Old Saybrook Homes for Sale

Welcome to Old Saybrook, Connecticut—a charming coastal town nestled in Middlesex County that effortlessly blends rich history with a vibrant community spirit. Known for its picturesque waterfront views and historic landmarks, Old Saybrook is a hidden gem that offers a unique lifestyle for those looking to settle down in a serene yet engaging environment.

Steeped in history, this quaint town is home to the iconic Katharine Hepburn Cultural Arts Center and the historic Saybrook Point, where the Connecticut River meets Long Island Sound. Outdoor enthusiasts will adore the stunning beaches, scenic parks, and nature trails that provide ample opportunities for hiking, biking, and water activities. The town’s welcoming atmosphere is complemented by a variety of local shops, restaurants, and cultural events, making it a perfect place for families, retirees, and everyone in between.

For those considering a move, Old Saybrook boasts a diverse range of homes for sale that cater to various tastes and budgets. From charming colonial-style houses with lush gardens to modern waterfront properties with breathtaking views, there’s something for everyone. The real estate market here is thriving, offering both historic homes that echo the town's rich past and contemporary builds that provide all the modern comforts.

Whether you’re seeking a cozy retreat or a vibrant community to call home, Old Saybrook invites you to discover its unique charm. Explore the homes for sale today and find the perfect place to create lasting memories in this enchanting coastal town!

Newest Old Saybrook Homes for Sale

$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. There is an adorable guest cottage which offers wonderful flexibility for visitors, or as an in-law suite or private studio. This building is not included in the total square footage or room count. 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

$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

$899,000

3 Beds ⋅ 2 Baths ⋅ 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

$675,000

4 Beds ⋅ 2 Baths ⋅ 24190279 MLS

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 investment. The existing home underwent a partial renovation in 2011 with a new roof, vinyl siding, replacement windows, and hardwood floors throughout. The septic system is appx 10 yrs old and is in front yard, so rear has room for a pool or building. The interior renovation was never completed, leaving the kitchen, bathrooms, and heating system gutted and ready for your vision. Whether you're looking to restore the existing home or explore the potential for a new custom residence, this property offers exceptional possibilities in a premier location. An added bonus is frontage along a state road at the rear of the property, which may offer the opportunity to create a rear driveway, subject to any required approvals. Bring your contractor, architect, and imagination to unlock the full potential of this exceptional Cornfield Point property just steps from Long Island Sound.

9 Old Colony Rd, Old Saybrook

$849,900

4 Beds ⋅ 3 Baths ⋅ 24189326 MLS

Life by the water starts here at 3 Anchorage Ln, a spacious Colonial in Old Saybrook set beside the marina with deeded 10-foot access for convenient boat loading and unloading. This 4-bedroom, 3 full bath home offers 2,496 sqft designed for everyday comfort and coastal living. The beautifully remodeled kitchen is the true anchor of the home, ideal for gatherings and seamlessly connected to the living and dining rooms. The first floor also features a family room, office or den, full bath, and laundry room for added flexibility and convenience. Upstairs, the primary suite offers a private retreat with an en-suite bath and three closets, joined by three refreshed bedrooms and another full bath. Major updates include a new oil boiler and water heater in 2024, oil tank in 2025, 200-amp service, and central air. There is also a 2-car garage and an unfinished basement, offering plenty of room for storage. Set on a 0.25-acre lot, this home puts you close to Saybrook Point, marinas, waterfront dining, Harvey's Beach, Main Street shops, and the charm of shoreline living with boating just steps from your door. Check out the virtual tour video!

3 Anchorage Ln, Old Saybrook

$599,000

4 Beds ⋅ 3 Baths ⋅ 24188934 MLS

Welcome to this classic home with a picturesque setting that is on a generous, level lot, the expansive backyard provides the perfect setting for outdoor entertaining, family gatherings, gardening, or simply relaxing and enjoying the outdoors. The backyard abuts the Old Saybrook preserve offering a private wooded backdrop with access to walking and hiking trails - an ideal setting! This home features four spacious bedrooms, hardwood floors throughout, a welcoming family room, a formal living room, and a dining room ideal for everyday living or holiday celebrations. The kitchen offers granite countertops, stainless steel appliances, and ample space for preparing meals and gathering with family and friends. Additional features include a Buderus furnace, updated electrical, generator ready, full basement offering abundant storage, a two-car garage, and in an area that is ideal for walking and biking. Conveniently located just minutes from two town beaches, marinas, restaurants, shopping, parks, and highways, this home offers the perfect combination of comfort, convenience, and location. Whether you're looking for your forever home or a place to enjoy all that the Connecticut shoreline has to offer, this Old Saybrook gem is ready to welcome its next owners!

22 Beaver Dam Trl, Old Saybrook

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