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Old Saybrook, CT Houses for Sale

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  • 86 Chalker Beach Rd, Old Saybrook, CT 06475
    86 Chalker Beach Rd, Old Saybrook, CT 06475
    86 Chalker Beach Rd, Old Saybrook, CT 06475
    /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,

    Agent Photo

    Jodi Serapilia

    William Raveis Real Estate

    (860) 809-5460

    86 Chalker Beach Rd, Old Saybrook, CT 06475
  • 5 Aladdin Ave, Old Saybrook, CT 06475
    5 Aladdin Ave, Old Saybrook, CT 06475
    5 Aladdin Ave, Old Saybrook, CT 06475
    /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

    Agent Photo

    Matt Diamond

    Houlihan Lawrence WD

    (860) 590-4441

    5 Aladdin Ave, Old Saybrook, CT 06475
  • 52 Chalker Beach Rd, Old Saybrook, CT 06475
    52 Chalker Beach Rd, Old Saybrook, CT 06475
    52 Chalker Beach Rd, Old Saybrook, CT 06475
    /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

    Agent Photo

    Patrick Farley

    Statewide Premier Prop. LLC

    (860) 718-4375

    52 Chalker Beach Rd, Old Saybrook, CT 06475
  • 45 Farview Ave, Old Saybrook, CT 06475
    45 Farview Ave, Old Saybrook, CT 06475
    45 Farview Ave, Old Saybrook, CT 06475
    /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

    Agent Photo

    Amy Rubin

    RE/MAX Legends

    (860) 854-9586

    45 Farview Ave, Old Saybrook, CT 06475
  • 12 4th Ave, Old Saybrook, CT 06475
    12 4th Ave, Old Saybrook, CT 06475
    12 4th Ave, Old Saybrook, CT 06475
    /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,

    Agent Photo

    Maddy Mattson

    Coldwell Banker Realty

    (860) 787-8257

    12 4th Ave, Old Saybrook, CT 06475
  • 96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    /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
  • 26 Meadowood Ln, Old Saybrook, CT 06475
    26 Meadowood Ln, Old Saybrook, CT 06475
    26 Meadowood Ln, Old Saybrook, CT 06475
    /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
  • 11 Osprey Rd, Old Saybrook, CT 06475
    11 Osprey Rd, Old Saybrook, CT 06475
    11 Osprey Rd, Old Saybrook, CT 06475
    /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
  • 8 Fenbrook Rd, Old Saybrook, CT 06475
    8 Fenbrook Rd, Old Saybrook, CT 06475
    8 Fenbrook 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
  • 23 Briarwood Dr, Old Saybrook, CT 06475
    23 Briarwood Dr, Old Saybrook, CT 06475
    23 Briarwood Dr, Old Saybrook, CT 06475
    /40

    $975,000

    • 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
  • 7 Sharon Ln, Old Saybrook, CT 06475
    7 Sharon Ln, Old Saybrook, CT 06475
    7 Sharon Ln, Old Saybrook, CT 06475
    /40

    $1,000,000

    • 4 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    7 Sharon Ln, Old Saybrook, CT 06475

    Welcome to 7 Sharon Lane, a classic Colonial on 1.35 acres, set against the tranquil backdrop of the Back River conservation marsh and located minutes from two town beaches. This inviting 4-bedroom, 2.5-bath, spacious home offers the perfect blend of formal entertaining, daily convenience and coastal lifestyle. Inside, the main entry foyer gives access to an open and welcoming floor plan; a

    Sara Venditto William Pitt Sotheby's Int'l

    7 Sharon Ln, Old Saybrook, CT 06475
  • 30 Watrous Point Rd, Old Saybrook, CT 06475
    30 Watrous Point Rd, Old Saybrook, CT 06475
    30 Watrous Point Rd, Old Saybrook, CT 06475
    /37

    $1,475,000

    • 4 Beds
    • 5 Baths
    • 4,546 Sq Ft

    30 Watrous Point Rd, Old Saybrook, CT 06475

    Framed by mature landscape and extensive hardscape, welcome to this private Watrous Point country home. Find a gracious, barrel-vaulted entry and a gallery-style foyer flanked by the library. Built to entertain, a solid cherry kitchen commands an 8-burner Wolf range, two Gaggenau convection ovens, warming drawers, dual Subzeros and a dream pantry. One of two fieldstone fireplaces anchors the

    Nancy Mesham Coldwell Banker Realty

    30 Watrous Point Rd, Old Saybrook, CT 06475
  • 1 Clark Ave, Old Saybrook, CT 06475
    1 Clark Ave, Old Saybrook, CT 06475
    1 Clark Ave, Old Saybrook, CT 06475
    /36

    $925,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 2,376 Sq Ft

    1 Clark Ave, Old Saybrook, CT 06475

    Imagine slipping your kayak into the tidal waters of Hagar Creek from your spacious backyard, and gliding through the morning's sun-dappled marsh to find yourself entering Long Island Sound. Maybe do a little fishing, or just drink in the stunning shoreline views? Time to head home for lunch. Check the newsletter to see what's going on at the community center tonight. Then it's a quick spin down

    Rick Weiner William Pitt Sotheby's Int'l

    1 Clark Ave, Old Saybrook, CT 06475
  • 24 Cottage Place, Old Saybrook, CT 06475
    24 Cottage Place, Old Saybrook, CT 06475
    24 Cottage Place, Old Saybrook, CT 06475
    /40

    $985,000

    • 4 Beds
    • 3 Baths
    • 2,516 Sq Ft

    24 Cottage Place, Old Saybrook, CT 06475

    Welcome to 24 Cottage Place - a luxury shoreline home offering the perfect blend of elegance, comfort, and an unbeatable Old Saybrook location. Tucked away on a quiet dead-end street, this move-in ready 4-bedroom, 3-bath residence is just minutes from Old Saybrook's vibrant Main Street, "The Kate" theater, library, fitness center, marinas, and train station. Walk or bike to popular beaches, the

    Jennifer Gurnell William Raveis Real Estate

    24 Cottage Place, Old Saybrook, CT 06475
  • 122 College St, Old Saybrook, CT 06475
    122 College St, Old Saybrook, CT 06475
    122 College St, Old Saybrook, CT 06475
    /26

    $998,868

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

    122 College St, Old Saybrook, CT 06475

    Iconic Old Saybrook 1890's Captain's home with it's own widow's walk-venture up and enjoy 360 degree views of the CT River, North Cove, and Long Island Sound-or relax on the wrap around porch and watch the world go by. Situated on .80 level acres w/an inground pool-2 car detached garage w/1/2 bath for the pool-possibly could be renovated for guest quarters. This home is like a blank slate w/3200

    Mary McDonald Coldwell Banker Realty

    122 College St, Old Saybrook, CT 06475
  • 1 Lighthouse Ln, Old Saybrook, CT 06475
    1 Lighthouse Ln, Old Saybrook, CT 06475
    1 Lighthouse Ln, Old Saybrook, CT 06475
    /39

    $1,045,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 3,286 Sq Ft

    1 Lighthouse Ln, Old Saybrook, CT 06475

    This spacious 3200 sq.ft. home offers SWEEPING WATER VIEWS and an UNBEATABLE LOCATION in one of the shoreline's most sought-after communities. Perfectly situated between Saybrook Point and Town Center, it's just a short walk in either direction to enjoy marinas, top-rated restaurants, boutique shopping, and local favorites like the Saybrook Inn. This cul-de-sac property features custom built-ins,

    Lynne Ferrigno Coldwell Banker Realty

    1 Lighthouse Ln, Old Saybrook, CT 06475
  • 26 College St, Old Saybrook, CT 06475
    26 College St, Old Saybrook, CT 06475
    26 College St, Old Saybrook, CT 06475
    /40

    $998,900

    • 5 Beds
    • 3 Baths
    • 2,898 Sq Ft

    26 College St, Old Saybrook, CT 06475

    Welcome to 26 College Street, a Nantucket-style haven nestled in the heart of historic Old Saybrook-a coastal village where charm meets convenience. With five spacious bedrooms and three full bathrooms, including a fully private in-law or au-pair suite, it's tailor-made for families or couples looking for multi-generational living, rental income, or a dedicated home office setup. Tucked between

    Joel Lucas Coldwell Banker Realty

    26 College St, Old Saybrook, CT 06475
  • 24 Seabreeze Rd, Old Saybrook, CT 06475
    24 Seabreeze Rd, Old Saybrook, CT 06475
    24 Seabreeze Rd, Old Saybrook, CT 06475
    /28

    $1,085,000

    • 2 Beds
    • 2 Baths
    • 1,952 Sq Ft

    24 Seabreeze Rd, Old Saybrook, CT 06475

    Nestled in the prestigious Cornfield Point Beach Association neighborhood, this upgraded ranch offers one-level living at its finest with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, central air, a huge bonus room you can convert to a third bedroom, this home provides comfort and style. A spacious open plan living room

    Brian Beaulieu KW Legacy Partners

    24 Seabreeze Rd, Old Saybrook, CT 06475
  • 20 Hill St, Old Saybrook, CT 06475
    20 Hill St, Old Saybrook, CT 06475
    20 Hill St, Old Saybrook, CT 06475
    /30

    $799,900 Open Sat 1PM - 3PM

    • 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
  • 18 Quarry St, Old Saybrook, CT 06475
    18 Quarry St, Old Saybrook, CT 06475
    18 Quarry St, Old Saybrook, CT 06475
    /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
  • 33 Fenwood Rd, Old Saybrook, CT 06475
    33 Fenwood Rd, Old Saybrook, CT 06475
    33 Fenwood Rd, Old Saybrook, CT 06475
    /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
  • 18 Lynde St, Old Saybrook, CT 06475
    18 Lynde St, Old Saybrook, CT 06475
    18 Lynde St, Old Saybrook, CT 06475
    /39

    $549,000

    • 3 Beds
    • 1 Bath
    • 1,185 Sq Ft

    18 Lynde St, Old Saybrook, CT 06475

    18 Lynde St is a classic cape style home, where vintage charm meets coastal living in the heart of downtown Old Saybrook. This home has timeless appeal with its original wood doors and classic glass doorknobs of the 1940's. Intimate in size, the space is inviting and brimming with potential, including the possibility of expansion. Less than a mile's walk to North Cove with access to the CT River,

    Liz Squillacote William Pitt Sotheby's Int'l

    18 Lynde St, Old Saybrook, CT 06475
  • 12 Bellaire Dr, Old Saybrook, CT 06475
    12 Bellaire Dr, Old Saybrook, CT 06475
    12 Bellaire Dr, Old Saybrook, CT 06475
    /23

    $799,000 Open Sat 11AM - 1PM

    • 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
  • 6 Trolley Crossing, Old Saybrook, CT 06475
    6 Trolley Crossing, Old Saybrook, CT 06475
    6 Trolley Crossing, Old Saybrook, CT 06475
    /34

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,662 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
  • 12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    /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
  • 2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    /40

    $1,685,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 3.5 Baths
    • 2,500 Sq Ft

    2 Old South Cove Rd, Old Saybrook, CT 06475

    Luxury, Lifestyle & Legacy in Old Saybrook's Most Stylish New Construction Welcome to 2 Old South Cove Road-a rare opportunity to own brand-new construction just steps from the water in one of Connecticut's most coveted shoreline towns. Designed in partnership with Saybrook Home and styled like a New York design editorial, this 2,400 sq ft single-level residence blends refined coastal luxury

    Michael Riccio Calcagni Real Estate

    2 Old South Cove Rd, Old Saybrook, CT 06475
  • 6 Pheasant Hill Ln, Old Saybrook, CT 06475
    6 Pheasant Hill Ln, Old Saybrook, CT 06475
    6 Pheasant Hill Ln, Old Saybrook, CT 06475
    /23

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,976 Sq Ft

    6 Pheasant Hill Ln, Old Saybrook, CT 06475

    Welcome to this beautifully maintained home. Set at the end of cul-de-sac and bordered by The Preserve Connecticut's largest coastal forest, this property offers privacy and natural beauty with direct access to miles of scenic hiking trails right outside your door. Minutes to I-95, close to Old Saybrook shops, top rated schools and beaches. Enjoy an open concept kitchen formal dining room, cozy

    Letessa Dion Coldwell Banker Realty

    6 Pheasant Hill Ln, Old Saybrook, CT 06475
  • 16 Lynde St, Old Saybrook, CT 06475
    16 Lynde St, Old Saybrook, CT 06475
    16 Lynde St, Old Saybrook, CT 06475
    /34

    $585,000

    • 2 Beds
    • 1.5 Baths
    • 1,258 Sq Ft

    16 Lynde St, Old Saybrook, CT 06475

    Unbeatable downtown Old Saybrook location! This well-maintained Cape Cod-style home at 16 Lynde Street is on the market for the first time in over 40 years. Offering 2+ bedrooms, 1+ baths, and a bright, flexible floor plan, this property places you in the heart of one of Connecticut's most desirable shoreline towns. Enjoy sidewalks leading to schools, the library, shops, restaurants, cafes, and

    Jennifer Gurnell William Raveis Real Estate

    16 Lynde St, Old Saybrook, CT 06475
  • 18 W King St, Old Saybrook, CT 06475
    18 W King St, Old Saybrook, CT 06475
    18 W King St, Old Saybrook, CT 06475
    /36

    $685,000 Open Sat 11:30AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 2,660 Sq Ft

    18 W King St, Old Saybrook, CT 06475

    Discover exceptional flexibility, Airbnb potential, and income opportunity at 18 King Street in the heart of Old Saybrook. This updated ranch-style home offers over four spacious bedrooms, three and a half modern baths, and two fully renovated kitchens-ideal for multigenerational living, private guest quarters, or short- and long-term rental income. Energy-efficient split systems and

    Jennifer Gurnell William Raveis Real Estate

    18 W King St, Old Saybrook, CT 06475
  • 122 Old Post Rd, Old Saybrook, CT 06475
    122 Old Post Rd, Old Saybrook, CT 06475
    122 Old Post Rd, Old Saybrook, CT 06475
    /40

    $1,199,000

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

    122 Old Post Rd, Old Saybrook, CT 06475

    Welcome home to your own exquisite coastal retreat. This award winning exceptional cedar 3,000 square feet home blends timeless craftsmanship with modern upgrades and includes a stunning 19 foot high great room with floor to wall ceilings, wrap around deck with effortless indoor-outdoor living, cozy fireplace, dining room and family room. The kitchen boasts custom counters and cabinetry,

    Sharon Linder Berkshire Hathaway NE Prop.

    122 Old Post Rd, Old Saybrook, CT 06475
  • 41 Watrous Point Rd, Old Saybrook, CT 06475
    41 Watrous Point Rd, Old Saybrook, CT 06475
    41 Watrous Point Rd, Old Saybrook, CT 06475
    /40

    $4,450,000

    • 6 Beds
    • 4.5 Baths
    • 5,536 Sq Ft

    41 Watrous Point Rd, Old Saybrook, CT 06475

    Presenting a single level light-filled mid-century modern masterpiece, set on a prominent 2.7 acre private waterfront peninsula! Enjoy 875' of frontage along the CT River and adjacent Turtle Creek nature preserve. This dreamlike property comes with two docks. A deep water dock on the river, plus a second dock on Turtle Creek! Drink in views from Essex Harbor to the north, across the river to Old

    Rick Weiner William Pitt Sotheby's Int'l

    41 Watrous Point Rd, Old Saybrook, CT 06475
  • 5 Oakwood Rd, Old Saybrook, CT 06475
    5 Oakwood Rd, Old Saybrook, CT 06475
    5 Oakwood Rd, Old Saybrook, CT 06475
    /38

    $1,800,000

    • 3 Beds
    • 2 Baths
    • 3,477 Sq Ft

    5 Oakwood Rd, Old Saybrook, CT 06475

    This spacious Knollwood Beach home is only ONE house from Long Island Sound featuring sweeping water views. Step into timeless elegance with this stunning home where classic craftsmanship meets modern convenience. The first floor features a gourmet kitchen and dining area complete with granite countertops, a center island with canopy, and high-end appliances. Original wainscoting ceilings and two

    Carol Ieronimo William Raveis Real Estate

    5 Oakwood Rd, Old Saybrook, CT 06475
  • 96 Chalker Beach Rd, Old Saybrook, CT 06475
    96 Chalker Beach Rd, Old Saybrook, CT 06475
    96 Chalker Beach Rd, Old Saybrook, CT 06475
    /36

    $649,900

    • 3 Beds
    • 1 Bath
    • 870 Sq Ft

    96 Chalker Beach Rd, Old Saybrook, CT 06475

    This FULLY FURNISHED charming cottage offers all the cozy beach vibes you've been looking for. Pull into the paver stone driveway with room for multiple vehicles, golf carts, or beach cruisers. A shed at the end of the driveway provides easy storage for all your beach gear. Step into the beautifully manicured, fully fenced backyard complete with a paver stone patio, open lawn for play or

    Danielle Spada Coldwell Banker Realty

    96 Chalker Beach Rd, Old Saybrook, CT 06475
  • 76 River St W, Old Saybrook, CT 06475
    76 River St W, Old Saybrook, CT 06475
    76 River St W, Old Saybrook, CT 06475
    /32

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft

    76 River St W, Old Saybrook, CT 06475

    Built to Last! Well Maintained Cape tucked away in a peaceful location backing up to Salt marshes. Nature lovers will enjoy the serene views of the salt meadows, wildlife and privacy of this quiet neighborhood. This property features 3 beds, 2 baths, over 1700 square feet of living space, a living room with vaulted ceilings and wall unit ac, dining area, kitchen, 3 good sized bedrooms, a private

    Robert Perriello Century 21 AllPoints Realty

    76 River St W, Old Saybrook, CT 06475
  • 14 Denmore Ln, Old Saybrook, CT 06475
    14 Denmore Ln, Old Saybrook, CT 06475
    14 Denmore Ln, Old Saybrook, CT 06475
    /25

    $549,900

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    14 Denmore Ln, Old Saybrook, CT 06475

    This beautifully revamped ranch style home provides a perfect blend of modern style and comfort. With 1,196 square feet of living space, this property boasts three spacious bedrooms and one full bathroom. The chef-inspired kitchen features sleek, new appliances, stylish cabinetry, and quartz countertops, ideal for both everyday meals and entertaining. The bright, airy living areas are enhanced

    Patrick Garrett Complete Real Estate

    14 Denmore Ln, Old Saybrook, CT 06475
  • 175 N Cove Rd, Old Saybrook, CT 06475
    175 N Cove Rd, Old Saybrook, CT 06475
    175 N Cove Rd, Old Saybrook, CT 06475
    /40

    $3,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,518 Sq Ft

    175 N Cove Rd, Old Saybrook, CT 06475

    Every home tells a story and the often admired c.1704 Black Horse Tavern in historic North Cove is no exception. Located at the waters edge and offering expansive water views, this stunning private residence is rich in both local history and architectural detail. Meticulously curated to perfection, quality of craftsmanship is evident throughout. A warm and welcoming entry leads to elegant

    Kyle Hinding Coldwell Banker Realty

    175 N Cove Rd, Old Saybrook, CT 06475
  • 3 4th Ave, Old Saybrook, CT 06475
    3 4th Ave, Old Saybrook, CT 06475
    3 4th Ave, Old Saybrook, CT 06475
    /13

    $399,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    3 4th Ave, Old Saybrook, CT 06475

    This home offers the one-level living you've been searching for! With a bit of repair work and thoughtful updates, you can transform this space into your perfect home. The property features a spacious backyard, complete with a generously sized outdoor shed for added storage and convenience. Close to marina, restaurants and highway access. Short drive to the beach!

    Phil Ledwith Century 21 AllPoints Realty

    3 4th Ave, Old Saybrook, CT 06475
  • 78 Hartford Ave, Old Saybrook, CT 06475
    78 Hartford Ave, Old Saybrook, CT 06475
    78 Hartford Ave, Old Saybrook, CT 06475
    /33

    $795,000

    • 3 Beds
    • 1 Bath
    • 890 Sq Ft

    78 Hartford Ave, Old Saybrook, CT 06475

    Beach living, redefined. Welcome to 78 Hartford Avenue, a rare coastal gem perched right on the water in the heart of Old Saybrook. With uninterrupted views, salty breezes, and your toes practically in the sand, this 3-bedroom beach retreat offers the kind of lifestyle most only dream about. Whether you're soaking in the sun from your patio, launching kayaks at sunrise, or hosting unforgettable

    Robert Perriello Century 21 AllPoints Realty

    78 Hartford Ave, Old Saybrook, CT 06475
  • 21 Wildwood Rd, Old Saybrook, CT 06475
    21 Wildwood Rd, Old Saybrook, CT 06475
    21 Wildwood Rd, Old Saybrook, CT 06475
    /33

    $1,150,000

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    21 Wildwood Rd, Old Saybrook, CT 06475

    Imagine waking up to breathtaking marsh views and stunning sunsets from your very own slice of paradise in the highly desirable Cornfield Point waterfront community. This nearly 1-acre lot offers endless possibilities - whether you choose to expand, rebuild, or simply enjoy the charm of the existing 1,408 square foot home. The current residence features 3 bedrooms, 1.5 baths, a spacious 2-car

    Marc Delise Coldwell Banker Realty

    21 Wildwood Rd, Old Saybrook, CT 06475
  • 4 Old Fenwick Rd, Old Saybrook, CT 06475
    4 Old Fenwick Rd, Old Saybrook, CT 06475
    4 Old Fenwick Rd, Old Saybrook, CT 06475
    /40

    $1,795,000

    • 5 Beds
    • 2.5 Baths
    • 2,994 Sq Ft

    4 Old Fenwick Rd, Old Saybrook, CT 06475

    Waterviews!!! Extraordinary Indirect Waterfront Home Overlooking Long Island Sound! Welcome to your dream home with stunning views of the Fenwick Lighthouses! This recently renovated home boasts panoramic views from every room and is move-in ready. Situated on a unique private water-view lot, the property features a lush green lawn, landscaped gardens, and is just steps away from the beautiful

    Joel Lucas Coldwell Banker Realty

    4 Old Fenwick Rd, Old Saybrook, CT 06475

Showing Results 1 - 40, Page 1 of 2

Connecticut Middlesex County Old Saybrook

Houses for Sale in Old Saybrook, CT

Why Live in Old Saybrook

Old Saybrook, Connecticut, is a tranquil town situated along the Long Island Sound, ideal for those seeking a waterside residence with ample beach and water activities. Housing options include colonials, ranch-style, and Cape Cod homes, with prices starting around $340,000 for single-family homes and peaking at $4.2 million for luxurious seaside properties. The town is known for its high foot traffic, especially near the beach and Main Street district. Old Saybrook Public Schools are highly rated, with Kathleen E. Goodwin Elementary School, Old Saybrook Middle School, and Old Saybrook High School all receiving commendable marks for academics and teacher quality. The town features several beautiful beaches, such as Cove Beach and Great Hammock, and recreational activities like golfing at Fenwick Golf Course. Dining options are concentrated along Route 1, with popular spots like the Parthenon Diner. The town hosts annual events, including holiday celebrations, a Fourth of July parade, and an art festival. Old Saybrook is accessible via Interstate 95, making it convenient for commuters. The town has a lower crime rate compared to the national average, contributing to its appeal as a safe place to live.

Learn more about living in Old Saybrook

Home Trends in Old Saybrook, CT

On average, homes in Old Saybrook, CT sell after 27 days on the market compared to the national average of 70 days. The median sale price for homes in Old Saybrook, CT over the last 12 months is $800,000, down 27% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$800,000
Median Single Family Sale Price
$1,685,000
Median Townhouse Sale Price
$920,000
Average Price Per Sq Ft
$389
Number of Homes for Sale
4
Last 12 months Home Sales
8
Months of Supply
6.00
Median List Price
$949,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-27%
How to Buy a Home How to Finance a Home How to Sell a Home

In Old Saybrook, there are currently 42 houses for sale, offering an array of options for potential buyers. With houses priced between $399,000 to $6,400,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Old Saybrook is $949,000, while the average sale price is $830,000, offering insights into the local housing market. On average, houses spend 27 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Old Saybrook, CT and find the perfect place to call home.

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