Old Saybrook Homes for Sale

Welcome to Old Saybrook, a charming town located in Middlesex County, Connecticut. Known for its picturesque coastal views and rich history, Old Saybrook offers a perfect blend of small-town charm and modern amenities.

If you are considering moving to this beautiful town, you'll be pleased to know that there are plenty of homes for sale in Old Saybrook. Whether you are looking for a cozy beachfront cottage, a historic colonial home, or a modern waterfront property, you are sure to find the perfect place to call home in Old Saybrook.

With its convenient location along the Connecticut shoreline, Old Saybrook offers residents easy access to beautiful beaches, quaint shops, delicious restaurants, and a variety of outdoor recreational activities. Whether you enjoy boating, fishing, hiking, or simply relaxing by the water, Old Saybrook has something for everyone.

Don't miss the opportunity to own a piece of this idyllic town. Explore the homes for sale in Old Saybrook and discover why so many people are proud to call this charming community their home.

Newest Old Saybrook Homes for Sale

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 24042457 MLS

Welcome to this exquisite Waterfront home located on North Cove. This timber frame home is a masterful blend of timeless elegance and state-of-the-art updates located . The exterior exudes sophistication with a freshly painted facade, new cedar siding, and Azek trim, while custom 9'6" garage doors and new bluestone walkway with landscaping add a grand touch. The newly rebuilt screened porch and an outdoor shower offer an open air retreat. As you step inside, the original maple floors guide you through a freshly painted interior that radiates warmth and character. The heart of the home, the kitchen, is a culinary dream with custom inset shaker cabinets painted in a bespoke Benjamin Moore hue, Calacatta marble island and backsplash, and black honed granite counters. Unlacquered brass hardware, open shelving, and a California faucets fixture enhance the space's charm. A custom-paneled integrated refrigerator, Thermador appliances, a Kohler farmhouse sink, and a Sharp microwave drawer fulfill any chef's desires. The adjoining dining area is illuminated by a custom brass chandelier, while a Devol pendant adds a touch of sophistication The primary bath is a luxurious sanctuary with antique limestone floors, an oversized built-in bathtub, and a microcement walk-in shower. Unlacquered Sigma brass hardware, custom visual comfort sconces, and a new window create an opulent atmosphere A custom walnut double vanity with macchia vecchia marble counter completes this lavish space.

502 Main Street, Old Saybrook

Listing courtesy of Teri Lewis from William Pitt Sotheby's Int'l

$899,900

3 Beds ⋅ 3 Baths ⋅ 24046553 MLS

Beautiful fully renovated L-shaped 3 bedroom ranch set in the Fenwood Beach Community. This home features an open floorpan, and is located on a quaint private cul-de-sac. Rare dock access into a marsh waterway that meanders thru the marsh into Saybrook's South Cove via kayak or small boat. Current owners completed renovations in 2015, including a custom kitchen with granite countertops, a living/dining room with a dual sided gas fireplace, a large combination family/mud room containing laundry/utility room. Home boasts central air, tankless water heater, 200 amp electrical, propane fired furnace with attic location, all new doors and windows with custom wood blinds, tiled and hardwood floors, custom built-in bookcase, crown moldings and more. All utilities are located on the first floor. Plug in portable generator ready. This forever home is one block to Fenwood's private beach; and a short golf cart ride to Fenwick golf. Enjoy quiet, peaceful and serene living at the beach. Relax and entertain on the large 1200+ sq ft private bluestone/brick patio offering spectacular evening sunsets. All 3 bedrooms feature direct sliding-door access to the patio. Other features include a private outdoor shower, fenced in dog area, a finished walk-out basement for an extra 1000+ finished bonus area, an outdoor storage/garage area below patio, and shed. You won't believe the quality, location and openness of this property until you see it.

14 Fenwood Place, Old Saybrook

Listing courtesy of Daniel Julian from Creative Realty of CT LLC

$674,000

4 Beds ⋅ 3 Baths ⋅ 24045022 MLS

Welcome to Old Saybrook! Enjoy this spacious and renovated 4 bedrooms, 2.1 baths home offers over 2,700 sq ft of flexible open concept space along with a unique lifestyle that can be enjoyed all year round! The main level features a large open-floor kitchen, dining, and living room with an electric double-sided fireplace. Great room boasting cathedral ceilings and brick fireplace. The updated kitchen is a chef's delight, equipped with stainless steel appliances, soft close cabinets, an over-sized island and elegant quartz countertops. primary bedroom with access to the deck located conveniently on the first floor. boasting a walk-in closet, and an ensuite bathroom with tiled shower and a floating tub. Three additional bedrooms and a full bath on the upper level offer comfort and privacy for family and guests. The finished basement features flex space for office, gym, storage... The cleared backyard offers a deck and patio perfect for grilling and hosting outdoor gatherings. This home update includes New roof, New windows, New exterior doors, freshly painted outside, New garage door and opener, New drywall, New gas forced hot air furnace, New central AC, Updated electric Custom kitchen, Quartz countertop, Natural gas appliances New hardwood floors, New carpet, fully renovated bathrooms.

1012 Boston Post Road, Old Saybrook

Listing courtesy of Naima Mazouzi from Eagle Eye Realty PLLC

$1,650,000

4 Beds ⋅ 5 Baths ⋅ 24043614 MLS

This quietly elegant property is well-sited in Watrous Point. Well-planned space features extensive millwork and lofted ceilings and allows for complete first floor living and plenty of second floor space for family and guests. A stunning hardscape and barrel-vaulted entry greets you with a heated lower landing. Enter a soaring gallery flanked by the library built to house the most extensive collections. The hexagonal cherry kitchen commands an 8-burner Wolf range, two Gaggenau convection ovens with warming drawers and dual Subzeros. The large eat in area with a fieldstone fireplace will be the center point of your gatherings. There is a dream pantry. The adjacent great room with the second fieldstone fireplace offers a bright, relaxing space. A beverage center with refrigeration and icemaker makes entertaining easy. The main level primary bedroom features a walk in with custom-built ins and a full bath. All rooms offer French doors leading to the bluestone patio. Completing the main level is the laundry room , mudroom, and a powder room. Upstairs, architectural angles provide interest and loft in all 3 bedrooms, all with ensuite baths. The lower level is partially finished as a bonus/craft room and half bath. Outside, find a gunite, heated pool with spa and a pool house and, for the craftsman, a heated woodshop. Extensive updates throughout include geothermal heating, Rinnai propane hot water heater, pool, pool house, woodshop and a new roof 2022.

30 Watrous Point Road, Old Saybrook

Listing courtesy of Nancy Mesham from Coldwell Banker Realty

$525,000

2 Beds ⋅ 1 Baths ⋅ 24042925 MLS

Welcome to 25 Elm Street, a charming 1950s ranch that perfectly blends classic appeal with modern updates. Renovated in 2014, this home features porcelain floors, a cozy fireplace, a modern kitchen with Carrara Marble countertops, and stainless steel appliances. With new HVAC, roof, windows, and 200-amp electrical service, it's ready for today's lifestyle. The spacious backyard is ideal for outdoor gatherings, and the whole-house generator offers peace of mind. Located just a short stroll from downtown Old Saybrook, this home offers both comfort and convenience. Make this your next home with its residential zoning, or explore AirBnB or business opportunities with its B1 Business zoning. Also listed as commercial MLS #24042932

25 Elm Street, Old Saybrook

Listing courtesy of Daniel Lussier from eXp Realty

$529,000

4 Beds ⋅ 3 Baths ⋅ 24042930 MLS

WELCOME TO YOUR NEW HOME IN OLD SAYBROOK! THIS IVITING FOUR-BEDROOM, SPLIT-LEVEL HOME OFFERS THE PERFECT BLEND OF CONVENIENCE.THE PRIMARY BEDROOM FEATURES A PRIVATE HALF BATHROOM,PROVIDING A LITTLE EXTRA PRIVACY.THE BONUS ROOM ON THE GROUND LEVEL INCLUDES AN ADDITIONAL BATHROOM AND DIRECT ACCESS TO THE BACK YARD,MAKING IT A GREAT SPACE FOR GUESTS OR A HOME OFFICE. YOU'LL LOVE THE GLEAMING HARDWOOD FLOORS THROUGHOUT THE HOME,ADDING A TOUCH OF ELEGANCE AND WARMTH.THE UPDATED KITCHEN IS PERFECTFOR COOKING UP FAVORITE MEALS,AND THE OPEN CONCEPT OF LIVING AND DINING AREAS CREATE A SPACIOUS FEEL THAT'S IDEAL FOR EVERYDAY LIVING.COZY UP BY THE FIREPLACE IN THE LIVING ROOM DURRING COOLER MONTHS,OR ENJOY THE OUTDOORS WITH EASY ACCESS TO THE BACKYARD-PERFECT FOR SUMMER BARBECUES OR RELAXING AFTERNOONS. OLD SAYBROOK IS MORE THAN JUST A PLACE TO LIVE, IT'S A COMMUNITY YOU'LL LOVE BEING PART OF. WITH TWO BEAUTIFUL BEACHES,CHARMING RESTAURANTS,GREAT SHOPPING AND LOCAL GOLF COURSE,THERE'S SOMETHING FOR EVERYONE. IT'S A WONDERFUL PLACE TO LIVE,WORK,AND RELAX.COME AND SEE WHAT MAKES THIS HOUSE A PERFECT HOME.

24 Connally Drive, Old Saybrook

Listing courtesy of Barbara Myslinski-Krucko from William Raveis Real Estate

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 24041853 MLS

This beautifully renovated ranch in the sought-after North Cove neighborhood offers an ideal lifestyle for those who cherish boating and picturesque water views. Situated on a serene .80-acre lot, this expansive home provides effortless one-floor living with stunning vistas of the Connecticut River. The large living room flows seamlessly into a modern kitchen, complete with a spacious island perfect for entertaining. With three generous bedrooms and a cozy den with an adjoining half bath, comfort and convenience are at your fingertips. The thoughtfully designed laundry room, located just off the attached two-car garage, adds an extra layer of practicality, while additional parking space is available for your boating equipment or recreational vehicles. This home is a rare find in a premier location, offering tranquility and a connection to the water that you'll love. Not in a flood zone, walk to both downtown or Saybrook Point amenities. Room for pool if needed. More photos to come.

40 Cromwell Place, Old Saybrook

Listing courtesy of Joel Lucas from Coldwell Banker Realty

$4,475,000

4 Beds ⋅ 5 Baths ⋅ 24038633 MLS

Charming Antique Colonial with North Cove and Connecticut River Views. Step into a piece of history with this enchanting Antique Colonial, gracefully positioned on 1.30 acres with captivating views. Spanning 3,518sqft this residence is a harmonious blend of classic charm featuring 4 bedrooms & 4.1 baths. The allure of this home begins with its landscaped grounds, complete with a private deep water dock, and in-ground pool, and a distinctive pool house. The beautifully designed blue stone patio is perfect for alfresco dining and entertaining amidst the tranquil backdrop of the cove. Inside, you'll be greeted by stunning wide board floors that flow throughout, leading you through light-filled rooms that boast views from every window. Culinary adventures await in the eat-in kitchen, where you can prepare meals by the fireside, surrounded by the home's historic elegance. The home has not one, but two primary suites - one conveniently located on the first floor and another on the second floor, each providing a serene sanctuary with their own unique charm. This Antique Colonial is more than just a home; it's a lifestyle that celebrates the past while offering the comforts and conveniences of modern living. Whether you're sailing from your private dock, lounging by the pool, or simply enjoying the view, this property is sure to captivate your heart and become your cherished waterfront haven

175 North Cove Road, Old Saybrook

Listing courtesy of Colette Harron from William Pitt Sotheby's Int'l

$599,000

4 Beds ⋅ 3 Baths ⋅ 24038453 MLS

This charming home features a new roof, open floor plan, hardwood floors, kitchen with island, stainless steel appliances, door that leads you to a covered deck to enjoy lazy afternoons, cozy eating area with windows allowing for natural sunlight, overlooks family room with inviting fireplace perfect for entertaining, spacious living room and dining room, primary bedroom with skylight and full bathroom, 3 additional generously sized bedrooms upstairs, 2 brand new garage doors, new water treatment system and new oil tank, full basement with plenty of storage. Old Saybrook has two town beaches, Main Street's shops, restaurants, The Kate Cultural Arts Center, Town Park, The Preserve for hiking trails, Saybrook Point and Fenwick Golf Course are a short drive away. Convenient to I95 and the train. Just a few hours from NYC or Boston! Come take a look! New roof next week!

3 Holly Drive, Old Saybrook

Listing courtesy of Sharon Linder from Berkshire Hathaway NE Prop.

$899,475

1 Beds ⋅ 1 Baths ⋅ 24035693 MLS

Your dream home awaits! Stunning year round waterfront property in Old Saybrook. Walk to Saybrook Point Inn and Marina, Main Street and "The Kate". Breathtaking views of South Cove and Saybrook Light House. Enjoy the natural wildlife including an osprey nest while sitting on your new deck with awning. The south cove is separated by the causeway so there are no motor boats coming in and out. Kayak, paddleboard, fish or go crabbing all from your front yard. Situated on a half acre, there is plenty of room to set up a tent for a formal affair or have a picnic with outdoor activities. Easy commute by train or car from NYC.

46 Soundview Avenue, Old Saybrook

Listing courtesy of Rick Loranger from Coldwell Banker Realty

$549,900

3 Beds ⋅ 2 Baths ⋅ 24036877 MLS

Welcome to 23 Clinton Ave, a beautiful home nestled in the beautiful Fenwick neighborhood of Old Saybrook, CT. This delightful residence offers the perfect blend of classic New England charm and modern convenience, all set in a picturesque location with stunning water views. Featuring 3 bedrooms and 2 full bathrooms, it has plenty of room for your family and friends. With a little cosmetic work make this cottage into your own modern summer retreat. This home at 23 Clinton Ave offers a unique opportunity to experience the best of Old Saybrook living. Whether you are looking for a peaceful retreat or a place to entertain family and friends, this property is sure to impress. Make your appointment ASAP!

23 Clinton Avenue, Old Saybrook

Listing courtesy of Victor Santana from Santana Realty Group LLC

$1,249,900

3 Beds ⋅ 2 Baths ⋅ 24035063 MLS

Experience coastal luxury in this stunning 3-bedroom, 2-bathroom home nestled in Knollwood Beach. Set on a rare .89-acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring a grand staircase with wrought iron and white oak railings/spindles, massive pine clad ceiling beams, and an expansive remodeled white kitchen with quartz counters, white washed wood ceiling, large center island and a charming coffee bar with live edge countertop. The family room boasts a dramatic propane fireplace, while a sunlit dining room/sunroom offers panoramic views of the marsh and Cove. Choose between a first-floor primary bedroom or an upstairs retreat with a sitting/dressing room, walk-in closet and gorgeous full bath with heated tile floors. The office loft is a dreamy space overlooking the first floor with views of South Cove. Additional features include a partially finished basement, central air, freshly painted exterior and main floor, remodelled baths, updated electrical, gutter guards and refinished hardwoods. Enjoy beach rights and clubhouse access, tennis/pickleball courts and playground through the Knollwood Beach Association, a golf cart community, enhancing your coastal lifestyle in this exceptional home.

41 Cypress Road, Old Saybrook

Listing courtesy of Lynn Toper from CR Premier Properties

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