Middlesex County CT Homes for Sale

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  /40

  $999,900

  $225K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,720 Sq Ft

  34 Briarcliffe Trail, Old Saybrook, CT 06475

  Welcome to this exceptional 3700 sq ft, move-in ready home, privately situated on a quiet private road and surrounded by landscaped grounds. Set on a beautifully maintained 1.3 acre lot with a lightly wooded backdrop and charming stone wall accents, this property offers the perfect blend of privacy, space, and timeless appeal. The brick exterior creates stunning curb appeal, while inside you'll

  Eric Schuell RE/MAX Right Choice

  34 Briarcliffe Trail, Old Saybrook, CT 06475
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  /32

  $699,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  No stone was left unturned at this turn key beach house in the Chalker Beach Association! Completely and professionally renovated from bottom to top, this 3 bedroom cottage is open, light and airy and ready for you to move in, just in time for summer! A spacious living room opens into the lovely eat-in kitchen with custom cabinets, stainless steel appliances and beautiful crown moulding. A bright

  Tina Rupp William Pitt Sotheby's Int'l

  52 Chalker Beach Rd, Old Saybrook, CT 06475
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  /9

  $229,000

  $21K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  77 Scenic View Dr Unit 17, Deep River, CT 06417

  Don't miss your opportunity for this affordable updated condo in Deep River! Peaceful location provides serenity, yet you are very close to vibrant town center with everything you could need including restaurants, shops, groceries, pharmacy and more! Close to Route 9 for convenience. Why rent when you can own in Deep River?!

  Joe Simmons Coldwell Banker Realty

  77 Scenic View Dr Unit 17, Deep River, CT 06417
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  /37

  $499,900

  $50K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft

  10 Glenwood Terrace, Cromwell, CT 06416

  Welcome to 10 Glenwood Terrace, a tranquilly located 3-bedroom, 2-bathroom ranch offering views overlooking the 3rd hole at TPC River Highlands from your front yard. Tucked away in a wooded nook on a cul-de-sac the lot offers a sense of neighborhood, while sill giving you the privacy. Walk into an open living-dining concept with hardwood floors throughout. This open space is great for

  Anthony LaCava Berkshire Hathaway NE Prop.

  10 Glenwood Terrace, Cromwell, CT 06416
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  /24

  $188,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 845 Sq Ft

  1221 Washington St Unit 8, Middletown, CT 06457

  This 2-bedroom loft-style townhouse at Woodgate offers a smart, functional layout in a community that recently completed a full exterior renovation - new roofs, siding, windows, decks, and doors throughout. The main level features a vaulted living room, galley kitchen, full bath, guest bedroom, and first-floor laundry. Upstairs, the primary suite includes large windows and an open balcony

  Cory Winkelmann William Pitt Sotheby's Int'l

  1221 Washington St Unit 8, Middletown, CT 06457
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  /6

  $129,000

  • Land
  • 3.17 Acres
  • $40,694 per Acre

  0 Porges Rd, East Haddam, CT 06423

  Beautiful approved building lot in the heart of East Haddam Village! All tests done & approved plot plan is available for up to a 4 bedroom home. Level, lightly wooded with historic foundation dating back to the 1700's. Get creative with it; possibly a fire pit area or a garden surrounded by stone!

  Melissa Chevalley Re/Max Valley Shore

  0 Porges Rd, East Haddam, CT 06423
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  /13

  $12,000,000

  • Land
  • 20.21 Acres
  • $593,765 per Acre

  1405-1445 Boston Post Rd, Old Saybrook, CT 06475

  Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the

  Casey Fisher Houlihan Lawrence WD

  1405-1445 Boston Post Rd, Old Saybrook, CT 06475
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  /5

  $169,900

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  7 Portland St, Middletown, CT 06457

  WELL MAINTAINED 3 BEDROOM, ONE BATH HOME WITH MANY RECENT UPDATES. FEATURES INCLUDE A LARGE EAT-IN KITCHEN, SPACIOUS LIVING ROOM. MAJOR IMPROVEMENTS INCLUDE A ROOF, CHIMNEY AND GUTTERS THAT ARE ONLY TWO YEARS OLD. ALONG WITH FURNACE AND OIL TANK THAT ARE JUST ONE YEAR OLD. MAIN SEWER REPLACED ONE YEAR AGO. A SOLID HOME THAT HAS BEEN CARED FOR OVER THE YEARS AND OFFERS AND EXCELLENT OPPORTUNITY

  Geraldine Mattera Luxe Realty LLC

  7 Portland St, Middletown, CT 06457
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  /38

  $929,900

  • 5 Beds
  • 3.5 Baths
  • 3,816 Sq Ft

  29 Buell Hill Rd, Killingworth, CT 06419

  Looking for a home with heart and soul? One that has been lovingly maintained and thoughtfully updated? This gracious 3,800 sqft Colonial sits proudly on a beautiful lot in one of Killingworth's most desirable neighborhoods. At the heart of the home is a beautifully appointed cook's kitchen that opens seamlessly to a sun-drenched family room, where expansive windows frame views of the private

  Phoebe Schreiner William Pitt Sotheby's Int'l

  29 Buell Hill Rd, Killingworth, CT 06419
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  /38

  $499,900

  • 9 Beds
  • 4 Baths
  • 3,720 Sq Ft

  356 Main St, Portland, CT 06480

  Investor alert in the heart of Portland! Welcome to 354-356 Main Street, a rare 4-unit multifamily offering incredible upside, strong rental potential, and a layout that works beautifully for both investors and owner-occupants. Priced with condition in mind, property is being sold as-is. Two units are currently month-to-month and well below market rent, creating a major value-add opportunity from

  Jennifer Mascaro LPT Realty

  356 Main St, Portland, CT 06480
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  /12

  $12,000,000

  • 4 Beds
  • 1 Bath
  • 2,059 Sq Ft

  1445 Boston Post Rd, Old Saybrook, CT 06475

  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

  Casey Fisher Houlihan Lawrence WD

  1445 Boston Post Rd, Old Saybrook, CT 06475
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  /39

  $599,900

  • 2 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  26 Mystique Ln Unit 26, Cromwell, CT 06416

  Welcome to this stunning single-family home located in a highly desirable 55+ community, built in 2014 and thoughtfully designed for comfortable, easy living. From the moment you step inside, you'll appreciate the open floor plan, abundant natural light, and beautiful hardwood floors that flow throughout the main level. The heart of the home is the gorgeous kitchen featuring granite countertops,

  Michelle Mazzotta eXp Realty

  26 Mystique Ln Unit 26, Cromwell, CT 06416
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  /13

  $499,900

  • 4 Beds
  • 3.5 Baths
  • 4,390 Sq Ft

  57 Summer St, Portland, CT 06480

  Set on a generous 1.2-acre lot in Portland, this expansive ranch offers an incredible amount of space and potential for someone ready to bring their vision to life. With over 4,300 square feet of living space, the home features 10 rooms including 4 bedrooms and 3 full baths plus a half bath, providing plenty of room for extended living, hobbies, or multi-generational needs. The layout offers the

  Carl Guild Carl Guild & Associates

  57 Summer St, Portland, CT 06480
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  /33

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  513 Essex Rd, Westbrook, CT 06498

  This 3-bedroom, 1-bath, 1-car garage ranch offers a full walk-out basement, 1,172 square feet of living space on a generous 0.52-acre lot. This property is ideal for first-time homebuyers, downsizers, or investors seeking a solid shoreline community home. sold as is. Subject to probate and lien holder approvalj

  Claude Cousins Berkshire Hathaway NE Prop.

  513 Essex Rd, Westbrook, CT 06498
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  /40

  $675,000

  • 4 Beds
  • 4 Baths
  • 2,671 Sq Ft

  76 Thimble Rock Rd, Middletown, CT 06457

  Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and

  Carl Guild Carl Guild & Associates

  76 Thimble Rock Rd, Middletown, CT 06457
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  /40

  $2,350,000

  • 3 Beds
  • 2.5 Baths
  • 3,700 Sq Ft

  18 Birch Mill Rd, Killingworth, CT 06419

  The Well Maiden Estate is an architecturally significant waterfront estate where cascading waterfalls, winding streams, and Kroopa Pond converge across 3.5 private acres to create one of Connecticut's most extraordinary residential settings. Positioned between New York City and Boston and minutes from the Connecticut shoreline, this private luxury retreat offers a rare opportunity to own a legacy

  Jennifer Gurnell William Raveis Real Estate

  18 Birch Mill Rd, Killingworth, CT 06419
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  /17

  $325,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  175 Newfield St, Middletown, CT 06457

  It has style, it has grace, it has a new roof (3 years old) - you will absolutely love this place!! THIS is the cape you've been waiting for! Ideal floorplan - the primary bedroom on the first floor faces the backyard; the relaxing living room has a wood burning fireplace; the renovated full bathroom has a bathtub; the beautifully modernized kitchen is fully applianced and the separate dining

  Vaiva Baltonis Coldwell Banker Realty

  175 Newfield St, Middletown, CT 06457
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  /40

  $2,899,900

  • 5 Beds
  • 4.5 Baths
  • 5,062 Sq Ft

  2 Captains Ln, Old Saybrook, CT 06475

  Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear

  Bill Heenan William Raveis Real Estate

  2 Captains Ln, Old Saybrook, CT 06475
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  /4

  $667,900

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  7A Freya Ln, East Hampton, CT 06424

  Lake Overlook Estates - an enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. Lot 4 - last home site available for Carma, LLC. Expanded Colonial III - this stately home offers a spacious and dramatic first floor with two story entry and double sided balcony overlook. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office

  Mark Toledo Berkshire Hathaway NE Prop.

  7A Freya Ln, East Hampton, CT 06424
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  /4

  $667,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  7B Freya Ln, East Hampton, CT 06424

  Lake Overlook Estates - an enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. Lot 4 - last home site available for Carma, LLC. Expanded Colonial III - this stately home offers a spacious and dramatic first floor with two story entry and double sided balcony overlook. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office

  Mark Toledo Berkshire Hathaway NE Prop.

  7B Freya Ln, East Hampton, CT 06424
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  /40

  $820,000

  • 2 Beds
  • 3 Baths
  • 1,795 Sq Ft

  199 E Shore Dr, Colchester, CT 06415

  Experience elevated, year-round waterfront living at 199 East Shore Drive. Positioned directly on the widest expanse of Lake Hayward, this exceptional property delivers a seamless blend of classic lake house charm and modern capability. The main level offers an inviting, open-concept living and dining space anchored by a gas fireplace, custom built-in bookshelves, and hardwood flooring. The

  Jonathan Archer William Raveis Real Estate

  199 E Shore Dr, Colchester, CT 06415
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  /10

  $299,000

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  11 Jobs Gate 1, Portland, CT 06480

  Investor's great opportunity!!!Must see this peaceful waterfront escape over looking Camp Ingersoll. This charming year-round home offers 2 bedrooms, 1 full bath, a cozy living room, and a kitchen overlooking the sparkling lake, creating the perfect setting to relax and unwind. Enjoy swimming, kayaking, and fishing right from your backyard while taking in the tranquil water views and natural

  Roseanne Scacca Dan Combs Real Estate

  11 Jobs Gate 1, Portland, CT 06480
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  /40

  $849,900

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  16 Glen Grove Rd, Deep River, CT 06417

  16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in desirable Deep River. Tucked well off the road and surrounded by beautiful stone walls, this property offers exceptional privacy and endless possibilities to enjoy the outdoors, from garden areas & gorgeous rock walls, to creating your own walking trails throughout the wooded landscape. Inside, you'll find

  Sara Tufano Real Broker CT, LLC

  16 Glen Grove Rd, Deep River, CT 06417
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  /35

  $329,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  20 Geromin Dr, Higganum, CT 06441

  Nestled on over an acre of beautiful, peaceful land in a private, quiet neighborhood, this 3-bedroom, 2-bath split-level home offers a wonderful opportunity to build equity and make it your own. The spacious floor plan features a large eat-in kitchen with oak cabinetry, ample storage - open to large living room. Head upstairs and find a family room that leads out to a deck and the beautiful

  Tracey Precourt Century 21 Clemens Group

  20 Geromin Dr, Higganum, CT 06441
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  $229,500

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,109 Sq Ft

  1231 Washington St Unit 2, Middletown, CT 06457

  Buyer Financing Fell Through - Enjoy one of only a select few of the largest townhouse end units in the complex offering 1,109 square feet of vast living space. Nestled in a popular, well-maintained community, this home combines convenience, comfort and peace of mind with nothing to do but unpack and enjoy. Recent complex-wide improvements include new roads with abundant guest parking, new

  Chris Hogan Century 21 Classic Homes

  1231 Washington St Unit 2, Middletown, CT 06457
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  /13

  $149,000

  • Land
  • 26,136 Sq Ft
  • $248,333 per Acre

  3 Island, East Hampton, CT 06424

  Own an island on Lake Pocotopaug! Scraggy Island or Blueberry Island is your in-lake dream picnic and camping destination! Tucked away on the northeast side of the lake, you can boat out for the afternoon, the day, or the weekend. Does a 360 degree water view sounds like a dream? It's not! Because it's a reality on this secluded island! Private, Private, private!

  

  Kevin Wilcox

  William Raveis Real Estate

  3 Island, East Hampton, CT 06424
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  /31

  $599,900

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  17 Grandview Terrace, Essex, CT 06426

  Discover the charm of Essex Village! Lovely inviting Ranch offering the ease of single-level living. Living Rm. with cozy Fireplace, 2BR, charming eat-in Kitchen, HW floors, Breezeway/Sun rm. and attached garage. Dining preferences also possible in LR nook or Sun Rm. Enjoy a level, easy-care yard and patio, perfect for outdoor dining, entertaining, or relaxing. Fun and adventure is just a short

  Diane Beckwith Popolizio William Raveis Real Estate

  17 Grandview Terrace, Essex, CT 06426
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  /16

  $275,000

  $6K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 876 Sq Ft

  28 Kickapoo Rd, Middlefield, CT 06455

  ATTENTION ALL INVESTORS AND RENOVATION SPECIALISTS- Being sold "AS IS". This is a Year-round ranch in the desirable Beseck Lake community offering water views and access to the lake, beach, and boat launch. The town shows this as a one bedroom home that features an eat-in kitchen, living room with fireplace, primary bedroom, den/possible 2nd bedroom, and a new updated full bath with Washer/Dryer

  Joselyn Valente Century 21 North East

  28 Kickapoo Rd, Middlefield, CT 06455
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  /39

  $875,000

  $124K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  13-21 Nott Ln Unit A3, Essex, CT 06426

  Enjoy the best of coastal living in this beautifully maintained waterfront condo, on Middle Cove, ideally located in the heart of a charming village of Essex. Wake up to stunning water views, relax on your private balcony, and stroll to nearby shops, restaurants, marinas, and local attractions. This light-filled home features an open floor plan, spacious living areas, and comfortable bedrooms

  Mary McDonald Coldwell Banker Realty

  13-21 Nott Ln Unit A3, Essex, CT 06426
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  /39

  $1,350,000

  $151K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,040 Sq Ft

  6 Fencove Ct, Old Saybrook, CT 06475

  Coastal living at its best in the desirable Fenwood District and Fenwood Beach Association! As a member, enjoy access to Fenwood Beach with panoramic views, sandy beach, and a picnic area.This move-in ready, updated home offers over 2,000 sq ft of thoughtfully designed living space, featuring 4 bedrooms, 3.5 baths, 2-car garage, central a/c, all nestled on a peaceful cul-de-sac with water views

  Laura Frisch Coldwell Banker Realty

  6 Fencove Ct, Old Saybrook, CT 06475
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  /40

  $269,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 564 Sq Ft

  1 West Blvd, East Hampton, CT 06424

  Enjoy Life at the Lake! Move right into this adorable year-round 2-bedroom, 1-bath ranch just a short walk to Lake Pocotopaug! The bright, open floor plan features a comfortable living room/dining room combination that lives larger than its footprint. Step out to the large deck overlooking the back yard, complete with a handy storage shed - the perfect spot to unwind after a day at the shore.

  Alexander Ugarte William Raveis Real Estate

  1 West Blvd, East Hampton, CT 06424
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  /31

  $529,000

  • 2 Beds
  • 1.5 Baths
  • 1,557 Sq Ft

  256 Hidden Cove Rd, Old Saybrook, CT 06475

  Discover effortless shoreline living at Summerwood in Old Saybrook. This beautifully maintained 2-bedroom, 1.5-bath condominium offers 1,557 SqFt of light-filled living space with tranquil marsh views and an upper-level loft perfect for a home office, guest space, or reading retreat. The updated kitchen features granite countertops, stainless steel appliances, and a center island, while hardwood

  Carla Mousch William Raveis Real Estate

  256 Hidden Cove Rd, Old Saybrook, CT 06475
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  /40

  $950,000

  • 4 Beds
  • 2.5 Baths
  • 2,841 Sq Ft

  10 Shelter Rock Rd, East Haddam, CT 06423

  A private approach which leads to this refined colonial home, set on more than four secluded acres. The property includes a heated mineral pool, expansive stone patios, Brazilian Ipe decking and full-property indoor/outdoor sound-an exceptional setting for effortless entertaining. With roughly 20 acres of protected association land as its backdrop, the grounds offer rare privacy along with

  Bill Moore Coldwell Banker Realty

  10 Shelter Rock Rd, East Haddam, CT 06423
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  /35

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 3,032 Sq Ft

  24 Indian Dr, Clinton, CT 06413

  Nestled along the shoreline where the Indian River meets Long Island Sound, the Country Club Estates neighborhood is one of Clinton's most sought-after waterfront communities. In the heart of Clinton, this established neighborhood offers a unique blend of coastal beauty, recreational opportunities, and small-town New England charm. Updates to this home in 2020 include a large addition (primary

  Bonnie Fillion Berkshire Hathaway NE Prop.

  24 Indian Dr, Clinton, CT 06413
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  /2

  $329,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft

  19 Winthrop Blvd, Cromwell, CT 06416

  6/3/1.5 split level. Located on .44 acres level chain link fence open yard.10x21 rear enclosed porch. Fireplace in living room. Great seasonal views. The home is in need of work. Currently filled with personal property and debris. Priced accordingly ! Roof is new in 2026.

  Arthur Forcier Vision Real Estate

  19 Winthrop Blvd, Cromwell, CT 06416
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  /36

  $315,000

  • Land
  • 4 Acres
  • $78,750 per Acre

  27 Hopyard Rd, East Haddam, CT 06423

  Beautiful 4 acre lot overlooking the fairways and greens of Fox Hopyard Golf Country Club. Water views from this property with privacy from other surrounding dwellings. Open level lot.

  Maddy Mattson Coldwell Banker Realty

  27 Hopyard Rd, East Haddam, CT 06423
• 

  

  /13

  $600,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  28 Church St, Old Saybrook, CT 06475

  This well-maintained 2-bedroom, 1-bathroom ranch is the ultimate turnkey opportunity in one of Connecticut's most beloved shoreline communities. Offered fully furnished - just move right in! Enjoy easy single-level living with a comfortable layout, all within minutes of Old Saybrook's downtown, local beaches, the Connecticut River, marinas, and charming shops and restaurants. Don't miss your

  Timothy Johnson Starr Team at LPT Realty

  28 Church St, Old Saybrook, CT 06475
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  /7

  $99,900

  • Land
  • 1.79 Acres
  • $55,810 per Acre

  0 Jobs Pond Rd, Portland, CT 06480

  One of the last lots available to build in this quaint neighborhood. Discover your perfect private escape on this nearly 2-acre approved building lot. Bordering a tranquil brook, this nature lover's paradise is just steps to the scenic Airline Trail for hiking and biking. Conveniently located just minutes from Route 66, providing easy access to local amenities, schools, and commuting routes.

  Julia King William Raveis Real Estate

  0 Jobs Pond Rd, Portland, CT 06480
• 

  

  /40

  $679,900

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  73 Long Hill Rd, Deep River, CT 06417

  Good design is all about the details and this well maintained custom Colonial is just what you have been looking for in the perfect shoreline home. Recently updated, the current owner's signature style has magically taken this charming home from ordinary to extraordinary with her colorful design. From the warm and welcoming entrance, to the well-appointed kitchen or the cozy family room centered

  Peg Mitchel Coldwell Banker Realty

  73 Long Hill Rd, Deep River, CT 06417
• 

  

  /40

  $849,900

  • 3 Beds
  • 3 Baths
  • 2,498 Sq Ft

  82 Pratt Rd, Clinton, CT 06413

  Nestled along a serene marsh & riverfront setting, this beautifully renovated home offers the rare balance of solitude paired seamlessly with ideal proximity to town. Enjoy breathtaking water & nature views from every room, and yet reside close to downtown & marinas, with dining, shopping & local amenities. Designed for both comfort & entertainment, the main floor features a spacious, renovated

  Leif Klein William Raveis Real Estate

  82 Pratt Rd, Clinton, CT 06413

Showing Results 161 - 200, Page 5 of 11