luxury real estate for sale Old Saybrook, United States

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.

Available for the first time in nearly 90 years, this exceptional 12 ACRES represents one of the very last large tracts of undeveloped land in the water community of Westbrook. The property features a striking combination of 7.5 level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded backdrop. The flat acreage provide an unobstructed southern view of 9 acre Lake Louise & borders the protected land of both Essex & Westbrook Land Trusts. Location & accessibility are unmatched. With 379 feet of clear-line frontage on Route 153, the parcel is positioned perfectly midway between I-95 & Route 9, just minutes to the Old Saybrook/Westbrook Amtrak & Shoreline East train station for seamless travel from Boston, New York & beyond. A local civil engineer believes the site is primed for high-yield development. The property offers remarkable flexibility: a possible 3-4 substantial luxury residential lots or leveraging under CT Affordable Housing Law 8-30g to construct high-density multi-unit complex ranging from 33 units to perhaps 100 units, mirroring successful transit-oriented development nearby. The land is also believed to have substantial on-site topsoil & gravel reserves for immediate asset value. NOTE This sale is contingent upon an adjoining actively listed for sale 20 acre parcel in Essex, owned by the same owners being sold individually, if not together. See related MLS numbers.

Welcome to Greystone, a masterpiece of modern architecture. Bordered by a protected wildlife area, this 4500 sf smart home offers peace and privacy. The main level features an open living room, dining area and kitchen, den, office, half bath, laundry room and primary bedroom suite. Two ensuite bedrooms and a rooftop deck comprise the upper level. The lower level affords access to the backyard and has finished space for a gym or home office as well as a rough-in for a full bath. The kitchen boasts a 10' x 4' island and large walk-in pantry and is well appointed with Wolf and Sub-Zero appliances. An expansive white limestone wrap-around deck and spacious lawn---with an irrigation system---are perfect for relaxing or entertaining. The attached two-car garage is heated. White oak radiant-heated flooring complements the oak Unilux windows and exterior doors. Interior pocket doors and custom cabinetry continue the sleek contemporary look. Kitchen and bathroom countertops are quartzite, some with waterfall edging. Bathrooms feature limestone floors and unique tadelakt plaster walls. Designed with energy efficiency in mind, Greystone uses a geothermal system for heating and cooling. Smart home technology includes programmable LED lighting, motorized shades, security system, and wiring for audio and AI systems. A whole-house generator connects automatically during power outages.

Step into timeless New England charm with this enchanting antique home, circa 1760, ideally set in the heart of the beloved shoreline community of Westbrook. Rich in character and history, this beautifully maintained residence blends classic period details with modern comforts for effortless coastal living. Featuring six inviting fireplaces, the home's warmth, ambiance and thoughtfully preserved architectural details celebrate this home's true heritage. An in-ground, heated pool creates a private backyard retreat while the "walk-to-everything" location makes this home a perfect escape from a hustle and bustle daily life. Just moments from the beach, charming town center, dining and community events, this home also features a two-story barn creating extra valuable storage or flexible space for hobbies, game room, beach gear or workshop space. Located in a desirable beach community, this special property also boasts a proven and successful rental history with excellent income potential or a seamless blend of personal use and investment opportunity. A rare chance to own a piece of history in a prime shoreline setting where coastal lifestyle, character and convenience come together beautifully.

Available for the first time in nearly 90 years, this exceptional 20.8 ACRES represent one of the very last large tracts of undeveloped land in historic Essex, widely celebrated as one of America's "Best Small Towns." The property features a striking combination of 8.5 level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded backdrop. & borders the protected land of both Essex & Westbrook Land Trusts. Location & accessibility are unmatched. Boasting over 800 feet of clear-line frontage on Route 153, the parcel is positioned perfectly midway between I-95 & Route 9, just minutes to the Old Saybrook/Westbrook Amtrak/Shoreline East train station for seamless travel from Boston, New York & beyond. Soil tested for water & drainage, a local civil engineer indicates the site is primed for high-yield development. The property offers remarkable flexibility: a possible 3-6 substantial luxury residential lots or leveraging under CT Affordable Housing Law 8-30g to construct a high density multi-unit complex ranging from 33 units to perhaps 100 units, mirroring successful transit-oriented developments nearby. The land is also believed to have substantial on-site topsoil & gravel reserves for immediate asset value. NOTE This sale is contingent upon an adjoining actively listed 12+ acre parcel in Westbrook, owned by the same sellers, being sold individually, if not together. See related MLS numbers.

Available for the first time in nearly 90 years, this exceptional 33 ACRES represents one of the very last large tracts of undeveloped land in Essex, widely celebrated as one of America's "Best Small Towns." Straddling the town line with parcels in both historic Essex & the water community of Westbrook, the property features a striking combination of 16 level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded backdrop. The flat acreage provides an unobstructed southern aspect view of 9 acre Lake Louise & borders the protected land of both Essex & Westbrook Land Trusts. Location & accessibility are unmatched. Boasting over 800 feet of clear-line frontage on Route 153, the parcel is positioned perfectly midway between I-95 & Route 9, minutes to the Old Saybrook/Westbrook Amtrak/Shoreline East train station for seamless travel from Boston, New York & beyond. Soil tested for water & drainage, a local civil engineer indicates the site is primed for high-yield development. The property offers remarkable flexibility: a possible 6-10 substantial luxury residential lots or leveraging under CT Affordable Housing Law 8-30g to construct a high density multi-unit complex ranging from 66 units to perhaps over 270 units, mirroring successful transit-oriented developments nearby. The land is also believed to have substantial on-site topsoil & gravel reserves for immediate asset value. This is a rare generational opportunity

This elegant and updated historic colonial is tucked away on a quiet road on 1.4 acres. The original two-story structure was built in the mid 1800s, and the additional first-story wing was later added in 1974. The main house has a cozy living room with a fireplace, a formal dining area with a window seat, reading room, a family room/den, and a powder room. The updated galley kitchen features upscale stainless-steel appliances, lots of cabinet space for storage, and plenty of counter space. There is a sunny breakfast nook just off of the kitchen. Upstairs are two bedrooms, including the primary with ensuite bath along with another bedroom and full bathroom. The addition offers a private and separate living space, with a kitchen, living room, bedroom with ensuite bath, a den and another full bathroom. As it is connected to the original house by a breezeway, it offers a good option for use an in-law apartment or for a multi-generational living arrangement. The main house has beautiful wide-plank floors and the apartment has hardwood floors. There is a spacious two-car garage located at the end of the addition. Outside is a lush mixture of mature landscaping, lawns, and shady trees. You can enjoy the outdoor setting from the covered front porch, a patio area off of the breakfast nook, or another patio by the pool area shaded by a vine-draped pergola leading directly to the sparkling in-ground gunite pool.

This charming and updated historic colonial is tucked away on a quiet road on 1.4 acres. The original two-story structure was built in the mid 1800s, and the additional first-story wing was later added in 1974. The main house has a cozy living room with a fireplace, a formal dining area with a window seat, reading room, a family room/den, and a powder room. The updated galley kitchen features upscale stainless-steel appliances, lots of cabinet space for storage, and plenty of counter space. There is a sunny breakfast nook just off of the kitchen. Upstairs are two bedrooms, including the primary with ensuite bath along with another bedroom and full bathroom. The addition offers a private and separate living space, with a kitchen, living room, bedroom with ensuite bath, a den and another full bathroom. As it is connected to the original house by a breezeway, it offers a good option for use an in-law apartment or for a multi-generational living arrangement. The main house has beautiful wide-plank floors and the apartment has hardwood floors. There is a spacious two-car garage located at the end of the addition. Outside is a lush mixture of mature landscaping, lawns, and shady trees. You can enjoy the outdoor setting from the covered front porch, a patio area off of the breakfast nook, or another patio by the pool area shaded by a vine-draped pergola leading directly to the sparkling in-ground gunite pool.

An elegant and lovingly maintained antique colonial situated on 1.2 secluded acres near the Old Lyme Country Club. Recent updates include new landscaping front and back, new hardscaping around the pool deck, a new cedar roof, well tank, and a HVAC system including ductwork. The interior preserves the historic aspects of the home while graciously blending all the amenities of modern life. A formal living room and cozy library frame the front entryway, and lead to a large family room lined with walls of windows and French doors that bring in loads of natural light. Thoughtful classic architectural details throughout the home include wide-plank hardwood floors, custom built-in cabinetry, crown molding, and front and back stairwells. The cheery kitchen is placed conveniently off the dining area, again filled with more windows and French doors leading to the outside patio. With plenty of room for outdoor seating and dining, it is the perfect spot for entertaining friends and hosting family gatherings around the in-ground gunite pool and spa. A lush lawn beyond beckons for yard games and playing fetch with the dog. Upstairs are four distinctive bedrooms. The primary suite has an ensuite bathroom and walk-in closet. There is another bedroom with a second ensuite bath, and two more rooms that share a third bathroom.

Welcome to 18 Orchard Heights Road, a charming modified saltbox colonial located at the end of a cul-de-sac in a desirable neighborhood. This home offers exceptional convenience, located just minutes from the boutique shops and historic charm of downtown Essex, with quick access to the vast amenities, dining, and shoreline conveniences of neighboring Old Saybrook. Inside, the home features a light-filled, functional layout designed for seamless main-level living including a first-floor primary suite, dedicated laundry space, and a recently updated kitchen with quartz countertops, stainless appliances, and ample cabinetry. A spacious family room opens to a private deck, located at the rear of the property. The second floor boasts two more bedrooms and a full bath with an additional 600 square feet (per tax card) of unfinished space, presenting an incredible opportunity to create a second primary suite, home office, play area, or bonus room tailored to your needs. Combining timeless character, thoughtful updates, and an unbeatable location near the best of the Lower Connecticut River Valley, 18 Orchard Heights Road is ready to welcome its next owners home.

Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a .45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers an exceptional sense of privacy and tranquility. Rich in architectural charm, the home features soaring ceilings, expansive windows, and elegant, light-filled interiors that reflect generations of thoughtful stewardship. Once known as one of the village's grand homes, its legacy continues today as a warm and inviting retreat with sophisticated style and historic integrity. Designed for both everyday living and entertaining, the property includes a spacious three-car garage and generous living areas that honor its past while accommodating modern lifestyles. The grounds unfold toward the water, offering a peaceful backdrop and a true connection to Essex's coastal beauty. This Historic Essex Village waterfront home is a rare offering where heritage, location, and lifestyle converge.

Enjoy the best of Shoreline living at Hammock Point, a distinctive 55+ community nestled along the Patchogue River in Westbrook. This exceptional, sun-filled end unit offers a wonderful combination of easy living, privacy and coastal charm. Stroll to the community dock to launch your kayak or canoe, enjoy morning coffee in the waterfront gazebo, or simply watch the egrets, herons and osprey along the river's edge. A nearby marina and Bill's Seafood are within walking distance, and Westbrook Town Beach is less than a mile away. Inside, the spacious kitchen features granite countertops, generous cabinetry and a breakfast bar opening to the dining and living areas with hardwood floors and a cozy gas fireplace. Sliders lead to a private, fenced backyard, perfect for outdoor dining, gardening, and relaxing. The oversized main-level primary suite features a walk-in closet and spacious bath with double sinks. A powder room, laundry area and charming home-office nook complete the first floor. Upstairs offers a generous second bedroom, full bath and large walk-in closet-ideal for guests. An attached one-car garage, Generac whole-house generator completes the package. Kayak from the community dock, walk to the marina, spend the afternoon at the beach, enjoy dinner along the Shoreline, or simply relax in your own private backyard. At Hammock Point, there's nothing left to do but unpack, settle in and enjoy the shoreline lifestyle. The light over the kitchen table does not convey.

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.

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. An inviting Family Room. A spectacular Living Room. And a 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.