Refine Search
Map
Sort by
$499,000
24206156 MLS
Fantastic Indian Town Association building lot. This one is cleared and flat. Looks beautiful as it is. Buy as a land bank or come build today.

65 Old Sea Ln, 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
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 24199678 MLS
Meticulously maintained and beautifully updated, this exceptional home offers refined coastal living in the desirable Fenwood Beach Association. Fully rebuilt and redesigned in 2008. Privately situated on a cul-de-sac with partial water views, the home showcases quality craftsmanship throughout, including hardwood floors and a stunning renovated kitchen featuring custom cabinetry, granite countertops, a generous center island including a renovated eating area with plenty of sunshine overlooking the backyard. The inviting main level offers wonderful spaces for both everyday living and entertaining, including a gracious dining room, living room with gas fireplace, family room with built-ins and charming reading nook. Upstairs, primary bedroom with luxurious fully renovated bathroom and oversized walk in closet. An additional three spacious bedrooms are complemented by a family room with built-ins and renovated bathroom. Additional improvements include a renovated half bath and laundry room, generator ready and multi room full house audio including outside, and new garage doors. Outdoors, enjoy a private patio with partial water views - an ideal setting for entertaining or relaxing after a day at the beach. Fenwood's kayak/paddle board launch is a minute away while the beach is a short stroll to enjoy the sunset. Close to golf, Saybrook Point, the causeway, two town beaches, Main Street restaurants and shops!

11 Fencove Ct, Old Saybrook
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 24199659 MLS
A Rare Coastal Opportunity Awaits! Set in the highly sought-after North Cove Historic District of Old Saybrook, this grand colonial offers something truly special: a coveted prime coastal location, spectacular water views, and incredible potential to create the home you've always envisioned. Originally built in 1930 and expanded in 1987, this property has the character, scale, and bones of a remarkable coastal residence-but today, it's ready for a new vision. With water views from nearly every room, spacious living areas, French doors leading out to a large deck, beautiful bay windows, a brick fireplace, a first-floor primary suite, four bedrooms, three and a half baths, a two-car garage with loft space, and an exceptional setting-there is truly so much to work with. The existing layout provides a strong foundation for someone looking to renovate, reimagine, and create a truly spectacular coastal retreat in one of Connecticut shoreline's most desirable neighborhoods. Located within walking distance of local restaurants, shops, beaches, and everything else that Main Street has to offer. Property being sold in "as is".

138 N Cove Rd, Old Saybrook
$799,500
3 Beds ⋅ 2 Baths ⋅ 24200281 MLS
KNOLLWOOD BEACH - Here is the opportunity! A recently sparkled-up home. This beach house lives on a wide, 0.98-acre lot offering possibilities rarely found this close to the shoreline. First time since it was built. Come and live it up now! This one can generate rental income, or land-bank this parcel while planning something much more commodious for tomorrow. Knollwood is renovation-active, with many projects currently underway surrounding this home-a proven location for substantial improvements and new construction. Recent upgrades include a new 200-AMP electrical panel, central A/C, and forced-air heat and vinyl siding. Downstairs is made for entertaining in the family room, featuring a newer wood stove, a '70s show bar with a sink, an office/mudroom from the garage, a workshop, laundry, and a half bath. The wide lot (97 feet of frontage) features a circular driveway leading to the one-car garage. Step onto the rear deck for marsh views and a spacious backyard with room for a fire pit and outdoor gatherings. Enjoy the association beach, pier and walkway, clubhouse, tennis/pickleball courts, basketball and baseball fields, and playground. Use it today while enjoying the tremendous fun this Old Saybrook location has to offer. There is plenty of upside for grand expansion tomorrow or simply making more fond memories every day.

71 Knollwood Dr, Old Saybrook
$285,000
24200155 MLS
Rare opportunity to create something special in the heart of Old Saybrook! Set on .25 acres on a quiet dead-end street, this in-town property offers the kind of location that is increasingly difficult to find along the Connecticut shoreline. Easily walkable to Main Street with sidewalk access along the way, enjoy morning coffee, restaurants, shopping, the library, and the charm of downtown Old Saybrook just moments from home. Beaches, marinas, the Connecticut River, Old Saybrook train station, and shoreline attractions are all just minutes away. The property is currently improved with an existing three-bedroom home that has been loved and occupied by the same owner for more than 40 years. The home requires extensive renovation and the entire property is being sold strictly AS IS. This is an opportunity for a builder, investor, or developer to consider a substantial renovation or explore the potential for a new home, subject to all town and zoning approvals. Whether searching for Old Saybrook land, an in-town building opportunity, investment property, renovation project, or a place to create a new year-round or shoreline home, this property offers location, walkability, and possibilities that are hard to duplicate. Bring your builder, your ideas, and your vision!

43 Quarry St, Old Saybrook
$285,000
3 Beds ⋅ 1 Baths ⋅ 24199926 MLS
43 Quarry Street, Loved and occupied by the same owner for more than 40 years, this three-bedroom home on Quarry Street presents a rare opportunity in the heart of Old Saybrook. Set on .25 acres on a quiet dead-end street, the real story here is the location. Enjoy an easy walk with sidewalk access into Old Saybrook's vibrant Main Street for coffee, restaurants, shopping, the library, and all the conveniences of town. Beaches, marinas, the Connecticut River, and Old Saybrook train station are just minutes away. The property is being sold strictly AS IS and requires extensive renovation, offering an opportunity for a builder or investor to reimagine the existing home or explore the potential for a new vision for the property, subject to town approvals. For those looking for an in-town Old Saybrook property, renovation project, investment opportunity, or potential building site, this is a location worth a closer look. Bring your ideas and vision to a property that has been held for decades in one of Old Saybrook's wonderfully convenient and walkable locations. Cash, proof of funds required.

43 Quarry St, Old Saybrook
$1,225,000
3 Beds ⋅ 1 Baths ⋅ 24199561 MLS
Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield Point, one of Connecticut's most desirable beach communities. Ideally located just steps from the beach. This move-in-ready home offers the perfect combination of comfort, coastal living, and breathtaking water views. The home features 3 bedrooms and 1 full bath, along with a bright living room showcasing stunning water views. The kitchen is equipped with new appliances, while the convenient laundry area includes all appliances. Recent improvements include a new boiler and hot water heater, providing added comfort and peace of mind. Enjoy the coastal lifestyle from the enclosed breezeway, which offers beautiful water views, or relax on the remodeled upper deck-perfect for morning coffee, entertaining, or taking in the surrounding scenery. A spacious one-car garage provides excellent storage and convenience. As a member of the Cornfield Point Beach Association, you'll enjoy an array of amenities, including a private beach, basketball court, tennis court, clubhouse, and private boat ramp. Whether you're looking for a year-round residence, weekend getaway, or a place to enjoy the best of shoreline living, this community offers an exceptional lifestyle.

24 W Shore Dr, Old Saybrook
$599,000
3 Beds ⋅ 2 Baths ⋅ 24196117 MLS
Location, location, location. Enjoy shoreline lifestyle in one of Old Saybrook's in demand neighborhoods. Level corner lot. Solid home ready for you to make it your own. Eight total room, three bedrooms, two full baths one updated. Fireplace in the Living room. Sunroom, one car attached garage. Full unfinished basement. Incredible opportunity to create the home of your dreams. Enjoy coastal living in Old Saybrook, around the corner from Kavanaugh Park, Trask Road area with tennis, splash pad, playground, ball field, basketball, picnic area. Short walk to beaches, Main Street, Schools Library and The Kate theatre. Close to train station for easy commute.

46 Farview Ave, Old Saybrook
$1,199,000
3 Beds ⋅ 2 Baths ⋅ 24197776 MLS
Enjoy coastal living in the sought-after Knollwood Beach Association. This well-maintained, sun-filled home is just a short stroll from the beach, where beautiful shoreline walks, golf cart rides and a vibrant neighborhood setting are just moments from home. Offering a gracious sense of space, comfort and versatility, the home is equally suited for year-round living or a memorable coastal retreat. The bright, open floor plan is filled with natural light and designed for easy everyday living and entertaining. Two bedrooms on the main level provide the option for one-floor living, while two additional spacious bedrooms upstairs offer flexibility for family and guests. The kitchen features granite countertops and generous seating for meals and holidays, while plantation shutters add a timeless finishing touch throughout the home. A partially finished lower level provides additional flexible living space. Outside, a fully fenced yard and expansive patio create an inviting setting for summer gatherings, outdoor dining and relaxed evenings after a day at the beach. Knollwood Beach Association amenities include private beach access, clubhouse, tennis and basketball courts, all just moments from your doorstep. An exceptional opportunity to enjoy the quintessential Old Saybrook coastal lifestyle in one of the shoreline's most sought after communities. Conveniently located minutes from Main Street, shops, restaurants, Saybrook Point, golf, highways and the train.

38 Jarvis Rd, Old Saybrook
$550,000
3 Beds ⋅ 1 Baths ⋅ 24198488 MLS
One floor living in Old Saybrook! This ranch home is a part of the Indian Town Beach association and also conveniently located on Boston Post Road which has beautiful new sidewalks connecting this property to both beaches and shops and restaurants all within walking distance. A picture window gives the living room lovely natural light and a wood burning fireplace for chilly winter nights. An open kitchen / dining room features sliding doors out to a nice large deck - great for entertaining. Hardwood floors throughout, 3 bedrooms and a bathroom with laundry complete the main level. The walk-out basement offers lots of possibilities with its high ceilings. A nice large private back yard includes a lovely deck, vegetable gardens and a one car garage. Come take a look as this property won't last!

1324 Boston Post Rd, Old Saybrook
$725,000
4 Beds ⋅ 2 Baths ⋅ 24189749 MLS
Rare opportunity to own a classic Connecticut shoreline beach cottage in the highly sought-after Cornfield Point Beach Association. Located just five homes from the water, this seasonal cottage offers water views from the enclosed breezeway and captures the timeless charm of Old Saybrook coastal living. Original hardwood floors, knotty pine walls, authentic beadboard, oversized rooms, and a stunning beach stone fireplace showcase the character and craftsmanship rarely found today. Designed for generations of summer memories, this vintage beach home also features a detached garage, outdoor shower, and inviting indoor and outdoor living spaces perfect for entertaining after a day at the private sandy beach. Enjoy one of the Connecticut shoreline's most desirable golf cart-friendly beach communities with easy access to the beach, boating, kayaking, swimming, fishing, and breathtaking sunsets. Surrounded by beautiful custom coastal homes, this property offers exceptional flexibility to preserve its historic New England charm, renovate, expand, or build your dream waterfront-inspired beach house. Whether you're searching for a seasonal retreat, vacation home, weekend getaway, investment property, or future new construction opportunity, this rare Old Saybrook offering combines water views, private beach association access, an unbeatable location, and endless potential in one of Connecticut's premier shoreline communities.

27 Gates Rd, Old Saybrook
$1,590,000
4 Beds ⋅ 3 Baths ⋅ 24197254 MLS
13 College Street | Old Saybrook, CT TO BE BUILT Discover the opportunity to build your dream home in one of Old Saybrook's most desirable locations-Saybrook Point. Thoughtfully designed with luxury, comfort, and flexibility in mind, this exceptional new construction home offers approximately 2,070 square feet, four bedrooms, two and one-half baths, and the ability to personalize finishes to suit your style. The open-concept floor plan is highlighted by a dramatic vaulted-ceiling living room that seamlessly flows into the dining area and gourmet kitchen, creating an inviting space for everyday living and entertaining. The kitchen is designed with quartz countertops, custom millwork cabinetry, a spacious butler's pantry, and an appliance allowance, giving buyers the opportunity to select the finishes that best reflect their vision. The desirable first-floor primary suite provides convenience and privacy, featuring a spacious layout and a luxurious en-suite bath. Hardwood flooring extends throughout the home, adding warmth and timeless appeal. Situated on a generously sized lot with approximately 200 feet of backyard depth, the property offers exceptional potential for future expansion, including space for a pool, outdoor entertaining area, or a possible accessory dwelling unit (ADU), subject to local approvals.

13 College St, Old Saybrook
$699,000
3 Beds ⋅ 3 Baths ⋅ 24197434 MLS
Tucked away on a peaceful cul-de-sac off School House Road, this beautifully maintained Cape offers over 2,700 square feet of finished living space in one of Old Saybrook's most desirable locations. Directly across from The Preserve trail access and just moments from Clark Park, this home is perfectly positioned for those who appreciate nature, recreation, and privacy. The inviting main level features a spacious living room with gleaming hardwood floors and a classic wood-burning fireplace, a formal dining room, convenient half bath, and an updated kitchen with rich cherry cabinetry and granite countertops that flows seamlessly into a warm and welcoming family room with a Garrison wood-burning stove. Sliders open to a stunning cedar-paneled three-season room overlooking the private backyard, expansive deck, and patio-an ideal setting for relaxing or entertaining. Upstairs, the spacious primary suite offers a beautifully sized en-suite bath with custom shower, while two additional bedrooms and a second full bath provide plenty of room for family and guests. A fully finished lower level is the perfect space for an at home gym, office or family room! Thoughtful updates throughout, including Andersen replacement windows, newer garage doors, enhanced attic insulation, 200amp service and ice dam heating cables, provide lasting value and peace of mind. A rare opportunity to enjoy timeless charm, modern updates, and an exceptional location...truly move-in ready.

11 Kitteridge Hill Rd, Old Saybrook
$649,000
2 Beds ⋅ 2 Baths ⋅ 24196847 MLS
Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Association. Offered As-Is and thoughtfully updated, this inviting home is ideal as a year-round residence, weekend escape, or classic summer getaway. With marsh views, salt air, and a relaxed beach-community setting, this is a turnkey opportunity designed for immediate enjoyment without the added cost or effort of furnishing the home. Inside, the home is bright, comfortable, and beautifully maintained. High-velocity central air conditioning adds a premium level of comfort not always found in beach-area homes, and the heating and cooling components are less than five years old. The living spaces are warm and efficient, offering the simple, low-maintenance lifestyle buyers seek near the shoreline. The surprise is downstairs, where approximately 221 square feet of finished lower-level space, not reflected in the public record square footage, provides valuable flexibility. Use it as a media room, home office, guest overflow area, hobby space, exercise area, or quiet retreat after a day at the beach. Outside, the deck, marsh views, and coastal breeze create the setting people come to Old Saybrook for. Spend mornings with coffee, afternoons enjoying Chalker Beach, and evenings relaxing in a home that is already set up and ready to enjoy. A rare chance to own a furnished, updated, move-in-ready coastal retreat in one of Old Saybrook's beloved beach communities.

8 Kenn Rd, Old Saybrook
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 24195903 MLS
Introducing a rare opportunity to build your dream home in one of Connecticut's most desirable shoreline communities. Located at 81 Essex Road in Old Saybrook, this to-be-built home by Silvin Homes offers the flexibility to choose from multiple thoughtfully designed floor plans and finishes, allowing you to create a home that fits your lifestyle and budget. What truly sets this property apart is something that's nearly impossible to find, your own deeded 47-foot boat slip in the sought-after Channelside Association. Launch into the Connecticut River, cruise to Long Island Sound, or enjoy waterfront dining by boat, all from your own backyard. Wake up to water views, spend summer evenings on the dock, and experience the boating lifestyle that makes Connecticut's shoreline so special. Whether you're looking for a year-round residence or a coastal retreat, you'll enjoy all that Old Saybrook has to offer, from charming downtown shops, award-winning restaurants, marinas, beaches, golf, and the historic Kate Theater, to convenient access to I-95 and rail service for an easy trip to New York or Boston. With the peace of mind, energy efficiency, and customization that come with new construction, combined with an included boat slip, this is a truly exceptional opportunity that's rarely available at this price point. Build the home you've always wanted and enjoy the shoreline lifestyle you've been dreaming of.

81 Essex Rd, Old Saybrook
$1,750,000
24195477 MLS
APPROVED OCEANFRONT LOT - WALK TO THE BEACH FROM YOUR BACKYARD Design the life you've always envisioned. Whether you dream of a timeless shingle-style coastal retreat or a striking modern waterfront masterpiece, this exceptional homesite offers the perfect canvas to bring your vision to life. This fully approved, level building lot is ready for construction, allowing you to move forward with confidence and begin creating the coastal home you've always imagined. Enjoy the rare opportunity to step from your backyard and take a short walk to the beach, embracing the very best of shoreline living. As a resident of the Borough, you'll enjoy exclusive access to exceptional amenities, including a beautifully maintained historic nine-hole golf course, private Borough tennis courts, and a charming coastal community known for its timeless New England character. Whether you're seeking a year-round residence or the ultimate seaside retreat, this is a rare opportunity to build in one of Connecticut's most desirable waterfront communities. Come walk the property and experience its exceptional setting and endless potential for coastal living.

101-A Sequassen Ave, Old Saybrook
$1,500,000
1 Baths ⋅ 24194226 MLS
Unique mixed-use investment and redevelopment opportunity. The ground-floor commercial spaces are fully occupied, providing immediate rental income, while the upper level offers approximately 3,540 square feet of office space. The expansive second floor may also offer the potential to be converted into two oversized three- or four-bedroom residential units, subject to zoning and municipal approvals. This property combines stable existing occupancy with significant value-add potential in a desirable shoreline location.

880 Boston Post Rd, Old Saybrook
$999,000
3 Beds ⋅ 3 Baths ⋅ 24192820 MLS
Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic 12-over-12 windows. It has been lovingly maintained for decades by a master craftsman and a devoted gardener, with a deep respect for historic properties. There is an adorable guest cottage which offers wonderful flexibility for visitors, or as an in-law suite or private studio. This building is not included in the total square footage or room count. The beautiful barn/carriage house holds two cars plus a unique blacksmith workshop. The picturesque grounds feature several gardens for seasonal color, mature shade trees, and a fenced vegetable garden area with a charming hand-built garden shed with running water. With its strong history and distinctive architecture, the home is listed on the National Registry of Historic Places. Rarely does a home of this significance become available - offering the perfect balance of history, craftsmanship, natural beauty, and timeless New England charm in a coastal community. The location is also ideal, close to Main St attractions, shopping, restaurants, beaches, and the train station. It is almost equal distance to Boston and New York.

170 Old Post Rd, Old Saybrook
$1,200,000
1 Baths ⋅ 24193657 MLS
90 foot conveyer belt tunnel system Large leeching field/water recycling tanks Prime shoreline retail corridor location (along US-1) Near major shopping destinations including big-box anchors and regional retail plazas Abutting & visible from I-95, 660 feet from ramp Traffic Count: 15,900 +/- ADT

277 Boston Post Rd, Old Saybrook
$750,000
2 Beds ⋅ 2 Baths ⋅ 24189175 MLS
Welcome to the desirable Indiantown Beach community, where endless possibilities await. This well-loved home offers a spacious floor plan featuring a bright sunroom, generous family room with a floor-to-ceiling gas fireplace and built-ins, and a large primary suite with its full bath and own private deck. Ready for cosmetic updates, this home presents an excellent opportunity to create your dream beach retreat in one of Old Saybrook's most sought-after shoreline neighborhoods. Enjoy outdoor living with a spacious deck, large patio, fenced yard and storage shed-perfect for entertaining, gardening, or relaxing after a day at the beach. As a resident of Indiantown Beach, you'll enjoy access to two private beaches, a marina, clubhouse, playground, and a variety of community events throughout the year. Conveniently located just minutes from Old Saybrook's Main Street, restaurants, shopping, marinas, and local amenities, this property offers the rare opportunity to personalize a home in an exceptional coastal location. Bring your vision and make this beach house your own!

25 Uncas Trl, 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.