Old Saybrook Real Estate

Welcome to Old Saybrook, Connecticut—a charming coastal town where history meets natural beauty. Nestled in Middlesex County, Old Saybrook is not just a place to live; it's a lifestyle steeped in rich maritime heritage and vibrant community spirit. With its picturesque views of the Long Island Sound and the Connecticut River, this town offers a serene backdrop for both relaxation and adventure.

Old Saybrook is renowned for its stunning beaches, including the popular Harvey's Beach, where families gather for sun-soaked days and breathtaking sunsets. The town’s historic district is a treasure trove of colonial architecture, featuring beautifully preserved homes and landmarks that tell the story of its founding in 1635. Stroll through the quaint streets lined with boutique shops, art galleries, and delightful eateries, each offering a taste of local flavor.

For those who appreciate the arts, Old Saybrook is home to the renowned Katharine Hepburn Cultural Arts Center, which hosts a variety of performances and events throughout the year. The town also boasts numerous parks and recreational areas, perfect for hiking, biking, and enjoying the great outdoors.

Education is a priority in Old Saybrook, with highly-rated schools that foster a nurturing environment for students. Whether you're looking for a peaceful retreat or a vibrant community to call home, Old Saybrook offers a unique blend of tranquility and charm. Discover your place in this lovely coastal gem, where every day feels like a vacation!

Newest Listings in Old Saybrook

$1,750,000

ACTIVE Status ⋅ 24195477 MLS

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 confidence and begin creating the coastal home you've always imagined. Enjoy the rare opportunity to step from your backyard and take a short walk to the beach, embracing the very best of shoreline living. As a resident of the Borough, you'll enjoy exclusive access to exceptional amenities, including a beautifully maintained historic nine-hole golf course, private Borough tennis courts, and a charming coastal community known for its timeless New England character. Whether you're seeking a year-round residence or the ultimate seaside retreat, this is a rare opportunity to build in one of Connecticut's most desirable waterfront communities. Come walk the property and experience its exceptional setting and endless potential for coastal living.

101-A Sequassen Ave, Old Saybrook

$1,500,000

1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ COMING SOON Status ⋅ 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

$675,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$899,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189317 MLS

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 eat-in kitchen flows into an adjacent family room, while a formal living room provides a more refined space for entertaining. The recently added sunroom is the standout: bright, expansive, and framed by multiple sliders & abundant windows that draw the outdoors in. Upstairs, the primary BR is a retreat unto itself - generously sized, with ample closets, a sitting area, and direct access to a personal balcony. Morning coffee or an evening glass of wine feels different from up here. Guests get a private 500-sq. ft guest house with a kitchenette, full bath, & living room. A spiral staircase leads to a large bdrm loft with its own small balcony. The location does the rest of the work. O S's Main St.- with its restaurants & shops - is close by, Fenwick Golf Course is minutes away for golfers. Harvey's Beach sits just 0.4 miles away, with OS's town beach just 0.2 miles beyond. For commuters, I-95 and Route 9 are both nearby, and Amtrak puts Boston and New York City within 2.5 hours. A home, a vacation, and a place for the people you love to visit - all in one address.

119 Great Hammock Rd, Old Saybrook

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.