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Old Saybrook, CT Homes for Sale

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  • 71 Knollwood Dr, Old Saybrook, CT 06475
    71 Knollwood Dr, Old Saybrook, CT 06475
    71 Knollwood Dr, Old Saybrook, CT 06475
    /35

    $770,000

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,856 Sq Ft

    71 Knollwood Dr, Old Saybrook, CT 06475

    KNOLLWOOD BEACH - Here is the opportunity! A recently sparkled-up home. This beach house lives on a wide, 0.98-acre lot offering possibilities rarely found this close to the shoreline. First time since it was built. Come and live it up now! This one can generate rental income, or land-bank this parcel while planning something much more commodious for tomorrow. Knollwood is renovation-active, with

    Agent Photo

    Matt Diamond

    Houlihan Lawrence WD

    71 Knollwood Dr, Old Saybrook, CT 06475
  • 8 Kenn Rd, Old Saybrook, CT 06475
    8 Kenn Rd, Old Saybrook, CT 06475
    8 Kenn Rd, Old Saybrook, CT 06475
    /40

    $649,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    8 Kenn Rd, Old Saybrook, CT 06475

    Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Association. Offered As-Is and thoughtfully updated, this inviting home is ideal as a year-round residence, weekend escape, or classic summer getaway. With marsh views, salt air, and a relaxed beach-community setting, this is a turnkey opportunity designed for immediate enjoyment

    Agent Photo

    Michael Marsden

    Compass Connecticut, LLC

    8 Kenn Rd, Old Saybrook, CT 06475
  • 25 River Ave, Old Saybrook, CT 06475
    25 River Ave, Old Saybrook, CT 06475
    25 River Ave, Old Saybrook, CT 06475
    /38

    $800,000

    • 2 Beds
    • 1 Bath
    • 1,478 Sq Ft

    25 River Ave, Old Saybrook, CT 06475

    Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants,

    Agent Photo

    Linda O'Hara

    William Raveis Real Estate

    25 River Ave, Old Saybrook, CT 06475
  • 25 Sunset Rd Unit D18, Old Saybrook, CT 06475
    25 Sunset Rd Unit D18, Old Saybrook, CT 06475
    25 Sunset Rd Unit D18, Old Saybrook, CT 06475
    /32

    $789,900

    • 2 Beds
    • 3.5 Baths
    • 1,565 Sq Ft

    25 Sunset Rd Unit D18, Old Saybrook, CT 06475

    Welcome to Oyster River Landing, a hidden shoreline retreat featuring just 20 distinctive townhomes. This peaceful community offers a private marina and a beautiful swimming pool overlooking the Oyster River. Spend quiet mornings on your private patio or embrace the coastal lifestyle with boating, kayaking, and paddleboarding along the river, which opens to Long Island Sound just a short distance

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    25 Sunset Rd Unit D18, Old Saybrook, CT 06475
  • 2 Captains Ln, Old Saybrook, CT 06475
    2 Captains Ln, Old Saybrook, CT 06475
    2 Captains Ln, Old Saybrook, CT 06475
    /40

    $2,899,900

    • 5 Beds
    • 4.5 Baths
    • 5,062 Sq Ft

    2 Captains Ln, Old Saybrook, CT 06475

    Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear

    Bill Heenan William Raveis Real Estate

    2 Captains Ln, Old Saybrook, CT 06475
  • 35 School House Rd, Old Saybrook, CT 06475
    35 School House Rd, Old Saybrook, CT 06475
    35 School House Rd, Old Saybrook, CT 06475
    /40

    $499,999

    • 3 Beds
    • 1 Bath
    • 2,718 Sq Ft

    35 School House Rd, Old Saybrook, CT 06475

    This Bright, freshly Painted, 1951 3 bedroom Ranch is located on Schoolhouse Road in Old Saybrook, Connecticut with quintessential New England charm, public beaches and parks, major access to interstate and state highways, commuter rails and long distance railways, and public transportation a short walk away. The property is situated on a .87 acre level lot, and has a two Car detached, oversized

    Edward Kelley Re/Max Valley Shore

    35 School House Rd, Old Saybrook, CT 06475
  • 61 Springbrook Rd, Old Saybrook, CT 06475
    61 Springbrook Rd, Old Saybrook, CT 06475
    61 Springbrook Rd, Old Saybrook, CT 06475
    /23

    $550,000

    • 3 Beds
    • 3 Baths
    • 1,296 Sq Ft

    61 Springbrook Rd, Old Saybrook, CT 06475

    Great opportunity to move into Old Saybrook! This spacious two level raised ranch offers 1 floor living - ranch style on the second floor with 3 bedrooms and two baths, kitchen and dining and living room with LOTS of closet space and a large deck. On the lower level a finished off family room and office complete with a full bath and a laundry room. A large two car detached garage with a large

    Tina Rupp William Pitt Sotheby's Int'l

    61 Springbrook Rd, Old Saybrook, CT 06475
  • 3 Anchorage Ln, Old Saybrook, CT 06475
    3 Anchorage Ln, Old Saybrook, CT 06475
    3 Anchorage Ln, Old Saybrook, CT 06475
    /40

    $799,900

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft

    3 Anchorage Ln, Old Saybrook, CT 06475

    Welcome to 3 Anchorage Ln, a spacious colonial designed with the flexibility, comfort, and space to grow into for years to come. This 4-bedroom, 3-full-bath home offers 2,496 sqft with a thoughtful layout that works for everyday family life, entertaining, and working from home. The beautifully remodeled kitchen is the heart of the house, opening to the living and dining rooms and creating an

    Arek Wtulich William Raveis Real Estate

    3 Anchorage Ln, Old Saybrook, CT 06475
  • 1405-1445 Boston Post Rd, Old Saybrook, CT 06475
    1405-1445 Boston Post Rd, Old Saybrook, CT 06475
    1405-1445 Boston Post Rd, Old Saybrook, CT 06475
    /13

    $12,000,000

    • Land
    • 20.21 Acres
    • $593,765 per Acre

    1405-1445 Boston Post Rd, Old Saybrook, CT 06475

    Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the

    Casey Fisher Houlihan Lawrence WD

    1405-1445 Boston Post Rd, Old Saybrook, CT 06475
  • 47 Maple Ave, Old Saybrook, CT 06475
    47 Maple Ave, Old Saybrook, CT 06475
    47 Maple Ave, Old Saybrook, CT 06475
    /21

    $549,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    47 Maple Ave, Old Saybrook, CT 06475

    Welcome to 47 Maple Ave., a charming 1958 ranch offering comfortable one-level living in a desirable Old Saybrook location. This three-bedroom, one-and-a-half-bath home features hardwood flooring throughout and a classic, easy-flowing floor plan. A full basement provides plenty of additional storage and possibilities. Step outside to a large deck overlooking the fenced yard-perfect for outdoor

    Maureen OGrady Compass Connecticut, LLC

    47 Maple Ave, Old Saybrook, CT 06475
  • 138 N Cove Rd, Old Saybrook, CT 06475
    138 N Cove Rd, Old Saybrook, CT 06475
    138 N Cove Rd, Old Saybrook, CT 06475
    /40

    $2,200,000

    $601K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,734 Sq Ft

    138 N Cove Rd, Old Saybrook, CT 06475

    A Rare Coastal Opportunity Awaits! Set in the highly sought-after North Cove Historic District of Old Saybrook, this grand colonial offers something truly special: a coveted prime coastal location, spectacular water views, and incredible potential to create the home you've always envisioned. Originally built in 1930 and expanded in 1987, this property has the character, scale, and bones of a

    Marcello Delmonaco Coldwell Banker Realty

    138 N Cove Rd, Old Saybrook, CT 06475
  • 81 Essex Rd, Old Saybrook, CT 06475
    81 Essex Rd, Old Saybrook, CT 06475
    81 Essex Rd, Old Saybrook, CT 06475
    /18

    $1,450,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,570 Sq Ft

    81 Essex Rd, Old Saybrook, CT 06475

    Introducing a rare opportunity to build your dream home in one of Connecticut's most desirable shoreline communities. Located at 81 Essex Road in Old Saybrook, this to-be-built home by Silvin Homes offers the flexibility to choose from multiple thoughtfully designed floor plans and finishes, allowing you to create a home that fits your lifestyle and budget. What truly sets this property apart is

    Rachael Cisz Serhant Connecticut, LLC

    81 Essex Rd, Old Saybrook, CT 06475
  • 9 Old Colony Rd, Old Saybrook, CT 06475
    9 Old Colony Rd, Old Saybrook, CT 06475
    9 Old Colony Rd, Old Saybrook, CT 06475
    /5

    $675,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    9 Old Colony Rd, Old Saybrook, CT 06475

    Rare opportunity to create your dream home in one of Old Saybrook's most sought-after beach communities! Located across from Cornfield Point Beach Association, with deeded beach rights, this .23-acre property includes access to the beautiful sandy beach a short walk away making daily walks to the shoreline effortless. Surrounded by attractive homes, the setting alone makes this a standout

    Joel Lucas Coldwell Banker Realty

    9 Old Colony Rd, Old Saybrook, CT 06475
  • 170 Old Post Rd, Old Saybrook, CT 06475
    170 Old Post Rd, Old Saybrook, CT 06475
    170 Old Post Rd, Old Saybrook, CT 06475
    /38

    $999,000

    $201K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    170 Old Post Rd, Old Saybrook, CT 06475

    Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic

    Rose McWaid William Raveis Real Estate

    170 Old Post Rd, Old Saybrook, CT 06475
  • 21 Fenbrook Rd, Old Saybrook, CT 06475
    21 Fenbrook Rd, Old Saybrook, CT 06475
    21 Fenbrook Rd, Old Saybrook, CT 06475
    /31

    $1,190,000

    $400K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    21 Fenbrook Rd, Old Saybrook, CT 06475

    Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first

    Ralph Harvey ListWithFreedom.com

    21 Fenbrook Rd, Old Saybrook, CT 06475
  • 104 Knollwood Dr, Old Saybrook, CT 06475
    104 Knollwood Dr, Old Saybrook, CT 06475
    104 Knollwood Dr, Old Saybrook, CT 06475
    /39

    $1,445,000

    $255K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    104 Knollwood Dr, Old Saybrook, CT 06475

    True tranquility awaits at this waterfront oasis! Unparalleled water views from every vantage point! Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access- perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm and character with thoughtful updates. Its architectural lines evoke a Normandy chalet vibe, while the

    Karen Lee Coldwell Banker Realty

    104 Knollwood Dr, Old Saybrook, CT 06475
  • 11 Cambridge Ct E, Old Saybrook, CT 06475
    11 Cambridge Ct E, Old Saybrook, CT 06475
    11 Cambridge Ct E, Old Saybrook, CT 06475
    /28

    $1,625,000

    $70K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,178 Sq Ft

    11 Cambridge Ct E, Old Saybrook, CT 06475

    SHORELINE YEAR-ROUND RETREAT - OLD SAYBROOK. Tucked away at the end of a quiet cul-de-sac with sweeping salt marsh and water views, this gracefully updated coastal haven offers exceptional privacy, natural beauty, and resort-style outdoor living in the heart of Old Saybrook. Set on a 1.6-acre lot and filled with natural light, the home features panoramic windows, open living and dining spaces,

    Linda Coyle William Raveis Real Estate

    11 Cambridge Ct E, Old Saybrook, CT 06475
  • 25 Uncas Trail, Old Saybrook, CT 06475
    25 Uncas Trail, Old Saybrook, CT 06475
    25 Uncas Trail, Old Saybrook, CT 06475
    /33

    $750,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    25 Uncas Trail, Old Saybrook, CT 06475

    Welcome to the desirable Indiantown Beach community, where endless possibilities await. This well-loved home offers a spacious floor plan featuring a bright sunroom, generous family room with a floor-to-ceiling gas fireplace and built-ins, and a large primary suite with its full bath and own private deck. Ready for cosmetic updates, this home presents an excellent opportunity to create your dream

    Sharon Linder Berkshire Hathaway NE Prop.

    25 Uncas Trail, Old Saybrook, CT 06475
  • 11 River Edge Rd, Old Saybrook, CT 06475
    11 River Edge Rd, Old Saybrook, CT 06475
    11 River Edge Rd, Old Saybrook, CT 06475
    /40

    $6,600,000

    • 6 Beds
    • 4 Baths
    • 7,169 Sq Ft

    11 River Edge Rd, Old Saybrook, CT 06475

    Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 7,239 square feet, including 1,500 finished square feet on the lower level including an ensuite bedroom and recreational room with French doors opening

    Colette Harron William Pitt Sotheby's Int'l

    11 River Edge Rd, Old Saybrook, CT 06475
  • 46 Fenwood Grove Rd, Old Saybrook, CT 06475
    46 Fenwood Grove Rd, Old Saybrook, CT 06475
    46 Fenwood Grove Rd, Old Saybrook, CT 06475
    /40

    $1,380,000

    • 5 Beds
    • 3 Baths
    • 2,969 Sq Ft

    46 Fenwood Grove Rd, Old Saybrook, CT 06475

    Step through the front door and experience a warm European inspired feel in this distinctive Fenwood Beach Association home. Offering exceptional flexibility and comfortable one-level living, the home features four bedrooms in the original residence, plus an additional bedroom and spacious in-law/primary suite in the addition, ideal for multi-generational living, guests, or a private retreat. The

    Mary Maffuid Berkshire Hathaway NE Prop.

    46 Fenwood Grove Rd, Old Saybrook, CT 06475
  • 43 Quarry St, Old Saybrook, CT 06475
    43 Quarry St, Old Saybrook, CT 06475
    /2

    $285,000

    • 3 Beds
    • 1 Bath
    • 941 Sq Ft

    43 Quarry St, Old Saybrook, CT 06475

    43 Quarry Street, Loved and occupied by the same owner for more than 40 years, this three-bedroom home on Quarry Street presents a rare opportunity in the heart of Old Saybrook. Set on .25 acres on a quiet dead-end street, the real story here is the location. Enjoy an easy walk with sidewalk access into Old Saybrook's vibrant Main Street for coffee, restaurants, shopping, the library, and all the

    Jennifer Gurnell William Raveis Real Estate

    43 Quarry St, Old Saybrook, CT 06475
  • 65 Knollwood Dr, Old Saybrook, CT 06475
    65 Knollwood Dr, Old Saybrook, CT 06475
    65 Knollwood Dr, Old Saybrook, CT 06475
    /32

    $925,000

    $175K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft

    65 Knollwood Dr, Old Saybrook, CT 06475

    The best of both worlds-enjoy the tranquility of a peaceful setting while being just a short stroll to the beach. Beautifully updated and impeccably maintained, this year-round home offers the perfect blend of coastal charm and modern comfort. A welcoming front porch invites you inside where you'll find beautifully renovated kitchen and baths as well as quality finishes throughout. You'll love

    Martha Quaratella Coldwell Banker Realty

    65 Knollwood Dr, Old Saybrook, CT 06475
  • 26 Willard Ave, Old Saybrook, CT 06475
    26 Willard Ave, Old Saybrook, CT 06475
    26 Willard Ave, Old Saybrook, CT 06475
    /40

    $1,100,000

    $195K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,904 Sq Ft

    26 Willard Ave, Old Saybrook, CT 06475

    Welcome to shoreline living at its finest in one of Old Saybrook's desirable beach communities, just minutes from the water, marinas, beaches, restaurants, and all that the Connecticut shoreline has to offer. This beautifully remodeled split-level ranch combines modern updates, flexible living space, and an exceptional outdoor setting. Step inside to an inviting open-concept floor plan filled

    Gigi Giordano Taylor Compass Connecticut, LLC

    26 Willard Ave, Old Saybrook, CT 06475
  • 13 College St, Old Saybrook, CT 06475
    13 College St, Old Saybrook, CT 06475
    13 College St, Old Saybrook, CT 06475
    /3

    $1,490,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,070 Sq Ft

    13 College St, Old Saybrook, CT 06475

    13 College Street | Old Saybrook, CT TO BE BUILT Discover the opportunity to build your dream home in one of Old Saybrook's most desirable locations-Saybrook Point. Thoughtfully designed with luxury, comfort, and flexibility in mind, this exceptional new construction home offers approximately 2,070 square feet, four bedrooms, two and one-half baths, and the ability to personalize finishes to suit

    Lisa Fekete William Raveis Real Estate

    13 College St, Old Saybrook, CT 06475
  • 46 Farview Ave, Old Saybrook, CT 06475
    46 Farview Ave, Old Saybrook, CT 06475
    46 Farview Ave, Old Saybrook, CT 06475
    /35

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,552 Sq Ft

    46 Farview Ave, Old Saybrook, CT 06475

    Location, location, location. Enjoy shoreline lifestyle in one of Old Saybrook's in demand neighborhoods. Level corner lot. Solid home ready for you to make it your own. Eight total room, three bedrooms, two full baths one updated. Fireplace in the Living room. Sunroom, one car attached garage. Full unfinished basement. Incredible opportunity to create the home of your dreams. Enjoy coastal

    Sheila Burke J.M. REALTY

    46 Farview 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

    $1,029,000

    $134K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,109 Sq Ft

    96 Ayers Point Rd, Old Saybrook, CT 06475

    Experience a rare combination of privacy, panoramic marsh and Connecticut River views, and resort-style living at 96 Ayers Point Road in Old Saybrook, with no flood insurance required. This exceptional 4/5-bedroom coastal home features an in-ground gunite pool, expansive wraparound deck, walls of glass, multiple fireplaces, and a flexible floor plan with the option for a main-level or

    Jennifer Gurnell William Raveis Real Estate

    96 Ayers Point Rd, 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
    /38

    $5,900,000

    • 4 Beds
    • 4 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
  • 101-A Sequassen Ave, Old Saybrook, CT 06475
    101-A Sequassen Ave, Old Saybrook, CT 06475
    101-A Sequassen Ave, Old Saybrook, CT 06475
    /9

    $1,750,000

    • Land
    • 20,037 Sq Ft
    • $3,804,348 per Acre

    101-A Sequassen Ave, Old Saybrook, CT 06475

    APPROVED OCEANFRONT LOT - WALK TO THE BEACH FROM YOUR BACKYARD Design the life you've always envisioned. Whether you dream of a timeless shingle-style coastal retreat or a striking modern waterfront masterpiece, this exceptional homesite offers the perfect canvas to bring your vision to life. This fully approved, level building lot is ready for construction, allowing you to move forward with

    Fationa Meco Houlihan Lawrence WD

    101-A Sequassen Ave, Old Saybrook, CT 06475
  • 5 Sand Creek Dr, Old Saybrook, CT 06475
    5 Sand Creek Dr, Old Saybrook, CT 06475
    5 Sand Creek Dr, Old Saybrook, CT 06475
    /40

    $1,249,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 3,684 Sq Ft

    5 Sand Creek Dr, Old Saybrook, CT 06475

    Welcome to 5 Sand Creek Drive, a truly unique coastal contemporary in Old Saybrook, beautifully positioned to capture stunning marsh and water views. Filled with natural light and designed around its exceptional setting, this distinctive home offers an open floor plan, brand-new windows throughout, and wonderful spaces for both everyday living and entertaining. The dramatic living room is a

    Gigi Giordano Taylor Compass Connecticut, LLC

    5 Sand Creek Dr, Old Saybrook, CT 06475
  • 5 Tudor Ct E, Old Saybrook, CT 06475
    5 Tudor Ct E, Old Saybrook, CT 06475
    5 Tudor Ct E, Old Saybrook, CT 06475
    /40

    $795,000

    • 3 Beds
    • 1 Bath
    • 2,002 Sq Ft

    5 Tudor Ct E, Old Saybrook, CT 06475

    Spectacular South Cove views, deeded beach rights and remarkably low taxes make this nicely updated shoreline home an exceptional opportunity! Set on a beautiful half-acre lot, this spacious split-level offers 3-4 bedrooms, a versatile floor plan and wonderful water views that bring the coastal setting right into your everyday life. Inside you'll find hardwood floors, double oven, a fireplace for

    Joel Lucas Coldwell Banker Realty

    5 Tudor Ct E, 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

    $1,025,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft

    37 Woodland Dr, Old Saybrook, CT 06475

    Experience coastal luxury in this stunning 3-bedroom, 2-bathroom ranch style home nestled in Knollwood Beach. Set on a rare .33 acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring an expansive remodeled white kitchen with quartz counters, large center island. The family room boasts a dramatic fireplace, while a sunlit dining

    Joel Lucas Coldwell Banker Realty

    37 Woodland Dr, Old Saybrook, CT 06475
  • 119 Great Hammock Rd, Old Saybrook, CT 06475
    119 Great Hammock Rd, Old Saybrook, CT 06475
    119 Great Hammock Rd, Old Saybrook, CT 06475
    /38

    $799,999

    $99K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    119 Great Hammock Rd, Old Saybrook, CT 06475

    Every Day a Getaway! Some properties ask you to choose between full-time living & vacation living. Not this one. Set in the heart of Old Saybrook, this fully furnished 7-room Cape Cod delivers the ease of a residence with the spirit of a seasonal retreat - and comes with a private guest house. The main home offers 3 bdrms,, 2 baths & includes a coveted 1st fl bdrm for single-level living. A large

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

    119 Great Hammock Rd, Old Saybrook, CT 06475
  • 256 Hidden Cove Rd, Old Saybrook, CT 06475
    256 Hidden Cove Rd, Old Saybrook, CT 06475
    256 Hidden Cove Rd, Old Saybrook, CT 06475
    /30

    $510,000

    $19K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,557 Sq Ft

    256 Hidden Cove Rd, Old Saybrook, CT 06475

    Discover effortless shoreline living at Summerwood in Old Saybrook. This beautifully maintained 2-bedroom, 1.5-bath condominium offers 1,557 SqFt of light-filled living space with tranquil marsh views and an upper-level loft perfect for a home office, guest space, or reading retreat. The updated kitchen features granite countertops, stainless steel appliances, and a center island, while hardwood

    Carla Mousch William Raveis Real Estate

    256 Hidden Cove 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
    /33

    $649,900

    • 3 Beds
    • 1 Bath
    • 968 Sq Ft

    96 Chalker Beach Rd, Old Saybrook, CT 06475

    Welcome to your seasonal sanctuary at Chalker Beach, where sun-soaked days and starry nights create lasting memories. Offered fully furnished and thoughtfully styled with relaxed coastal charm, this seasonal cottage is the perfect place to slow down, unwind, and enjoy easy shoreline living. Just a short walk or golf cart ride to the beach, the home is tucked into one of the shoreline's most loved

    Danielle Spada Coldwell Banker Realty

    96 Chalker Beach Rd, Old Saybrook, CT 06475
  • 0 Middlesex Turnpike, Old Saybrook, CT 06475
    0 Middlesex Turnpike, Old Saybrook, CT 06475
    0 Middlesex Turnpike, Old Saybrook, CT 06475
    /7

    $495,000

    • Land
    • 32.66 Acres
    • $15,156 per Acre

    0 Middlesex Turnpike, Old Saybrook, CT 06475

    32.66 ac at a prime intersection in Old Saybrook right off I-95. W/ Plans for various layouts of multiple building to totaling as much as 50,000 sqft +/-. B4 Zone offers a wide variety of uses. A large portion of this parcel is wetlands.

    Craig Milton Re/Max Valley Shore

    0 Middlesex Turnpike, Old Saybrook, CT 06475
  • 100 Dudley Ave Unit F30, Old Saybrook, CT 06475
    100 Dudley Ave Unit F30, Old Saybrook, CT 06475
    100 Dudley Ave Unit F30, Old Saybrook, CT 06475
    /40

    $779,000

    $18K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,565 Sq Ft

    100 Dudley Ave Unit F30, Old Saybrook, CT 06475

    Spectacular North Cove unobstructed water views and downtown village living come together in this beautifully renovated townhouse-style condo, offering an exceptional opportunity for shoreline buyers seeking a turn-key home under $1 million. Enjoy captivating water views and wildlife from the open kitchen, dining and living areas, with a stylish renovated kitchen featuring a breakfast bar and

    Joel Lucas Coldwell Banker Realty

    100 Dudley Ave Unit F30, Old Saybrook, CT 06475
  • 1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    /6

    $695,000

    $300K PRICE DROP
    • Land
    • 1.16 Acres
    • $599,138 per Acre

    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475

    1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900.

    Maxwell Lyman Lyman Real Estate

    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
  • 24 W Shore Dr, Old Saybrook, CT 06475
    24 W Shore Dr, Old Saybrook, CT 06475
    24 W Shore Dr, Old Saybrook, CT 06475
    /40

    $1,225,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 884 Sq Ft

    24 W Shore Dr, Old Saybrook, CT 06475

    Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield Point, one of Connecticut's most desirable beach communities. Ideally located just steps from the beach. This move-in-ready home offers the perfect combination of comfort, coastal living, and breathtaking water views. The home features 3 bedrooms and 1 full bath, along with a

    David Rodriguez William Pitt Sotheby's Int'l

    24 W Shore Dr, Old Saybrook, CT 06475
  • 18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    /40

    $899,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,569 Sq Ft

    18 Old South Cove Rd, Old Saybrook, CT 06475

    Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the

    Steven Koleno Beycome of Connecticut

    18 Old South Cove Rd, Old Saybrook, CT 06475
  • 81 Hartford Ave, Old Saybrook, CT 06475
    81 Hartford Ave, Old Saybrook, CT 06475
    81 Hartford Ave, Old Saybrook, CT 06475
    /40

    $1,995,000

    $300K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,440 Sq Ft

    81 Hartford Ave, Old Saybrook, CT 06475

    Experience the pinnacle of Connecticut shoreline living in this exquisitely remodeled coastal retreat, ideally located just three homes from the private association beach in the Saybrook Manor Beach community. Blending timeless coastal elegance with today's most desirable amenities, this exceptional four-bedroom, two-bath home provides the perfect balance of luxury, comfort, and effortless

    Gigi Giordano Taylor Compass Connecticut, LLC

    81 Hartford Ave, Old Saybrook, CT 06475
Connecticut Middlesex County

Real Estate & Homes 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

Old Saybrook, CT Home Prices

Old Saybrook, CT
Median Home Price
$779,950
Median Sale Price
$723,750
+3% YoY
Avg. Price per Square Foot
$536
Median Single Family Price
$799,949
Median Townhouse Price
$717,500
Median Condo Price
$637,500
Total Active Listings
40 listings
Market Conditions
3 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Old Saybrook, CT?
Homes for sale in Old Saybrook, CT have an average home price of $1,013,111.
How many homes have sold over the last 12 months in Old Saybrook, CT?
156 homes have sold in Old Saybrook, CT over the last 12 months.
What is the average household income in Old Saybrook, CT?
The average household income in Old Saybrook, CT is $136K.
What are the most popular zip codes in Old Saybrook, CT?
The most popular zip codes in Old Saybrook, CT include 06475, 06498, 06371, 06426 and 06442.
How much do you need to make to afford a house in Old Saybrook?
The median home price in Old Saybrook is $779,950. If you put a 20% down payment of $156,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $4,130 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $177K a year to afford the median home price in Old Saybrook. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Old Saybrook is $136K.
How are the schools in Old Saybrook, CT?
Old Saybrook, CT has highly rated public and private schools. Some of the best schools in Old Saybrook based on Niche Grades are Oxford Academy, Lyme-Old Lyme Middle School and Lyme-Old Lyme High School. Browse all the schools in Old Saybrook, CT to learn more.
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