Old Saybrook, CT Homes

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  /33

  $575,000 Open Sun 12PM - 2PM

  • 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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  /32

  $3,500 per month

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Apartment for Rent

  725 Boston Post Rd, Old Saybrook, CT 06475

  Updated 4-Bedroom, 2-Bathroom Year-Round Rental in the Heart of Old Saybrook Enjoy the convenience of living just steps from downtown Old Saybrook, with easy access to restaurants, shops, and stunning beaches. This beautifully updated home features a newly renovated kitchen with an open-concept design, Corian countertops, stainless steel appliances, and a spacious island with additional seating.

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 905-0075

  725 Boston Post Rd, Old Saybrook, CT 06475
• 

  $505,000 Sold Jul 07, 2025

  • 1,557 Sq Ft
  • $324/SF
  • 101 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475

  NEW PRICE!! Owners say "SELL"!! You can't miss this.... Newly remodeled home at an amazing new price!!!! COME SEE .... A wonderful transformation has been made ...Two New baths! New quartz kitchen counters, new HARDWOOD floors installed on first floor, new carpeting and tile; even the "popcorn" ceilings are gone! Freshly painted, this home is waiting for its new owners! WELCOME to Summer Wood

  Lisa Genovali Re/Max Valley Shore

  104 Sandy Point Rd Unit 104, 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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  /37

  $499,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  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

  (860) 773-4719

  14 Meadowood Ln, Old Saybrook, CT 06475
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  /23

  $2,666 - $3,550 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
• 

  $520,000 Sold Jul 07, 2025

  • 922 Sq Ft
  • $564/SF
  • 122 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  25 Chalker Beach Rd, Old Saybrook, CT 06475

  Cute and Compact! This delightful cape is snuggled back from the street on a half-acre lot of serene comfort and convenience. A perfect starter home, downsizer, city retreat or condo alternative. Built in 1986 with approximately 1144 square feet, (HOUSEMEASURES 768 FIRST FLOOR & 376 SECOND FLOOR - TOTAL 1144 SQ FT). Two bedrooms, 2 full bathrooms, a two-car garage and storage shed with power.

  Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, 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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  /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
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  /40

  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft
  • House for Rent

  2 Whitney Ave, Old Saybrook, CT 06475

  Available for rent in one of Old Saybrook's most desirable shoreline communities, this charming single-family home delivers relaxed coastal living with everyday functionality. Just moments from the water, this 2-bedroom, 2-bath property offers an airy, open layout with durable tile flooring and a bright kitchen outfitted with white cabinetry, granite countertops, and coordinating appliances. Step

  Danielle Turrell eXp Realty

  2 Whitney Ave, Old Saybrook, CT 06475
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  $215,000 Sold Jul 03, 2025

  • 880 Sq Ft
  • $244/SF
  • 9 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1979

  174 Old Boston Post Rd Unit 10, Old Saybrook, CT 06475

  Discover this quaint unit at Saybrook Village Condominiums! Set in the "B" building with just four units, your humble abode awaits. With just under 900 square feet, enjoy a spacious living room featuring a wood-burning fireplace, a galley kitchen, and a comfortably sized bedroom and bathroom. Additional features include a washer/dryer, balcony, assigned parking, and a personal storage unit in the

  Kayla Chasse Compass Connecticut, LLC

  174 Old Boston Post Rd Unit 10, 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

  $695,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,830 Sq Ft

  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

  (860) 385-8517

  100 Sheffield St Unit B4, 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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  $885,000 Sold Jul 01, 2025

  • 2,843 Sq Ft
  • $311/SF
  • 16 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1974

  4 Ridgewood Dr, Old Saybrook, CT 06475

  This meticulously maintained home welcomes you with warm pine floors, chef's kitchen with granite countertops, expansive island and gas stove top with a seamless flow to the family room with cozy fireplace, cathedral ceilings, French doors to beautiful patio and dining room with breakfast bar. Fully renovated primary bedroom suite on the first floor featuring dual walk-in closets, bathroom with

  Sharon Linder Berkshire Hathaway NE Prop.

  4 Ridgewood Dr, Old Saybrook, CT 06475
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  Est $756,263 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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  /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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  /26

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft
  • House for Rent

  94 Nehantic Trail, Old Saybrook, CT 06475

  Welcome to the popular Indian Town Beach Association in Old Saybrook. This is a fully furnished academic rental available from September 15, 2025, to May 15, 2026. Bright and neat, this home has been well taken care of both inside and out. The home features central air, propane heat, 2 bedrooms, a living room, a generously sized eat-in kitchen, a full set of laundry on the main floor, and a full

  Sang Jee William Raveis Real Estate

  94 Nehantic Trail, Old Saybrook, CT 06475
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  $1,625,000 Sold Jul 01, 2025

  • 3,556 Sq Ft
  • $457/SF
  • 105 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  9 Overlook Dr, Old Saybrook, CT 06475

  Welcome to your dream home! Nestled on a private, gated 1.36-acre lot, this magnificent recently completed Coastal-Inspired home blends coastal charm with New England elegance. Featuring 4 bedrooms and 4.5 baths, this home is designed for both luxury and comfort. The secluded primary suite on the main level offers an expansive walk-in closet and a spa-like bathroom with a large shower, a

  Mary Ann Hebert BHGRE Bannon & Hebert

  9 Overlook Dr, Old Saybrook, CT 06475
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  Est $1,567,430 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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  /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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  /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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  $810,000 Sold Jun 30, 2025

  • 2,100 Sq Ft
  • $386/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1977

  27 Birch St, Old Saybrook, CT 06475

  Welcome to this beautifully updated 4 bedroom, 3 full bath home nestled in the heart of picturesque Old Saybrook. This property is perfectly situated within walking distance to town and close to beaches, yet tucked away on a quiet dead end street that feels worlds apart. Enjoy the best of both worlds, convenience and tranquility. Step onto the charming front porch, perfect for enjoying your

  Jennifer Pagan RE/MAX One

  27 Birch St, Old Saybrook, CT 06475
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  Est $6,957,382 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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  /2

  $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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  /31

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 1,665 Sq Ft
  • House for Rent

  38 Mohican Rd, Old Saybrook, CT 06475

  This home is just one short block from the beach and has a nice sized yard with a patio and outdoor shower. The roomy kitchen opens to a large great room with a gas burning stove. There is also a separate living room to the front of the house. This home has plenty of room for parking and is a member of Cornfield Point with two beaches, a club house, pickleball court, tennis court and activities

  Bonnie Fillion Berkshire Hathaway NE Prop.

  38 Mohican Rd, Old Saybrook, CT 06475
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  $670,000 Sold Jun 27, 2025

  • 1,870 Sq Ft
  • $358/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1980

  7 Beaver Dam Trail, Old Saybrook, CT 06475

  Welcome to your dream shoreline home in Old Saybrook-where small-town charm meets modern luxury. Set on a quiet cul de sac just minutes from the beach, schools, and shops, this like-new Colonial has been fully renovated and offers everything a young family could want. Inside, you'll find gleaming hardwood floors, a stunning new kitchen with leathered granite counters, center island, and breakfast

  Joel Lucas Coldwell Banker Realty

  7 Beaver Dam Trail, Old Saybrook, CT 06475
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  Est $395,633 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

  $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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  /15

  $2,650 per month

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • House for Rent

  9 Denmore Ln, Old Saybrook, CT 06475

  3 bedroom Ranch-YEAR ROUND RENTAL! Come take a look -- South of Rt. 1 is this 3 bedroom ranch located close to restaurants and shopping and just a few minutes to the town beaches and I-95. This home has had some recent work done to be ready for its new tenants ... whole house freshly painted, new flooring and carpeting in entire house, professionally cleaned!! Exterior has been power washed and

  Lisa Genovali Re/Max Valley Shore

  9 Denmore Ln, Old Saybrook, CT 06475
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  $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
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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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  /34

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 3,404 Sq Ft

  6 Trolley Crossing, Old Saybrook, CT 06475

  Love to entertain, or just spend time relaxing in your extensive living areas, including the newly added inground pool with deck and patio surround? Check out the spacious front to back living room with fireplace, formal dining room, open concept great room with a renovated kitchen and family room with fireplace, and a stunning sunroom with a cathedral ceiling and brand new skylights. The kitchen

  Donald Holland William Pitt Sotheby's Int'l

  6 Trolley Crossing, Old Saybrook, CT 06475
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  /37

  $7,500 per month

  • 1 Bed
  • 1 Bath
  • 1,133 Sq Ft
  • Apartment for Rent

  18 Riverside Ave, Old Saybrook, CT 06475

  Welcome to "The Boathouse", offered as a seasonal monthly rental: May, June, July or August! Situated on the West bank of the Connecticut River at a "boat-ique" boatyard on Ferry Point, is this 2016 custom built, fully furnished Nantucket style 1 bedroom luxury apartment which captures stunning views of Long Island Sound. Enter through a custom mahogany door into a mudroom w/ heated floors,

  Jessica Blancato William Pitt Sotheby's Int'l

  18 Riverside Ave, Old Saybrook, CT 06475
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  $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
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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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  /40

  $975,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  23 Briarwood Dr, Old Saybrook, CT 06475

  Mid-Century Modern Gem with Marsh Views and sunsets in Cornfield Point. Welcome to this stunning mid-century modern split-level home, perfectly situated on a serene half-acre lot in the sought-after Cornfield Point waterfront community. Backing directly to the marsh with water access to Long Island Sound, this beautifully updated home offers the ideal blend of timeless architectural style and

  Marc Delise Coldwell Banker Realty

  23 Briarwood Dr, Old Saybrook, CT 06475
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  /14

  $3,180 per month

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Apartment for Rent

  109 Lynde St Unit 1, Old Saybrook, CT 06475

  WELCOME TO THE LUXURY HANFORD COMMONS, LOCATED IN THE TOWN OF OLD SAYBROOK WHICH IS KNOWN FOR ITS BEACHES, MARINAS, SHOPPING, FINE DINING, GALLERIES AND THE FAMOUS KATHERINE HEPBURN THEATER, MOST OF WHICH IS WALKING DISTANCE FROM THE APARTMENT COMPLEX. THIS FIRST FLOOR UNIT IS A TWO BEDROOM, TWO BATH, RANCH STYLE APARTMENT WITH LOTS OF NATURAL LIGHT FROM THE OVERSIZED WINDOWS. UNIT ALSO HAS

  Tracy Bonito William Raveis Real Estate

  109 Lynde St Unit 1, Old Saybrook, CT 06475
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  $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 $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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