6,223

Old Saybrook, CT Homes

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  • 69 Essex Rd, Old Saybrook, CT 06475
    69 Essex Rd, Old Saybrook, CT 06475
    69 Essex Rd, Old Saybrook, CT 06475
    /36

    $550,000

    • 4 Beds
    • 2 Baths
    • 2,112 Sq Ft

    69 Essex Rd, Old Saybrook, CT 06475

    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 for added convenience, and a cozy pellet stove in

    Brittany O'Hara William Raveis Real Estate

    69 Essex Rd, Old Saybrook, CT 06475
  • 2 Point Rd, Old Saybrook, CT 06475
    2 Point Rd, Old Saybrook, CT 06475
    2 Point Rd, Old Saybrook, CT 06475
    /29

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 1,972 Sq Ft
    • House for Rent

    2 Point Rd, Old Saybrook, CT 06475

    The Iconic 2 Point Road Old Saybrook. Enjoy the breathtaking water views from every room! There are two full suites on the main level. The primary suite with French doors opening to its own balcony with breathtaking panoramic views will leave you speechless. The outside grounds boasts stunning views of Long Island Sound, Orient Point, Plum Island and more. Cornfield Point Association allows

    David Rodriguez William Pitt Sotheby's Int'l

    2 Point Rd, Old Saybrook, CT 06475
  • 4 Patterson Place, Old Saybrook, CT 06475

    $555,000 Sold Mar 28, 2025

    • 1,752 Sq Ft
    • $317/SF
    • 60 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    4 Patterson Place, Old Saybrook, CT 06475

    Classic contemporary style in move in condition! Sitting pretty on a lovely landscaped lot in a super cul de sac location close to everything Old Saybrook has to offer! Light and bright with soaring ceilings, skylights, hardwood floors, central air, pretty kitchen all refreshed with new appliances, flooring and paint, remodeled baths, first floor master suite with walk-in closet and private bath.

    Lynn Lehrman REMAX Valley Shore

    4 Patterson Place, Old Saybrook, CT 06475
  • 62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475
    62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475
    62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475
    /8

    $850,000

    • Land
    • 26 Acres
    • $32,185 per Acre

    62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475

    Beautiful 26+ Acre Wooded Lot with Subdivision Potential. This stunning 26+ acre wooded parcel offers incredible potential for a variety of uses-from a private gentleman's farm to a multi-generational compound or subdivision development. Bucolic stone walls and mature trees create a serene, timeless setting. The sale includes parcels identified as Tax Map 62, Lots 14, 15, and 16. Access is

    Kevin Kennedy Kennedy Real Estate Solutions

    62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475
  • 157 Plum Bank Rd, Old Saybrook, CT 06475
    157 Plum Bank Rd, Old Saybrook, CT 06475
    157 Plum Bank Rd, Old Saybrook, CT 06475
    /25

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • House for Rent

    157 Plum Bank Rd, Old Saybrook, CT 06475

    Spend the winter at the beach! Enjoy wonderful views and sunsets. Convenient Old Saybrook location. Spacious living areas. Large windows provide natural sunlight and great views. Galley kitchen complete with a dishwasher. Laundry on the main level. A full bathroom completes the first floor. Upstairs there are three bedrooms and a full bathroom. A fourth bedroom is not available to tenants.

    Beth Brewer Compass Connecticut, LLC

    157 Plum Bank Rd, Old Saybrook, CT 06475
  • 9 Trolley Crossing, Old Saybrook, CT 06475

    $600,000 Sold Mar 24, 2025

    • 1,453 Sq Ft
    • $413/SF
    • 40 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    9 Trolley Crossing, Old Saybrook, CT 06475

    Welcome to this charming home located on a quiet cul- de-sac convenient to 95 and Route 9. Just a 5 minute drive to quaint downtown Main Street where you will find shopping, restaurants, The Kate Theater and so much more. This home has an open concept floor plan with a cozy gas fireplace in the family room. There's an office/den, or could even be used as a bedroom with glass doors onto a deck,

    Jackie Lyman Lyman Real Estate

    9 Trolley Crossing, 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
    /39

    $1,575,000 Open Sat 2PM - 3:30PM

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

    26 Meadowood Ln, Old Saybrook, CT 06475

    Welcome to The Sunset House-a truly exceptional shoreline retreat where refined craftsmanship meets the natural beauty of Long Island Sound and Hagar Creek. Perfectly situated in a premier Old Saybrook location, this stunning new construction Colonial offers panoramic views while remaining outside the flood plain-a rare and valuable combination offering both luxury and peace of mind. Thoughtfully

    Jennifer Gurnell William Raveis Real Estate

    26 Meadowood Ln, Old Saybrook, CT 06475
  • 3 Wilson Ave, Old Saybrook, CT 06475
    3 Wilson Ave, Old Saybrook, CT 06475
    3 Wilson Ave, Old Saybrook, CT 06475
    /40

    $6,500 per month

    • 5 Beds
    • 4 Baths
    • 3,154 Sq Ft
    • House for Rent

    3 Wilson Ave, Old Saybrook, CT 06475

    Academic Rental in desirable Fenwick! Available from September 2024 through May 2025 at 4,000 per month; and available from September 2025 through May 2026 at $6,500 per month ~ we are looking for tenants for full academic term. This exceptional property offers the ultimate in Shoreline living. Set privately on a knoll overlooking open marshlands to water views of Long Island Sound and the outer

    Lynn Lehrman REMAX Valley Shore

    3 Wilson Ave, Old Saybrook, CT 06475
  • 11 Evans Ln, Old Saybrook, CT 06475

    $445,000 Sold Mar 21, 2025

    • 684 Sq Ft
    • $651/SF
    • 40 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1938

    11 Evans Ln, Old Saybrook, CT 06475

    Whether single or taken, this year round beach cottage is sure to steal your Heart this Valentines Day week! Nestled in the Beach Community of Saybrook Manor, 11 Evans Ln. oozes with Beach Vibes through out all of her heart and is complimented by deeded rights to Cove Beach. Remodeled home from top to bottom, offering two bedrooms and a cleverly placed 3rd bedroom loft, she offers a lot for the

    Jordan Ostrofsky KW Legacy Partners

    11 Evans Ln, 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

    $1,895,000 Open Thu 5PM - 7PM

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

    2 Old South Cove Rd, Old Saybrook, CT 06475

    A Rare Coastal Masterpiece in Saybrook Point! Welcome to a once-in-a-generation opportunity to own brand new custom construction in the heart of prestigious Saybrook Point-where coastal elegance meets cutting-edge design. Inspired by the pages of a New York design magazine and brought to life in collaboration with Saybrook Home, this residence showcases the pinnacle of quality, American-made

    Ralph Riccio Calcagni Real Estate

    2 Old South Cove Rd, Old Saybrook, CT 06475
  • 8 Belaire Manor, Old Saybrook, CT 06475
    8 Belaire Manor, Old Saybrook, CT 06475
    8 Belaire Manor, Old Saybrook, CT 06475
    /36

    $18,000 per month

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

    8 Belaire Manor, Old Saybrook, CT 06475

    Summer 2025! -- Current availability: June 1-14 ($9,000) + entire month of September ($18,000). 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 here. Upon pulling into the driveway, you'll be greeted by breathtaking

    Erika Raffles William Pitt Sotheby's Int'l

    8 Belaire Manor, Old Saybrook, CT 06475
  • 73 Ayers Point Rd, Old Saybrook, CT 06475

    $625,000 Sold Mar 20, 2025

    • 1,861 Sq Ft
    • $336/SF
    • 34 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    73 Ayers Point Rd, Old Saybrook, CT 06475

    The spacious 3 bedroom/2 bath RANCH home you've been waiting for in a great location! Flexible floor plan includes a bonus room over the garage - perfect flex space for an in-home office, possible in-law; large eat-in kitchen/dining area with french door to 18x14 deck; cozy den also with access to deck. Generous-sized living room with large bay window; remodeled bath with walk-in shower and two

    Lisa Genovali REMAX Valley Shore

    73 Ayers Point Rd, Old Saybrook, CT 06475
  • 37 Woodland Dr, Old Saybrook, CT 06475
    37 Woodland Dr, Old Saybrook, CT 06475
    37 Woodland Dr, Old Saybrook, CT 06475
    /40

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    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
  • 17 Agawam Ave, Old Saybrook, CT 06475
    17 Agawam Ave, Old Saybrook, CT 06475
    17 Agawam Ave, Old Saybrook, CT 06475
    /40

    $6,500 per month

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

    17 Agawam Ave, Old Saybrook, CT 06475

    Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September 4, 2024, through June 20, 2025! 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 walls of windows and French door access to a spacious

    Lynn Lehrman REMAX Valley Shore

    17 Agawam Ave, Old Saybrook, CT 06475
  • 35 Sherwood Terrace, Old Saybrook, CT 06475

    $610,000 Sold Mar 10, 2025

    • 1,834 Sq Ft
    • $333/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    35 Sherwood Terrace, Old Saybrook, CT 06475

    Welcome to 35 Sherwood Terrace, a charming shoreline Cape nestled in the heart of downtown Old Saybrook, CT! This delightful home perfectly combines convenience and comfort, with sidewalks leading you to the town green, Main Street, library, restaurants, schools, and the renowned "The Kate" theater. Plus, enjoy easy access to Harvey's or Town Beach for those sunny days! As you step inside, you'll

    Jennifer Gurnell William Raveis Real Estate

    35 Sherwood Terrace, Old Saybrook, CT 06475
  • 9 Whisper Cove Rd, Old Saybrook, CT 06475
    9 Whisper Cove Rd, Old Saybrook, CT 06475
    9 Whisper Cove Rd, Old Saybrook, CT 06475
    /40

    $3,400,000

    • 4 Beds
    • 5 Baths
    • 4,768 Sq Ft

    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
  • 8 Nibang Ave, Old Saybrook, CT 06475
    8 Nibang Ave, Old Saybrook, CT 06475
    8 Nibang Ave, Old Saybrook, CT 06475
    /39

    $6,000 per month

    • 3 Beds
    • 3.5 Baths
    • 1,710 Sq Ft
    • House for Rent

    8 Nibang Ave, Old Saybrook, CT 06475

    Direct waterfront in fabulous Fenwick! Academic Rental available from September 4, 2024 to May 28, 2025 at $4,000 per month and again from September 2025 to May, 2026 at $6,000 per month. Spectacular setting on South Cove. Enjoy beautiful sunrises and sunsets in this idyllic water front home in the Borough of Fenwick. Completely renovated in 2007, open floor plan kitchen, great room and dining

    Lynn Lehrman REMAX Valley Shore

    8 Nibang Ave, Old Saybrook, CT 06475
  • 1 Connolly Dr, Old Saybrook, CT 06475

    $397,000 Sold Mar 07, 2025

    • 2,060 Sq Ft
    • $193/SF
    • 76 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    1 Connolly Dr, Old Saybrook, CT 06475

    Welcome to this charming cape-style home, perfectly situated less than a mile from Main Street. The land and home have only had one owner and have been meticulously maintained. This property offers a unique opportunity to create your dream home with some personal touches. Featuring 3 bedrooms and 2 bathrooms, the first floor includes a formal living room and dining room with hardwood floors, a

    Chloe White KW Legacy Partners

    1 Connolly Dr, Old Saybrook, CT 06475
  • 25 Sherman St, Old Saybrook, CT 06475
    25 Sherman St, Old Saybrook, CT 06475
    25 Sherman St, Old Saybrook, CT 06475
    /27

    $528,000

    • 3 Beds
    • 1.5 Baths
    • 1,225 Sq Ft

    25 Sherman St, Old Saybrook, CT 06475

    Ideally situated just a short walk from Main Street and moments from the shoreline, this home offers coastal charm and fully renovated comfort. This sun-filled 3-bedroom ranch, delivers the ease of one-level living with a modern, designer touch throughout.The welcoming great room features a cozy fireplace and flows effortlessly into a eat-in kitchen. Outfitted with white shaker cabinetry,

    Ginny Proft William Raveis Real Estate

    25 Sherman St, Old Saybrook, CT 06475
  • 136 Sandy Point Rd, Old Saybrook, CT 06475
    136 Sandy Point Rd, Old Saybrook, CT 06475
    136 Sandy Point Rd, Old Saybrook, CT 06475
    /28

    $3,450 per month

    • 2 Beds
    • 1.5 Baths
    • 1,288 Sq Ft
    • Townhouse for Rent

    136 Sandy Point Rd, Old Saybrook, CT 06475

    Spring is in the air....beautiful year-round rental maintenance free with GORGEOUS VIEWS! It's all about the lifestyle here at Summerwood, a community offering a private beach, inground pool, cabana, tennis/pickleball courts. Wake up each morning to the calming views -- this year-round rental unit offers amazing views of Long Island Sound, nature at its best with the ever-changing marsh and

    Lisa Genovali REMAX Valley Shore

    136 Sandy Point Rd, Old Saybrook, CT 06475
  • 28 Cypress Rd, Old Saybrook, CT 06475

    $705,000 Sold Mar 03, 2025

    • 1,070 Sq Ft
    • $659/SF
    • 16 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    28 Cypress Rd, Old Saybrook, CT 06475

    Beach Living at its finest with marsh views and no flood insurance! Just steps from a private beach in Knollwood Beach Association, this charming 2 bedroom, 1 bathroom ranch offers the perfect blend of seaside tranquility and convenient access to town amenities. Interior features include hardwood floors, a fireplace, generator hook up, and ample storage in the under-house garage. A spacious four

    Julia King William Raveis Real Estate

    28 Cypress Rd, Old Saybrook, CT 06475
  • 254 Hidden Cove Rd, Old Saybrook, CT 06475
    254 Hidden Cove Rd, Old Saybrook, CT 06475
    254 Hidden Cove Rd, Old Saybrook, CT 06475
    /23

    $499,000

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

    254 Hidden Cove Rd, Old Saybrook, CT 06475

    Nestled in the picturesque town of Old Saybrook, this two bedroom, one and a half bath townhouse provides a blend of comfort and leisure. Spanning 1,557sf of thoughtfully designed living space, this residence is perfect for those seeking a tranquil lifestyle by the shore. A community swimming pool is great on warm summer days. Stay Active with on-site tennis and pickleball courts, catering to

    Bonnie Foster William Pitt Sotheby's Int'l

    254 Hidden Cove Rd, Old Saybrook, CT 06475
  • 35 Old Boston Post Rd, Old Saybrook, CT 06475

    $998,120 Sold Feb 28, 2025

    • 3,046 Sq Ft
    • $328/SF
    • 101 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1979

    35 Old Boston Post Rd, Old Saybrook, CT 06475

    Welcome to 35 Old Boston Post Road --- gorgeous colonial with an accessory apartment! You've been waiting for this! Steps to Old Saybrook's vibrant Main Street, elementary and middle schools, Acton Library, the gracious main home has so much to offer besides the amazing location -- 9 rooms --all generous in size with gleaming hardwood floors throughout. The kitchen offers great space for the avid

    Lisa Genovali REMAX Valley Shore

    35 Old Boston Post Rd, Old Saybrook, CT 06475
  • 2 Whitney Ave, Old Saybrook, CT 06475
    2 Whitney Ave, Old Saybrook, CT 06475
    2 Whitney Ave, Old Saybrook, CT 06475
    /40

    $599,000

    • 2 Beds
    • 2 Baths
    • 920 Sq Ft

    2 Whitney Ave, Old Saybrook, CT 06475

    Nestled in one of Old Saybrook's most coveted shoreline neighborhoods, this updated 2-bedroom, 2-bath home offers beachside living with year-round comfort. Just a short stroll to the water, this property combines coastal convenience with everyday practicality-featuring a spacious open layout, tile flooring throughout, and a bright kitchen with white cabinetry, granite countertops, and matching

    William Chase eXp Realty

    2 Whitney Ave, Old Saybrook, CT 06475
  • 37 Sheffield St, Old Saybrook, CT 06475

    $737,500 Sold Feb 24, 2025

    • 2,360 Sq Ft
    • $312/SF
    • 36 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1923

    37 Sheffield St, Old Saybrook, CT 06475

    Live in the heart of charming historic Old Saybrook center. Steps away from Main Street, The Kate Theater, farmers market, town green, library, schools, shops and restaurants. Short walk to train station with Amtrak and Shoreline East service. At the end of the street take in gorgeous harbor views at the town's kayak-friendly boat launch. This 1920's gem oozes charm, starting with its arched

    Phoebe Finch William Pitt Sotheby's Int'l

    37 Sheffield St, Old Saybrook, CT 06475
  • 142 Ferry Rd Unit 6-1, Old Saybrook, CT 06475
    142 Ferry Rd Unit 6-1, Old Saybrook, CT 06475
    142 Ferry Rd Unit 6-1, Old Saybrook, CT 06475
    /8

    $17,000

    • 50 Sq Ft

    142 Ferry Rd Unit 6-1, Old Saybrook, CT 06475

    This beautiful dock slip can accommodate (per owner) a 25 foot boat with motor. Unit is Dock #6. Slip #1. Located at the "Ferry Landing Marina" in Old Saybrook CT. Situated on the Connecticut River about two miles from the mouth of Long Island Sound. This is a full service marina and boatyard that offers rack and winter storage, sales, rentals, and repairs provided by certified master

    Crystal McGrath Carl Guild & Associates

    142 Ferry Rd Unit 6-1, Old Saybrook, CT 06475
  • 12 Forest Glen Rd, Old Saybrook, CT 06475

    $476,000 Sold Feb 19, 2025

    • 2,248 Sq Ft
    • $212/SF
    • 207 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1979

    12 Forest Glen Rd, Old Saybrook, CT 06475

    Welcome to your dream home! Nestled in the heart of an established and highly sought-after neighborhood, this charming 3-bedroom Dutch Colonial offers the perfect blend of classic elegance and modern potential. With deeded beach rights to the pristine Cornfield Point Beach, you can enjoy coastal living at its finest just steps from your front door. As you enter, you'll be greeted by a warm,

    Nick Prevost William Raveis Real Estate

    12 Forest Glen Rd, Old Saybrook, CT 06475
  • 104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
    104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
    104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
    /34

    $524,900

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

    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 REMAX Valley Shore

    104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
  • 152 N Cove Rd, Old Saybrook, CT 06475

    $1,700,000 Sold Feb 18, 2025

    • 2,256 Sq Ft
    • $754/SF
    • 17 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1994

    152 N Cove Rd, Old Saybrook, CT 06475

    Introducing a rare gem on the market - a breathtaking waterfront property located in the highly coveted North Cove area of Old Saybrook, Connecticut. This exquisite home offers beautiful views of North Cove, creating a serene and picturesque living experience. Inside you will find a beautifully designed space that maximizes the views with large windows and an open floor plan that flows seamlessly

    Tammy Tinnerello William Pitt Sotheby's Int'l

    152 N Cove Rd, Old Saybrook, CT 06475

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