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 offers an idyllic setting for those seeking the perfect place to call home. This quaint town is situated at the mouth of the Connecticut River, where it meets the Long Island Sound, providing residents with stunning waterfront views and a plethora of recreational opportunities.

Old Saybrook boasts a delightful blend of historic charm and modern amenities. Stroll down Main Street, where you’ll find an array of local boutiques, cafes, and restaurants, each offering a taste of the town’s unique character. The area is also home to several beautiful parks, scenic beaches, and nature trails, perfect for outdoor enthusiasts and families alike.

For those considering a move to Old Saybrook, you’ll be pleased to discover a diverse selection of homes for sale. From charming colonial-style houses to contemporary waterfront properties, there’s something to suit every taste and budget. Many homes in the area feature beautiful architectural details, spacious yards, and easy access to local amenities. Whether you’re looking for a cozy retreat or a family-friendly abode, Old Saybrook has it all.

With its welcoming community, excellent schools, and a strong sense of history, Old Saybrook is more than just a place to live; it’s a place to thrive. Explore the homes for sale today and discover why so many have chosen to make this enchanting town their forever home!

Newest Old Saybrook Homes for Sale

$2,495,000

4 Beds ⋅ 4 Baths ⋅ 24197382 MLS

Welcome to 514 Main Street, a waterfront custom-crafted home built in 2006 with unobstructed, expansive views of North Cove. This coastal-inspired retreat blends sophisticated elegance with everyday functionality. Boasting 3,766 square feet, this home has 4-bedrooms, 3.1-baths with an open-air concept that centers around a spectacular great room, setting the stage for seamless entertaining and comfortable daily living. Steeped in high-end finishes, the main level features an expansive chef's kitchen equipped with granite countertops, a large island, a dedicated walk-in pantry, separate bar/prep sink and double wall ovens. It transitions effortlessly into the dining area, which opens onto a tranquil screened porch directly overlooking North Cove-your future favorite spot for morning coffee or relaxing summer evenings. The highly desirable first-floor layout includes a luxurious primary master suite complete with a spa-like bath. Ideal for modern remote work, the main level offers a dedicated home office plus a separate quiet study. Upstairs, the home continues to impress with a playroom/rec room outfitted with custom built-in bookshelves. Tucked away on yet another level is a unique "Crow's Nest"-a perfect reading nook or a great space for a spin cycle with an amazing view of both North and South Coves. Complete your day with your favorite beverage on the balcony, watching the sailboats as they return to their moorings in the protected cove.

514 Main St, Old Saybrook

$679,000

3 Beds ⋅ 3 Baths ⋅ 24216599 MLS

Discover the charm and comfort of this beautifully maintained Cape, ideally situated on a quiet cul-de-sac off School House Road in one of Old Saybrook's desirable locations. Offering over 2,700 square feet of finished living space, this inviting home is just across from The Preserve trail access and moments from Clark Park, making it easy to enjoy nature, recreation, and the outdoors. Inside, gleaming hardwood floors, a spacious living room with a wood-burning fireplace, and a formal dining room create a warm, welcoming atmosphere. The updated kitchen features rich cherry cabinetry and granite countertops and opens to a cozy family room with a Garrison wood stove. Sliders lead to a cedar-paneled three-season room overlooking the private backyard, deck, and patio-perfect for entertaining or relaxing outdoors. Upstairs, the spacious primary suite features an en-suite bath with a custom shower and tons of storage, along with two additional bedrooms and a full bath. The finished lower level offers flexible space for a home office, gym, media room, or additional living area. Thoughtful updates include Andersen replacement windows, newer garage doors, enhanced attic insulation, and ice dam heating cables. Blending classic New England charm, versatile living spaces, and an exceptional location near trails and recreation, this move-in-ready home is a wonderful place to enjoy the best of Old Saybrook living.

11 Kitteridge Hill Rd, Old Saybrook

$574,000

1 Beds ⋅ 1 Baths ⋅ 24212897 MLS

Escape to your own private country retreat along the beautiful Connecticut shoreline! Nestled on over two acres of gorgeous, level land, this newly renovated 1,100-square-foot home offers a rare opportunity to enjoy the serenity of country living with all the conveniences of Old Saybrook just minutes away. Imagine creating magnificent gardens, hosting summer gatherings and picnics on the expansive lawn, or simply relaxing with your favorite book surrounded by nature. There's plenty of room for pets to play, outdoor hobbies, and perhaps even a horse, subject to town approval. The beautifully refreshed home offers comfortable, easy living, whether as a full-time residence, charming weekend escape, or potential income-producing Airbnb. With over two acres of usable land, the possibilities for creating your own personal sanctuary are truly exciting. Enjoy peaceful mornings, star-filled evenings, and the luxury of space and privacy, all within easy reach of beautiful beaches, marinas, waterfront dining, boutique shopping, and Amtrak service connecting to New York and Boston. Perfect for those seeking a relaxed lifestyle away from the hustle and bustle, this special property offers the best of country and coastal living. A wonderful opportunity to enjoy the shoreline on your own terms!

121 Bokum Rd, Old Saybrook

$1,190,000

3 Beds ⋅ 3 Baths ⋅ 24211568 MLS

Welcome to easy year-round coastal living in the desirable Knollwood Beach Association! Ideally located near a beautiful private sandy beach. this spacious home offers the perfect opportunity for a full-time residence, weekend getaway or shoreline retreat. The bright, inviting interior features a vaulted ceiling, fireplace and large east-facing windows that fill the home with morning sunlight. Offering approximately 1,916 square feet of finished living space, including a finished above-grade lower level, the home provides plenty of room for family and guests. Ceramic tile enhances the lower level, while hardwood flooring extends throughout the upper floors. Comfort is assured year-round with oil forced-air heat, central air conditioning and supplemental electric heat. Additional features include newer windows, useful storage and an oversized septic system with a 4-bedroom capacity tank. Best of all is the Knollwood lifestyle! The association is situated on approximately five acres and offers a private beach, clubhouse, pickleball, tennis and basketball courts, playscape and sea kayak storage/stand. Enjoy morning walks by the water, beach days with friends and family, kayaking and an active coastal lifestyle-all just minutes from Old Saybrook's Main Street, restaurants, shops and amenities. A wonderful opportunity to enjoy the Connecticut shoreline in every season.

21 Fenbrook Rd, Old Saybrook

$995,000

4 Beds ⋅ 4 Baths ⋅ 24211855 MLS

LONG ISLAND SOUND VIEWS,2.02 PRIVATE ACRES & EXCEPTIONAL CONDITION!Perched on a sunny hilltop, this beautifully maintained Colonial Contemporary offers approximately 3,300 sq. ft. of thoughtfully designed living space, coastal breezes and a fabulous open floor plan. The heart of the home is the impressive chef's kitchen featuring a large granite island, commercial-size side-by-side Sub-Zero refrigerator/freezer, Thermador double convection ovens, 6-burner gas cooktop with custom-paneled hood and Bosch dishwasher. The kitchen opens seamlessly to the dining area and spacious family room with gas fireplace-perfect for entertaining or simply enjoying the view. Vaulted ceilings, beautiful hardwood floors, a dramatic foyer and French doors leading to a private deck add to the bright, open feel. A rare floor plan offers BOTH first- and second-floor primary bedroom suites! Four bedrooms and 3 1/2 baths, with every bedroom enjoying direct access to a bathroom, provide wonderful flexibility for family, guests or multi-generational living. Additional highlights include first-floor laundry; central air; 2-zone gas heat; oversized 2-car garage; front porch; spacious, dry, partially finished basement; generator; basketball court; and lighted pea-stone driveway. Set on 2.2 secluded acres, yet close to beaches and everything that makes Old Saybrook and the Connecticut shoreline so special.This beautifully maintained home presents an exceptional opportunity to enjoy coastal living at its best

12 Drummers Trl, Old Saybrook

$659,000

3 Beds ⋅ 3 Baths ⋅ 24208801 MLS

Tucked away on a beautiful, wooded 1.5-acre lot, this home offers a rare blend of absolute privacy and everyday convenience. Step inside to a freshly painted, 2,606sqft 3 bed and 3 bath open-concept floor plan designed for seamless modern living and effortless entertaining. The heart of the home is anchored by a large kitchen featuring granite countertops, an island with high-top seating, ample cabinet space, and a functional layout that flows beautifully into the main living space. This main living space features a dramatic living room with a wall of windows that frame peaceful nature views and a soaring cathedral ceiling that maximize the sense of space and light. A dedicated home office, or potentially a first floor bedroom, a distinct step-down dining room, and a gorgeous full bathroom complete the first floor. Three generous bedrooms and two more full baths upstairs provide plenty of room for family or guests. The finished walkout basement allows for seamless outdoor access, making it a perfect rec room, gym, or media center. Outside, the expansive deck serves as the ideal backdrop for al-fresco dining, summer barbecues, or quiet mornings enjoying your peaceful, private outdoor space. Situated just minutes from Old Saybrook's vibrant town center and train station, this home provides a quiet escape with upscale dining, boutique shopping, beautiful shoreline beaches and a 1,000 acre nature preserve just a short distance away.

5 Connally Dr, Old Saybrook

$485,000

4 Beds ⋅ 2 Baths ⋅ 24208270 MLS

This warm and inviting Cape offers the perfect blend of comfort, space, and convenience in a highly desirable Old Saybrook location. Just one mile from Main Street's charming shops, restaurants, and local attractions, this home features an open-concept main level highlighted by vaulted ceilings in the living room that seamlessly flows into the kitchen and dining area, creating an ideal space for everyday living and entertaining. Beautiful hardwood floors extend throughout the main living areas, while two first-floor bedrooms provide flexible living options. Upstairs, you'll find two additional bedrooms offering plenty of room for family, guests, or a home office. The partially finished basement adds valuable bonus space for recreation, fitness, or storage. Energy-conscious buyers will appreciate the solar panels, helping to offset utility costs. Conveniently located with easy access to Routes 9 and I-95, this home is perfect for commuters while still enjoying all the coastal charm and amenities that make Old Saybrook such a special place to call home.

1 Briarcliffe Trl, Old Saybrook

$935,000

4 Beds ⋅ 4 Baths ⋅ 24207853 MLS

Step into this farmhouse with a bright, open and inviting floor plan. A welcoming grand foyer sets the tone, leading into sun-filled living spaces accented by hardwood floors, skylights and abundant windows throughout. The stunning wraparound deck is a true focal point of the home, offering the perfect setting for entertaining, relaxing or simply enjoying the peaceful surroundings. The main level features a spacious first-floor primary suite with a walk-in closet, laundry and a renovated bathroom. Upstairs, a loft overlooks the living space and is complemented by generously sized bedrooms and beautifully updated bathroom with heated floor. The full walkout basement provides excellent storage and additional possibilities.This home offers convenient access to the restaurants, shops, beaches, highways and train station. Enjoy all that Old Saybrook has to offer while coming home to a property that feels warm, distinctive and made for both entertaining and relaxing. Deferred maintenance needed. Professional photos coming.

6 Overlook Dr, Old Saybrook

$955,000

3 Beds ⋅ 3 Baths ⋅ 24208689 MLS

Discover the perfect blend of comfort, style, and convenience in this beautifully remodeled home. Tucked in a prime location just minutes from fine dining, shopping, the golf course, and the train station, this property offers unparalleled access to everything you need. Walking along the shore to Saybrook Point Inn and Saybrook Lighthouse. Step into the heart of the home: a chef's kitchen with high-end appliances, designed to make cooking and entertaining a breeze. Enjoy seasonal waterviews that bring a touch of tranquility to your everyday life. The lushly landscaped yard is an ideal setting for summer evenings-whether you're hosting friends, enjoying a quiet moment, or taking a dip in your very own swim spa. This home isn't just gorgeous; it's energy-efficient too, featuring solar panels that help reduce your carbon footprint and save on utility costs. With every inch thoughtfully updated, all that's left to do is move in and make it your own.

17 College St, Old Saybrook

$995,000

4 Beds ⋅ 3 Baths ⋅ 24205576 MLS

Welcome to 5 Sand Creek Drive, a truly unique coastal contemporary in Old Saybrook, beautifully positioned to capture stunning marsh and water views. Filled with natural light and designed around its exceptional setting, this distinctive home offers an open floor plan, brand-new windows throughout, and wonderful spaces for both everyday living and entertaining. The dramatic living room is a standout, featuring a vaulted ceiling and stunning stone wood-burning fireplace that creates a warm and inviting focal point. A separate den offers another comfortable gathering space with a gas log stove, while the open layout allows the main living areas to flow seamlessly together. The first floor provides exceptional flexibility with a spacious primary suite, plus a second first-floor bedroom and an additional full bath-ideal for guests, extended family, or one-level living. Upstairs, a loft-style second level offers three additional bedrooms, a full bath, and a bonus room, providing plenty of space for family, guests, a home office, or recreation. Outdoor living is just as special. Step onto the deck and take in the peaceful marsh and water views or follow the exterior spiral staircase to the widow's-walk-style upper deck, where the elevated vantage point showcases the surrounding coastal landscape. A 3-car attached garage provides generous parking and storage, while the home's contemporary architecture beautifully complements its shoreline setting.

5 Sand Creek Dr, Old Saybrook

$475,000

3 Beds ⋅ 2 Baths ⋅ 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 ⋅ 24205326 MLS

3-2-1 BUYDOWN PROGRAM OFFERED. 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, 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

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Old Saybrook Homes for Sale

Newest Old Saybrook Homes for Sale

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