meticulous landscaping, stone walls, and timeless architecture create an unmistakable sense of arrival. Inside, walls of floor-to-ceiling windows bathe the home in natural light while perfectly framing the ever-changing river views. French doors throughout the rear of the home open onto expansive decks and outdoor living spaces, seamlessly blending indoor and outdoor entertaining. The main level is anchored by an expansive waterfront dining room that flows effortlessly into both the living room and dramatic vaulted-ceiling family room. The chef's kitchen is exceptionally well appointed with stunning burl walnut cabinetry and premium appliances. The luxurious primary suite serves as a private retreat, complete with a spa-inspired bath, gas fireplace, private balcony, and soaking tub overlooking the water. Upstairs, two spacious ensuite bedrooms enjoy sweeping river views & access to a charming screened porch. Tucked away nearby, a private home office offers an inspiring setting for work or creativity. A rooftop deck crowns the home, providing unmatched views up and down the river - the perfect setting for sunset cocktails, stargazing, or quiet summer evenings. The walk-out lower level offers a warm and inviting game room/family room with fireplace, kitchenette, abundant storage for waterfront activities, and an additional ensuite bedroom or office. Stone patios lead directly to the dock and riverfront beyond. Complementing the main home is a stunning two-bedroom guest house featuring vaulted ceilings, beautiful finishes, Large well appointed full bath and a three-car garage below. Also included is a remarkable two-story post-and-beam barn featuring a huge game room with a soaring 20-foot ceiling, designed to host gatherings both large and intimate. The upper level offers exceptional open entertaining space along with a separate room, full bath, and kitchenette, while the expansive lower level provides ample space for vehicles, boats, and equipment storage, as well as a climate-controlled storage room. Additional structures include a substantial utility shed with workshop and wood-burning stove, plus a separate woodshed. Rarely does a property combine this level of craftsmanship, functionality, privacy, and waterfront beauty. Completely turnkey and truly one of a kind, this is a home designed to be enjoyed for generations. A setting this spectacular feels like a year-round oasis, you may never want to leave home!

Incredible investment opportunity. Mixed use/flex space including two existing apartments. Historic building that has had multiple uses including an antique book store and once a brush factory. Many updates in recent years with a variety of potential uses. Level .74 acre lot, gravel parking lot, great visibility and signage. There are two apartments and multiple office/flex spaces. The property has a total of six bathrooms, 3 full and 3 half. The owner of this property for the last 40 years has not had any flooding issues. The property is in a flood zone, there is no existing flood insurance policy.

Nestled in the heart of Essex Village along one of its most picturesque streets, this iconic c.1818 home welcomes you with a charming wraparound covered front porch, an inviting place to sit and relax. Inside, you'll find a perfect blend of timeless character and thoughtful modern updates, creating a home is both beautiful and comfortable. At its heart is a custom chef's kitchen featuring solid wood cabinetry, granite countertops, a Wolf 6-burner range, dual sinks, and complete with a well appointed butler's pantry. The kitchen flows seamlessly into a dining and seating area that opens to the patio & backyard. A sun filled, cozy family room with a stone floor and fireplace provides the perfect setting for quiet evenings or casual gatherings. Formal living and dining rooms, along with, half bath, and mudroom, complete this level. Upstairs, the spacious primary suite serves as a true retreat, offering dual walk-in closets, a fireplace, and a spa like bathroom. Three additional bedrooms and two full baths provide plenty of space for family and guests, while a walk-up attic adds convenient storage. French doors open to a beautiful bluestone patio overlooking the spacious fenced backyard-ideal for outdoor entertaining or simply enjoying peaceful moments at home. A handsome two-car carriage house includes a heated garage and a finished (permitted/legal) upper level apartment with a full bath, perfect for a guest suite, studio, or private office.

Welcome to 150 Joshuatown Road in Lyme, a stunning, custom built residence sited on over 30 acres of bucolic land, with specimen trees, beautiful landscaping, and over 1/4 mile of impressive rebuilt stone walls. The main level features a welcoming foyer, Chef's kitchen with breakfast room, a cherry paneled library with vaulted ceiling and warming fireplace, commodious dining room, living room with separate seating areas, and a first floor primary suite. The second level has additional bedrooms and a beautiful family room, currently used as an art studio. In addition to the Main house, there is an incredible Guest house, fully functioning with full kitchen and adequate bedroom space. This is a property that needs to be seen to be believed! Simply amazing!

Perched over the CT River on one of the largest lots on Main, the David Watrous House offers water views from each room. This 1850 architectural treasure offers over 4,000 square feet of living space, plus an additional 1,500+ square foot walkout lower level. A detached oversized 3-bay post-and-beam carriage house offers exceptional workshop/studio space, stained glass windows and crowned by a copper cupola with antique weathervane. A side porch entry leads to chef's kitchen with handcrafted Vermont solid cherry cabinetry, granite countertops, stainless appliances, a tin ceiling and dramatic 10-foot island. Formal dining with antique chandelier and fireplace make for elevated home entertaining. The dramatic riverfront great room with wall-to-wall windows, a river-facing 2nd kitchen, fireplace, and expansive deck captures ever-changing water views. A den, living room, office with cherry built-ins, 10+ foot ceilings and full bath offer flexibility on 1st flr. Upstairs, restored original chestnut floors lead to multiple living spaces, full laundry, a 3rd kitchen and a primary suite with gas fireplace with marble en suite. Recent upgrades include new windows, patio, driveway, refreshed landscaping, Buderus furnace, upgraded 400-amp electrical, restored chimneys, whole-house generator, and updated roofing. Stone pathways lead to private riverside seating areas for amazing sunsets. Rare chance to claim a home of notable architectural significance with recognized press coverage.

Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. And the sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

Discover the perfect blend of income potential and small-town charm with this centrally located two-unit property. Ideal for investors or owner-occupants seeking rental income, this well-maintained home offers flexibility and walkable convenience in the heart of Centerbrook. First Floor - Private entrance with direct access from the parking area. Freshly painted and flooded with natural light, this unit features a spacious living room, one bedroom, full bath, and kitchen. Hardwood floors lie beneath the carpet, ready to be uncovered. Enjoy bonus living or storage space on the private front porch. Second Floor - Accessed through the main entrance, this cozy unit is carpeted throughout for warmth and comfort. Both the living room and bedroom are generously sized with closet space in each. The large bathroom and efficient galley kitchen complete the layout. Walk-up attic access provides abundant storage. Additional features include, private outdoor space perfect for al fresco dining, garage for parking or extra storage, additional driveway parking and washer/dryer hookup in basement. This is an unbeatable Location, walk to local restaurants, shops, the post office, and galleries. Quick access to Route 9 and I-95 makes commuting a breeze. Whether you're building your investment portfolio or looking for a live-in income property, this Centerbrook gem delivers on all fronts.

Nestled in the heart of the quaint village of Ivoryton, this circa 1920 home offers timeless charm and exceptional opportunity. Featuring 4 bedrooms, 2.5 bathrooms, and over 1,800 square feet of living space, this home has been in the same family since 1966 and is ready for its next chapter. The main level includes a traditional living room, dining room, kitchen, and fireplace, while all bedrooms are located on the second floor. Hardwood floors run throughout much of the home, and a large unfinished attic offers added potential. Enjoy relaxing on the welcoming wraparound front porch or entertaining on the rear patio overlooking the expansive .61-acre lot. Additional outbuildings include a detached garage and storage shed. Priced with updating in mind, this property presents a wonderful opportunity to make it your own in one of the shoreline's most picturesque communities. Ivoryton offers local restaurants, the renowned Ivoryton Playhouse, and Copper Beech Inn, scenic beauty, and easy access to the CT River and nearby shoreline beaches.

Wonderful waterfront antique home on 1.6 acres. The Parker Bull House, circa 1754 located in Ivoryton overlooking the Falls River, this gracious home is a unique blend of original antique features with updated modern amenities. The large sunlit kitchen has granite countertops and stainless-steel appliances, hardwood floors, and is adjacent to a spacious pantry/laundry room, heated sunroom, and a covered porch. The living room has a fireplace and leads to a formal dining room, both rooms with American Chestnut wide board flooring, and the dining room also has a fireplace and a beehive oven. A parlor serves as a comfortable family room, and there is also a powder room on the first floor. Upstairs, the primary bedroom has an ensuite updated full bath; two additional bedrooms and another updated full bathroom. A large walk-up attic has plenty of room for storage, and a back staircase leads to the kitchen. The property includes a barn/garage, fabulous antique shed and an original outhouse. This home is next to Prive Swiss and across the street from Copper Beech Inn.

Fresh Update for a Classic Connecticut Home - Discover a beautifully restored 1955 waterfront classic. Stunning panoramic water views, privacy and walk-to-town convenience. Ascend to the family room, crowned with cathedral ceilings and expansive windows that invite the breathtaking views of the Connecticut River. A Danish gas fireplace adds a touch of sophistication, creating a cozy yet chic atmosphere year-round. At the heart of the home lies a vast chef's kitchen, a culinary masterpiece equipped with top-tier appliances and exquisite millwork by a master craftsman, ensuring both style and functionality. There is a butler's pantry, an elegant paneled library with water views, as well as an outdoor shower in the garden. The entertainment quotient soars in the spacious playroom, complete with a vaulted ceiling, a chic bar, and a sub-zero wine cooler, setting the stage for memorable games of ping pong and billiards. This riverside haven is graced with two large, sumptuous en-suite guest rooms. An entirely new primary bedroom suite was added to the original house in 2021. Gorgeous views from the primary bed as well as an extra-large dressing area and jaw-dropping primary bathroom with vaulted ceilings. Part of the restoration and renovation was the addition of a sleek new garage, housing a gym designed to cater to the wellness-minded.

Signature building in Essex Village. Originally the EE Dickinson corporate offices; grandfathered use in a residential zone. Reimagine this amazing space, water views, Essex Village, .78 acres of land, large footprint. Rare opportunity to own a cherished piece of Essex history

Tucked away on 2.53 picturesque acres in Ivoryton, this inviting Cape Cod offers the perfect blend of privacy, space, and natural beauty. With 3 bedrooms, 3 baths, and over 3,400 square feet, the home is surrounded by gardens, beautiful meadow, a tranquil pond, and plenty of space to simply enjoy the peaceful setting. Entertain or unwind on the expansive patio and deck while taking in the serene surroundings. A detached 3-car garage and well-maintained interiors complete this truly special property - offering a rare opportunity to enjoy secluded country living with timeless charm.

Welcome to the reimagined John Miner House on North Main Street in the charming Connecticut River Valley Village of Essex. Originally built in 1880 as a residence and tailor shop, this historic property has evolved over the years into a unique investment and lifestyle opportunity. Ideally located in the Heart of the Village, you'll enjoy a short stroll to the Connecticut River, marinas, quaint shops, and wonderful restaurants. The building now offers three beautifully updated units. The showpiece is the entire second floor-an elegant, light-filled two-bedroom apartment featuring soaring ceilings, two full baths, a spacious living room and kitchen, and an expansive deck that spans the length of the building. Perfect as your own private residence while enjoying the convenience of rental income. On the first floor, you'll find two additional units. A bright apartment with an open floor plan, two bedrooms, 1.5 baths, and its own private deck. A professional office space with flexible use potential. Recent updates include new appliances, newer roof, upgraded mechanicals, lighting, and ceiling fans. The property sits on a professionally landscaped village lot with two off-street parking spaces. Whether you're seeking a historic Essex residence, an income-producing property, or both, the John Miner House offers a rare opportunity to live in The Best Small Town in America. Located midway between Boston and New York.

Hilltop Cottage c.1900 The Perfect pied a terre in the heart of the historic Essex CT yachting village welcomes you in each season. In spring, see your professional perennial cottage garden come alive with roses, irises, and peonies. In summer, entertain friends on your large private deck overlooking more gardens and catching the breeze off Long Island Sound. In fall, join in the village Halloween parade then cozy up in front of your carefree gas fireplace. As winter arrives, stroll down to Main Street for holiday shopping in a Hallmark movie town, then watch the twinkling lights on the opposite shore of the mighty Connecticut River from your English cottage dining area. Two bedrooms, 1.5 baths, chic galley kitchen, mini splits, living room with year-round sun porch. One-car garage plus ample street parking. Freshly painted in Farrow & Ball. Window treatments and stair runner included. Furnishings are negotiable. Lock-and-leave charm and convenience minutes from I-95, Amtrak, and Tweed Airport.