Old Saybrook Real Estate Search

Old Saybrook Properties for Sale

Our website features the best Old Saybrook real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

Old Saybrook is a coastal Connecticut shoreline town with a population around 11,000.  Old Saybrook has a long rich history which dates back to its founding in 1635.

One significant note is that Yale University was originally chartered in Old Saybrook in 1701 under the name the Collegiate School of Connecticut.  It was later renamed Yale University when it moved to New Haven in 1716.

Located in between New York City and Boston, Old Saybrook is easily commutable by train or I95.

Golf enthusiasts will love the Fenwick Golf Course which is a 9 hole course on the Connecticut shoreline.

Notable resident to the Fenwick borough is Katharine Hepburn who lived in Old Saybrook her entire life until 2003.

Old Saybrook’s cute downtown area is full of unique stores and high quality restaurants.  Fresh Salt directly on the water and Liv’s Oyster Bar are two town favorites.   The coast is adorned with sprawling beaches and beautiful luxury homes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Old Saybrook real estate market? Sign up for a  Old Saybrook Real Estate Market Report to see what’s active, under contract, and sold!

Newest Old Saybrook Properties for Sale

1 Beds 1 Baths 24000133 MLS
Welcome to your dream getaway in the sought-after Chalker Beach Association of Old Saybrook, CT. This fully updated home a serene and compact living space. Bask in the sun, jump in for cooling swims, or indulge in a leisurely stroll along the shoreline just steps away from your front door. A year round home. Now with a propane fireplace and tankless hotwater heater. Ductless A/C and New Appliances! This home gives a life of beachy and beautiful. There's a wonderful yard, not too much to mow, and the deck overlooking the lush plantings. Flowers abound with the wonderful nectar in the air - dazzling your eyes; right here, right now. Convenience and entertainment in Old Saybrook - a wide range of fantastic local restaurants nearby. Savor delicious seafood. Looking for investment potential? This property offers the flexibility to rent it out, allowing you to generate income while enjoying your own private retreat. Seize the opportunity to own this fully furnished beach house, complete with updated HVAC systems, a beautiful bath and kitchen, and a stunning backyard deck for enjoying picturesque sunsets. With its exceptional location and hassle-free lifestyle, this home represents the epitome of value in Old Saybrook. Included with puchase will be; survey, permitting, zoning and construction due diligence. This has has been done to be able to lift the house to meet the Town's FEMA requirement. Lifting the house may allow the new owner to add an additional bedroom etc...

15 Cranton Avenue, Old Saybrook

2 Beds 2 Baths 170623827 MLS
Nestled in the prestigious Cornfield Point Beach Association neighborhood, this upgraded ranch offers one-level living at its finest with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, central air, this home provides comfort and style. A spacious open plan living room welcomes you home with a wall of windows that flood the space with light and air; durable wood-look plank flooring offers easy maintenance. With vaulted ceilings, gas log fireplace, and ceramic tile flooring, your family room offers a cozy, inviting atmosphere. An immaculate updated kitchen with cherry cabinetry, breakfast bar island, stainless appliances, and granite counters is perfect for hosting. Spacious and light-filled, bedrooms feature updated carpeting and ample storage. A large driveway and detached garage provide plenty of off-street parking, while mature privacy hedging and greenspace creates an ideal space to relax with friends and family. HOA fees include trash, playground, tennis court & snow removal on the main road! Experience the incomparable quality of life Old Saybrook has to offer: blocks from the ocean, enjoy magnificent sunsets, local eateries, and beautiful nature preserves. With easy access to the train station for a quick commute into NYC, this home is perfect for year-round living, or seasonal enjoyment. Don't miss your opportunity to own this superlative one-level property; schedule your showing today!

24 Seabreeze Road, Old Saybrook

4 Beds 3 Baths 170622784 MLS
Enter enchanting Otter Cove and find this stunning, well updated mid-century ranch. A brick rotunda drive sets the tone. Architectural details enhance functional design. The hallmark entry foyer glows. Beyond, the living room is wrapped with sliding doors creating terrific ambiant light. A central fireplace anchors the space. A well designed, updated kitchen sits adjacent the dining room which comfortably accommodates a party of 12! Sliders to the decks offer great transition space overlooking private grounds. Four bedrooms include a primary with superbly renovated bath, a custom bamboo vanity and glass shower. A second BR features an ensuite bath. The fourth bedroom doubles as an office with extensive built ins. Everywhere, there is light and space and a warmth only exceptional design creates. The three-season porch creates a welcoming transition from the home to the garage. The daylight lower level is unfinished with heat and central air opening a host of opportunities for expansion and finishing. There is a second central fireplace, banks of sliders opening to ground level and high ceilings. Currently serving as a woodshop, the space is flanked left and right by terrific storage and mechanical space. Take extra time to tour Otter Cove, an enclave of fine homes with a private beach access (yes, a beach on the CT River!) and open spaces making this an exceptional place to call home. 5 minutes to Saybrook Station rail access and 2 hours to NY and Boston.

11 Crest Road, Old Saybrook

3 Beds 3 Baths 170614449 MLS
Charming Colonial with something for everyone. Serene location on private street but only a short distance to the center of town. Beautiful living room with hardwood floors, raised panels and coffered ceiling along with built in bookcases. Large formal dining room with bay window offering an abundance of natural sunlight. The fully applianced country kitchen has a pantry and fireplace, recessed lighting and access to a glass sunroom with tile floor. Access to the deck and rear yard enhance the desirability of this room. Perfect room to sit and just relax or locate your piano here and make it a stunning music room. Upstairs you will find 3 spacious bedrooms and 2 full bathrooms. Primary bedroom includes a full bath with tub, two walk in closets and an atrium door to access the second sunroom with views of South Cove. New carpet in the primary bedroom, both walk in closets and the sunroom make this enclave a warm and cozy area to enjoy a good book or private office. Perfect size deck on the rear of the house with quick and easy access to the inground pool on those warm summer nights. Full basement, Oil forced hot air heat and Central Air. With the proximity to the town center you will be able to catch a show at "The Kate", hit the gym or use the pickleball courts for a quick game or just meander along visiting all of the great shops and restaurants on Main St. This house offers the complete package. Don't let this opportunity pass you by.

2 Trails End, Old Saybrook

6 Beds 5 Baths 170618144 MLS
Welcome to a stunning property nestled in the heart of Old Saybrook! This expansive home, discreetly tucked in a secure enclave, offers not just a residence but a lifestyle. Boasting 6 bedrooms and 4.5 baths, this meticulously maintained home features a legal accessory apartment, a coveted asset generating excellent income. Beyond its spacious interiors, this residence emphasizes convenience and leisure. Picture-perfect for summer days, the just-completed summer porch invites you to relax and savor the tranquility of the serene front yard. For beach enthusiasts, the proximity to the Town Beach in Old Saybrook makes it an ideal spot for endless summer fun. Discover the allure of Old Saybrook's vibrant amenities! Indulge in culinary delights at the renowned Fresh Salt restaurant located at Saybrook Point, offering exquisite dining overlooking picturesque views. Explore the evolving charm of Main Street, a hub teeming with eclectic eateries and shopping options, creating a dynamic destination right at your doorstep.Old Saybrook is celebrated for its reputation as a safe town, ensuring peace of mind for residents and visitors alike. Additionally, this property's versatile layout offers the opportunity for effortless conversion into a spectacular single-family home. The three-car garage is not something you'll always find. Here's your chance for versatile living, income potential, and prime location, perfectly encapsulating the sought-after lifestyle in Old Saybrook.

15 Cricket Court, Old Saybrook

5 Baths 170595498 MLS
The landmark James Pharmacy building is fully occupied, operating as the James Pharmacy Bed & Breakfast and restaurant on vibrant Main Street, Old Saybrook. Anna James, daughter of a slave and the first African American female pharmacist owned and operated the iconic pharmacy for decades, residing upstairs. Her niece, noted novelist Anna Petry, was born here and assisted Miss James. The main floor restaurant retains the historic pharmacy built-ins and soda fountain. Arched glass windows offer diners a Main Street view. Three B&B guest rooms are well appointed and upscale, each with a fully renovated bath and a gas fireplace. Max. occupancy 6 guests. Innkeeper quarters are on the main level. The building underwent extensive updates and renovations, bringing it to current standards while preserving its beauty and historic architecture. Exterior painting two sides slated for October. A full basement houses mechanicals, exceptional storage and clean storage. Old Saybrook is a popular weekend destination. Sidewalks access a plethora of restaurants, shops, The Kate cultural arts center and Saybrook Station just 2 hours from NY/Boston. Find exceptional beaches, boating, Fenwick or Fox Hopyard Golf a short drive. A vibrant Chamber of Commerce works tirelessly ensuring Old Saybrook businesses have the support they need with Main Street events throughout the year. Limited area lodging ensures the James Pharmacy Bed & Breakfast and restaurant are an option with provenance year-round.

323 Main Street, Old Saybrook

4 Beds 3 Baths 170575167 MLS
This traditional Fenwick cedar shingle style home has spectacular water views of the Connecticut River and South Cove. It also enjoys Fenwick’s unique lifestyle: beach, tennis courts, Yacht Club and famed golf course. The 2,634 home built in 2006 with the highest craftsmanship and state-of-the-art materials has wideboard floors throughout. The great room with a coffered ceiling has a wall of windows above the long banquette, a large beach stone fireplace and built-in cabinets. French doors on the main level open to a full width porch, which overlook the long water views and beautiful professionally landscaped gardens. The open kitchen is flooded with sunlight and is a chef’s delight with all top of the line appliances. Rich mahogany cabinetry and marble counters and sit down island are custom made. The first floor 15x15 master suite has built-ins, and has access to the porch. A guest room/office off the kitchen has a beadboard ceiling, shiplap walls, and state-of-the-art Murphy bed built into custom cabinetry. Mudroom side entrance with outdoor shower, includes extra built-in cabinets, farm sink and washer/dryer. Two guest rooms on the second level, one with built-in beds have access to the balcony with views of the hydrangea border gardens and water. This beautiful dream home sits on a private .46 acre parcel and has full mechanicals including a full house generator. Located half way between New York and Boston and is only minutes to all major transportation.

102b Sequassen Avenue, Old Saybrook

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