Refine Search
Map
Sort by
$2,899,900
5 Beds ⋅ 5 Baths ⋅ 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
$775,000
2 Beds ⋅ 1 Baths ⋅ 24180696 MLS
Saybrook Point! Welcome to the coastal lifestyle you've been dreaming of! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is just steps away. Set on a generous sized lot this home is move-in ready filled with natural sunlight and thoughtfully updated throughout creating a bright welcoming interior which includes a 3-season sunroom where you can slow down and enjoy the coastal air and a full basement. With engineered plans already in place for future expansion, the possibilities are endless - whether you are looking for a year round residence, weekend getaway, or investment in one of shoreline's most coveted locations. Close to highways, trains and amenities. This is truly a hidden gem in the heart of Old Saybrook where every day feels like vacation!

13-A Cove St, Old Saybrook
$1,425,000
3 Beds ⋅ 3 Baths ⋅ 24176301 MLS
DEEDED BEACH RIGHTS TO CORNFIELD POINT! One of Old Saybrook's most sought after beach communities! Enjoy beach days, sunset strolls, and the relaxed charm of shoreline living. This impeccably maintained Nantucket-style reverse floor plan home promotes scenic views from upper level main living space with private primary ensuite and 1st floor indoor/outdoor entertainment suite below offering timeless coastal charm and thoughtfully designed living spaces with breathtaking, expansive marsh views, features a spectacular, fully renovated chef's kitchen featuring premium appliances, Thermadore oven, a wine chiller, ice maker, breakfast bar, and an impressive oversized leathered quartzite stone island! An inviting living room with a wood-burning fireplace, which offers warmth and character, and a deck seamlessly extending from the kitchen features remote controlled retractable screens and integrated LED rail lighting, offering the flexibility of an open-air retreat or fully screened outdoor living space. Equipped with a premium partial Lutron smart lighting system and integrated Sonos 5-zone sound system. Every detail has been thoughtfully curated with high-end finishes and exceptional craftsmanship throughout. The primary suite includes a renovated bathroom with walk-in shower and installed California Closets.

4 Beach Rd, Old Saybrook
$1,495,000
3 Beds ⋅ 4 Baths ⋅ 24178761 MLS
Set on .62 acres along a protected canal just off the Connecticut River, this well built and maintained waterfront offers more than 100 feet of bulkhead frontage, along with a floating dock equipped with power and water suitable for a variety of boats and watercraft. Updated systems including central air and solar roof panels. Master bedroom on main floor with large closet, walk-in shower, sliders to private outside deck and direct water views. Large living room with cathedral ceiling, fireplace and direct access to outdoor deck and water. Large kitchen with modern appliances, center island, bar sink, wine fridge and eating area with sliders to deck and waterfront. Separate formal dining room. Three and half baths. Hardwood floors in excellent condition. Lower level has good sized den with fireplace and brick hearth, large rec room, laundry/ bath combo and well organized utility room all with convenient walk out via sliders to lawn and dock. Oversized 2 bay garage and landscaped for privacy. Solar panel system installed in 2024 and fully transferable. Documentation available.

77 Essex Road Rd, Old Saybrook
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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
$1,049,900
4 Beds ⋅ 2 Baths ⋅ 24176978 MLS
95 Middletown Avenue offers a rare opportunity to enjoy four season living in the heart of Saybrook Manor, one of Old Saybrook's most sought after shoreline communities. Renovated in 2022 with thoughtful attention to comfort and design, this beautifully updated home combines timeless coastal character with modern amenities and sweeping views of the Oyster River & Long Island Sound. With approx. 1,600 sq ft. of living space, the home features a reverse floor plan designed to maximize natural light and take advantage of the water views. The main living spaces feel bright and open, w/ hardwood floors, updated finishes, and open layout. A spacious deck with full panoramic views provides the perfect setting for morning coffee, outdoor dining, or relaxing while overlooking the water & shoreline. The home includes four bedrooms and two full bathrooms, offering flexibility for guests, remote work, or year round living. The updated kitchen opens comfortably into the living/dining areas, creating an inviting atmosphere. Modern conveniences including central air and mini split. The property includes a rare two car garage along w/ 400 square foot barn full of charm and potential perfect for a studio, workshop, gym, storage. An outdoor shower after a day at the beach. Residents enjoy a private beach exclusive to the community steps away! This home does not require flood ins adding long term value. Just minutes from marinas, restaurants, shopping the location is best CT shoreline living.

95 Middletown Ave, Old Saybrook
$649,900
3 Beds ⋅ 1 Baths ⋅ 24174666 MLS
Welcome to your seasonal sanctuary at Chalker Beach, where sun-soaked days and starry nights create lasting memories. Offered fully furnished and thoughtfully styled with relaxed coastal charm, this seasonal cottage is the perfect place to slow down, unwind, and enjoy easy shoreline living. Just a short walk or golf cart ride to the beach, the home is tucked into one of the shoreline's most loved beach communities where summer days are spent by the water, riding bikes through the neighborhood, and gathering with friends and family for community events and beach nights. The outdoor spaces are designed for relaxing and entertaining, featuring a spacious paver patio, beautifully manicured open lawn, outdoor shower, and a private firepit deck beside peaceful marsh grasses--the perfect setting for morning coffee, summer dinners, or evenings under the stars. Inside, cathedral ceilings, natural light, and custom wood paneling create a warm and welcoming atmosphere with a cozy beach-house feel throughout. Every space has been thoughtfully designed to make the home feel comfortable, inviting, and ready to enjoy from the moment you arrive. Located within the Chalker Beach Association with private beach access, clubhouses, playgrounds, basketball court, golf cart parades, and cherished summer traditions.

96 Chalker Beach Rd, Old Saybrook
$1,440,000
3 Beds ⋅ 3 Baths ⋅ 24173257 MLS
Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first floor, offering even more usable space than reflected. Inside, you'll find a warm and inviting layout highlighted by a vaulted ceiling, large open windows that capture beautiful morning sunlight from the east-facing front exposure, and a cozy fireplace. The first floor features durable ceramic tile, while the second and third floors showcase classic hardwood flooring throughout. Designed for comfort in every season, the home is equipped with oil forced air heating and central air conditioning, with supplemental electric baseboard heating. An oversized septic system, including a 4-bedroom capacity tank, adds peace of mind and functionality. Additional features include new windows, a storage crawlspace beneath the second floor, and thoughtful construction throughout. Knollwood Beach Association residents enjoy exclusive amenities including a private beach, clubhouse, tennis courts, basketball courts, pickleball, and a kayak stand.

21 Fenbrook Rd, Old Saybrook
$415,000
1 Beds ⋅ 2 Baths ⋅ 24169155 MLS
Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless living, with an eat-in kitchen showcasing a center island and newer appliances. Off the kitchen, a slider leads to a spacious back deck, perfect for outdoor dining or soaking in the coastal air. Built-in shelves add both charm and function to the main living area, which also features a convenient first-floor half bath and laundry. Head upstairs to discover a spacious bedroom paired with a full bath featuring a stall shower. The property doesn't stop impressing there-a full basement offers storage or potential, while the flat lot includes a versatile barn/garage and an adorable gazebo perfect for relaxing or entertaining. With public water and an unbeatable location, this home is ready to be your seaside escape or year-round haven. Welcome to the best of Old Saybrook living!

61 Ingham Hill Rd, Old Saybrook
$460,000
3 Beds ⋅ 3 Baths ⋅ 24170006 MLS
Attention Investors and Motivated Home Buyers. Welcome to 6 Watch Hill. Home offers eclectic feel. New owner will build off of this design. Home boast beautiful views and you can not help but to feel peace as you appreciate all the nature around you. Great stand alone garage with wonderful workspace on 2nd level. Sale is subject to probate approval.

6 Watch Hill Rd, Old Saybrook
$559,000
2 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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
$5,900,000
4 Beds ⋅ 4 Baths ⋅ 24165905 MLS
Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy fireplace, floor to ceiling windows and opens to a 750 square foot inviting deck ideal for relaxing, entertaining, soaking in the hot tub, peaceful sunsets or simply taking in the ever-changing river views. A lower level 750 square foot patio overlooks landscaped grounds, gardens and new stone fire pit area. The chef's kitchen is a dream featuring an oversized granite island, high-end stainless-steel appliances, custom cabinetry, wet bar, wine chiller that invites both gourmet cooking and effortless hosting. Designed for comfort, the home offers multiple luxurious bedroom suites each with sweeping views, spa like bathrooms, walk in closets, hardwood floors and high ceilings. It is perfect for an in-law bedroom or an au pair suite. Spacious additional bedrooms with views, entertainment room, private office with views, a loft, 4.5 bathrooms. A 5-car garage provides ample space for cars, outdoor lawn equipment or storage. A luxury lifestyle experience unlike any other on the Connecticut shoreline.

12 Rocky Point Rd, Old Saybrook
$6,600,000
6 Beds ⋅ 4 Baths ⋅ 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
$3,995,000
6 Beds ⋅ 5 Baths ⋅ 24162782 MLS
Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and wildlife lovers alike. The dual shoreline offers the river side with tidal rhythms and sweeping panoramas stretching from Essex Harbor north to Old Lyme across the water, then south toward Long Island Sound. The marsh side along Turtle Creek hums with avian life-majestic Bald Eagles perch in the trees while Herons, Egrets, Osprey, and migrating songbirds create a symphony that changes with the seasons. Two private docks provide endless boating possibilities: launch from the deep-water river dock for open-water adventure, or drift into the tranquil creek for kayaking and wildlife observation. Inside, 5,536 square feet of light-drenched living space unfolds with effortless grace. The architecture celebrates both gathering and solitude-a chef's kitchen designed for culinary artistry flows seamlessly to indoor and outdoor dining areas, while five fireplaces anchor intimate retreats throughout.

41 Watrous Point Rd, Old Saybrook
$899,000
4 Beds ⋅ 3 Baths ⋅ 24163559 MLS
Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the largest water-view coastal lot in South Cove! Situated in Old Saybrook's most protected and prominent corridor, 18 Old South Cove Road provides the rare opportunity for you to embrace your dream of living by the water and realizing your vision of Moving-in, Renovating, or Custom Building a "Luxury Estate" where privacy and scenic integrity are guaranteed by zoning. As one of the largest parcels in the protective Gateway Zone, you are granted 15% building coverage. This translates to a massive potential footprint of approximately 2,744 sq. ft., allowing for a custom build that far exceeds the scale of neighboring homes. And by leveraging the 35-foot (2.5 story) scale-up potential, you have the incredible opportunity to capture dramatic, unencumbered panoramic sunrises and water views of South Cove. With Residence A designation, this lot represents the perfect 'Coastal Canvas' for a luxury home up to 4,000 sq. ft. featuring 3-car garage, sweeping verandas, and all the best in coastal living!

18 Old S Cove Rd, Old Saybrook
$1,099,000
3 Beds ⋅ 3 Baths ⋅ 24161065 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
$2,195,000
1 Beds ⋅ 2 Baths ⋅ 24138056 MLS
Great mixed-use opportunity. Fully leased office building with town-approved one-bedroom apartment on Second Floor with kitchen, full bath including washer/dryer. Great opportunity to own a mixed-use property on beautiful Main Street in Old Saybrook. Established salon with long term lease on first floor. The one bedroom apartment on the second floor has been carpeted and painted and has separate heat control from all office spaces. Opportunities exist for additional apartments with proper permitting. The front of the building faces the heart of Downtown Old Saybrook with shops, restaurants, art and dance studios and The Kate all within walking distance. The rear of the building faces Pine Street and boasts a 25-car parking lot surrounded by chain link fencing and a storage shed. Opportunities exist for other uses of this area with proper permitting. The building has a full sprinkler system with associated central station alarms. Easy access to RT. 95 and RT.9.

125 Main St, Old Saybrook
$9,850,000
5 Beds ⋅ 8 Baths ⋅ 24125295 MLS
YOUR OWN PRIVATE COUNTRY CLUB! Enjoy the expansive 3500 sf granite terrace, a heated saltwater swimming pool, a deep water dock and a pool house with a full kitchen and seating for 10! This modern masterpiece, sited to take full advantage of a private 1.6 acre waterfront location overlooking North Cove and the Connecticut River has been constructed with the best curated materials. 20 Saltus Drive offers a luxurious, comfortable lifestyle with panoramic water views from almost every room. The great room (30' x 40') has soaring ceilings, a remarkable, double sided stone fireplace and a window wall creating an expanse of glass facing picture perfect water views. Glass pocket doors open to the dining room which flows into the impressive kitchen with table and counter seating. Additional notable spaces on this level are a home theater with an 8'+ screen and two bedroom suites (all five bedrooms have ensuite baths; four also enjoy separate sitting rooms). Access the second level either by elevator or a striking marine stainless steel, floating staircase. To the left are two additional bedroom suites while to the right is the palatial primary suite which includes a bedroom with fireplace, a large bathroom, walk-in closets, a laundry, an office and a sitting room. These three suites also have water view decks. Nearby is downtown Old Saybrook with its restaurants, shops and the Hepburn Cultural Arts Center.

20 Saltus Dr, Old Saybrook

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.