Middlesex County CT Homes for Sale

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  /38

  $3,150,000

  • 4 Beds
  • 6 Baths
  • 4,926 Sq Ft

  288 Middlesex Ave, Chester, CT 06412

  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

  Nancy Mesham Coldwell Banker Realty

  288 Middlesex Ave, Chester, CT 06412
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  /21

  $699,900

  • 6 Beds
  • 3 Baths
  • 3,152 Sq Ft

  226 W High St, East Hampton, CT 06424

  Discover a rare and exceptional opportunity with this unique property featuring two homes on one lot-a spacious 1,726 sq ft single-family residence paired with a separate three-unit multi-family on a beautiful 2.32 Acre lot with stone walls! 4 car detached garage! Perfect for owner-occupants, investors, multigenerational living, or anyone seeking added income potential, this versatile setup

  Cathyann Schulte Countryside Realty

  226 W High St, East Hampton, CT 06424
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  /40

  $1,179,900

  • 4 Beds
  • 2.5 Baths
  • 4,109 Sq Ft

  96 Ayers Point Rd, Old Saybrook, CT 06475

  Discover the serenity of Ayers Point in this spacious 3400 sq ft home with captivating views of the Connecticut River and surrounding marshland. Privately set with a beautiful inground pool and lush gardens, this retreat is perfect for those seeking a coastal lifestyle near boating and village charm. The home features both main and upper level primary suites, offering flexibility and comfort for

  Joel Lucas Coldwell Banker Realty

  96 Ayers Point Rd, Old Saybrook, CT 06475
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  /2

  $750,000

  • Land
  • 7.5 Acres
  • $100,000 per Acre

  0 Middle St, Middletown, CT 06457

  7.5 Acres Commercial Industrial Land. Zoning: IOP (Industrial Office Park including office, warehouse, industrial & recreation. This parcel is going to be split off of a larger piece consisting of 28.96 acres. 8 acres of abutting residential land off Bell Street available for assemblage * Total Potential Assemblage: 41 acres * Immediate Access: Minutes to I-91 (Exit 20) Highly flexible IOP zoning

  Nancy Newman LPT Realty

  0 Middle St, Middletown, CT 06457
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  /32

  $300,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,283 Sq Ft

  78 Highland Ave, Middletown, CT 06457

  Well maintained and thoughtfully updated, this home offers a combination of space, functionality, and value that's getting harder to find. Hardwood floors run throughout much of the home, adding warmth and character, while the layout provides flexibility for a variety of living needs. The main level features an updated kitchen that connects comfortably to the living space, where a fireplace

  Rob Paskiewicz CT Home Pro, LLC

  78 Highland Ave, Middletown, CT 06457
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  /34

  $1,045,000

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft

  224 Salt Island Rd, Westbrook, CT 06498

  Tucked away in a charming shoreline setting, this retreat on Salt Island Road is directly across the street from Long Island Sound with breathtaking unobstructed water views. Enjoy coastal living in this inviting home featuring bright and comfortable living spaces designed for relaxing summer days and peaceful evenings by the shore. Wake up to refreshing sea breezes and take in stunning views of

  Jackie Lyman Lyman Real Estate

  224 Salt Island Rd, Westbrook, CT 06498
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  /36

  $845,000

  • 4 Beds
  • 1.5 Baths
  • 2,070 Sq Ft

  110 Freeman Rd, Middletown, CT 06457

  VERY unique property. Use to be a goat farm. Contains 6 outbuildings consisting of a 3 bay open shed - perfect for storing just about anything, a 3 story red bank barn, a 1 car detached heated garage with an office and a furnace with a separate oil tank, a feed shed, a detached garage for the house and an outhouse. The home has 4 bedroom on the 2nd floor, a walk up attic that is floored , a large

  Pam Rizy Berkshire Hathaway NE Prop.

  110 Freeman Rd, Middletown, CT 06457
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  /25

  $548,000

  • 3 Beds
  • 2 Baths
  • 1,833 Sq Ft

  9 Ben Merrill Rd, Clinton, CT 06413

  Welcome to 9 Ben Merrill Rd . A fully renovated 3-bed, 2 full bath ranch on 1.86 private acres. The house has a brand new roof, vinyl siding, gutters, windows, exterior doors, full electrical and plumbing overhaul, new water heater, 200- amp meter panel, and much more! The open-concept kitchen features a large island, quartz countertops, Hardwood custom cabinetry, and all-new stainless appliances

  Ruben Vallejo Golden Ribbon Realty

  9 Ben Merrill Rd, Clinton, CT 06413
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  /29

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft

  49 River St, Old Saybrook, CT 06475

  Spacious village area colonial with lot's of space and in what a location, a short stroll to Main Street and convenient to shops, highways and the railroad station. Featuring 9 rooms and 4 bedrooms with a second upper level kitchenette, this floorplan suits all of your housing needs at a price which won't bust the budget. Could potentially accommodate an in-law use with the second kitchen.

  Rick Allen William Raveis Real Estate

  49 River St, Old Saybrook, CT 06475
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  /40

  $1,589,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,472 Sq Ft

  2 Old South Cove Rd, Old Saybrook, CT 06475

  At Saybrook Point, life is defined by the water. Morning walks by the marina, kayaking on quiet coves, beach days, coffee downtown, dinner at the Saybrook Point Inn, and summer evenings that feel like a resort vacation without ever leaving home. New construction in this location is nearly impossible to find, and the photos tell the story better than words ever could. Set where water, light, and

  Michael Riccio Calcagni Real Estate

  2 Old South Cove Rd, Old Saybrook, CT 06475
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  /36

  $1,090,000

  • 7 Beds
  • 6 Baths
  • 2,942 Sq Ft

  23 Main St, East Haddam, CT 06423

  Completely remodeled inside in 2025, this historic building has the potential for multiple uses. It was approved as a tavern on the first floor, and B+B units on the 2nd and 3rd floor or long term rentals. but can be easily adapted into a number of different uses, including commercial. Currently it has been adapted into gorgeous, modern residential units, With a two-bedroom unit, 4 one-bedroom

  Stephanie Jacobs Sunset Creek Realty, LLC

  23 Main St, East Haddam, CT 06423
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  /20

  $319,900 Pre-Foreclosure

  • 5 Beds
  • 2 Baths
  • 1,912 Sq Ft

  116 Howd Rd, Durham, CT 06422

  Set on a generous 1+ acre lot in scenic Durham, this Colonial offers a fantastic opportunity to create your dream home. Featuring a spacious layout with an open living/dining area, updated kitchen, and multiple bedrooms and baths, the home provides a solid foundation with great potential. The expansive yard and wooded backdrop offer privacy and room to expand outdoor living spaces. Ideal for

  Michael Sirochman Coldwell Banker Realty

  116 Howd Rd, Durham, CT 06422
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  /2

  $279,900

  • Land
  • 20,037 Sq Ft
  • $608,478 per Acre

  8 Cortland Way, Cromwell, CT 06416

  Last lot available in new subdivision of beautiful custom built homes! 8 lot subdivision located off of Woodside Road in Cromwell. Lot is .46 acres in size; is easy to work with and sewer and water are on site! Lot has all the topsoil you will need and then some. Bring your builder, bring your dream home plans and make it a dream come true! Don't wait, there's nothing else out there like this - a

  Jennifer Hussey Century 21 Clemens Group

  8 Cortland Way, Cromwell, CT 06416
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  /28

  $1,275,000

  • 3 Beds
  • 3 Baths
  • 2,475 Sq Ft

  6 Leeway Dr, Westbrook, CT 06498

  Pristine year round Contemporary home with views of the Marina at Pilots Point. Relax on the 12'x35' deck with an electric retractable awning or just enjoy the evening setting sun. The back patio has an enclosed shower and an area to grill. This home has been renovated and features many upgrades. The family room on the first floor could have an office. The Great room on the 2nd level has windows

  Salome Kirkutis SKS Realty

  6 Leeway Dr, Westbrook, CT 06498
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  /14

  $229,900

  • 3 Beds
  • 1 Bath
  • 1,238 Sq Ft

  103 Grand St, Middletown, CT 06457

  Perfect opportunity for home ownership in Middletown! This 3 bedroom home offers an updated kitchen with quartz countertops and stainless steel appliances, large dining room perfect for entertaining, and beautiful living room arrangement with custom shiplap wall! Level lot with off street parking. Stop by for a showing today!

  Sylvia Narciso Bottom Line Realty

  103 Grand St, Middletown, CT 06457
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  /40

  $2,800,000

  • 5 Beds
  • 5.5 Baths
  • 5,234 Sq Ft

  88 Main St, Ivoryton, CT 06442

  Move into this elegantly designed, meticulously restored estate in the nationally registered historic village of Ivoryton in the town of Essex. Built by the prominent Essex industrialist, Samuel Comstock, the 5,234 sq. ft. property on 1.86 acres offers history and grandeur to those seeking privacy and tasteful opulence. Preserved in the same family for five generations and recently completely

  Kirsten Adams William Pitt Sotheby's Int'l

  88 Main St, Ivoryton, CT 06442
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  /31

  $875,000

  • 3 Beds
  • 3 Baths
  • 1,560 Sq Ft

  100 2nd Ave, Westbrook, CT 06498

  Welcome to 100 Second Avenue, located in sought-after Stannard Beach. A coastal gem offering the perfect blend of lifestyle and location. Enjoy water views that bring a sense of calm and coastal charm to everyday living. This property is ideally situated to take advantage of a vibrant, community. Amenities at Stannard Beach include a new playground, pickleball, tennis, basketball courts, and it's

  Jackie Lyman Lyman Real Estate

  100 2nd Ave, Westbrook, CT 06498
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  /15

  $134,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  44 Linden Ave N, Westbrook, CT 06498

  Welcome to easy coastal living in the highly desirable 55+ beach community in Westbrook, CT. This charming 2-bedroom, 1 full bathroom mobile home offers the perfect opportunity to enjoy a relaxed shoreline lifestyle just steps from the water. Inside, you'll find a bright and inviting living space with a functional layout that makes the most of every square foot. The home features new appliances,

  Tyler Amann Social & Co Realty

  44 Linden Ave N, Westbrook, CT 06498
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  /6

  $118,000

  • Land
  • 19,602 Sq Ft
  • $262,222 per Acre

  28 & 33 River Rd, Cromwell, CT 06416

  Riverfront property! Building lot with 80 feet of private direct waterfront access just steps away. Perfect setting to build your new home and enjoy recreational water activities.Buyers to conduct own due diligence.Make appointment to view.

  Julie Keithan Group Four Realty

  28 & 33 River Rd, Cromwell, CT 06416
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  /37

  $749,900 Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 5,165 Sq Ft

  13 Copper Knoll Ln, Cromwell, CT 06416

  Tucked away at the end of a cul-de-sac, this beautiful and bright contemporary colonial offers the perfect blend of space, comfort, & functionality! Freshly painted throughout, this expansive home features a desirable open layout filled with natural light and thoughtful living spaces for today's lifestyle. The main level offers a spacious eat-in kitchen w abundant cabinet storage and counter

  Cheryl Bergeron-Lucca LPT Realty - IConn Team

  13 Copper Knoll Ln, Cromwell, CT 06416
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  /20

  $729,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  151 E Main St Unit 22, Clinton, CT 06413

  Welcome to Sterling Sand Village - Coastal Living in Clinton Township. Discover the charm of Sterling Sand Village, a community under development, perfectly situated along the shoreline of Clinton Beach and Marina. Nestled in tranquil Clinton Township, this new development combines modern comfort with coastal beauty, offering an exceptional lifestyle just minutes from Clinton Premium Outlets,

  Gavin Sudhakar RE/MAX Right Choice

  151 E Main St Unit 22, Clinton, CT 06413
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  /19

  $750,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  2 Town Line Dr, East Hampton, CT 06424

  Brand new construction by M&R Custom Homes offering 2,500 sq ft. of thoughtfully designed living space in one of the area's most sought-after subdivisions Whispering Woods. In the process of construction, the pictures show a similar to be completed home. This four-bedroom, 2.5-bath home features a bright, open-concept layout perfect for both everyday living and entertaining. The spacious kitchen

  Tracy Molloy Coldwell Banker Realty

  2 Town Line Dr, East Hampton, CT 06424
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  /40

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  89 Book Hill Rd, Essex, CT 06426

  Welcome to 89 Book Hill Road in the heart of Essex Village. This beautifully updated Cape offers a perfect blend of classic New England charm and modern comfort. Set on a private lot surrounded by mature trees, the home features a spacious and light-filled layout with hardwood floors, two fireplaces, and a flexible floor plan. The kitchen has been tastefully updated with modern finishes, flowing

  Tyler Lynch RE/MAX RISE

  89 Book Hill Rd, Essex, CT 06426
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  /32

  $139,900

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  55 Mountainview Rd, East Hampton, CT 06424

  Welcome to Hampton Homes, a 55+ community near Lake Pocotopaug in East Hampton. This well-maintained 2001-built home offers 924 square feet of comfortable living with community lake access and move-in ready condition so you can be in by summer. Inside, an open-concept living and kitchen area with laminate floors feels generous for the size. The peninsula with bar seating makes the kitchen a

  Nick Gilham Real Broker CT, LLC

  55 Mountainview Rd, East Hampton, CT 06424
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  /2

  $400,000

  • Land
  • 6.73 Acres
  • $59,435 per Acre

  0 Dinatale Dr, Durham, CT 06422

  Build your dream home in a quiet residential neighborhood on DiNatale Drive in Durham. This approved building lot offers a peaceful setting with a blend of privacy and convenience. Surrounded by attractive homes and natural scenery, the property provides an ideal opportunity for custom construction. Located just minutes from Durham town center, schools, and local amenities, with easy access to

  Jennifer Ferri Berkshire Hathaway NE Prop.

  0 Dinatale Dr, Durham, CT 06422
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  /38

  $479,900

  • 2 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  9 Pear Orchard Rd, Portland, CT 06480

  Wonderful Bartlett Hill Home set in the best location near the pool and backing up to acres of woods. Step inside to the perfect floorplan with the Living room, dining room, kitchen, laundry and primary bedroom, plus a two car garage, all on the same level! As you walk around the open floorplan, the sunlight flows in and the view of the woods can be seen from everywhere... The efficient chef's

  Wendy Anderson William Pitt Sotheby's International Realty

  9 Pear Orchard Rd, Portland, CT 06480
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  /37

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,309 Sq Ft

  11 Webster Ln Unit 6, Middletown, CT 06457

  Beautifully maintained single-family home located in a desirable 55+ community offering comfort, style & easy living. This open floor plan features a stunning kitchen with granite countertops, abundant cabinetry & a natural gas fireplace that creates a warm, inviting living space. Hardwood floors extend throughout the main level, including the spacious primary suite complete with a walk-in

  Michelle Mazzotta eXp Realty

  11 Webster Ln Unit 6, Middletown, CT 06457
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  /24

  $1,700,000

  • 13 Beds
  • 8 Baths
  • 7,641 Sq Ft

  170 Main St, Deep River, CT 06417

  Exciting investment package in the heart of downtown Deep River! This rare offering includes two nicely renovated multifamily/mixed-use buildings plus a well-established laundromat business, all conveyed together in one sale. 170 Main Street sits on a beautiful corner lot and features a turnkey 5-unit multifamily property with a unit mix of (2) two-bedroom units and (3) one-bedroom units. All

  Amanda Sheehan Oxford Realty

  170 Main St, Deep River, CT 06417
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  /39

  $775,000

  • 3 Beds
  • 3 Baths
  • 2,407 Sq Ft

  112 Main St, Centerbrook, CT 06409

  Nestled on a prime 0.5-acre corner lot in the heart of Centerbrook, 112 Main Street is a meticulously maintained 3-bedroom home that perfectly blends classic charm with serious modern utility. The residence has been extensively updated, featuring an exterior professionally painted in August 2025 with a three-year guarantee and a refreshed kitchen boasting new countertops and a functional kitchen

  Adam Zak Century 21 Classic Homes

  112 Main St, Centerbrook, CT 06409
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  /36

  $924,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  15 Pent Rd, Deep River, CT 06417

  Welcome to 15 Pent Rd in Deep River, a truly captivating property that feels like a private retreat from the moment you arrive. Set in a peaceful, natural setting surrounded by trees and scenic outdoor views, this home offers a rare blend of charm, character, and everyday comfort. This home features 4 bedrooms and a finished attic for added living space. Inside, the home is warm, bright, and full

  Nadia Martinez Ki Property Group

  15 Pent Rd, Deep River, CT 06417
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  /40

  $629,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,010 Sq Ft

  58 Middle Haddam Rd, East Hampton, CT 06424

  Dreaming of a stylish country retreat with history? Look no further than the charming Captain Elijah Johnson house, nestled in the bucolic village of Middle Haddam, CT and located just two hours from New York City and Boston. This property blends modern amenities, including a swimming pool, with the carefully restored original features of a house built in 1780 and listed on the National Registry

  Teri Lewis William Pitt Sotheby's Int'l

  58 Middle Haddam Rd, East Hampton, CT 06424
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  /40

  $1,320,000

  • 4 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  1572 Saybrook Rd, Haddam, CT 06438

  Unique Investment Opportunity! Discover this charming antique two-family home with timeless appeal, featuring a welcoming wraparound porch. Zoned for residential or commercial use, the property also comes with special permit approvals for 24 additional units, creating endless potential. Set on two lots totaling 1.26 acres, this rare offering provides flexibility to purchase together, separately,

  Craig Milton Re/Max Valley Shore

  1572 Saybrook Rd, Haddam, CT 06438
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  /40

  $559,000

  • 2 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  92 Bokum Rd, Old Saybrook, CT 06475

  A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and

  Linda Toscano Coldwell Banker Realty

  92 Bokum Rd, Old Saybrook, CT 06475
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  /39

  $775,000

  • 3 Beds
  • 3.5 Baths
  • 3,476 Sq Ft

  74 Bushy Hill Rd, Ivoryton, CT 06442

  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

  Susan Malan William Pitt Sotheby's Int'l

  74 Bushy Hill Rd, Ivoryton, CT 06442
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  /37

  $2,100,000

  • 11 Beds
  • 12 Baths
  • 8,500 Sq Ft

  163 Main St, Deep River, CT 06417

  A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

  Connor Wenchell VC Property Group, LLC

  163 Main St, Deep River, CT 06417
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  /40

  $729,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,177 Sq Ft

  1340 Old Clinton Rd Unit 12, Westbrook, CT 06498

  Highly sought-after freestanding condo at Spencer's Landing with scenic views of the Patchogue River. The first floor features a spacious primary suite complete with a double vanity, whirlpool tub, and walk-in closet. The remodeled kitchen offers granite countertops, a natural gas range, and a bright eat-in area. The living room impresses with vaulted ceilings and a cozy gas fireplace-perfect for

  Shane Bonanno William Raveis Real Estate

  1340 Old Clinton Rd Unit 12, Westbrook, CT 06498
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  /4

  $89,900

  • Land
  • 3.72 Acres
  • $24,167 per Acre

  00 Stockburger Rd, East Haddam, CT 06423

  Looking for peaceful, picturesque property to build your home? This lot is located on a beautiful, country road that travels along Salmon River Forest. View of the river valley is across the road. Was tested in 1981 with updated testing done in 2025. Treed lot of 3.72 acres with 313 ft of road frontage. Lot is part of the Salmon Ridge Subdivision.

  Dee Hasuly KW Legacy Partners

  00 Stockburger Rd, East Haddam, CT 06423
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  /6

  $350,000

  • 2 Beds
  • 1 Bath
  • 573 Sq Ft

  41 Trolley Rd, Westbrook, CT 06498

  Tucked along Trolley Road in Westbrook, this year-round cottage offers a rare opportunity in one of the shoreline's most sought-after locations. The home itself is ready for a new owner's vision and care, but it's the walk-to-town lifestyle that makes this property truly special. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, and the Westbrook train station, you'll enjoy the

  Jennifer Gurnell William Raveis Real Estate

  41 Trolley Rd, Westbrook, CT 06498
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  /4

  $499,000

  • Land
  • 13.27 Acres
  • $37,604 per Acre

  0 Fairy Dell Rd, Clinton, CT 06413

  Nestled on 13.27 acres of pristine raw land, this parcel boasts 617 feet of road frontage, making it easily accessible and highly visible. Situated in a prime location, it offers the perfect balance of tranquility and convenience, with wooded areas providing a serene backdrop while still being close to town amenities and beautiful beaches. The property's ample size provides ample opportunities

  Gigi Giordano Taylor Compass Connecticut, LLC

  0 Fairy Dell Rd, Clinton, CT 06413
• 

  

  /40

  $1,295,000

  • 4 Beds
  • 5 Baths
  • 4,465 Sq Ft

  53 Oakridge Dr, Westbrook, CT 06498

  Can you imagine 8 acres of privacy surrounding your own pristine 3 acre lake, stocked with bass, just steps from your 4 bedroom home and minutes from Long Island Sound and walking distance from the high school? It's one thing to live on a lake. It's quite another to own and enjoy one. Welcome to the Lake House at 53 Oakridge Drive in the Shoreline Town of Westbrook, Connecticut. Imagine, waking

  John Campbell Compass Connecticut, LLC

  53 Oakridge Dr, Westbrook, CT 06498

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