Old Saybrook Homes for Sale

Welcome to Old Saybrook, Connecticut, a charming coastal town nestled in the heart of Middlesex County. With its rich history, picturesque landscapes, and vibrant community, Old Saybrook is a hidden gem that offers a perfect blend of small-town charm and modern amenities.

Known for its stunning waterfront views along the Connecticut River and Long Island Sound, Old Saybrook boasts a unique coastal lifestyle that attracts both families and retirees alike. Enjoy leisurely strolls along the scenic beaches, explore the quaint shops and boutiques in the historic downtown area, or savor fresh seafood at one of the local restaurants. The town is also home to several parks and nature preserves, providing ample opportunities for outdoor enthusiasts to hike, bike, and birdwatch.

For those looking to call Old Saybrook home, the real estate market offers an array of options to suit every taste and budget. From charming colonial-style homes to contemporary waterfront properties, you’ll find a diverse selection of homes for sale that cater to your unique lifestyle. Many of these residences feature spacious yards, modern amenities, and stunning views, allowing you to fully embrace the coastal living experience.

With its top-rated schools, friendly community, and easy access to nearby cities like New Haven and Hartford, Old Saybrook is an ideal place to settle down. Whether you’re searching for a year-round residence or a vacation retreat, Old Saybrook welcomes you with open arms and endless possibilities. Discover your dream home in this idyllic coastal town today!

Newest Old Saybrook Homes for Sale

$549,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24206696 MLS

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 dining, entertaining, gardening or simply relaxing. Best of all, enjoy the convenience of being within walking distance to town, with Old Saybrook's shops, restaurants, cafes and local amenities close by. A wonderful opportunity to enjoy shoreline living with the charm, convenience and potential of a classic New England ranch.

47 Maple Ave, Old Saybrook

$799,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205326 MLS

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 inviting space for gatherings. The first floor offers a versatile den/family room, dedicated office space, full bath, and laundry room, providing plenty of options as your needs evolve. The office could easily serve as a first-floor bedroom, with the convenience of a full bathroom nearby. Upstairs, the spacious primary suite offers a private retreat with an en-suite bath and three closets, along with three additional bedrooms and another full bath. Major updates include a new oil boiler and water heater in 2024, oil tank in 2025, 200-amp electrical service, and central air. A 2-car garage and unfinished basement provide abundant storage. Enjoy the added benefit of deeded 10-foot access for convenient passenger loading and unloading, along with the opportunity to launch and enjoy kayaks. Set on a 0.25-acre lot, the home is close to Saybrook Point, marinas, waterfront dining, Harvey's Beach, Main Street shops, and all that makes Old Saybrook such a wonderful place to call home. A home with room to grow, spaces that adapt with you, and coastal amenities right nearby.

3 Anchorage Ln, Old Saybrook

$1,380,000

5 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24205169 MLS

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 gourmet kitchen is the heart of the home, featuring granite countertops, custom cabinetry, a Viking refrigerator, Bertazzoni ovens and cooktop, and Vitev alkaline filtration system. A large eat-in area accommodates a long dining table, while the nearby laundry room adds everyday convenience. A wood-burning stove brings warmth and charm to the kitchen area. Just off the kitchen, the inviting family room flows into a bright three-season/Florida room, extending the living and entertaining space. The spacious in-law/primary suite offers privacy with a large living room, full kitchen with pocket doors, private bedroom and bath, and fireplace. Outside, enjoy a beautiful backyard with patio, large storage shed, and outdoor hot-water shower-perfect after a day at the beach. An oversized two-car garage and two separate attics provide excellent storage. Located in the desirable Fenwood private beach association, this home offers a relaxed coastal lifestyle with private beach access, character, flexibility, and exceptional one-level living.

46 Fenwood Grove Rd, Old Saybrook

$699,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24202240 MLS

Spacious ranch with an impressive second-story primary suite, set in Old Saybrook's desirable Saybrook Point area and close to some of the town's best-loved destinations. Stroll to Main Street for restaurants, boutique shopping and a show at The Kate, or head toward Saybrook Point and the nearby marinas. The town beach is just minutes away. Inside, hardwood floors and abundant natural light welcome you into the main living area, where a pellet stove creates a warm focal point. The kitchen and dining area flow easily into the living room, while a first-floor office with sliders to the patio provides flexible space for working from home, a den or exercise. Two bedrooms and a full bath complete the main level. Upstairs, the spacious private primary suite features 9+ foot ceilings, a walk-in closet, laundry hookup and space for a full en-suite bath. The double vanity and toilet are already installed, with the shower roughed in and ready for the next owner to complete. Outside, enjoy a level .29-acre lot enclosed by 6-foot vinyl fencing, along with a large Klotter Farms shed for additional storage. The oversized 29' x 24' attached garage is another standout, offering exceptional room for vehicles, a golf cart, workshop, lawn equipment and storage. Enjoy central air, public water, 200-amps and a septic system installed in 2023. This is a fantastic opportunity to enjoy the OS lifestyle with Main Street, Saybrook Point, marinas, beaches, dining, and shopping all nearby.

6 Willard St, Old Saybrook

$550,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204068 MLS

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 loft above would be great for a home office, gym or studio. Come take a look and jump on this opportunity! Professional photos coming soon!

61 Springbrook Rd, Old Saybrook

$899,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190267 MLS

Live every day like you're on vacation in sought-after Knollwood Beach! Lovingly enjoyed by the same family for nearly 50 years, this attractive four-bedroom, one-and-a-half-bath home offers a wonderful opportunity to become part of one of Old Saybrook's most desirable beach communities. Inside, the comfortable floor plan features a welcoming living room with built-in bookcases, and a cozy fireplace that add warmth and character. Sunlight pours into the adjoining sunroom, offering a peaceful retreat overlooking the outdoors. The inviting kitchen is filled with natural light and has been meticulously maintained, featuring warm wood cabinetry, stainless steel appliances, and Corian countertops. A welcoming breakfast nook at one end provides a comfortable spot for morning coffee or casual meals, while the adjoining first-floor laundry room adds everyday convenience and valuable storage. Just off the kitchen, the sun-filled dining room offers a comfortable setting for entertaining and gathering. Updates include a newer roof and heated bathroom floor, irrigation system and vinyl siding. Wood floors lie beneath much of the existing carpeting-ready to be revealed. A brick driveway and walkway wind toward the side entrance, setting a welcoming tone from the moment you arrive. The detached one-car garage and shed adds valuable storage for bikes, beach chairs, umbrellas, and all the essentials for a day by the water. No flood insurance.

30 Neptune Dr, Old Saybrook

$795,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24204260 MLS

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 cozy evenings and air conditioning for summer comfort. The flexible layout provides plenty of room for family and guests, a home office or additional living space. A 2-car garage offers excellent parking and storage, while major improvements including a newer roof , heating system and septic system add peace of mind. Enjoy the generous half-acre setting and beautiful views of South Cove, or take advantage of your deeded beach access and embrace the shoreline lifestyle. Whether you're looking for a year-round residence, weekend escape or summer retreat, this property offers the hard-to-find combination of water views, beach rights, an updated home, 2-car garage and sizable lot. With annual property taxes just under $5,000, this is an outstanding value for coastal living!

5 Tudor Ct E, Old Saybrook

$1,550,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24203677 MLS

Contemporary coastal elegance meets remarkable privacy along South Cove in Old Saybrook. Set well back from the road on 1.8 acres, this distinctive 3,188-square-foot cedar-sided residence captures sweeping water views from nearly every room. Originally built in 1965 and completely rebuilt in 1991, the home was thoughtfully designed to embrace its spectacular setting, with vaulted ceilings, expansive windows, and seamless connections to the outdoors. The living room features custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a vaulted family room and opens to a 300-square-foot enclosed porch-an inviting space for entertaining or relaxing. The main-level primary suite is a private retreat with vaulted ceilings, deck access, water views, dual bathrooms, and an impressive 120-square-foot walk-in closet. A formal dining room, additional bedroom, and separate laundry room complete the first floor. Upstairs, two bedrooms share a Jack-and-Jill bath. With 1.8 private acres and 278 feet of frontage along South Cove, this property offers a rare blend of waterfront, space, and seclusion. Whether enjoyed as a year-round residence or treasured coastal retreat, this is a setting that simply cannot be replicated.

108 Maple Ave, Old Saybrook

$499,999

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24202909 MLS

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 garage with a lean two shed. The basement includes a workshop area and porcelain wash sink, plenty of storage to boot. Please schedule your appointment today using Showtime!

35 School House Rd, Old Saybrook

$2,200,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24199659 MLS

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 remarkable coastal residence-but today, it's ready for a new vision. With water views from nearly every room, spacious living areas, French doors leading out to a large deck, beautiful bay windows, a brick fireplace, a first-floor primary suite, four bedrooms, three and a half baths, a two-car garage with loft space, and an exceptional setting-there is truly so much to work with. The existing layout provides a strong foundation for someone looking to renovate, reimagine, and create a truly spectacular coastal retreat in one of Connecticut shoreline's most desirable neighborhoods. Located within walking distance of local restaurants, shops, beaches, and everything else that Main Street has to offer. Property being sold in "as is".

138 N Cove Rd, Old Saybrook

$770,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24200281 MLS

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 many projects currently underway surrounding this home-a proven location for substantial improvements and new construction. Recent upgrades include a new 200-AMP electrical panel, central A/C, and forced-air heat and vinyl siding. Downstairs is made for entertaining in the family room, featuring a newer wood stove, a '70s show bar with a sink, an office/mudroom from the garage, a workshop, laundry, and a half bath. The wide lot (97 feet of frontage) features a circular driveway leading to the one-car garage. Step onto the rear deck for marsh views and a spacious backyard with room for a fire pit and outdoor gatherings. Enjoy the association beach, pier and walkway, clubhouse, tennis/pickleball courts, basketball and baseball fields, and playground. Use it today while enjoying the tremendous fun this Old Saybrook location has to offer. There is plenty of upside for grand expansion tomorrow or simply making more fond memories every day.

71 Knollwood Dr, Old Saybrook

$285,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24199926 MLS

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 conveniences of town. Beaches, marinas, the Connecticut River, and Old Saybrook train station are just minutes away. The property is being sold strictly AS IS and requires extensive renovation, offering an opportunity for a builder or investor to reimagine the existing home or explore the potential for a new vision for the property, subject to town approvals. For those looking for an in-town Old Saybrook property, renovation project, investment opportunity, or potential building site, this is a location worth a closer look. Bring your ideas and vision to a property that has been held for decades in one of Old Saybrook's wonderfully convenient and walkable locations. Cash, proof of funds required.

43 Quarry St, Old Saybrook

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