luxury real estate for sale Chester, United States

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.

Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot compound, completed in 2018, was conceived to inspire creativity, wellness, and a connection to the outdoors. Protected by parkland, Nature Conservancy, and Land Trust preserves, the heart of the home is defined by extensive, floor-to-ceiling glass walls that command uninterrupted, panoramic vistas of the Connecticut River while a scenic jeep road offers direct access to Chapman Creek and the River beyond. A seamless flow connects the breathtaking entertaining and living areas with a variety of outdoor decks and terraces. The estate offers a rare sanctuary designed to fuel both the mind and the body. It features an unparalleled suite of dedicated, professional- grade spaces that defy the ordinary. The Creative Hub: Fulfill your creative inspirations in one of four dedicated studios: a sky-lit art studio, a sky-lit writing/drawing studio, a fabrication studio, and a fully equipped woodworking shop.

Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

Welcome to the charming Gingerbread House, a custom-built home in the desirable Hadlyme section of East Haddam. Set back from the road and surrounded by beautifully landscaped grounds, this distinctive property offers privacy, character, and thoughtful updates throughout. The main level features an open floor plan with wide-plank flooring, a country kitchen, dining area, and a comfortable family room with custom built-ins and a gas fireplace. The expansive primary suite is the home's centerpiece, offering over 800 square feet of private living space with cathedral ceilings, stained-glass accents, a gas fireplace, and a full bath with a jacuzzi tub and double shower. A staircase leads to a third-floor loft, perfect for a home office, reading nook, fitness area, or creative space. The partially finished lower level adds flexibility with a bedroom, full bath, and additional storage or expansion potential. Outside, a wraparound deck overlooks the level yard, creating an ideal setting for relaxing or entertaining. The detached garage features 12-foot ceilings and a floored second story, making it ideal for a workshop, hobbyist, craftsman, or home-based business. Recent improvements include a new roof (2025), complete exterior painting (2026), propane water heater (2023), well pump (2020), and updated appliances (2020-2021). A truly special property offering charm, space, and privacy in one of Connecticut's most picturesque settings.

Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled with natural light and captures river views, seamlessly blending the ever-changing beauty of the water with miles of pristine, undeveloped landscape. Whether watching boats glide along the river, bald eagles and ospreys soar overhead, or vibrant sunsets reflect across the water, the connection to nature is simply unrivaled. The luxurious primary suite is a private sanctuary, perfectly positioned to showcase the breathtaking riverfront setting and spectacular sunset views. Inside, three fireplaces create warmth and ambiance, offering intimate gathering spaces for cozy evenings and seasonal get-togethers. This unique Deep River property is conveniently located to Essex Village, which is recognized as one of America's Best Small Towns where one can enjoy boutique shopping, restaurants, marinas and quintessential New England charm, all while returning to the peace and privacy of your own waterfront retreat. This stunning property is situated two hours from Boston and New York City, and offers convenient access to airports in New haven, Hartford and Providence.

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

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.

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!

This wonderful one bedroom ranch home is the perfect condo alternative, offering over 1100 sf of easy one floor living, just minutes from Essex village. The sun-filled living room flows seamlessly into a charming kitchen featuring a large pantry closet with laundry, as well as a spacious dining area. Spend your down time in the three season sunroom overlooking the mature trees and plantings on the .69 acre level lot. The expansive bedroom has ample closet storage, and could easily be converted to two bedrooms. Additional features include a fenced area, an attached two car garage, storage shed, generator hook-up, central air conditioning. This move-in-ready home will not last long! SHOWINGS BEGIN AT NOON SUNDAY 7/12

Extremely rare! Peaceful, tranquil waterfront lot available. This special location is on Falls River Cove with a shared dock and consists of 1+ acres ready for new construction. View restrictions in place. Please see declaration of restrictions, covenants and easements in the attached. The lot is not visible from the road; shown by appointment only.

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.

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.

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.

24 New City Street is by far one of the most admired riverfront homes in Essex. This gracious Gambrel Cape was built in 1953 with just two owners since. The lush setting commands sweeping views overlooking the CT River from every room in the house. Enter the house through the front door and step into the foyer, which leads to the heart of the home. There are beautiful wide-board floors throughout the house, custom millwork, and other thoughtful architectural touches. There is a large and well-appointed chef's kitchen, formal dining room, and a full bathroom with a laundry area. There is also a formal living room, a den/family room, and lovely sunroom, and three wood burning fireplaces. Upstairs is the primary bedroom featuring an ensuite bath and two roomy walk-in closets. There are also two more bedrooms, both with ensuite bathrooms. A two-car (plus) garage and basement on the lower level. Outside is a boathouse built in 1992 with an expansive first-floor workshop with high ceilings. A charming spiral staircase leads to two more rooms and a bathroom on the second floor. The first floor is heated by a wood-burning stove, and the second floor is heated with propane heater. This offering includes a second land parcel of .83 acres of land and a dock.

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

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.