Old Saybrook Real Estate

Welcome to Old Saybrook, Connecticut – a charming coastal town that beautifully marries rich history with modern living. Nestled in Middlesex County, Old Saybrook is ideally situated at the confluence of the Connecticut River and Long Island Sound, making it a picturesque destination for both residents and visitors alike.

Founded in 1635, Old Saybrook boasts a vibrant history that is palpable as you stroll through its quaint streets. The town is home to several historic landmarks, including the iconic Saybrook Point Lighthouse, which has stood sentinel over the waters for over a century. The lush landscapes and scenic waterfront not only provide breathtaking views but also offer a myriad of recreational activities, from sailing and fishing to hiking along the picturesque trails of the nearby Preserve.

Old Saybrook is also known for its tight-knit community and excellent schools, making it an ideal place for families. The town hosts a variety of local events throughout the year, including farmers' markets, art festivals, and summer concerts, fostering a sense of belonging and camaraderie among residents.

Culturally rich, Old Saybrook is home to the renowned Katharine Hepburn Cultural Arts Center, where art, theater, and music come together to create unforgettable experiences. With its charming boutiques, delightful dining options, and serene beaches, Old Saybrook offers a perfect blend of relaxation and excitement.

Whether you're looking for a peaceful retreat or an active lifestyle, Old Saybrook invites you to explore all that this enchanting town has to offer. Come discover your next home in this idyllic slice of Connecticut!

Newest Listings in Old Saybrook

$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

$495,000

4 Beds ⋅ 3 Baths ⋅ 24215261 MLS

Enjoy the best of Old Saybrook living with this charming ranch ideally situated within walking distance to Main Street's wonderful restaurants, shops, and local attractions, and walking distance to seee beautiful water views. Offering easy one-floor living, spacious living areas, hardwood floors, and a full basement with partially finished space, this home is filled with possibilities! A lovely private backyard provides the perfect setting for relaxation or entertaining. Bring your personal style and vision to make this home your own. Whether you're looking for a year-round residence or a shoreline retreat, this is a wonderful opportunity to enjoy the Old Saybrook lifestyle in a fantastic, walkable location. Convenient to beaches, shopping, the train station, and major highways!

50 Dudley Ave, Old Saybrook

$1,777,000

3 Beds ⋅ 4 Baths ⋅ 24213563 MLS

***HIGHEST AND BEST DUE BY MONDAY 10/26 by 5PM**** Beautifully maintained Cape in the sought after Fenwood Beach community, offering ocean views and a short walk to the community's private beach. Enjoy the best of shoreline living with timeless charm, spacious interiors, and versatile living spaces. Cherry hardwood floors, a custom kitchen with breakfast nook opening to the backyard entertaining patio, formal dining room, living room with fireplace, and a cozy family room create a warm, inviting atmosphere. First-floor bedroom w/full bath and convenient laundry room add flexibility. Upstairs the primary suite features a walk-in closet, full bath w/soaking tub and separate walk-in shower, and private balcony with awning and ocean views. The family den offers its own fireplace and balcony access, creating an ideal second gathering space. Room to grow and space for everyone! A versatile bonus room, accessible from both levels, offers options for a home office, playroom, added bedroom or hobby space. Along with the upstairs den and separate exercise room, these flexible areas adapt to a growing family, remote work, guests, and changing needs. Enjoy a three-season enclosed porch, abundant closets, walk-up attic, and spacious two-bay garage with extra storage. Professionally landscaped grounds feature an irrigation system and patio for outdoor entertaining. Experience the charm of Old Saybrook, beautiful ocean views, and private beach access.

22 Fenwood Dr, Old Saybrook

$375,000

1 Beds ⋅ 1 Baths ⋅ 24215648 MLS ⋅ Summerwood Condo BLDG.

Discover the perfect blend of coastal living, comfort, and convenience in this beautiful condo offering exceptional amenities, including a private beach, swimming pool, and tennis courts! Thoughtfully updated and filled with charm, this inviting home features an open floor plan, beautiful hardwood floors, and a cozy fireplace that creates a warm and welcoming atmosphere. The delightful enclosed front sunporch offers the perfect spot to enjoy your morning coffee, unwind with a good book, or simply relax. The main level features a spacious bedroom with oversized closet and full bath in hallway , while the finished upper-level bonus room offers wonderful versatility as an office or family room. There is plenty of storage upstairs with a large walk in closet. A one-car garage and plenty of storage add to the appeal. Enjoy easy, low-maintenance living with the added benefit of a fantastic community and amenities just steps from your door. Ideally situated minutes from Old Saybrook's restaurants, shopping, beaches, train station, and major highways. Whether you're looking for a year-round residence or a relaxing coastal escape, this hidden gem offers an incredible opportunity to enjoy all that Old Saybrook has to offer!

78 Sandy Point 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

$140,000

24206910 MLS

Tina Perma Beauty Spa is a turnkey, fully equipped beauty studio in the heart of Old Saybrook's Main Street corridor in one of the most affluent shoreline markets in the Northeast. Established in 2020, the studio has built a loyal repeat clientele across permanent makeup, laser treatments, lash and brow services, waxing, and full nail care. What makes this offering unusual is the combination of three things a buyer rarely finds together: demonstrated growth, an exceptionally low fixed cost base, and clear untapped pricing capacity. Revenue climbed 26% in 2025 while occupancy cost held at roughly $800 per month - under 9% of gross revenue. The result is a discretionary earnings margin near 50% on a business that has never carried a marketing budget above $2,300 a year. The studio conveys fully equipped, including two commercial laser platforms, an established website and social presence, and a client database with booking system. A qualified buyer steps into an operating business with revenue on day one.

15 N Main St, Old Saybrook

$699,000

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, 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

Start Your Search

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.

Old Saybrook Real Estate

Newest Listings in Old Saybrook

How much is your home worth?

How much is your home worth?