Old Saybrook Homes with Colonial Style

Welcome to Old Saybrook, Connecticut—a charming coastal town nestled in Middlesex County, where the serene beauty of nature meets rich historical heritage. Known for its picturesque views of the Connecticut River and Long Island Sound, Old Saybrook is a delightful blend of quaint New England charm and modern conveniences. With its vibrant arts scene, delightful local eateries, and scenic parks, this town offers a lifestyle that is both relaxing and engaging.

One of the standout features of Old Saybrook is its stunning collection of Colonial-style homes. These architectural treasures, characterized by their symmetrical facades, classic gable roofs, and inviting front porches, reflect the town’s deep-rooted history dating back to the 17th century. Each Colonial home tells a story, showcasing craftsmanship and timeless elegance that appeals to both history enthusiasts and modern homeowners alike.

Imagine sipping your morning coffee on a sun-drenched porch, surrounded by lush gardens and the gentle sounds of nature. Whether you’re drawn to the historic charm of a well-preserved Colonial or the allure of a new build inspired by traditional designs, Old Saybrook offers a diverse array of real estate options that cater to every taste and lifestyle.

With its welcoming community, excellent schools, and proximity to beautiful beaches, Old Saybrook is not just a place to live; it's a place to thrive. Explore the enchanting streets lined with Colonial homes and discover why so many are proud to call this quintessential New England town their home. Your dream home awaits in Old Saybrook!

Newest Old Saybrook Homes with Colonial Style

$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

$849,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$949,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184811 MLS

Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrook's most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic cottage offers timeless shoreline charm and standout curb appeal. The spacious enclosed front porch is the heart of the home, perfect for morning coffee, afternoon reading, and relaxing summer evenings. A cozy wood-burning fireplace adds warmth for cool nights by the shore. The expansive backyard is ideal for family gatherings, lawn games, and picnics, while your own "his and hers" beach sheds offer room for bikes, kayaks, beach gear, and more. The larger shed also includes a washer, dryer, refrigerator, and golf cart ramp. An outdoor shower makes rinsing off after beach days a breeze. Thoughtful updates including a new septic system (2019), new hot water heater (2021), new roof (2021), new refrigerator and microwave (2024), plus custom kitchen cabinetry and woodwork throughout. As a Cornfield Point resident, you'll enjoy private sandy and rocky beaches, a clubhouse, playground, basketball, tennis and pickleball courts, plus a full calendar of community events. Whether you're looking for the perfect summer getaway or a place to create lifelong family traditions, 28 Gates Road offers the entire package! Seasonal property. All furniture/TVs convey with sale. As-Is.

28 Gates Rd, Old Saybrook

$1,499,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185199 MLS

Welcome to one of Old Saybrook's most compelling brand-new luxury opportunities. Built by one of Connecticut's premier shoreline designers and builders, this exceptional coastal residence showcases a level of craftsmanship, architectural detail, and thoughtful design rarely found in today's market. Summer is in full swing, and with immediate occupancy and flexible closing arrangements available for qualified buyers, you can still enjoy the very best of the season at Saybrook Point. Perfectly positioned in the heart of this renowned waterfront community, the home offers something increasingly difficult to find along the Connecticut shoreline: brand-new luxury construction, timeless coastal architecture, and an unmatched waterfront lifestyle all without the maintenance, uncertainty, and costly renovations often associated with older shoreline homes. Designed for both everyday living and effortless entertaining, the residence is filled with natural light, soaring ceilings, expansive walls of glass, and carefully curated finishes throughout. The open-concept floor plan flows seamlessly from elegant living spaces into a spectacular chef's kitchen, creating the perfect setting for everything from intimate evenings to holiday gatherings and summer weekends with family and friends.

2 Old S Cove Rd, Old Saybrook

$999,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182838 MLS

Welcome to this exceptional 3700 sq ft, move-in ready home, privately situated on a quiet private road and surrounded by landscaped grounds. Set on a beautifully maintained 1.3 acre lot with a lightly wooded backdrop and charming stone wall accents, this property offers the perfect blend of privacy, space, and timeless appeal. The brick exterior creates stunning curb appeal, while inside you'll find a thoughtfully designed floor plan with generous living spaces throughout. The expansive eat-in kitchen features a center island, pantry, abundant cabinetry and counter space, making it ideal for everyday living and entertaining. The bright formal dining room showcases beautiful hardwood flooring, while the formal living room provides additional gathering space. The impressive family room features vaulted ceilings, a wood-burning fireplace, and French doors that open to the picturesque backyard. A sun-filled living room with a second wood-burning fireplace offers the perfect place to relax year-round. The main level also includes a full bathroom and a spacious first-floor bedroom, providing flexibility for guests or multi-generational living. Upstairs, the expansive primary suite offers a private retreat complete with a walk-in closet, dressing area and full en-suite bath. Two additional generously sized bedrooms, including one with a walk-in closet, share a full bath. Convenient upper-level laundry adds to the home's functionality. 2 car attached garage and huge basement.

34 Briarcliffe Trl, Old Saybrook

$12,000,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24183764 MLS

A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a local treasure for generations. The improvements require significant modernization and renovation, presenting an ideal opportunity for someone seeking to preserve and enhance a historic property. Whether envisioned as a private estate, hospitality-related use, office, wellness concept, or other permitted use, the property offers exceptional potential for those with a vision for restoration and stewardship. Ideally situated on Boston Post Road with convenient access to Interstate 95, Route 9, shoreline beaches, marinas, shopping, and restaurants, the property benefits from excellent visibility and accessibility within one of Connecticut's most desirable shoreline communities. This offering is subject to the property's historic designation and must be purchased together with the adjoining Bushnell Farm land parcel (MLS #24183765). The combined offering presents a truly unique opportunity to preserve, restore, and shape the future of one of the Connecticut shoreline's most recognizable historic properties.

1445 Boston Post Rd, Old Saybrook

$2,899,900

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24182941 MLS

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 Fireplace, Gleaming Hardwoods, Whole House Sound & Security, Irrigation, Super Efficient Natural Gas Heat, Three Car Garage w/ Radiant Floor Heat, On Demand Hot Water, & Custom Built-Ins every where you look! Gourmet Kitchen featuring Floor to Ceiling Double Box Cabinetry, Tile Backsplash, Accent Lighting, Stainless, 1.25" Quartz Counters, Huge Breakfast Island & a 'To Be Jealous For' Chef's Pantry. The Primary Double Floor Suite needs to be seen to be fully appreciated w/ it's Vaulted Balcony Ceilings, Circular stairs that lead to a Private Office & Sitting Room & a Luxurious & Relaxing En-Suite Bathroom! Incredible Bright & Spacious In-Law Apartment w/ a Custom Granite & Stainless Kitchen, Separate Laundry, Hardwoods & Beautiful Light at every turn! Indian Town Beach Association (indiantownassociation. org) is one of the most unique associations in the area w/ it's Golf Cart Friendly Mindset, 3 Beautiful Beaches, 100 Slip Marina, Large Waterfront Clubhouse & a Playground for the Little Ones. It is a great time to buy your Dream Home in Old Saybrook! We are always here to help!

2 Captains Ln, Old Saybrook

$1,695,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178785 MLS

SHORELINE 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, refinished hardwood floors, high-end kitchen appliances, and a seamless connection to its natural surroundings. The outdoor setting is no less impressive with an oversized saltwater pool, newly laid Techo-Bloc paver patio, generous deck for outdoor dining, professionally landscaped grounds, koi pond, mature trees, and multiple spaces for relaxation and entertaining. Thoughtful improvements include a new roof, economical electric heat pump HVAC system, refurbished free-standing studio, updated pool systems, hand-painted tilework, custom linen curtains, and more. Just minutes from beaches, Saybrook Point Marina, restaurants, and shops, this special shoreline property offers the feel of a private year-round retreat while remaining close to all that Old Saybrook has to offer.

11 Cambridge Ct E, Old Saybrook

$850,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24177311 MLS

This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California closets, dressing room, cathedral ceilings and a cozy loft. Gourmet kitchen with full pantry, granite countertops, island, stainless steel appliances, a stunning double-sided gas fireplace that creates warmth and ambiance between the main living spaces. Upstairs, a second private primary suite with a walk-in closet, full bath, two additional spacious bedrooms, another full bath, a charming terrace completes the upper level. A walk-up attic offers abundant additional storage, while the full basement and oversized two-car garage provide even more functionality. Surrounded by beautiful landscaping, a spacious deck perfect for entertaining, privacy, on a cul-de-sac minutes from town, beaches and highways.

9 Barley Hill Rd, Old Saybrook

$559,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24164864 MLS

A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and updated plumbing and septic, it offers modern peace of mind while preserving its timeless character. Rich in personality, the home evokes the romance of a countryside Tuscan Villa, from its ivy draped exterior to the layered, designer interiors originally re envisioned by Charles Spada in the 1990s. The private backyard is a tranquil escape, featuring exquisite stonework and curated plantings meant for quiet moments or intimate gatherings. Ideally situated just moments from boutique shopping, galleries, dining, Old Saybrook Town Beach, and the Katharine Hepburn Cultural Arts Center, this exceptional home offers both lifestyle and convenience. Featured in House Beautiful and Home Decorating Ideas, it is a true one of a kind residence ready to be enjoyed immediately, with furnishings available for purchase if desired.

92 Bokum Rd, Old Saybrook

$1,595,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24167090 MLS

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 interior reflects a coastal sensibility. Features include oak hardwood floors, a striking coastal river rock fireplace, and a sun-filled enclosed porch with a wall of windows. Kitchen is in the process of being completely updated including new cabinetry and countertops. Enjoy vibrant sunsets from the comfort of your family room. A versatile first-floor room offers flexibility as a private office or bedroom, complete with a nearby full bath. Adding to the home's unique appeal, a staircase leads to a charming hideaway-an ideal retreat or reading nook. The kitchen is light and bright with its own panoramic views. A lovely dining room provides entertainment options. A haven for bird lovers and outdoor enthusiasts alike, this property just awaits thoughtful updates. This home truly has it all. Knollwood Beach Association amenities include a sandy beach with raft, tennis and pickleball courts, a clubhouse, guest parking, and kayak storage. Conveniently located in Old Saybrook, just two hours from both New York City and Boston

104 Knollwood Dr, Old Saybrook

$6,600,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24151590 MLS

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 to the expansive back yard. This residence combines timeless architectural sophistication with the serene beauty of nature. Leave the world behind as you travel up the winding driveway that sets this home back from the road for ultimate privacy. The exterior is a master class in curb appeal, featuring a three-car garage and a porte cochere, all framed by lush landscaping and your own private pond and a dock. Step through the front door into a soaring cathedral ceiling foyer. As the heart of the home, this space is open to the floor above and finished with exquisite marble flooring, offering a regal welcome to guests. The floor plan is defined by wide-open spaces that flow seamlessly from one room to the next, making it as ideal for grand-scale entertaining as it is for quiet relaxation. With six spacious bedrooms, there is ample room for family, guests. There is also a home office and a sun room both overlooking the Connecticut River. Embrace the river breeze from your choice of outdoor vantage points: This isn't just a home; it's a lifestyle.

11 River Edge Rd, Old Saybrook

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