Refine Search
Map
Sort by
$829,000
3 Beds ⋅ 2 Baths ⋅ 24189317 MLS
Every Day a Getaway! Some properties ask you to choose between full-time living & vacation living. Not this one. Set in the heart of Old Saybrook, this fully furnished 7-room Cape Cod delivers the ease of a residence with the spirit of a seasonal retreat - and comes with a private guest house. The main home offers 3 bdrms,, 2 baths & includes a coveted 1st fl bdrm for single-level living. A large eat-in kitchen flows into an adjacent family room, while a formal living room provides a more refined space for entertaining. The recently added sunroom is the standout: bright, expansive, and framed by multiple sliders & abundant windows that draw the outdoors in. Upstairs, the primary BR is a retreat unto itself - generously sized, with ample closets, a sitting area, and direct access to a personal balcony. Morning coffee or an evening glass of wine feels different from up here. Guests get a private 500-sq. ft guest house with a kitchenette, full bath, & living room. A spiral staircase leads to a large bdrm loft with its own small balcony. The location does the rest of the work. O S's Main St.- with its restaurants & shops - is close by, Fenwick Golf Course is minutes away for golfers. Harvey's Beach sits just 0.4 miles away, with OS's town beach just 0.2 miles beyond. For commuters, I-95 and Route 9 are both nearby, and Amtrak puts Boston and New York City within 2.5 hours. A home, a vacation, and a place for the people you love to visit - all in one address.

119 Great Hammock Rd, Old Saybrook
$675,000
4 Beds ⋅ 2 Baths ⋅ 24190279 MLS
Rare opportunity to create your dream home in one of Old Saybrook's most sought-after beach communities! Located across from Cornfield Point Beach Association, with deeded beach rights, this .23-acre property includes access to the beautiful sandy beach a short walk away making daily walks to the shoreline effortless. Surrounded by attractive homes, the setting alone makes this a standout investment. The existing home underwent a partial renovation in 2011 with a new roof, vinyl siding, replacement windows, and hardwood floors throughout. The septic system is appx 10 yrs old and is in front yard, so rear has room for a pool or building. The interior renovation was never completed, leaving the kitchen, bathrooms, and heating system gutted and ready for your vision. Whether you're looking to restore the existing home or explore the potential for a new custom residence, this property offers exceptional possibilities in a premier location. An added bonus is frontage along a state road at the rear of the property, which may offer the opportunity to create a rear driveway, subject to any required approvals. Bring your contractor, architect, and imagination to unlock the full potential of this exceptional Cornfield Point property just steps from Long Island Sound.

9 Old Colony Rd, Old Saybrook
$1,995,000
4 Beds ⋅ 2 Baths ⋅ 24186858 MLS
Experience the pinnacle of Connecticut shoreline living in this exquisitely remodeled coastal retreat, ideally located just three homes from the private association beach in the Saybrook Manor Beach community. Blending timeless coastal elegance with today's most desirable amenities, this exceptional four-bedroom, two-bath home provides the perfect balance of luxury, comfort, and effortless entertaining. From the moment you arrive, you'll appreciate the impressive circular paver driveway with parking for up to nine vehicles. The inviting oversized Trex front deck sets the stage for relaxing and enjoying the refreshing sea breeze just steps from the beach. Inside, thoughtfully designed living spaces showcase quality craftsmanship and a welcoming open flow. The beautifully remodeled eat-in kitchen is a chef's dream, featuring abundant cabinetry, generous counterspace, 2 wine chillers, oversized island and 6 burner gas stove/cooktop. The spacious living room is anchored by a gas log fireplace with space for gatherings and adjacent to the large dining area perfect for entertaining. With four generously sized bedrooms aloft and two beautifully updated baths, this home provides ample space for family and guests alike. Modern mechanical updates include efficient propane heat, central air conditioning, and on-demand hot water, ensuring year-round comfort. The backyard is nothing short of a private resort. Completely reimagined into a landscaped lot that screams bring on Summer!!!

81 Hartford Ave, Old Saybrook
$1,029,000
4 Beds ⋅ 3 Baths ⋅ 24188114 MLS
Experience the best of Old Saybrook shoreline living at 96 Ayers Point Road. This exceptional 4/5-bedroom coastal home offers panoramic marsh and Connecticut River views from a private setting with no flood insurance required. Recently painted and designed for effortless indoor-outdoor living, the home features an in-ground gunite pool, an expansive wraparound deck, walls of glass and oversized windows, multiple fireplaces, and a flexible floor plan with a main-level or second-floor primary suite. Rich Saltillo terracotta tile flooring adds warmth, character, and timeless coastal style. Walls of glass fill the home with natural light while framing the ever-changing marsh and Connecticut River views. Spend hours relaxing on the wraparound deck overlooking the peaceful marsh, enjoying spectacular sunsets, abundant wildlife, and tranquil water views, or entertain poolside in your private backyard oasis. The updated eat-in kitchen features new quartz countertops, a 6-burner gas cooktop, and French doors opening to the deck for seamless indoor-outdoor entertaining. A vaulted main level room offers flexible space for a family room, home office, studio, or guest suite. The walkout lower level provides additional living, recreation, or fitness potential. Additional highlights include a new roof, central A/C just over one year old, a 2-car garage, and both gas and wood-burning fireplaces. Minutes from Safe Harbor Saybrook Marina, the public boat launch, beaches, downtown

96 Ayers Point Rd, Old Saybrook
$1,025,000
3 Beds ⋅ 2 Baths ⋅ 24186222 MLS
Experience coastal luxury in this stunning 3-bedroom, 2-bathroom ranch style home nestled in Knollwood Beach. Set on a rare .33 acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring an expansive remodeled white kitchen with quartz counters, large center island. The family room boasts a dramatic fireplace, while a sunlit dining room/sunroom offers panoramic views of the marsh and Cove. A first-floor primary bedroom a two additional bedrooms, and 2 gorgeous full bathrooms. Additional features a patio and a large deck, new exterior vinyl siding with Azek trim, a 1000 sq ft basement for storage, central air, freshly painted exterior and main floor, remodelled baths, updated electrical, gutter guards and refinished flooring. Roof and septic are newer. No flood insurance needed. Appears to have room for a garage if needed. 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.

37 Woodland Dr, Old Saybrook
$800,000
2 Beds ⋅ 1 Baths ⋅ 24183581 MLS
Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants, shopping, and all that Old Saybrook has to offer. The inviting outdoor spaces include a spacious patio, firepit area, beautiful gardens, and plenty of room to entertain family and friends. A detached shed provides additional storage, while ample parking accommodates guests with ease. A special feature of this property is access to private beach parking, making your beach days effortless. Boaters will appreciate the opportunity for a boat slip, subject to availability-simply inquire for details. Spend your days strolling to the beach, enjoying nearby boating and fishing, or taking a golf cart ride through one of Old Saybrook's most beloved shoreline neighborhoods. Whether you're looking for a year-round residence, weekend retreat, or investment opportunity, this home offers the very best of Connecticut shoreline living. Relax, entertain, and enjoy the peaceful coastal surroundings while being just minutes from everything Old Saybrook has to offer. A rare opportunity to own in one of Old Saybrook's most sought-after beach communities.

25 River Ave, Old Saybrook
$859,900
2 Beds ⋅ 3 Baths ⋅ 24185294 MLS
Your Beach Retreat Awaits! Completely renovated and thoughtfully redesigned, 86 Fenwood Drive offers the perfect opportunity for a year-round residence or summer getaway. Ideally located just minutes from the kayak launch, cove, and beach, this charming home sits on a beautifully landscaped, level lot filled with mature plantings and inviting outdoor spaces. Step inside to discover a stunning custom kitchen featuring GE Cafe appliances, white shaker cabinetry, quartz countertops, and character-grade flooring that flows throughout the home. The bright and welcoming front living room is anchored by a cozy wood-burning fireplace, creating the perfect gathering space. At the rear of the home, the spacious family room showcases soaring ceilings, exposed beams, shiplap accents, and an abundance of windows overlooking the backyard. This versatile space could easily be converted into an additional bedroom if desired. Adjacent to the family room is a beautifully updated full bath featuring a new vanity with marble top and a stylish tiled shower. Convenient first-floor laundry is located just off the hallway leading to the bedroom wing. Both bedrooms offer generous proportions, while the primary suite boasts an oversized walk-in closet and a luxurious en-suite bath complete with heated floors, a soaking tub, updated vanity, and a large walk-in shower. The updates continue throughout the property, including a new propane tank, new septic system, central air condition

86 Fenwood Dr, Old Saybrook
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 24182151 MLS
Welcome to shoreline living at its finest in one of Old Saybrook's desirable beach communities, just minutes from the water, marinas, beaches, restaurants, and all that the Connecticut shoreline has to offer. This beautifully remodeled split-level ranch combines modern updates, flexible living space, and an exceptional outdoor setting. Step inside to an inviting open-concept floor plan filled with natural light, featuring gleaming hardwood floors, a stunning center island, ample dining space, and a cozy gas fireplace that serves as the focal point of the main living area. The thoughtfully designed kitchen is perfect for both everyday living and entertaining, with easy access to the rear deck and backyard oasis. Upstairs, you'll find three spacious bedrooms, including an oversized primary suite complete with convenient laundry facilities and generous closet space. A full bath serves the additional bedrooms as well. The fully finished walkout lower level offers incredible versatility with a large family room, media room, additional finished living space, a second full bath, and a second laundry area-ideal for guests, recreation, home offices, or multi-generational living. There is a pellet stove for additional heating too! Adding tremendous value is the detached garage featuring a one-bedroom, one-bath accessory apartment above-perfect for extended family, guests, au pair, or rental income. Recent improvements include a brand-new septic system and driveway.

26 Willard Ave, Old Saybrook
$12,000,000
4 Beds ⋅ 1 Baths ⋅ 24183764 MLS
A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a local treasure for generations. The improvements require significant modernization and renovation, presenting an ideal opportunity for someone seeking to preserve and enhance a historic property. Whether envisioned as a private estate, hospitality-related use, office, wellness concept, or other permitted use, the property offers exceptional potential for those with a vision for restoration and stewardship. Ideally situated on Boston Post Road with convenient access to Interstate 95, Route 9, shoreline beaches, marinas, shopping, and restaurants, the property benefits from excellent visibility and accessibility within one of Connecticut's most desirable shoreline communities. This offering is subject to the property's historic designation and must be purchased together with the adjoining Bushnell Farm land parcel (MLS #24183765). The combined offering presents a truly unique opportunity to preserve, restore, and shape the future of one of the Connecticut shoreline's most recognizable historic properties.

1445 Boston Post Rd, Old Saybrook
$12,000,000
24183765 MLS
Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the renowned Elisha Bushnell House, creating a setting unlike any other currently available along the shoreline. With its historic designation and deep connection to Connecticut's heritage, Bushnell Farm offers the opportunity to preserve a remarkable legacy while creating a meaningful future. Zoned B-4 Commercial, the property allows for a wide variety of potential uses, including hospitality, Independent Living Community, office, medical, retail, and destination-oriented development. The site is particularly well suited for a boutique hotel, wellness retreat, destination resort, or mixed-use concept that embraces the property's unique character and sense of place. Strategically located just minutes from Interstate 95 and Route 9, Bushnell Farm benefits from exceptional accessibility between New York City and Boston while remaining within one of Connecticut's most desirable shoreline communities. Nearby beaches, marinas, golf courses, and cultural attractions further enhance its appeal. Large-scale commercial development opportunities of this caliber are increasingly rare on

1405-1445 Boston Post Rd, Old Saybrook
$2,899,900
5 Beds ⋅ 5 Baths ⋅ 24182941 MLS
Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear Fireplace, Gleaming Hardwoods, Whole House Sound & Security, Irrigation, Super Efficient Natural Gas Heat, Three Car Garage w/ Radiant Floor Heat, On Demand Hot Water, & Custom Built-Ins every where you look! Gourmet Kitchen featuring Floor to Ceiling Double Box Cabinetry, Tile Backsplash, Accent Lighting, Stainless, 1.25" Quartz Counters, Huge Breakfast Island & a 'To Be Jealous For' Chef's Pantry. The Primary Double Floor Suite needs to be seen to be fully appreciated w/ it's Vaulted Balcony Ceilings, Circular stairs that lead to a Private Office & Sitting Room & a Luxurious & Relaxing En-Suite Bathroom! Incredible Bright & Spacious In-Law Apartment w/ a Custom Granite & Stainless Kitchen, Separate Laundry, Hardwoods & Beautiful Light at every turn! Indian Town Beach Association (indiantownassociation. org) is one of the most unique associations in the area w/ it's Golf Cart Friendly Mindset, 3 Beautiful Beaches, 100 Slip Marina, Large Waterfront Clubhouse & a Playground for the Little Ones. It is a great time to buy your Dream Home in Old Saybrook! We are always here to help!

2 Captains Ln, Old Saybrook
$510,000
2 Beds ⋅ 2 Baths ⋅ 24180111 MLS ⋅ Summerwood Condo BLDG.
Discover effortless shoreline living at Summerwood in Old Saybrook. This beautifully maintained 2-bedroom, 1.5-bath condominium offers 1,557 SqFt of light-filled living space with tranquil marsh views and an upper-level loft perfect for a home office, guest space, or reading retreat. The updated kitchen features granite countertops, stainless steel appliances, and a center island, while hardwood floors and spacious living and dining areas create an inviting atmosphere throughout. Wake up to peaceful water views, then unwind on your private rear deck overlooking the natural beauty of the marsh. Summerwood residents enjoy private beach rights, an in-ground pool, tennis and pickleball courts, and beautifully maintained grounds. Conveniently located just minutes from downtown Old Saybrook's shops, restaurants, marinas, and beaches, this is the perfect year-round residence or weekend getaway where every day feels like a vacation.

256 Hidden Cove Rd Unit 256, Old Saybrook
$1,625,000
4 Beds ⋅ 3 Baths ⋅ 24178785 MLS
SHORELINE YEAR-ROUND RETREAT - OLD SAYBROOK. Tucked away at the end of a quiet cul-de-sac with sweeping salt marsh and water views, this gracefully updated coastal haven offers exceptional privacy, natural beauty, and resort-style outdoor living in the heart of Old Saybrook. Set on a 1.6-acre lot and filled with natural light, the home features panoramic windows, open living and dining spaces, refinished hardwood floors, high-end kitchen appliances, and a seamless connection to its natural surroundings. The outdoor setting is no less impressive with an oversized saltwater pool, newly laid Techo-Bloc paver patio, generous deck for outdoor dining, professionally landscaped grounds, koi pond, mature trees, and multiple spaces for relaxation and entertaining. Thoughtful improvements include a new roof, economical electric heat pump HVAC system, refurbished free-standing studio, updated pool systems, hand-painted tilework, custom linen curtains, and more. Just minutes from beaches, Saybrook Point Marina, restaurants, and shops, this special shoreline estate offers a peaceful sense of privacy and the comfort of a year-round retreat while remaining close to all that Old Saybrook has to offer.

11 Cambridge Ct E, Old Saybrook
$749,900
4 Beds ⋅ 4 Baths ⋅ 24177311 MLS
This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California closets, dressing room, cathedral ceilings and a cozy loft. Gourmet kitchen with full pantry, granite countertops, island, stainless steel appliances, a stunning double-sided gas fireplace that creates warmth and ambiance between the main living spaces. Upstairs, a second private primary suite with a walk-in closet, full bath, two additional spacious bedrooms, another full bath, a charming terrace completes the upper level. A walk-up attic offers abundant additional storage, while the full basement and oversized two-car garage provide even more functionality. Surrounded by beautiful landscaping, a spacious deck perfect for entertaining, privacy, on a cul-de-sac minutes from town, beaches and highways.

9 Barley Hill Rd, Old Saybrook
$649,900
3 Beds ⋅ 1 Baths ⋅ 24174666 MLS
Welcome to your seasonal sanctuary at Chalker Beach, where sun-soaked days and starry nights create lasting memories. Offered fully furnished and thoughtfully styled with relaxed coastal charm, this seasonal cottage is the perfect place to slow down, unwind, and enjoy easy shoreline living. Just a short walk or golf cart ride to the beach, the home is tucked into one of the shoreline's most loved beach communities where summer days are spent by the water, riding bikes through the neighborhood, and gathering with friends and family for community events and beach nights. The outdoor spaces are designed for relaxing and entertaining, featuring a spacious paver patio, beautifully manicured open lawn, outdoor shower, and a private firepit deck beside peaceful marsh grasses--the perfect setting for morning coffee, summer dinners, or evenings under the stars. Inside, cathedral ceilings, natural light, and custom wood paneling create a warm and welcoming atmosphere with a cozy beach-house feel throughout. Every space has been thoughtfully designed to make the home feel comfortable, inviting, and ready to enjoy from the moment you arrive. Located within the Chalker Beach Association with private beach access, clubhouses, playgrounds, basketball court, golf cart parades, and cherished summer traditions.

96 Chalker Beach Rd, Old Saybrook
$1,290,000
3 Beds ⋅ 3 Baths ⋅ 24173257 MLS
Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first floor, offering even more usable space than reflected. Inside, you'll find a warm and inviting layout highlighted by a vaulted ceiling, large open windows that capture beautiful morning sunlight from the east-facing front exposure, and a cozy fireplace. The first floor features durable ceramic tile, while the second and third floors showcase classic hardwood flooring throughout. Designed for comfort in every season, the home is equipped with oil forced air heating and central air conditioning, with supplemental electric baseboard heating. An oversized septic system, including a 4-bedroom capacity tank, adds peace of mind and functionality. Additional features include new windows, a storage crawlspace beneath the second floor, and thoughtful construction throughout. Knollwood Beach Association residents enjoy exclusive amenities including a private beach, clubhouse, tennis courts, basketball courts, pickleball, and a kayak stand.

21 Fenbrook Rd, Old Saybrook
$375,000
1 Beds ⋅ 2 Baths ⋅ 24169155 MLS
Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless living, with an eat-in kitchen showcasing a center island and newer appliances. Off the kitchen, a slider leads to a spacious back deck, perfect for outdoor dining or soaking in the coastal air. Built-in shelves add both charm and function to the main living area, which also features a convenient first-floor half bath and laundry. Head upstairs to discover a spacious bedroom paired with a full bath featuring a stall shower. The property doesn't stop impressing there-a full basement offers storage or potential, while the flat lot includes a versatile barn/garage and an adorable gazebo perfect for relaxing or entertaining. With public water and an unbeatable location, this home is ready to be your seaside escape or year-round haven. Welcome to the best of Old Saybrook living!

61 Ingham Hill Rd, Old Saybrook
$460,000
3 Beds ⋅ 3 Baths ⋅ 24170006 MLS
Attention Investors and Motivated Home Buyers. Welcome to 6 Watch Hill. Home offers eclectic feel. New owner will build off of this design. Home boast beautiful views and you can not help but to feel peace as you appreciate all the nature around you. Great stand alone garage with wonderful workspace on 2nd level. Sale is subject to probate approval.

6 Watch Hill Rd, Old Saybrook
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 24167090 MLS
True tranquility awaits at this waterfront oasis! Unparalleled water views from every vantage point! Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access- perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm and character with thoughtful updates. Its architectural lines evoke a Normandy chalet vibe, while the interior reflects a coastal sensibility. Features include oak hardwood floors, a striking coastal river rock fireplace, and a sun-filled enclosed porch with a wall of windows. Kitchen has been completely renovated including new cabinetry, countertops, lighting and fresh paint. Popcorn ceiling has been removed. Enjoy vibrant sunsets from the comfort of your family room. A versatile first-floor room offers flexibility as a private office or bedroom, complete with a nearby full bath. Adding to the home's unique appeal, a staircase leads to a charming hideaway-an ideal retreat or reading nook. The kitchen is light and bright with its own panoramic views. A lovely dining room provides entertainment options. A haven for bird lovers and outdoor enthusiasts alike, this property just awaits thoughtful updates. This home truly has it all. Knollwood Beach Association amenities include a sandy beach with raft, tennis and pickleball courts, a clubhouse, guest parking, and kayak storage. Conveniently located in Old Saybrook, just two hours from both New York City and Boston

104 Knollwood Dr, Old Saybrook
$1,050,000
2 Baths ⋅ 24167568 MLS
VERSATILE MIXED-USE OPPORTUNITY | PRIME OLD SAYBROOK LOCATION. Welcome to 93 Elm Street, Old Saybrook - a rare mixed-use asset offering strong in-place income, exceptional visibility, and significant upside potential for investors and owner-operators alike. Strategically positioned at the entrance to the high-traffic Stop & Shop/Walmart Plaza and directly across from a newly developed 250+ unit apartment community, this property benefits from consistent traffic flow and immediate access to I-95 via the Elm Street exit. NEW SEPTIC! The well-maintained building offers a flexible configuration suited for multiple income streams and uses: Two fully leased residential apartments with separate utilities and brand-new Navien heating systems, providing stable, consistent cash flow. One private office space ideal for professional or administrative use * Two commercial units currently combined into a turnkey restaurant, featuring a full dining room, takeout area, prep space, commercial kitchen, liquor license, new FF&E, ANSUL fire suppression system, walk-in cooler, multiple sinks, and ADA-compliant restrooms - easily adaptable for restaurant, cafe, deli, or alternative food concepts. Garage with conversion potential, additional warehouse/storage space, and a partially finished basement/cellar offering operational flexibility and expansion capability. The exterior features a newly paved parking lot with 16 spaces, a finished outdoor patio ideal for dining or gathering.

93 Elm St, Old Saybrook
$5,900,000
4 Beds ⋅ 4 Baths ⋅ 24165905 MLS
Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy fireplace, floor to ceiling windows and opens to a 750 square foot inviting deck ideal for relaxing, entertaining, soaking in the hot tub, peaceful sunsets or simply taking in the ever-changing river views. A lower level 750 square foot patio overlooks landscaped grounds, gardens and new stone fire pit area. The chef's kitchen is a dream featuring an oversized granite island, high-end stainless-steel appliances, custom cabinetry, wet bar, wine chiller that invites both gourmet cooking and effortless hosting. Designed for comfort, the home offers multiple luxurious bedroom suites each with sweeping views, spa like bathrooms, walk in closets, hardwood floors and high ceilings. It is perfect for an in-law bedroom or an au pair suite. Spacious additional bedrooms with views, entertainment room, private office with views, a loft, 4.5 bathrooms. A 5-car garage provides ample space for cars, outdoor lawn equipment or storage. A luxury lifestyle experience unlike any other on the Connecticut shoreline.

12 Rocky Point Rd, Old Saybrook
$6,600,000
6 Beds ⋅ 4 Baths ⋅ 24151590 MLS
Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 7,239 square feet, including 1,500 finished square feet on the lower level including an ensuite bedroom and recreational room with French doors opening to the expansive back yard. This residence combines timeless architectural sophistication with the serene beauty of nature. Leave the world behind as you travel up the winding driveway that sets this home back from the road for ultimate privacy. The exterior is a master class in curb appeal, featuring a three-car garage and a porte cochere, all framed by lush landscaping and your own private pond and a dock. Step through the front door into a soaring cathedral ceiling foyer. As the heart of the home, this space is open to the floor above and finished with exquisite marble flooring, offering a regal welcome to guests. The floor plan is defined by wide-open spaces that flow seamlessly from one room to the next, making it as ideal for grand-scale entertaining as it is for quiet relaxation. With six spacious bedrooms, there is ample room for family, guests. There is also a home office and a sun room both overlooking the Connecticut River. Embrace the river breeze from your choice of outdoor vantage points: This isn't just a home; it's a lifestyle.

11 River Edge Rd, Old Saybrook
$899,000
4 Beds ⋅ 3 Baths ⋅ 24163559 MLS
Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the largest water-view coastal lot in South Cove! Situated in Old Saybrook's most protected and prominent corridor, 18 Old South Cove Road provides the rare opportunity for you to embrace your dream of living by the water and realizing your vision of Moving-in, Renovating, or Custom Building a "Luxury Estate" where privacy and scenic integrity are guaranteed by zoning. As one of the largest parcels in the protective Gateway Zone, you are granted 15% building coverage. This translates to a massive potential footprint of approximately 2,744 sq. ft., allowing for a custom build that far exceeds the scale of neighboring homes. And by leveraging the 35-foot (2.5 story) scale-up potential, you have the incredible opportunity to capture dramatic, unencumbered panoramic sunrises and water views of South Cove. With Residence A designation, this lot represents the perfect 'Coastal Canvas' for a luxury home up to 4,000 sq. ft. featuring 3-car garage, sweeping verandas, and all the best in coastal living!

18 Old S Cove Rd, Old Saybrook
$225,000
3 Baths ⋅ 24154768 MLS
This sale includes two commercial office units (Units 1300 and 1400), offering a combined total of approximately 2,400 square feet across two floors. Unit 1300 is a first-floor unit, while Unit 1400 is located on the second floor. Well-maintained and updated, this bright, professional space spans both levels, each featuring brand-new flooring, private restrooms, and a clean, turnkey feel throughout. The layout lends itself well to professional offices, medical or wellness services, creative studios, or a variety of commercial uses. Conveniently located near the center of town yet tucked away for added privacy, the property offers plenty of off-street parking and a quiet, productive setting. An ideal opportunity for investors seeking stable income or business owners looking to secure their own space while offsetting expenses with an in-place tenant.

123 Elm St Unit 13 & 14, Old Saybrook
$495,000
24143476 MLS
32.66 ac at a prime intersection in Old Saybrook right off I-95. W/ Plans for various layouts of multiple building to totaling as much as 50,000 sqft +/-. B4 Zone offers a wide variety of uses. A large portion of this parcel is wetlands.

Middlesex Tpke, Old Saybrook
$139,000
2 Baths ⋅ 24138058 MLS
Clean, updated office space featuring approximately 1,200 square feet across two levels, plus a lower-level basement ideal for storage. This bright, professional unit offers brand-new flooring throughout, two restrooms, and plenty of off-street parking. Conveniently located near the center of town yet tucked away for added privacy-ideal for a quiet and productive work environment. A great fit for professional offices, wellness services, or other commercial uses seeking a well-maintained and accessible location. Also for sale is unit 13 MLS #24138052 and unit 14 MLS #24138054. These spaces can be combined for a total of 3600 square feet.

123 Elm St Unit 15, Old Saybrook
$695,000
24139358 MLS
1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900.

1333 Boston Post Rd Unit 1, Old Saybrook
$925,000
170061418 MLS
Gas station and repair facility for sale in B-2 Zoned location. 6 Gas tanks were removed by seller in July 2019: 3 gas (3,000 gal each), 1 diesel (3,000 gal), 1 waste oil (550 gal), 1 fuel oil (550 gal). Clean environmental report. Building # 1 = 1856 SF with 3 bay overhead doors, Ceiling height: 12 Ft. Building #2 (rear) = 2,400 SF with 2 overhead doors, Ceiling height: 18 Ft. Acres: 0.51. Heating: oil & waste oil / hot air. Taxes: $10,831. Items remaining: compressors, sign, storage containers, canopy, POS terminal, furniture, kerosene pump/tank, heaters. 200 amp electric service for both. Well & septic. City water available. Frontage: 100 Ft. Traffic Count: 14,100. Next to intersection to Main Street & Old Saybrook Shopping Center. Abuts Burger King. Up the street from the train station.

621 Boston Post Rd, Old Saybrook
$599,500
1 Baths ⋅ 24110306 MLS
ALSO FOR LEASE $3,000/month NNN Property Overview: Building Size: 4,157 SF (Three Stories) Lot Size: 0.23 Acres Zoning: B-2 (General Business District) Heating & Cooling: Oil Heat, Window A/C Units Access: Multiple ground-floor entrances Key Highlights: -High-visibility corner location at a traffic light Directly across from CVS and a Ford dealership -Located on busy Route 1 near Main Street -Just 0.5 miles from I-95 on/off ramp Traffic Count: 21,000 vehicles per day (ADT) -This is a strong retail or office opportunity in a high-traffic area with excellent visibility and accessibility. Ideal for businesses seeking a presence on a major commercial corridor.

523 Boston Post Rd, 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.