Old Saybrook Real Estate

Welcome to Old Saybrook, Connecticut, a charming coastal gem nestled in Middlesex County. This picturesque town, steeped in history, offers a unique blend of small-town charm and vibrant community life, making it an ideal place to call home.

Founded in 1635, Old Saybrook boasts a rich historical tapestry that is beautifully woven into its scenic landscapes. The town is situated at the confluence of the Connecticut River and Long Island Sound, providing stunning waterfront views and an abundance of recreational opportunities. Whether you enjoy sailing, fishing, or simply strolling along the picturesque shoreline, Old Saybrook offers a plethora of outdoor activities to savor.

The town’s historic downtown area features an array of boutique shops, delightful cafes, and restaurants that serve everything from fresh seafood to artisanal coffee. The local farmers’ market, held weekly, showcases the best of Connecticut’s produce and artisanal goods, fostering a sense of community and supporting local businesses.

Old Saybrook is also home to several cultural attractions, including the renowned Katharine Hepburn Cultural Arts Center, which hosts a variety of performances and events throughout the year. Nature enthusiasts will appreciate the nearby parks and nature preserves, such as the scenic Saybrook Point and the expansive Hammonasset Beach State Park, perfect for hiking and picnicking.

With its excellent schools, friendly neighborhoods, and a strong sense of community, Old Saybrook presents an inviting atmosphere for families, retirees, and everyone in between. Discover the charm of Old Saybrook, where history meets modern living, and find your perfect home in this delightful coastal town!

Newest Listings in Old Saybrook

$749,000

3 Beds ⋅ 3 Baths ⋅ 24204473 MLS

This meticulously maintained hidden gem features an inviting open floor plan with a dramatic double-sided fireplace creating warmth and character between the main living areas. The living room is enhanced by beautiful built-ins and a charming reading nook, while the spacious kitchen features an expansive island, built in china cabinets with plenty of room for family gatherings, casual dining and entertaining. Just beyond, the sunroom with skylights is filled with natural light and provides a peaceful place to relax throughout the seasons. The recently updated bathrooms add a fresh, polished feel, while a new roof and a newer heating and cooling system installed has five mini-split units offering added comfort and peace of mind. The full basement is partially finished, providing flexible space for a home gym or casual hangout, while still offering excellent storage. Outdoors, this hidden gem continues to impress. A fenced in yard enhances privacy, along with an expansive deck and heated Gunite saltwater pool and surrounding entertaining areas create a wonderful setting for summer enjoyment. You are on vacation every day in your backyard! Backing directly to a nature preserve this home enjoys a natural peaceful setting and access to nearby trails and outdoor recreation. Ideally located just minutes from Old Saybrook's vibrant Main Street, shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living

6 Nutmeg Cir Old, Old Saybrook

$549,000

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

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, Main Street shops, 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

$1,380,000

5 Beds ⋅ 3 Baths ⋅ 24205169 MLS

Step through the front door and experience a warm European inspired feel in this distinctive Fenwood Beach Association home. Offering exceptional flexibility and comfortable one-level living, the home features four bedrooms in the original residence, plus an additional bedroom and spacious in-law/primary suite in the addition, ideal for multi-generational living, guests, or a private retreat. The gourmet kitchen is the heart of the home, featuring granite countertops, custom cabinetry, a Viking refrigerator, Bertazzoni ovens and cooktop, and Vitev alkaline filtration system. A large eat-in area accommodates a long dining table, while the nearby laundry room adds everyday convenience. A wood-burning stove brings warmth and charm to the kitchen area. Just off the kitchen, the inviting family room flows into a bright three-season/Florida room, extending the living and entertaining space. The spacious in-law/primary suite offers privacy with a large living room, full kitchen with pocket doors, private bedroom and bath, and fireplace. Outside, enjoy a beautiful backyard with patio, large storage shed, and outdoor hot-water shower-perfect after a day at the beach. An oversized two-car garage and two separate attics provide excellent storage. Located in the desirable Fenwood private beach association, this home offers a relaxed coastal lifestyle with private beach access, character, flexibility, and exceptional one-level living.

46 Fenwood Grove Rd, Old Saybrook

$789,900

2 Beds ⋅ 4 Baths ⋅ 24205240 MLS ⋅ Oyster River Landing BLDG.

Welcome to Oyster River Landing, a hidden shoreline retreat featuring just 20 distinctive townhomes. This peaceful community offers a private marina and a beautiful swimming pool overlooking the Oyster River. Spend quiet mornings on your private patio or embrace the coastal lifestyle with boating, kayaking, and paddleboarding along the river, which opens to Long Island Sound just a short distance away. Boat slips and storage are available and included for owners. The beautifully updated residence features a fully renovated eat-in kitchen, hardwood flooring throughout the main living level and bedroomsnt. The spacious dining room is ideal for entertaining, while the inviting living room offers a wood-burning fireplace and sliders leading to the private patio. Upstairs, two generously sized bedrooms each include a private full bathroom, along with the convenience of upper-level laundry. Additional highlights include a main-level powder room, a finished lower-level family room with a full bath, workshop and storage space, and a detached garage. Two sandy beaches are just a short stroll away, while Old Saybrook's charming village, restaurants, shops, The Kate Cultural Arts Center, Saybrook Point, marinas, fishing, and scenic walking and biking trails are all nearby. Conveniently located within a few hours of New York City and Boston by car or train, this exceptional shoreline oasis is ready to welcome you

25 Sunset Rd Unit 18, Old Saybrook

$699,900

3 Beds ⋅ 2 Baths ⋅ 24202240 MLS

Spacious ranch with an impressive second-story primary suite, set in Old Saybrook's desirable Saybrook Point area and close to some of the town's best-loved destinations. Stroll to Main Street for restaurants, boutique shopping and a show at The Kate, or head toward Saybrook Point and the nearby marinas. The town beach is just minutes away. Inside, hardwood floors and abundant natural light welcome you into the main living area, where a pellet stove creates a warm focal point. The kitchen and dining area flow easily into the living room, while a first-floor office with sliders to the patio provides flexible space for working from home, a den or exercise. Two bedrooms and a full bath complete the main level. Upstairs, the spacious private primary suite features 9+ foot ceilings, a walk-in closet, laundry hookup and space for a full en-suite bath. The double vanity and toilet are already installed, with the shower roughed in and ready for the next owner to complete. Outside, enjoy a level .29-acre lot enclosed by 6-foot vinyl fencing, along with a large Klotter Farms shed for additional storage. The oversized 29' x 24' attached garage is another standout, offering exceptional room for vehicles, a golf cart, workshop, lawn equipment and storage. Enjoy central air, public water, 200-amps and a septic system installed in 2023. This is a fantastic opportunity to enjoy the OS lifestyle with Main Street, Saybrook Point, marinas, beaches, dining, and shopping all nearby.

6 Willard St, Old Saybrook

$550,000

3 Beds ⋅ 3 Baths ⋅ 24204068 MLS

Great opportunity to move into Old Saybrook! This spacious two level raised ranch offers 1 floor living - ranch style on the second floor with 3 bedrooms and two baths, kitchen and dining and living room with LOTS of closet space and a large deck. On the lower level a finished off family room and office complete with a full bath and a laundry room. A large two car detached garage with a large loft above would be great for a home office, gym or studio. Come take a look and jump on this opportunity! Professional photos coming soon!

61 Springbrook Rd, Old Saybrook

$899,000

4 Beds ⋅ 2 Baths ⋅ 24190267 MLS

Live every day like you're on vacation in sought-after Knollwood Beach! Lovingly enjoyed by the same family for nearly 50 years, this attractive four-bedroom, one-and-a-half-bath home offers a wonderful opportunity to become part of one of Old Saybrook's most desirable beach communities. Inside, the comfortable floor plan features a welcoming living room with built-in bookcases, and a cozy fireplace that add warmth and character. Sunlight pours into the adjoining sunroom, offering a peaceful retreat overlooking the outdoors. The inviting kitchen is filled with natural light and has been meticulously maintained, featuring warm wood cabinetry, stainless steel appliances, and Corian countertops. A welcoming breakfast nook at one end provides a comfortable spot for morning coffee or casual meals, while the adjoining first-floor laundry room adds everyday convenience and valuable storage. Just off the kitchen, the sun-filled dining room offers a comfortable setting for entertaining and gathering. Updates include a newer roof and heated bathroom floor, irrigation system and vinyl siding. Wood floors lie beneath much of the existing carpeting-ready to be revealed. A brick driveway and walkway wind toward the side entrance, setting a welcoming tone from the moment you arrive. The detached one-car garage and shed adds valuable storage for bikes, beach chairs, umbrellas, and all the essentials for a day by the water. No flood insurance.

30 Neptune Dr, Old Saybrook

$795,000

3 Beds ⋅ 1 Baths ⋅ 24204260 MLS

Spectacular South Cove views, deeded beach rights and remarkably low taxes make this nicely updated shoreline home an exceptional opportunity! Set on a beautiful half-acre lot, this spacious split-level offers 3-4 bedrooms, a versatile floor plan and wonderful water views that bring the coastal setting right into your everyday life. Inside you'll find hardwood floors, double oven, a fireplace for cozy evenings and air conditioning for summer comfort. The flexible layout provides plenty of room for family and guests, a home office or additional living space. A 2-car garage offers excellent parking and storage, while major improvements including a newer roof , heating system and septic system add peace of mind. Enjoy the generous half-acre setting and beautiful views of South Cove, or take advantage of your deeded beach access and embrace the shoreline lifestyle. Whether you're looking for a year-round residence, weekend escape or summer retreat, this property offers the hard-to-find combination of water views, beach rights, an updated home, 2-car garage and sizable lot. With annual property taxes just under $5,000, this is an outstanding value for coastal living!

5 Tudor Ct E, Old Saybrook

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 24203677 MLS

Contemporary coastal elegance meets remarkable privacy along South Cove in Old Saybrook. Set well back from the road on 1.8 acres, this distinctive 3,188-square-foot cedar-sided residence captures sweeping water views from nearly every room. Originally built in 1965 and completely rebuilt in 1991, the home was thoughtfully designed to embrace its spectacular setting, with vaulted ceilings, expansive windows, and seamless connections to the outdoors. The living room features custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a vaulted family room and opens to a 300-square-foot enclosed porch-an inviting space for entertaining or relaxing. The main-level primary suite is a private retreat with vaulted ceilings, deck access, water views, dual bathrooms, and an impressive 120-square-foot walk-in closet. A formal dining room, additional bedroom, and separate laundry room complete the first floor. Upstairs, two bedrooms share a Jack-and-Jill bath. With 1.8 private acres and 278 feet of frontage along South Cove, this property offers a rare blend of waterfront, space, and seclusion. Whether enjoyed as a year-round residence or treasured coastal retreat, this is a setting that simply cannot be replicated.

108 Maple Ave, Old Saybrook

$499,999

3 Beds ⋅ 1 Baths ⋅ 24202909 MLS

This Bright, freshly Painted, 1951 3 bedroom Ranch is located on Schoolhouse Road in Old Saybrook, Connecticut with quintessential New England charm, public beaches and parks, major access to interstate and state highways, commuter rails and long distance railways, and public transportation a short walk away. The property is situated on a .87 acre level lot, and has a two Car detached, oversized garage with a lean two shed. The basement includes a workshop area and porcelain wash sink, plenty of storage to boot. Please schedule your appointment today using Showtime!

35 School House Rd, Old Saybrook

$779,000

2 Beds ⋅ 3 Baths ⋅ 24200662 MLS ⋅ Sheltered Cove BLDG.

Spectacular North Cove unobstructed water views and downtown village living come together in this beautifully renovated townhouse-style condo, offering an exceptional opportunity for shoreline buyers seeking a turn-key home under $1 million. Enjoy captivating water views and wildlife from the open kitchen, dining and living areas, with a stylish renovated kitchen featuring a breakfast bar and wonderful natural light. The spacious two-bedroom layout includes a primary bedroom with its own full bath and spectacular views overlooking North Cove. With 2.5 baths, a wood-burning fireplace, central air, one-car garage and a dry full basement offering excellent potential for additional finished space, this home has everything you need for year-round or weekend living. Ideally located in the heart of the village, walk to downtown restaurants, shops and more, while the train station, golf course and town beach are just minutes away. The association also offers a large clubhouse with kitchen for gatherings and a wonderful in-ground pool. Best of all, enjoy spectacular shoreline views without the need for flood insurance. By appointment only.

100 Dudley Ave Unit F30, Old Saybrook

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