Middlesex, CT Homes

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  /40

  $929,000

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  86 Chalker Beach Rd, Old Saybrook, CT 06475

  Welcome to Year-Round Beach Living with Room to Spare! Welcome to 86 Chalker Beach Rd. Do you desire a year-round beach home with plenty of space? Look no further! Welcome to 86 Chalker Beach Rd-your gateway to coastal living in one of Old Saybrook's most vibrant beach communities. With nearly 2,300 square feet of living space, this rare find offers four spacious bedrooms and two full bathrooms,

  

  Jodi Serapilia

  William Raveis Real Estate

  (860) 809-5460

  86 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  Explore Old Saybrook

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  /22

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  18 Belaire Manor, Old Saybrook, CT 06475

  Fantastic opportunity to spend the "off season" at the beach. Come and see this completelyRenovated to the hilt beachhouse. High ceilings, the finest of everything! This is a Academic Rental available from 9/1/25-5/31/26. It is not available for yearly rental. NOT Annual Rental. But for 9 Months come and enjoy the vistas of the Long Island sound. Put your toes in the sand every morning. This home

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 864-4132

  18 Belaire Manor, Old Saybrook, CT 06475
• 

  $620,000 Sold Jul 31, 2025

  • 1,500 Sq Ft
  • $413/SF
  • 94 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1945

  37 Woodland Dr, Old Saybrook, CT 06475

  Welcome to Knollwood Beach Association, where charm, comfort, and nature meet in this beautifully updated year-round ranch-style home. Just two blocks from the sandy shores of Knollwood Beach, kayaking stands, tennis , pickleball and basketball courts, a playground, and the association clubhouse, this home is nestled along the Beamon Creek Estuary-a vital migratory stopover for birds that empties

  Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
• 

  Est $522,503 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,930 Sq Ft

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475
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  /33

  $560,000

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  5 Aladdin Ave, Old Saybrook, CT 06475

  GET YOUR SPOT AT THE BEACH! The perfect getaway, just a short walk from the Chalker Beach Sandy Shoreline. Ready for love, sun, swim, and enjoying all the fun-with no traffic and plenty of relaxation right outside this home. A spacious deck overlooks a beautiful backyard, ideal for entertaining family and friends. Rinse off the day in the outdoor shower. Chalker Beach offers an abundance of

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 590-4441

  5 Aladdin Ave, Old Saybrook, CT 06475
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  /35

  $2,950 - $4,270 per month

  Hanford Commons

  1 - 2 Beds

  99 Lynde St, Old Saybrook, CT 06475

  Welcome to Hanford Commons – The Definition of LuxuryDiscover modern living at its finest with our brand-new apartments in the picturesque town of Old Saybrook. Hanford Commons perfectly blends style, convenience, and comfort, offering you a home that exceeds expectations. Each thoughtfully designed unit features stainless steel appliances, an in-unit washer and dryer, central heating and

  99 Lynde St, Old Saybrook, CT 06475
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  $499,000 Sold Jul 30, 2025

  • 1,812 Sq Ft
  • $275/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1962

  14 Meadowood Ln, Old Saybrook, CT 06475

  Make this warm, inviting home your own this spring! Ideally located in one of the most desirable neighborhoods in town and conveniently located a short walk to the high school and close to beaches and the village. This home offers a very flexible floor plan with hardwood floors, a new roof and recently replaced septic system. A spacious, private deck with a hot tub complete the package! Schedule

  Rick Allen William Raveis Real Estate

  14 Meadowood Ln, Old Saybrook, CT 06475
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  Est $678,665 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  24 Willard St, Old Saybrook, CT 06475

  24 Willard St, Old Saybrook, CT 06475
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  /19

  $449,900 Pre-Foreclosure

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

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  This property is located in the private Chalker Beach community. This 3 Bedroom / 1.5 Bathroom house is a short walk from the white sandy Beaches and all the fun that comes with this Beach Community. Imagine all the unforgettable moments you'll create in this incredibly desirable location! Property is being sold As Is. Property Offered for the First 30 Days to prospective buyers making less than

  

  Patrick Farley

  Statewide Premier Prop. LLC

  (860) 718-4375

  52 Chalker Beach Rd, Old Saybrook, CT 06475
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  /8

  $1,200 per month

  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  1500 Boston Post Rd Unit 11, Old Saybrook, CT 06475

  Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach. Credit must be good.

  Brian Botti Botti Realty

  1500 Boston Post Rd Unit 11, Old Saybrook, CT 06475
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  $800,000 Sold Jul 29, 2025

  • 1,810 Sq Ft
  • $442/SF
  • 2 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1958

  92 Fenwood Dr, Old Saybrook, CT 06475

  Location! Location! Location! Nestled in the desirable Fenwood Beach District, this inviting ranch style home offers serene views of South Cove and a lifestyle of comfort and coastal charm. Set on a level .25 acre lot, the property features a fenced, private backyard with mature plantings and a shed for your tools and beach gear. There are 2 bedrooms and 3 full baths. The home has hardwood floors

  Fran Manganello Coldwell Banker Realty

  92 Fenwood Dr, Old Saybrook, CT 06475
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  Est $644,959 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  40 Bokum Rd, Old Saybrook, CT 06475

  40 Bokum Rd, Old Saybrook, CT 06475
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  /40

  $875,000 Open Sat 3PM - 4:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft

  45 Farview Ave, Old Saybrook, CT 06475

  A Refined Coastal Estate in the Heart of Old Saybrook, Connecticut. Set on nearly an acre along a tranquil tidal inlet leading into the Ferry Point Marsh Wildlife Management Area, this coastal estate offers a rare blend of privacy, natural beauty, and enduring craftsmanship. A true retreat, where every element has been curated with care and intention. Inside, the layout is designed for effortless

  

  Amy Rubin

  RE/MAX Legends

  (860) 854-9586

  45 Farview Ave, Old Saybrook, CT 06475
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  /28

  $2,468 - $3,326 per month

  Saybrook Station Apartments

  1 - 2 Beds

  7 N Main St, Old Saybrook, CT 06475

  Located in Old Saybrook, with easy access to Main Street and Boston Post Road, Saybrook Station Apartments are just a quick jaunt to the train station, a four-minute drive to the historic Town Green, and minutes away from 1000 acres of coastal forest at The Preserve. Not to mention, all of the shopping, dining, and entertainment that nearby New Haven has to offer. Picture coming home every day to

  7 N Main St, Old Saybrook, CT 06475
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  $1,025,000 Sold Jul 25, 2025

  • 3,730 Sq Ft
  • $275/SF
  • 58 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1957

  8 Cromwell Place, Old Saybrook, CT 06475

  Location, Location, Location. Set in the coveted North Cove neighborhood, only a 2-minute walk away CT River meets the Long Island Sound, awaits an exceptional residence-no flood required. Mature gardens and stunning trees welcome you. Your backyard faces a beautiful park. Just a few steps away lies the Saybrook Point Marina and Health Club. This one-of-a-kind MIDCENTURY MODERN HOME is

  Roxanne Quinn Coldwell Banker Realty

  8 Cromwell Place, Old Saybrook, CT 06475
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  Est $756,176 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,502 Sq Ft

  456 Main St, Old Saybrook, CT 06475

  456 Main St, Old Saybrook, CT 06475
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  /40

  $899,000

  • 3 Beds
  • 2 Baths
  • 2,297 Sq Ft

  12 4th Ave, Old Saybrook, CT 06475

  Huge Price reduction! Nestled on Ferry Point, where the Ct River meets the L.I. Sound, this charming waterfront home offers breathtaking views and direct access to the water. The private dock, complete with Jet ski port and well suited to an array of different boat designs,invites endless maritime adventures. Enjoy watching Osprey on their nest along with boats drifting by from the kitchen,

  

  Maddy Mattson

  Coldwell Banker Realty

  (860) 787-8257

  12 4th Ave, Old Saybrook, CT 06475
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  /9

  $4,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,732 Sq Ft
  • House for Rent

  5 Knollwood Dr, Old Saybrook, CT 06475

  Waterviews. Recently renovated year-round Cottage in Knollwood Beach Association 2 doors down from the waterfront. Incredible views of Long Island Sound. You will love the large covered porch and the designer white kitchen. Beautiful open flow on first floor with large dining area and gas fireplace in living-room. Home has 3 Bedrooms and 2.1 bathrooms. Nice back yard with outdoor shower. Tenant

  Joel Lucas Coldwell Banker Realty

  5 Knollwood Dr, Old Saybrook, CT 06475
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  $805,000 Sold Jul 18, 2025

  • 1,900 Sq Ft
  • $424/SF
  • 35 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1957

  8 Edwards Rd, Old Saybrook, CT 06475

  Your perfect beachside retreat awaits in the desirable Cornfield Point Beach community, offering deeded beach rights and a fully renovated, move-in-ready home. Ideal for retirement, a second home, or year-round living, this charming ranch sits on a professionally landscaped .20-acre lot with a fenced backyard, paved driveway, carport garage, and large shed. Relax on the welcoming rear patio,

  Joel Lucas Coldwell Banker Realty

  8 Edwards Rd, Old Saybrook, CT 06475
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  Est $1,647,437 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,580 Sq Ft

  23 Red Bird Trail, Old Saybrook, CT 06475

  23 Red Bird Trail, Old Saybrook, CT 06475
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  /23

  $699,500 Under Contract

  • Land
  • 8 Acres
  • $86,252 per Acre

  60 Ingham Hill Rd, Old Saybrook, CT 06475

  Picturesque waterfront 8.1-acre lot on the tranquil Oyster River in historic Old Saybrook. 1,400 feet of river frontage leading to Long Island Sound. Currently set as farmland, this could be a home run for builders sensitive to the needs of the land. With its beauty, you have 50-plus feet of road frontage and large footprint within the 50-foot tidal wetlands setback. I-95 is easily accessible,

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 735-1229

  60 Ingham Hill Rd, Old Saybrook, CT 06475
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  /15

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • House for Rent

  116 Chalker Beach Rd, Old Saybrook, CT 06475

  Gorgeous Academic Rental Home at Chalker Beach, 2 bedrooms with Queen Beds, 3rd bedroom is currently used as an office andworkout space. Offering vinyl plank flooring, with an open living concept; living room with LP gas fireplace, kitchen and sun porch!Gorgeous updated kitchen, stainless steel appliances, beautiful butcher block counters all with an updated bathroom along with

  116 Chalker Beach Rd, Old Saybrook, CT 06475
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  $600,000 Sold Jul 18, 2025

  • 1,830 Sq Ft
  • $328/SF
  • 33 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1940

  62 Lynde St, Old Saybrook, CT 06475

  A Rare in-town GEM ! Come visit this special property. 4 Bedroom 2 Full Bath Colonial, plus first floor bedroom. This charming 1940 Colonial has a large eat-in Country Kitchen, full bathroom on the first floor has a walk-in shower. Dining Room just off the Kitchen has a lot of light. Formal living room with fireplace. Hardwood floors in most rooms throughout this special place to make this YOUR

  Jan Murray J.M. REALTY

  62 Lynde St, Old Saybrook, CT 06475
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  Est $6,598,966 Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 7,465 Sq Ft

  9 Pettipaug Ave, Old Saybrook, CT 06475

  9 Pettipaug Ave, Old Saybrook, CT 06475
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  /40

  $529,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  25 King St, Old Saybrook, CT 06475

  NEW to the market in Old Saybrook is this Like-New Ranch within minimal walking distance to Main Street! This home is meticulously cared for with many desirable (recent) upgrades. Gleaming hardwood floors throughout the entire main level, a spotless kitchen featuring Granite countertops and a generously sized island for gathering, newer appliances, custom cabinetry, and a dining room that was a

  Joe Loguidice William Raveis Real Estate

  25 King St, Old Saybrook, CT 06475
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  /36

  $2,600 per month

  • 3 Beds
  • 1.5 Baths
  • 864 Sq Ft
  • House for Rent

  4 Elinor Rd, Old Saybrook, CT 06475

  CHALKER BEACH ACADEMIC RENTAL AVAILABLE 10/1/24 - 5/31/25. Adorable fully furnished 3 bedroom, 1.1 bathroom Cape featuring kitchen open to dining room, living room, 1 bedroom on the main level, 2 bedrooms on the 2nd floor, 3 season screened in porch, outdoor shower, off street parking for 4 cars. Tenants will be responsible for water, electric (lights, hot water, AC & Heat) and snow removal. The

  Chloe White KW Legacy Partners

  4 Elinor Rd, Old Saybrook, CT 06475
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  $925,000 Sold Jul 18, 2025

  • 4,559 Sq Ft
  • $203/SF
  • 28 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  134 School House Rd, Old Saybrook, CT 06475

  A private estate minutes from the shore-welcome to 134 School House Road. Tucked away on a beautiful 3.4 acres, this 4,500 sq ft custom Colonial offers timeless elegance and unparalleled privacy in one of Old Saybrook's most coveted locations. A winding driveway leads you to a stately residence surrounded by nature. Inside, hardwood floors, three fireplaces, and formal living and dining spaces

  Tina Rupp William Pitt Sotheby's Int'l

  134 School House Rd, Old Saybrook, CT 06475
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  Est $408,443 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  310 Springbrook Rd, Old Saybrook, CT 06475

  310 Springbrook Rd, Old Saybrook, CT 06475
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  /40

  $1,395,000 Open Sat 1:30PM - 3PM

  • 4 Beds
  • 3 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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  /22

  $3,200 per month

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  4 Old Colony Rd, Old Saybrook, CT 06475

  Cornfield Point Beach area, October 1- May 15 2026. Furnished. Academic Rental.Conveniently located near town, restaurants and train station. You will fall in love with this Old Saybrook 3 bedroom, 2 full bathroom home. Newly renovated. Fully furnished, move in ready. Washer and dryer in basement. Open concept kitchen with stainless steel appliances, dishwasher, microwave, hardwood

  4 Old Colony Rd, Old Saybrook, CT 06475
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  $3,400,000 Sold Jul 18, 2025

  • 4,768 Sq Ft
  • $713/SF
  • 74 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2008

  9 Whisper Cove Rd, Old Saybrook, CT 06475

  Nestled in the picturesque town of Old Saybrook, this exquisite Colonial-style home offers a blend of traditional charm and modern living. With captivating views of the nearby cove, residents can enjoy the serene beauty of waterfront living. The home's stately presence is complemented by its elegant architectural details, creating a timeless appeal. Inside, spacious rooms flow seamlessly,

  Tammy Tinnerello William Pitt Sotheby's Int'l

  9 Whisper Cove Rd, Old Saybrook, CT 06475
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  Est $696,523 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,813 Sq Ft

  5 Crowley Dr, Old Saybrook, CT 06475

  5 Crowley Dr, Old Saybrook, CT 06475
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  /35

  $1,498,777 Open Sat 1:30PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  26 Meadowood Ln, Old Saybrook, CT 06475

  Rare opportunity to own a newly built luxury residence with unobstructed water views, high-end finishes, and an exceptional location. Homes of this caliber in Old Saybrook are limited-don't miss your chance to experience elevated shoreline living. 26 Meadowood Lane, is an unparalleled blend of upscale shoreline living and architectural excellence in a premier Old Saybrook location. 2025

  Jennifer Gurnell William Raveis Real Estate

  26 Meadowood Ln, Old Saybrook, CT 06475
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  /18

  $2,400 per month

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

  9 Red Bird Trail, Old Saybrook, CT 06475

  ACADEMIC RENT (mid Sept to mid May) 3 BR Colonial with Sun Room is located in the beautiful Indian Town Association with views of LIS and harbor. Bright and spacious rooms. This location is perfect for walking, biking or strolling along the beach. Conveniently located to I95, Train Station, Shopping and The Kate. Sorry NO pets or smokers allowed

  Sandy Orsie Berkshire Hathaway NE Prop.

  9 Red Bird Trail, Old Saybrook, CT 06475
• 

  $700,000 Sold Jul 15, 2025

  • 1,830 Sq Ft
  • $383/SF
  • 54 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1976

  100 Sheffield St Unit B4, Old Saybrook, CT 06475

  This creek/estuary facing unit at "The Cove" in the heart of Old Saybrook has been completely & tastefully remodeled! Enjoy shoreline living on North Cove within walking distance of North Cove Yacht Club as well as Main Street with it's restaurants, shops & of course the "Kate". It features water views of North Cove along with access to launch your kayak just outside your slider door! Amenities

  Kevin Geysen William Pitt Sotheby's Int'l

  100 Sheffield St Unit B4, Old Saybrook, CT 06475
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  Est $599,555 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,290 Sq Ft

  21 Baum Ave, Old Saybrook, CT 06475

  21 Baum Ave, Old Saybrook, CT 06475
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  /39

  $1,375,000

  • 3 Beds
  • 3.5 Baths
  • 2,578 Sq Ft

  11 Osprey Rd, Old Saybrook, CT 06475

  Oasis On Osprey! Hardly ever does a trophy property with the finest quality building materials, flawless craftsmanship and a true sense of ownership pride hit the shoreline market. Situated on immaculately manicured, park-like grounds in the Knollwood beach community, this crown jewel that underwent an extensive renovation from 2021-2022 is an entertainer's delight! This coastal retreat's

  Matthew Guida Eagle Eye Realty PLLC

  11 Osprey Rd, Old Saybrook, CT 06475
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  /26

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,139 Sq Ft
  • House for Rent

  54 Hartford Ave, Old Saybrook, CT 06475

  Immaculate home at the beach available for rent October 1, 2025 - May 15, 2026 (negotiable). Spacious ranch with an open living, dining, and kitchen. The primary bedroom has access to the backyard and is next to the full bathroom which has a walk in shower and washer/dryer. On the other side of the home you will find 2 generous sized bedrooms and a full bathroom with bath/tub combo. Central air.

  Kate Lombardi Coccomo Real Estate LLC

  54 Hartford Ave, Old Saybrook, CT 06475
• 

  $410,000 Sold Jul 15, 2025

  • 826 Sq Ft
  • $496/SF
  • 111 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  6 West St, Old Saybrook, CT 06475

  It is all about location! Discover this cozy ranch within walking distance to Saybrook Point and Main Street to enjoy walks to restaurants, mini golf, golfing, shops and the Katherine Hephburn Cultural arts center. This home features a brand new roof, whole house generator, stainless steel appliances, new sump pump, updated bathroom, inviting stone fireplace adding warmth and character, new barn

  Sharon Linder Berkshire Hathaway NE Prop.

  6 West St, Old Saybrook, CT 06475
• 

  Est $655,364 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  34 Coulter St, Old Saybrook, CT 06475

  34 Coulter St, Old Saybrook, CT 06475

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