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$435,000

27-29 East High Street offers a strong investment opportunity in the heart of East Hampton, combining established first-floor retail with professional office space above. The approximately 3,816-square-foot building features two street-level retail spaces totaling roughly 2,300 square feet, along with approximately 1,386 square feet of second-floor office space divided into multiple suites. The property already has established tenants in place, while current office vacancies provide an opportunity to increase income through additional leasing. The level .16-acre site includes paved parking for approximately 12 vehicles, two points of ingress and egress, city sewer, and excellent exposure along Route 66 (East High Street). Recent improvements include second-floor windows, vinyl siding on the front exterior, and paving in the parking area. With a mix of retail and professional office uses, existing income, and room to improve occupancy, this is a compelling opportunity for an investor looking to add a manageable commercial property to their portfolio.

2 Baths ⋅ 24205780 MLS

27-29 East High Street offers a strong investment opportunity in the heart of East Hampton, combining established first-floor retail with professional office space above. The approximately 3,816-square-foot building features two street-level retail spaces totaling roughly 2,300 square feet, along with approximately 1,386 square feet of second-floor office space divided into multiple suites. The property already has established tenants in place, while current office vacancies provide an opportunity to increase income through additional leasing. The level .16-acre site includes paved parking for approximately 12 vehicles, two points of ingress and egress, city sewer, and excellent exposure along Route 66 (East High Street). Recent improvements include second-floor windows, vinyl siding on the front exterior, and paving in the parking area. With a mix of retail and professional office uses, existing income, and room to improve occupancy, this is a compelling opportunity for an investor looking to add a manageable commercial property to their portfolio.

27-29 E High St, East Hampton

$479,500

Move right into this beautifully maintained Contemporary Cape in the popular Spice Hill subdivision! Freshly painted throughout with gleaming hardwood floors, this inviting home combines modern updates with timeless appeal. A cathedral ceiling, skylights, ceiling fans, and a fireplace create a bright, airy atmosphere, perfect for relaxing or entertaining. The open living and dining areas flow into the updated kitchen featuring granite countertops, stainless steel appliances, and additional skylights that fill the space with natural light. A versatile first-floor room offers the flexibility to serve as a primary bedroom, home office, den, or guest space. Sliders from the dining room lead to a charming three-season porch - easy to convert into a year-round sunroom. Upstairs you'll find two spacious bedrooms, a remodeled full bath, and an open loft overlooking the living room, ideal for a reading nook or workspace. Both bathrooms have been tastefully updated. The roof and skylights are 2 years old. Outside, enjoy beautifully landscaped gardens filled with mature shrubs and colorful perennials. The subdivision has 80 acres of open space and is within easy reach of major routes, the town center, Sears Park on Lake Pocotopaug and other attractions and amenities. Don't miss this superb home!

3 Beds ⋅ 2 Baths ⋅ 24204479 MLS

Move right into this beautifully maintained Contemporary Cape in the popular Spice Hill subdivision! Freshly painted throughout with gleaming hardwood floors, this inviting home combines modern updates with timeless appeal. A cathedral ceiling, skylights, ceiling fans, and a fireplace create a bright, airy atmosphere, perfect for relaxing or entertaining. The open living and dining areas flow into the updated kitchen featuring granite countertops, stainless steel appliances, and additional skylights that fill the space with natural light. A versatile first-floor room offers the flexibility to serve as a primary bedroom, home office, den, or guest space. Sliders from the dining room lead to a charming three-season porch - easy to convert into a year-round sunroom. Upstairs you'll find two spacious bedrooms, a remodeled full bath, and an open loft overlooking the living room, ideal for a reading nook or workspace. Both bathrooms have been tastefully updated. The roof and skylights are 2 years old. Outside, enjoy beautifully landscaped gardens filled with mature shrubs and colorful perennials. The subdivision has 80 acres of open space and is within easy reach of major routes, the town center, Sears Park on Lake Pocotopaug and other attractions and amenities. Don't miss this superb home!

47 Spice Hill Dr, East Hampton

$450,000

Enjoy refreshments on the deck and a boat ride to boot while taking in beautiful views of the community's private beach, docks, gazebo and Lake Pocotopaug! Located within an intimate, self-managed lakefront community of just 19 seasonal and year-round homes, this spacious two-bedroom, two-bath condominium offers 1,152 square feet of comfortable living space and a generous awning-covered deck. With only a limited number of year-round residences, this shared community setting offers a distinctive alternative to the expense and responsibility often associated with owning a traditional standalone waterfront home. Whether you're searching for a year-round residence or a weekend retreat, this special property invites you to enjoy swimming, boating and relaxing by the lake-even taking your boat to a nearby lakeside restaurant-all while remaining conveniently close to East Hampton's shops, restaurants and other amenities. The spacious upper level is currently configured as one bedroom with a private bath and offers flexibility for a possible additional bedroom, office or playroom, subject to town and association approvals.

2 Beds ⋅ 2 Baths ⋅ 24205103 MLS ⋅ Island View Community BLDG.

Enjoy refreshments on the deck and a boat ride to boot while taking in beautiful views of the community's private beach, docks, gazebo and Lake Pocotopaug! Located within an intimate, self-managed lakefront community of just 19 seasonal and year-round homes, this spacious two-bedroom, two-bath condominium offers 1,152 square feet of comfortable living space and a generous awning-covered deck. With only a limited number of year-round residences, this shared community setting offers a distinctive alternative to the expense and responsibility often associated with owning a traditional standalone waterfront home. Whether you're searching for a year-round residence or a weekend retreat, this special property invites you to enjoy swimming, boating and relaxing by the lake-even taking your boat to a nearby lakeside restaurant-all while remaining conveniently close to East Hampton's shops, restaurants and other amenities. The spacious upper level is currently configured as one bedroom with a private bath and offers flexibility for a possible additional bedroom, office or playroom, subject to town and association approvals.

1 Day Point Rd Unit 19, East Hampton

$424,900

Completely remodeled from top to bottom and showing like brand-new construction, this beautifully refreshed home offers bright, inviting living spaces and a fantastic location in the Pocotopaug Lake community. The first floor features hardwood flooring and an open, comfortable layout with a spacious kitchen, dining area and sun-filled living room with access to the covered deck. Upstairs, generously sized bedrooms continue the home's fresh, move-in-ready feel. The heated 672 sq. ft. walkout lower level provides valuable additional living space along with storage and flexibility for a recreation room, home office, gym or more. Outside, a huge 24 x 32 detached two-car garage with workshop space and a loft is an exceptional bonus. Enjoy beach rights and the ability to walk to Pocotopaug Lake and the boat launch for swimming, kayaking, canoeing and fishing. Conveniently located close to shopping, businesses and Route 66, this is an opportunity to enjoy a beautifully remodeled home along with the lifestyle of a true lake community. New roof!

4 Beds ⋅ 3 Baths ⋅ 24197501 MLS

Completely remodeled from top to bottom and showing like brand-new construction, this beautifully refreshed home offers bright, inviting living spaces and a fantastic location in the Pocotopaug Lake community. The first floor features hardwood flooring and an open, comfortable layout with a spacious kitchen, dining area and sun-filled living room with access to the covered deck. Upstairs, generously sized bedrooms continue the home's fresh, move-in-ready feel. The heated 672 sq. ft. walkout lower level provides valuable additional living space along with storage and flexibility for a recreation room, home office, gym or more. Outside, a huge 24 x 32 detached two-car garage with workshop space and a loft is an exceptional bonus. Enjoy beach rights and the ability to walk to Pocotopaug Lake and the boat launch for swimming, kayaking, canoeing and fishing. Conveniently located close to shopping, businesses and Route 66, this is an opportunity to enjoy a beautifully remodeled home along with the lifestyle of a true lake community. New roof!

28 Tennyson Rd, East Hampton

$499,999

Welcome to Laurel Ridge, a desirable 55+ community in East Hampton! Built in 2005, this spacious 2,108 sq. ft. home offers 3 bedrooms, 2 full baths, plus a versatile bonus room and a thoughtfully designed floor plan with several upgrades that set it apart. Cathedral ceilings, five skylights and large windows bring an abundance of natural light in the main living space, while the gas fireplace creates a warm and inviting focal point. The kitchen features under-cabinet lighting and newer appliances, and Hunter Douglas blinds and ceiling fans can be found throughout. Designed with aging in place in mind, the home features widened doorways for wheelchair accessibility, grab bars in the primary bath and additional railings for added convenience. A newer deck includes a built-in gas line, and the grill stays! One of the home's standout features is the walkout basement with additional windows, offering excellent natural light and tremendous potential for future finished space, a workshop, hobbies or storage. Enjoy comfortable, low-maintenance living in one of East Hampton's established 55+ communities, with a flexible floor plan and features you won't find in every Laurel Ridge home. Come look today!

3 Beds ⋅ 2 Baths ⋅ 24202387 MLS

Welcome to Laurel Ridge, a desirable 55+ community in East Hampton! Built in 2005, this spacious 2,108 sq. ft. home offers 3 bedrooms, 2 full baths, plus a versatile bonus room and a thoughtfully designed floor plan with several upgrades that set it apart. Cathedral ceilings, five skylights and large windows bring an abundance of natural light in the main living space, while the gas fireplace creates a warm and inviting focal point. The kitchen features under-cabinet lighting and newer appliances, and Hunter Douglas blinds and ceiling fans can be found throughout. Designed with aging in place in mind, the home features widened doorways for wheelchair accessibility, grab bars in the primary bath and additional railings for added convenience. A newer deck includes a built-in gas line, and the grill stays! One of the home's standout features is the walkout basement with additional windows, offering excellent natural light and tremendous potential for future finished space, a workshop, hobbies or storage. Enjoy comfortable, low-maintenance living in one of East Hampton's established 55+ communities, with a flexible floor plan and features you won't find in every Laurel Ridge home. Come look today!

26 Laurel Ridge, Unit 26, East Hampton

$499,999

Welcome to Laurel Ridge, a desirable 55+ community in East Hampton! Built in 2005, this spacious 2,108 sq. ft. home offers 3 bedrooms, 2 full baths, plus a versatile bonus room and a thoughtfully designed floor plan with several upgrades that set it apart. Cathedral ceilings, five skylights and large windows bring an abundance of natural light in the main living space, while the gas fireplace creates a warm and inviting focal point. The kitchen features under-cabinet lighting and newer appliances, and Hunter Douglas blinds and ceiling fans can be found throughout. Designed with aging in place in mind, the home features widened doorways for wheelchair accessibility, grab bars in the primary bath and additional railings for added convenience. A newer deck includes a built-in gas line, and the grill stays! One of the home's standout features is the walkout basement with additional windows, offering excellent natural light and tremendous potential for future finished space, a workshop, hobbies or storage. Enjoy comfortable, low-maintenance living in one of East Hampton's established 55+ communities, with a flexible floor plan and features you won't find in every Laurel Ridge home. Come look today!

3 Beds ⋅ 2 Baths ⋅ 24202086 MLS ⋅ Laurel Ridge BLDG.

Welcome to Laurel Ridge, a desirable 55+ community in East Hampton! Built in 2005, this spacious 2,108 sq. ft. home offers 3 bedrooms, 2 full baths, plus a versatile bonus room and a thoughtfully designed floor plan with several upgrades that set it apart. Cathedral ceilings, five skylights and large windows bring an abundance of natural light in the main living space, while the gas fireplace creates a warm and inviting focal point. The kitchen features under-cabinet lighting and newer appliances, and Hunter Douglas blinds and ceiling fans can be found throughout. Designed with aging in place in mind, the home features widened doorways for wheelchair accessibility, grab bars in the primary bath and additional railings for added convenience. A newer deck includes a built-in gas line, and the grill stays! One of the home's standout features is the walkout basement with additional windows, offering excellent natural light and tremendous potential for future finished space, a workshop, hobbies or storage. Enjoy comfortable, low-maintenance living in one of East Hampton's established 55+ communities, with a flexible floor plan and features you won't find in every Laurel Ridge home. Come look today!

26 Laurel Ridge, Unit 26, East Hampton

$475,000

Discover lake-community living in this distinctive California-style hi-ranch, where thoughtful design and careful stewardship come together in this unique home. Expansive windows bring natural light to both floors, including the walk-out lower level, creating more than 3,000 sq ft of bright, heated living space. The open main level features vaulted ceilings, exposed beams, and hardwood floors, while the spacious kitchen offers concrete counters, stainless appliances, and direct deck access. Four bedrooms and three full baths include a generous primary suite with two walk-in closets, deck access, and a spa-inspired bath with a claw-foot tub, tiled shower, and double vanity. The lower level offers a family room, recreation space, two bedrooms, a full bath, a fireplace, and excellent flexibility for work, hobbies, or guests. Full central air was installed in April 2024, with an additional mini-split for enhanced comfort, and the hot-water tank was replaced in July 2025. Enjoy private beach, swimming and dock access through the Lake Pocotopaug Terrace Association.

4 Beds ⋅ 3 Baths ⋅ 24200823 MLS

Discover lake-community living in this distinctive California-style hi-ranch, where thoughtful design and careful stewardship come together in this unique home. Expansive windows bring natural light to both floors, including the walk-out lower level, creating more than 3,000 sq ft of bright, heated living space. The open main level features vaulted ceilings, exposed beams, and hardwood floors, while the spacious kitchen offers concrete counters, stainless appliances, and direct deck access. Four bedrooms and three full baths include a generous primary suite with two walk-in closets, deck access, and a spa-inspired bath with a claw-foot tub, tiled shower, and double vanity. The lower level offers a family room, recreation space, two bedrooms, a full bath, a fireplace, and excellent flexibility for work, hobbies, or guests. Full central air was installed in April 2024, with an additional mini-split for enhanced comfort, and the hot-water tank was replaced in July 2025. Enjoy private beach, swimming and dock access through the Lake Pocotopaug Terrace Association.

8 Mountain Trl, East Hampton

$425,000

Welcome to 18 Crestwood Dr., a beautifully maintained & thoughtfully updated 3-bedroom, 2-full-bath home over the 33 year ownership. Nestled on more than a half-acre this property brings a wonderful & thoughtful blend of comfort, functionality, and modern updates, designed for the way you live today. All in a peaceful neighborhood setting. The home has benefited from an impressive list of improvements, with many of the major systems and finishes updated in recent years. The kitchen has been remodeled within the past year, complete with updated appliances, while the main level has been freshly painted. The flooring has been redone within the past 5 years, complementing the home's refreshed interior. The bathrooms have also been remodeled, and a newer furnace adds to the home's comfort and efficiency. The lower level walk-out adds an entirely different dimension to the home, featuring both a "Man Cave" and a "Diva Den," offering fantastic flexible space for entertaining, hobbies, recreation, a home office, or simply having separate areas to relax and unwind. Or maybe someone's screaming "teen suite"! Peace of mind comes with the whole-house Generac generator system, installed approximately 4 years ago, along with an upgraded 220-amp electrical service. New gutters & garage door openers add further convenience and value. The main house roof & windows are approximately 15 years old, along with an impressive, freshly paved driveway. Within minutes of everything that East Hampton

3 Beds ⋅ 2 Baths ⋅ 24200325 MLS

Welcome to 18 Crestwood Dr., a beautifully maintained & thoughtfully updated 3-bedroom, 2-full-bath home over the 33 year ownership. Nestled on more than a half-acre this property brings a wonderful & thoughtful blend of comfort, functionality, and modern updates, designed for the way you live today. All in a peaceful neighborhood setting. The home has benefited from an impressive list of improvements, with many of the major systems and finishes updated in recent years. The kitchen has been remodeled within the past year, complete with updated appliances, while the main level has been freshly painted. The flooring has been redone within the past 5 years, complementing the home's refreshed interior. The bathrooms have also been remodeled, and a newer furnace adds to the home's comfort and efficiency. The lower level walk-out adds an entirely different dimension to the home, featuring both a "Man Cave" and a "Diva Den," offering fantastic flexible space for entertaining, hobbies, recreation, a home office, or simply having separate areas to relax and unwind. Or maybe someone's screaming "teen suite"! Peace of mind comes with the whole-house Generac generator system, installed approximately 4 years ago, along with an upgraded 220-amp electrical service. New gutters & garage door openers add further convenience and value. The main house roof & windows are approximately 15 years old, along with an impressive, freshly paved driveway. Within minutes of everything that East Hampton

18 Crestwood Dr, East Hampton

$429,000

Welcome to this well-maintained raised ranch nestled on a peaceful cul-de-sac in one of East Hampton's most desirable neighborhoods. Situated on approximately one acre, this 3-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and convenience, just minutes from Lake Pocotopaug, local parks, shopping, and restaurants. The main level features a bright and inviting living room with hardwood floors and a fireplace, a spacious eat-in kitchen, and comfortable bedrooms designed for everyday living. Step outside to a large deck overlooking the private backyard-ideal for entertaining, relaxing, or enjoying the peaceful surroundings. Home includes include a newer roof, along with a paved driveway and attached garage. The finished lower level provides additional flexible living space that can accommodate a variety of needs, such as a recreation room, home office, gym, hobby space, or guest area. Don't miss this opportunity to own a move-in-ready home in a quiet neighborhood with plenty of indoor and outdoor space to enjoy

3 Beds ⋅ 2 Baths ⋅ 24197522 MLS

Welcome to this well-maintained raised ranch nestled on a peaceful cul-de-sac in one of East Hampton's most desirable neighborhoods. Situated on approximately one acre, this 3-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and convenience, just minutes from Lake Pocotopaug, local parks, shopping, and restaurants. The main level features a bright and inviting living room with hardwood floors and a fireplace, a spacious eat-in kitchen, and comfortable bedrooms designed for everyday living. Step outside to a large deck overlooking the private backyard-ideal for entertaining, relaxing, or enjoying the peaceful surroundings. Home includes include a newer roof, along with a paved driveway and attached garage. The finished lower level provides additional flexible living space that can accommodate a variety of needs, such as a recreation room, home office, gym, hobby space, or guest area. Don't miss this opportunity to own a move-in-ready home in a quiet neighborhood with plenty of indoor and outdoor space to enjoy

54 Midwood Farm Rd, East Hampton

$449,000

Beautifully remodeled and move-in ready, this exceptional home is waiting for its new owner! Situated on 5.3 picturesque acres that abut a state forest, this property offers privacy, scenic surroundings, and the potential to be used as horse property. The home has been thoughtfully updated with a newer roof, newer siding, a beautifully remodeled kitchen, two recently renovated full bathrooms, and fresh paint throughout, creating a modern and inviting living space. Step outside to enjoy the beautifully landscaped grounds featuring a spacious Trex deck with a fully waterproof patio below-perfect for entertaining, relaxing, or taking in the peaceful setting. The versatile lower-level room offers endless possibilities and can easily be converted into a garage or kept as a workshop, hobby space, or arts and crafts studio. Whether you're looking for room to roam, space for horses, or simply a beautifully updated home surrounded by nature, this one checks all the boxes. Don't miss this must-see property!

2 Beds ⋅ 2 Baths ⋅ 24195513 MLS

Beautifully remodeled and move-in ready, this exceptional home is waiting for its new owner! Situated on 5.3 picturesque acres that abut a state forest, this property offers privacy, scenic surroundings, and the potential to be used as horse property. The home has been thoughtfully updated with a newer roof, newer siding, a beautifully remodeled kitchen, two recently renovated full bathrooms, and fresh paint throughout, creating a modern and inviting living space. Step outside to enjoy the beautifully landscaped grounds featuring a spacious Trex deck with a fully waterproof patio below-perfect for entertaining, relaxing, or taking in the peaceful setting. The versatile lower-level room offers endless possibilities and can easily be converted into a garage or kept as a workshop, hobby space, or arts and crafts studio. Whether you're looking for room to roam, space for horses, or simply a beautifully updated home surrounded by nature, this one checks all the boxes. Don't miss this must-see property!

138 Clark Hill Rd, East Hampton

$409,995

Comfort, convenience, and efficiency on nearly 1 acre are the highlights of this well-maintained 3-bedroom, 2 full bath Ranch. This home is equipped with energy money saving systems. Home includes a whole house electric heat pump, central air, hybrid heat pump water heater, automated water filtration system and updated well pump tank for year-round comfort. This single level home boasts an open layout with a bright eat-in kitchen opening directly to a deck overlooking a fenced in yard, ideal for family and furry friends. Step inside a bright living room with fireplace that transitions into a den or dedicated office. The primary bedroom includes attached full bath, while second full bath serves the additional bedrooms. Set back in a quiet neighborhood, moments from Lake Pocotopaug, Salmon River, and Airline Trail, with easy access to area schools and conveniences. Don't miss this rare opportunity to own this one!

3 Beds ⋅ 2 Baths ⋅ 24192346 MLS

Comfort, convenience, and efficiency on nearly 1 acre are the highlights of this well-maintained 3-bedroom, 2 full bath Ranch. This home is equipped with energy money saving systems. Home includes a whole house electric heat pump, central air, hybrid heat pump water heater, automated water filtration system and updated well pump tank for year-round comfort. This single level home boasts an open layout with a bright eat-in kitchen opening directly to a deck overlooking a fenced in yard, ideal for family and furry friends. Step inside a bright living room with fireplace that transitions into a den or dedicated office. The primary bedroom includes attached full bath, while second full bath serves the additional bedrooms. Set back in a quiet neighborhood, moments from Lake Pocotopaug, Salmon River, and Airline Trail, with easy access to area schools and conveniences. Don't miss this rare opportunity to own this one!

165 Colchester Ave, East Hampton

$495,000

Step into the perfect blend of timeless New England charm and modern convenience in this beautifully maintained circa-1869 Colonial, ideally located in the heart of East Hampton. Offering over 2,275 square feet of living space, this 4-bedroom, 2.5-bath home showcases the character of a bygone era while featuring numerous thoughtful updates throughout. The custom kitchen is equipped with stainless steel appliances, corian countertops, and ample cabinetry, creating a functional space for everyday living and entertaining. Wide-plank hardwood floors, updated bathrooms, and a flexible floor plan provide warmth and versatility. Major improvements include a high-efficiency natural gas boiler with on-demand hot water, updated electrical service, newer windows, and newer roof, providing peace of mind for years to come. Outside, enjoy a level yard with detached garage and off-street parking. Conveniently situated within a very short distance to the Air Line State Park Trail, local shops, restaurants, schools, the town beach, and all that East Hampton's vibrant village center has to offer. Rich in history, thoughtfully updated, and ideally located, this is a wonderful opportunity to own a home that truly offers the best of old-world character and modern comfort.

4 Beds ⋅ 3 Baths ⋅ 24192604 MLS

Step into the perfect blend of timeless New England charm and modern convenience in this beautifully maintained circa-1869 Colonial, ideally located in the heart of East Hampton. Offering over 2,275 square feet of living space, this 4-bedroom, 2.5-bath home showcases the character of a bygone era while featuring numerous thoughtful updates throughout. The custom kitchen is equipped with stainless steel appliances, corian countertops, and ample cabinetry, creating a functional space for everyday living and entertaining. Wide-plank hardwood floors, updated bathrooms, and a flexible floor plan provide warmth and versatility. Major improvements include a high-efficiency natural gas boiler with on-demand hot water, updated electrical service, newer windows, and newer roof, providing peace of mind for years to come. Outside, enjoy a level yard with detached garage and off-street parking. Conveniently situated within a very short distance to the Air Line State Park Trail, local shops, restaurants, schools, the town beach, and all that East Hampton's vibrant village center has to offer. Rich in history, thoughtfully updated, and ideally located, this is a wonderful opportunity to own a home that truly offers the best of old-world character and modern comfort.

124 Main St, East Hampton

$400,000

Build your dream home-or explore subdivision potential-on this exceptional 37+ acre parcel featuring 54 feet of road frontage. This beautiful wooded setting offers privacy, natural charm, and endless possibilities. Best of all, scenic Pine Brook winds along the rear of the property, creating a peaceful backdrop and a truly special connection to nature.

24166202 MLS

Build your dream home-or explore subdivision potential-on this exceptional 37+ acre parcel featuring 54 feet of road frontage. This beautiful wooded setting offers privacy, natural charm, and endless possibilities. Best of all, scenic Pine Brook winds along the rear of the property, creating a peaceful backdrop and a truly special connection to nature.

139 Chestnut Hill Rd, East Hampton