Middlesex, CT Homes

• 

  

  

  /19

  $949,900 Pending

  • 3 Beds
  • 1 Bath
  • 762 Sq Ft

  27 Barnes Rd, Old Saybrook, CT 06475

  After being cherished by the same family for 70 years, this quintessential New England cottage ON THE WATER of Long Island Sound is ready for its next chapter. Located in the much sought after summer beach community of Great Hammock Beach, this property, situated on an oversized lot, offers direct access to fishing, swimming, kayaking and breathtaking sunset views from the deck. Inside, you'll

  Debra Pliego Essentia Realty

  27 Barnes Rd, Old Saybrook, CT 06475
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  /15

  $6,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • House for Rent

  25 W Shore Dr, Old Saybrook, CT 06475

  BEACHFRONT Beautifully renovated Furnished luxury waterfront monthly rental for annually $10,500 or winter for $6900 a month 9/30/25 to 5/15/26 (some flexibility with dates). Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new gourmet kitchen, generator, in beautiful

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
• 

  $900,000 Sold Jun 23, 2025

  • Land
  • 17 Acres
  • $52,941 per Acre

  • 468 Days On Market

  382 Middlesex Turnpike, Old Saybrook, CT 06475

  Builders and Developers Take Notice! Development Opportunity. 17 Acre Residential building lot on Middlesex Turnpike in a very convenient location near I95. Right behind multiple available Commercial and Residential building lots.

  Michael Hvizdo Coldwell Banker Realty

  382 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  Est $1,113,610 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,278 Sq Ft

  300 Cromwell Ct N, Old Saybrook, CT 06475

  300 Cromwell Ct N, Old Saybrook, CT 06475
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  /30

  $799,900 Open Sun 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  20 Hill St, Old Saybrook, CT 06475

  This FEMA compliant coastal residence in Old Saybrook offers panoramic views of South Cove at the mouth of the Connecticut River, where the river meets the sound. The property features a new deck, providing an ideal vantage point for observing the sunrise and local wildlife each morning, as well as evening views of Lynde Lighthouse and passing boats.The interior has been thoughtfully remodeled

  Pardi & Zucco Team William Pitt Sotheby's Int'l

  20 Hill St, Old Saybrook, CT 06475
• 

  

  /14

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,052 Sq Ft
  • House for Rent

  16 Clearwater Rd, Old Saybrook, CT 06475

  *Academic Rental August - June* Welcome to 16 Clearwater Rd, Academic Rental that's fully furnished with 3 Bedrooms and 2 full baths. New flooring throughout the main floor with brand new bay windows that really make you feel at home. Open spaced living room that flows right into your dining room with plenty of space to sit and relax. Updated kitchen with all the cooking appliances you need to

  Marco Rondinone Berkshire Hathaway NE Prop.

  16 Clearwater Rd, Old Saybrook, CT 06475
• 

  $575,000 Sold Jun 20, 2025

  • 912 Sq Ft
  • $630/SF
  • 36 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  3 Clark Ave, Old Saybrook, CT 06475

  Welcome to this beautifully updated 2-bedroom ranch located in the desirable Chalker Beach Association. Enjoy peaceful mornings watching the sunrise over the water from the back of the home, where eastern views create the perfect setting for coffee on the deck or relaxing in the hot tub. Set on a spacious 0.24-acre lot, this home offers a rare combination of privacy and community, just a short

  Lorenda DiMeo Century 21 AllPoints Realty

  3 Clark Ave, Old Saybrook, CT 06475
• 

  Est $948,749 Not Listed For Sale

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

  39 Hill St, Old Saybrook, CT 06475

  39 Hill St, Old Saybrook, CT 06475
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  /4

  $399,000

  • Land
  • 1.00 Acre
  • $399,000 per Acre

  396 Middlesex Turnpike, Old Saybrook, CT 06475

  Builders and Developers Take Notice! 1 Acre Commercial building lot on Middlesex Turnpike in a very convenient location. Right next to multiple available Commercial and Residential building lots.

  Michael Hvizdo Coldwell Banker Realty

  396 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  

  /19

  $2,400 per month

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  38 Seabreeze Rd, Old Saybrook, CT 06475

  Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with three bedrooms, an updated bathroom, eat-in kitchen, living room with fireplace, a wonderful sun porch and an outside

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
• 

  $1,500,000 Sold Jun 20, 2025

  • 3,529 Sq Ft
  • $425/SF
  • 14 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2016

  20 Otter Cove Dr, Old Saybrook, CT 06475

  Discover this contemporary Cape, set on 2 acres in Otter Cove, a tranquil enclave nestled along the CT River. This custom-built gem is a testament to sophisticated design paired with practical elegance, offering a versatile living experience that caters to both casual relaxation and upscale entertaining. Blending style with functionality, this 7-year-young home features a sunlit main level with a

  MJ Derisio William Pitt Sotheby's Int'l

  20 Otter Cove Dr, Old Saybrook, CT 06475
• 

  Est $1,153,989 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  11 Beechwood Rd, Old Saybrook, CT 06475

  11 Beechwood Rd, Old Saybrook, CT 06475
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  /34

  $675,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  18 Quarry St, Old Saybrook, CT 06475

  This home located in the center of town features a perfect blend of coastal charm and modern comfort including hardwood floors, a first floor primary bedroom suite with full bath that includes floor to ceiling shelving , 3 additional generous sized bedrooms upstairs, a redesigned kitchen with granite countertops, stainless steel new appliances and new cabinetry. Renovated bathrooms. The living

  Sharon Linder Berkshire Hathaway NE Prop.

  18 Quarry St, Old Saybrook, CT 06475
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  /12

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 609 Sq Ft
  • House for Rent

  41 Town Beach Rd, Old Saybrook, CT 06475

  Academic lease only. Fully furnished rental available 9/2/25. Sparkling clean, hurry, this one won't last! Remodeled kitchen, fenced in back yard, new furniture, fireplace. Owner is a licensed Broker in the State of Connecticut. a great little place to live amazing sunsets trash pick up included

  George Agnelli Agnelli Real Estate

  41 Town Beach Rd, Old Saybrook, CT 06475
• 

  $662,500 Sold Jun 18, 2025

  • 2,002 Sq Ft
  • $331/SF
  • 62 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1976

  100 Sheffield St Unit D4, Old Saybrook, CT 06475

  The ease of a condo lifestyle in the absolute perfect location! Come home to incredibly relaxing water views. Everday will feel like a vacation!! From your patio to the balcony off your bedroom you're sure to feel the days stress melt away as you look out to the spectacular views. There's just something therapeutic in the breeze off the water! This townhome offers a lovely entry foyer, efficient

  Dawn Satagaj William Raveis Real Estate

  100 Sheffield St Unit D4, Old Saybrook, CT 06475
• 

  Est $611,812 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475

  175 Ferry Rd Unit 8, Old Saybrook, CT 06475
• 

  

  /40

  $799,000

  • 2 Beds
  • 3.5 Baths
  • 2,090 Sq Ft

  25 Sunset Rd Unit C12, Old Saybrook, CT 06475

  Looking for a home that feels like vacation every day? This beautiful townhouse overlooks the river, with incredible sunsets and bird watching. The small complex offers an inground pool and private marina. Its a short distance to both the town beach and town restaurants and shops, offering the best of coastal living and convenience. This beae townhouse has been updated throughout. The main level

  Rose McWaid William Raveis Real Estate

  25 Sunset Rd Unit C12, Old Saybrook, CT 06475
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  /36

  $4,500 per month

  • 4 Beds
  • 3 Baths
  • 1,120 Sq Ft
  • House for Rent

  8 Belaire Manor, Old Saybrook, CT 06475

  Academic rental available November 1, 2025 - May 28, 2026 (year-round possible as well). This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and watch the panoramic sunrises and sunsets which are magical with colors ranging from cotton candy on one side of the beach to deep orange on

  Erika Raffles William Pitt Sotheby's Int'l

  8 Belaire Manor, Old Saybrook, CT 06475
• 

  $1,230,000 Sold Jun 17, 2025

  • 2,557 Sq Ft
  • $481/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1966

  5 Cromwell Ct, Old Saybrook, CT 06475

  Welcome to the relaxed coastal lifestyle you've been dreaming of. Nestled in the prestigious North Cove community, this charming Cape Cod-style home offers comfort, space, and the perfect setting for a peaceful, yet active, life by the water. Built in 1966 and lovingly maintained this 2,600 square foot home is set on a beautifully landscaped .48-acre lot at the end of a quiet cul-de-sac, just a

  Joel Lucas Coldwell Banker Realty

  5 Cromwell Ct, Old Saybrook, CT 06475
• 

  Est $1,295,748 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,952 Sq Ft

  9 Watrous Point Rd, Old Saybrook, CT 06475

  9 Watrous Point Rd, Old Saybrook, CT 06475
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  /37

  $829,900 Open Sun 10AM - 11:30AM

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft

  33 Fenwood Rd, Old Saybrook, CT 06475

  Fenwood Beach Association! This beautifully renovated home is ready for you to move right in to this newly updated home. The light-filled interior offers an open flow between the kitchen, dining, and living areas, perfect for relaxed coastal living. The primary suite features a gorgeous new full bath, while the finished lower level adds 700 sq ft of flexible space currently used as a family room

  Joel Lucas Coldwell Banker Realty

  33 Fenwood Rd, Old Saybrook, CT 06475
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  /40

  $40,000 per month

  • 4 Beds
  • 3 Baths
  • 3,762 Sq Ft
  • House for Rent

  17 Agawam Ave, Old Saybrook, CT 06475

  Fantastic Opportunity to Rent for the month of July in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage offers Fenwick's unique lifestyle: beach, tennis courts, yacht club and famed golf course. Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with

  Lynn Lehrman Re/Max Valley Shore

  17 Agawam Ave, Old Saybrook, CT 06475
• 

  $550,000 Sold Jun 09, 2025

  • 2,112 Sq Ft
  • $260/SF
  • 44 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  69 Essex Rd, Old Saybrook, CT 06475

  ***OFFERING A $5000 closing cost credit to buyers!!! Welcome to this spacious Cape-style home offering over 2,000 sq ft of living space, nestled in the desirable Ferry Point neighborhood. Just steps from a 10' right of way to the Connecticut River, this home is perfect for those who love the water and the outdoors. Inside, you'll find beautiful hardwood floors, a first-floor bedroom and full bath

  Brittany O'Hara William Raveis Real Estate

  69 Essex Rd, Old Saybrook, CT 06475
• 

  Est $552,442 Not Listed For Sale

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

  1 Dwayne Rd, Old Saybrook, CT 06475

  1 Dwayne Rd, Old Saybrook, CT 06475
• 

  

  /40

  $1,565,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,467 Sq Ft

  8 Fenbrook Rd, Old Saybrook, CT 06475

  Live the coastal lifestyle in this Knollwood Beach Association gem, just one house from the sand! This charm-filled, tastefully reconstructed home offers 4 bedrooms and 2 full baths with original fir hardwood floors throughout. Enjoy modern comforts including new central air, a newer roof, and a transferable solar system for just $109/month. Relax on the gorgeous rear patio surrounded by

  Joel Lucas Coldwell Banker Realty

  8 Fenbrook Rd, Old Saybrook, CT 06475
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  /16

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  1 Cedarwood Ln, Old Saybrook, CT 06475

  Beautifully redone ranch in the sought after Cornfield Point neighborhood on a fantastic corner lot. Completely renovated kitchen with ceramic floors, refurbished cabinets, and fresh paint throughout. 3 Bedrooms, two full baths and a large finished basement this property also comes with a 1 car attached garage. Enjoy the private beach association of the Cornfield Point Association while still

  Jack Pandolfe Coldwell Banker Realty

  1 Cedarwood Ln, Old Saybrook, CT 06475
• 

  $745,000 Sold Jun 06, 2025

  • 2,152 Sq Ft
  • $346/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  107 Ayers Point Rd, Old Saybrook, CT 06475

  Enjoy the ease of one-floor living in a serene, private setting with this charming ranch style home nestled on a full acre just moments from the Connecticut River and the scenic Turtle Creek Preserve-perfect for daily walks and enjoying nature. Designed with comfort and convenience in mind, this spacious residence features generously sized rooms, both formal and informal living spaces, and ample

  Joel Lucas Coldwell Banker Realty

  107 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $712,439 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,911 Sq Ft

  32 Cricket Ct, Old Saybrook, CT 06475

  32 Cricket Ct, Old Saybrook, CT 06475
• 

  

  /23

  $749,000

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  12 Bellaire Dr, Old Saybrook, CT 06475

  Cornfield Point Beach Association! Steps to beach! Two doors away from Clubhouse & its amenities. Totally renovated year round ranch style home with new everything! Septic, siding, roof, Air Conditioning, flooring - all new! Large parking area to accommodate all your guests. Great Air B&B potential. The park like fenced back yard is a special oasis! currently with a refreshing above ground pool

  Joel Lucas Coldwell Banker Realty

  12 Bellaire Dr, Old Saybrook, CT 06475
• 

  

  /22

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  28 Beach Rd W, Old Saybrook, CT 06475

  Amazing views every day at 28 Beach Rd West, Old Saybrook! This beautiful Academic Rental beach home has 3 bedrooms and 2 baths and is available for your enjoyment ... across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

  Terry McDonald McDonald Real Estate, LLC

  28 Beach Rd W, Old Saybrook, CT 06475
• 

  $490,000 Sold Jun 04, 2025

  • 1,740 Sq Ft
  • $282/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1972

  10 Cricket Ct, Old Saybrook, CT 06475

  A Diamond in the Rough that offers Tremendous Potential! Located in the desirable Cricket Court neighborhood of Old Saybrook, this traditional 3-bedroom, 1 & 1/2 bath colonial offers 1,740 square feet of living space on a spacious 1/2-acre lot with a fenced in back yard. With a 2-car attached garage, an oversized deck, underground utilities and a prime location close to town, Saybrook Point, and

  Kevin Kennedy Kennedy Real Estate Solutions

  10 Cricket Ct, Old Saybrook, CT 06475
• 

  Est $582,277 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft

  6 Willard St, Old Saybrook, CT 06475

  6 Willard St, Old Saybrook, CT 06475
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  /38

  $615,000

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

  143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475

  Welcome to SummerWood on the Sound, a premier waterfront community in Old Saybrook offering resort-style living on the Long Island Sound. This beautifully maintained 2-story condo with a 3rd-floor sleeping loft is perfect for year-round living or a cozy coastal getaway. Features include 2 bedrooms, with a primary suite and en-suite full bath, an updated guest bath, and a half bath on the main

  Lorenda DiMeo Century 21 AllPoints Realty

  143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
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  /25

  $6,000 per month

  • 5 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • House for Rent

  1200 Boston Post Rd, Old Saybrook, CT 06475

  october- may!!!!!The historic Nathaniel Clark House in Old Saybrook, Connecticut, has a taste of New England charm. Large families or people who require additional space to work from home will love this roomy five-bedroom house. Savor a tranquil setting for your winter getaway with warm fires, a spacious porch, a lovely garden, and a quiet greenhouse. This house is perfect for family

  Marina Kokis William Raveis Real Estate

  1200 Boston Post Rd, Old Saybrook, CT 06475
• 

  $5,995,000 Sold Jun 03, 2025

  • 5,592 Sq Ft
  • $1072/SF
  • 4 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 1732

  91 N Cove Rd, Old Saybrook, CT 06475

  A masterful fusion of Colonial New England heritage and refined modernity, this landmark estate has been meticulously reimagined through a comprehensive 2020 restoration. Every element has been crafted with precision, marrying historic authenticity with world-class design. Upon entry, the home reveals a breathtaking harmony of 18th-century character and contemporary sophistication-oak floors,

  Angela Ruel Berkshire Hathaway NE Prop.

  91 N Cove Rd, Old Saybrook, CT 06475
• 

  Est $466,164 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  10 Cliff Dr, Old Saybrook, CT 06475

  10 Cliff Dr, Old Saybrook, CT 06475
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  /39

  $6,400,000

  • 4 Beds
  • 4.5 Baths
  • 5,651 Sq Ft

  12 Rocky Point Rd, Old Saybrook, CT 06475

  Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy

  Sharon Linder Berkshire Hathaway NE Prop.

  12 Rocky Point Rd, Old Saybrook, CT 06475
• 

  

  /22

  $2,395 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • House for Rent

  163 Ferry Rd, Old Saybrook, CT 06475

  Price Reduction. Completely renovated, Upstairs Ranch-Style unit offers a rare opportunity for waterfront living, with views of the Ferry Landing Marina, Connecticut River, and Long Island Sound. Located directly across from the marina. This 2-bedroom, 1-bathroom home combines modern updates with an unbeatable location for boating, fishing, and outdoor enjoyment. The open-concept newly remodeled

  David Boudinot Berkshire Hathaway NE Prop.

  163 Ferry Rd, Old Saybrook, CT 06475
• 

  $697,000 Sold Jun 03, 2025

  • 2,315 Sq Ft
  • $301/SF
  • 18 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1948

  57 Lynde St, Old Saybrook, CT 06475

  Did I say FABULOUS?! A Cape with a contemporary twist and oozing with charm! You will be pleasantly surprised to discover spacious, sunny and inviting rooms with an open floor plan. The main living space boasts a tremendous great room with a large bay window and built ins. This room can accommodate a sitting area, a reading nook and dining area that opens into the kitchen. Culinary delights can

  Susan Malton Coldwell Banker Realty

  57 Lynde St, Old Saybrook, CT 06475
• 

  Est $696,433 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  21 Nehantic Trail, Old Saybrook, CT 06475

  21 Nehantic Trail, Old Saybrook, CT 06475

Showing Results 81 - 120, Page 3 of 18