Refine Search
Map
Sort by
$775,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24180696 MLS
Saybrook Point! Welcome to the coastal lifestyle you've been dreaming of! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is just steps away. Set on a generous sized lot this home is move-in ready filled with natural sunlight and thoughtfully updated throughout creating a bright welcoming interior which includes a 3-season sunroom where you can slow down and enjoy the coastal air and a full basement. With engineered plans already in place for future expansion, the possibilities are endless - whether you are looking for a year round residence, weekend getaway, or investment in one of shoreline's most coveted locations. Close to highways, trains and amenities. This is truly a hidden gem in the heart of Old Saybrook where every day feels like vacation!

13-A Cove St, Old Saybrook
$1,495,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24178761 MLS
Set on .62 acres along a protected canal just off the Connecticut River, this well built and maintained waterfront offers more than 100 feet of bulkhead frontage, along with a floating dock equipped with power and water suitable for a variety of boats and watercraft. Updated systems including central air and solar roof panels. Master bedroom on main floor with large closet, walk-in shower, sliders to private outside deck and direct water views. Large living room with cathedral ceiling, fireplace and direct access to outdoor deck and water. Large kitchen with modern appliances, center island, bar sink, wine fridge and eating area with sliders to deck and waterfront. Separate formal dining room. Three and half baths. Hardwood floors in excellent condition. Lower level has good sized den with fireplace and brick hearth, large rec room, laundry/ bath combo and well-organized utility room all with convenient walk out via sliders to lawn and dock. Oversized 2 bay garage and landscaped for privacy. Solar panel system installed in 2024 and fully transferable. Latest six months electricity bills have been zero, monthly panel lease is $137.00. Documentation available.

77 Essex Road Rd, Old Saybrook
$1,695,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178785 MLS
SHORELINE 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 property offers the feel of a private year-round retreat while remaining close to all that Old Saybrook has to offer.

11 Cambridge Ct E, Old Saybrook
$850,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$1,375,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$1,595,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 is in the process of being completely updated including new cabinetry and countertops. 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$1,099,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24161065 MLS
Discover the perfect blend of comfort, style, and convenience in this beautifully remodeled home. Tucked in a prime location just minutes from fine dining, shopping, the golf course, and the train station, this property offers unparalleled access to everything you need. Walking along the shore to Saybrook Point Inn and Saybrook Lighthouse. Step into the heart of the home: a chef's kitchen with high-end appliances, designed to make cooking and entertaining a breeze. Enjoy seasonal waterviews that bring a touch of tranquility to your everyday life. The lushly landscaped yard is an ideal setting for summer evenings-whether you're hosting friends, enjoying a quiet moment, or taking a dip in your very own swim spa. This home isn't just gorgeous; it's energy-efficient too, featuring solar panels that help reduce your carbon footprint and save on utility costs. With every inch thoughtfully updated, all that's left to do is move in and make it your own.

17 College St, Old Saybrook
$225,000
3 Baths ⋅ ACTIVE Status ⋅ 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
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
ACTIVE Status ⋅ 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
$9,850,000
5 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24125295 MLS
YOUR OWN PRIVATE COUNTRY CLUB! Enjoy the expansive 3500 sf granite terrace, a heated saltwater swimming pool, a deep water dock and a pool house with a full kitchen and seating for 10! This modern masterpiece, sited to take full advantage of a private 1.6 acre waterfront location overlooking North Cove and the Connecticut River has been constructed with the best curated materials. 20 Saltus Drive offers a luxurious, comfortable lifestyle with panoramic water views from almost every room. The great room (30' x 40') has soaring ceilings, a remarkable, double sided stone fireplace and a window wall creating an expanse of glass facing picture perfect water views. Glass pocket doors open to the dining room which flows into the impressive kitchen with table and counter seating. Additional notable spaces on this level are a home theater with an 8'+ screen and two bedroom suites (all five bedrooms have ensuite baths; four also enjoy separate sitting rooms). Access the second level either by elevator or a striking marine stainless steel, floating staircase. To the left are two additional bedroom suites while to the right is the palatial primary suite which includes a bedroom with fireplace, a large bathroom, walk-in closets, a laundry, an office and a sitting room. These three suites also have water view decks. Nearby is downtown Old Saybrook with its restaurants, shops and the Hepburn Cultural Arts Center.

20 Saltus Dr, Old Saybrook
$925,000
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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.