Old Saybrook Real Estate

Welcome to Old Saybrook, a picturesque town nestled in Middlesex County, Connecticut. Known for its historic charm and stunning waterfront views, Old Saybrook offers residents a unique blend of small-town atmosphere and modern amenities.

Located along the scenic Connecticut shoreline, Old Saybrook boasts a rich history dating back to the 1600s when it was first settled. Today, the town is a vibrant community with a thriving downtown area featuring boutique shops, cozy cafes, and delicious restaurants serving up fresh seafood caught locally.

Outdoor enthusiasts will appreciate the abundance of recreational activities available in Old Saybrook. From boating and fishing on the Connecticut River to relaxing on the sandy beaches of Long Island Sound, there is no shortage of ways to enjoy the natural beauty of the area.

Old Saybrook is also home to a variety of cultural attractions, including the Katharine Hepburn Cultural Arts Center, named in honor of the legendary actress who called the town home. Residents can enjoy live performances, art exhibits, and film screenings at this beloved venue.

With its convenient location just a short drive from major cities like New Haven and Hartford, Old Saybrook offers the perfect balance of tranquility and accessibility. Whether you're looking for a peaceful retreat or a place to call home, Old Saybrook has something for everyone. Come discover the beauty and charm of this historic New England town.

Newest Listings in Old Saybrook

$1,500,000

1 Baths ⋅ 24194226 MLS

Unique mixed-use investment and redevelopment opportunity. The ground-floor commercial spaces are fully occupied, providing immediate rental income, while the upper level offers approximately 3,540 square feet of office space. The expansive second floor may also offer the potential to be converted into two oversized three- or four-bedroom residential units, subject to zoning and municipal approvals. This property combines stable existing occupancy with significant value-add potential in a desirable shoreline location.

880 Boston Post Rd, Old Saybrook

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 24192820 MLS

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 12-over-12 windows. It has been lovingly maintained for decades by a master craftsman and a devoted gardener, with a deep respect for historic properties. Granite steps lead to the entries and there is a brick patio overlooking the grounds. There is an adorable guest cottage which offers wonderful flexibility for visitors, or as an in-law suite or private studio. The beautiful barn/carriage house holds two cars plus a unique blacksmith workshop. The picturesque grounds feature several gardens for seasonal color, mature shade trees, and a fenced vegetable garden area with a charming hand-built garden shed with running water. With its strong history and distinctive architecture, the home is listed on the National Registry of Historic Places. Rarely does a home of this significance become available - offering the perfect balance of history, craftsmanship, natural beauty, and timeless New England charm in a coastal community. The location is also ideal, close to Main St attractions, shopping, restaurants, beaches, and the train station It is almost equal distance to Boston and New York.

170 Old Post Rd, Old Saybrook

$575,000

3 Beds ⋅ 2 Baths ⋅ 24192318 MLS

This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endless potential, this well-maintained home features one bedroom and a full bath on the main level and 3 additional bedrooms upstairs. An inviting open floor plan where the kitchen flows seamlessly into the dining area and family room. The kitchen has granite counter tops, island and double ovens. A cozy living room with a classic fireplace creating the perfect gathering space. Hardwood floors throughout, while the sunroom provides a bright retreat for reading or relaxing. The fully finished basement offers flexible living space ideal for a family room, home office, gym, or playroom. A spacious private yard includes a shed and outdoor shower set on a corner lot is perfect for outdoor barbecues or Summer evenings. Generator ready. Move right in and enjoy its charm while adding your own personal touches over time. Ideally located just minutes from Old Saybrook's vibrant Main Street, boutique shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living! Come make this home your own!

2 Half Penny Ln, Old Saybrook

$675,000

3 Beds ⋅ 2 Baths ⋅ 24193791 MLS

Located in the highly sought-after shoreline town of Old Saybrook, this charming Cape offers character, comfort, and exceptional curb appeal. Set on 1.14 beautiful acres in the desirable Otter Cove neighborhood, this well-maintained three-bedroom, two-bath home is ready for its next owners. The updated kitchen features heated tiled floors, while the main level offers a spacious bedroom with a cedar-lined closet, convenient first-floor laundry, a bright den/library with a bay window, a welcoming living room with a stone propane fireplace, and a separate dining room. Upstairs you'll find two generously sized bedrooms, each with cozy dormer sitting areas, plus a walk-in attic for additional storage. A full basement, detached two-car garage, two storage sheds and abundant space for hobbies, storage, or a workshop. Lovingly cared for over the years, this special property is ready for you to make it your own.

84 Ayers Point Rd, Old Saybrook

$585,000

4 Beds ⋅ 2 Baths ⋅ 24193207 MLS

A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwood floors, and central air conditioning. Step inside to a welcoming living room featuring a classic wood-burning fireplace and oversized windows that fill the space with natural light while overlooking the beautifully landscaped front gardens. The eat-in kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive dining room-an ideal layout for holiday gatherings, dinner parties, and everyday entertaining. One of the home's standout features is the 280-square-foot, four-season sunporch, offering beautiful views of the private backyard and providing the perfect space to relax year-round. It is important to note the this sq. footage is not included in the Tax Record totals for the home. Situated on a picturesque 1.1-acre lot, this property also includes a partially finished basement with plenty of room for storage as well as an attached two-car garage. The home is freshly painted throughout with newly refinished hardwood floors, offering a bright, move-in-ready interior while providing the perfect canvas to make it your own. Offering space, quality, and exceptional care in a sought-after setting, this is a home you'll be proud to call your own.

207 School House Rd, Old Saybrook

$1,200,000

1 Baths ⋅ 24193657 MLS

90 foot conveyer belt tunnel system Large leeching field/water recycling tanks Prime shoreline retail corridor location (along US-1) Near major shopping destinations including big-box anchors and regional retail plazas Abutting & visible from I-95, 660 feet from ramp Traffic Count: 15,900 +/- ADT

277 Boston Post Rd, Old Saybrook

$399,500

1 Baths ⋅ 24193626 MLS

1,590 SF 0.47 Acre (1) Garage Clear Height Outdoor storage area for vehicles/equipment Recently renovated interior Located right off Route 1 0.6 mile/2 min drive to I-95 ramp

9-19 King St, Old Saybrook

$699,000

2 Beds ⋅ 2 Baths ⋅ 24191828 MLS ⋅ Chatham BLDG.

This sun-drenched ranch unit at Chatham balances modern style with unmatched convenience, situated moments from the vibrant shops and dining on Main Street. The beautifully updated, open-concept floor plan features soaring vaulted ceilings, gleaming hardwoods, and a natural gas fireplace with custom built-ins. Retreat to one of two private bedroom suites, or step outside from the main living area onto your expansive, privately-sited deck. Complete with an attached garage, pristine modern bathrooms, main-level laundry, and a massive, dry unfinished basement for seamless storage, this home delivers the freedom of condo living without sacrificing space. Embrace a relaxed lifestyle in one of the most dynamic and sought-after towns on the Connecticut Shoreline.

11 Coulter St Unit 7, Old Saybrook

$799,900

2 Beds ⋅ 2 Baths ⋅ 24189175 MLS

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 beach retreat in one of Old Saybrook's most sought-after shoreline neighborhoods. Enjoy outdoor living with a spacious deck, large patio, fenced yard and storage shed-perfect for entertaining, gardening, or relaxing after a day at the beach. As a resident of Indiantown Beach, you'll enjoy access to two private beaches, a marina, clubhouse, playground, and a variety of community events throughout the year. Conveniently located just minutes from Old Saybrook's Main Street, restaurants, shopping, marinas, and local amenities, this property offers the rare opportunity to personalize a home in an exceptional coastal location. Bring your vision and make this beach house your own!

25 Uncas Trl, Old Saybrook

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 24191006 MLS

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 the four-season sunroom, with French doors and a wall of windows offering marsh views and spectacular sunsets year-round. Some recent updates include a newly added one-car garage, windows, siding, roof, rear deck, electrical panel, A/C, and sprinkler system. A deck off the living room and sunroom provides the perfect place to relax, entertain, or simply enjoy the peaceful surroundings. The full walkout lower level offers flexibility with an additional bedroom, family room, full bath and separate laundry room. Easy access to Beamon's Creek where you can launch a kayak and explore South Cove. The Knollwood Beach Association includes a private beach, clubhouse, tennis/pickleball, basketball court, a playground and the charm of a golf cart-friendly community. Low-maintenance and truly move-in ready, this exceptional shoreline home offers a lifestyle that's hard to beat.

65 Knollwood Dr, Old Saybrook

$775,000

4 Beds ⋅ 2 Baths ⋅ 24190439 MLS

Welcome to 14 Seagull Road, where the best of Connecticut shoreline living begins just outside your front door. Tucked within the sought-after Knollwood Beach community, this updated cape is just a 3-minute walk to the ocean. Enjoy waterfront strolls, kayaking, swimming, pickleball at the clubhouse, and spectacular sunsets over Long Island Sound. Knollwood Beach is more than a neighborhood... it's a lifestyle. With four-season beach access, scenic shoreline walks, and a welcoming community, every season offers a new reason to enjoy life by the water. From the street, this charming cape feels warm and inviting. Inside, discover a home that lives larger than it appears, featuring an open floor plan, gas fireplace, enclosed porch, and spaces that invite you to slow down, hang your hat, and feel at home. Offering four bedrooms and two full baths, with two bedrooms and a full bath on the main level, the flexible layout suits guests, a home office, or everyday living. A spacious laundry room and low-maintenance, shaded backyard complete the home. Recent updates include a new septic system, central air, Vaughn hot water heater, refinished hardwood floors, added upstairs hardwood, fresh paint, updated lighting, upstairs bath updates, newer kitchen appliances, rebuilt screened porch roof, and a bluestone walkway. Not in a flood zone. Strong rental history. Ideal as a year-round home, weekend retreat, or investment.

14 Seagull Rd, Old Saybrook

$1,950,000

3 Beds ⋅ 3 Baths ⋅ 24183797 MLS

Welcome to a coastal sanctuary where changing, panoramic views of the Long Island Sound greet you from almost every room. Situated directly across from the shore with no homes across the street to block your view, this remarkable year-round residence offers a permanent, front-row seat to the water. Enjoy all the benefits of an unobstructed marine horizon and instant beach access, completely free from the requirement of flood insurance. Inside, an incredible open floor plan boasts generous, light-filled spaces throughout. The seamless living and dining area is warmed by a cozy propane fireplace and flows effortlessly into a fully heated and cooled front porch-the ultimate sun-soaked perch for watching the waves. Brand-new windows throughout perfectly frame the water vistas, leading you to the heart of the home: a delightful eat-in kitchen just steps from a oversized side deck designed for effortless indoor-outdoor entertaining and more views. Upstairs, beautiful historic fir floors sweep through the three spacious bedrooms, including a primary suite that serves as a private oasis, hosting its own unique, glassed-bookcase sitting room overlooking the Sound. Two full baths complete the second level. Every coastal convenience has been thoughtfully considered, including an attached two-car garage, a partial basement for mechanicals, a built-in sprinkler system, a storage shed equipped with electricity, and an outdoor hot/cold shower for rinsing off after a day in the sand....

420 Maple Ave, Old Saybrook

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