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71 Knollwood Dr, Old Saybrook
$750,000
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
1333 Boston Post Rd Unit 1, 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
11 Kitteridge Hill Rd, Old Saybrook
$679,000
3 Beds ⋅ 3 Baths ⋅ 24216599 MLS
Discover the charm and comfort of this beautifully maintained Cape, ideally situated on a quiet cul-de-sac off School House Road in one of Old Saybrook's desirable locations. Offering over 2,700 square feet of finished living space, this inviting home is just across from The Preserve trail access and moments from Clark Park, making it easy to enjoy nature, recreation, and the outdoors. Inside, gleaming hardwood floors, a spacious living room with a wood-burning fireplace, and a formal dining room create a warm, welcoming atmosphere. The updated kitchen features rich cherry cabinetry and granite countertops and opens to a cozy family room with a Garrison wood stove. Sliders lead to a cedar-paneled three-season room overlooking the private backyard, deck, and patio-perfect for entertaining or relaxing outdoors. Upstairs, the spacious primary suite features an en-suite bath with a custom shower and tons of storage, along with two additional bedrooms and a full bath. The finished lower level offers flexible space for a home office, gym, media room, or additional living area. Thoughtful updates include Andersen replacement windows, newer garage doors, enhanced attic insulation, and ice dam heating cables. Blending classic New England charm, versatile living spaces, and an exceptional location near trails and recreation, this move-in-ready home is a wonderful place to enjoy the best of Old Saybrook living.

11 Kitteridge Hill Rd, Old Saybrook
9 Old Colony 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
25 Sunset Rd Unit 18, Old Saybrook
$669,900
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
5 Connally Dr, Old Saybrook
$659,000
3 Beds ⋅ 3 Baths ⋅ 24208801 MLS
Tucked away on a beautiful, wooded 1.5-acre lot, this home offers a rare blend of absolute privacy and everyday convenience. Step inside to a freshly painted, 2,606sqft 3 bed and 3 bath open-concept floor plan designed for seamless modern living and effortless entertaining. The heart of the home is anchored by a large kitchen featuring granite countertops, an island with high-top seating, ample cabinet space, and a functional layout that flows beautifully into the main living space. This main living space features a dramatic living room with a wall of windows that frame peaceful nature views and a soaring cathedral ceiling that maximize the sense of space and light. A dedicated home office, or potentially a first floor bedroom, a distinct step-down dining room, and a gorgeous full bathroom complete the first floor. Three generous bedrooms and two more full baths upstairs provide plenty of room for family or guests. The finished walkout basement allows for seamless outdoor access, making it a perfect rec room, gym, or media center. Outside, the expansive deck serves as the ideal backdrop for al-fresco dining, summer barbecues, or quiet mornings enjoying your peaceful, private outdoor space. Situated just minutes from Old Saybrook's vibrant town center and train station, this home provides a quiet escape with upscale dining, boutique shopping, beautiful shoreline beaches and a 1,000 acre nature preserve just a short distance away.

5 Connally Dr, Old Saybrook
96 Chalker Beach 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
8 Kenn 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
14 Cinnamon Rdg, Old Saybrook
$625,000
3 Beds ⋅ 3 Baths ⋅ 24217273 MLS
Available to be shown 10/31 --- NEW LISTING in beautiful Cinnamon Ridge! This absolutely charming cape on picturesque 1+/- acre lot has undergone several wonderful transformations with fresh paint, newer windows, Buderus boiler, newer water heater, newer floors and carpets, along with stunning kitchen and baths with gorgeous cabinetry, granite countertops, stainless steel appliances including a beverage/wine refrigerator. The entry foyer is bright with full-lite front door and skylights, coat closet and new half bath; the front to back family room has a fireplace for cozy fall-time fires and french door to large 40x14 deck; both the dining room (also with french door to deck) and the living room have beautiful hardwood floors. On the second floor is the Primary bedroom complete with it's new personal bath; two additional bedrooms plus the main bath also newly remodeled. Beautiful drive along Cinnamon Ridge with trees laden with fall leaves ... Don't miss this once-in-while opportunity to be in one of Old Saybrook's prime locations - off country roads yet close to all that Old Saybrook has to offer -- town parks, beaches, quaint Main Street, The Kate theater, restaurants, shopping, train station etc.

14 Cinnamon Rdg, Old Saybrook
523 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
1324 Boston Post Rd, Old Saybrook
$515,000
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
256 Hidden Cove Rd Unit 256, 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
61 Springbrook Rd, Old Saybrook
$495,000
3 Beds ⋅ 3 Baths ⋅ 24204068 MLS
Great opportunity to move into Old Saybrook! Need an in-law suite? This home has that possibility!!! The town of Old Saybrook is very open to ADUs, and this would be perfect- all you need to add is a kitchenette. 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
Middlesex Tpke, 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
1 Briarcliffe Trl, Old Saybrook
$485,000
4 Beds ⋅ 2 Baths ⋅ 24208270 MLS
This warm and inviting Cape offers the perfect blend of comfort, space, and convenience in a highly desirable Old Saybrook location. Just one mile from Main Street's charming shops, restaurants, and local attractions, this home features an open-concept main level highlighted by vaulted ceilings in the living room that seamlessly flows into the kitchen and dining area, creating an ideal space for everyday living and entertaining. Beautiful hardwood floors extend throughout the main living areas, while two first-floor bedrooms provide flexible living options. Upstairs, you'll find two additional bedrooms offering plenty of room for family, guests, or a home office. The partially finished basement adds valuable bonus space for recreation, fitness, or storage. Energy-conscious buyers will appreciate the solar panels, helping to offset utility costs. Conveniently located with easy access to Routes 9 and I-95, this home is perfect for commuters while still enjoying all the coastal charm and amenities that make Old Saybrook such a special place to call home.

1 Briarcliffe Trl, Old Saybrook
43 Quarry St, 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
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
123 Elm St Unit 13 & 14, 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
no property photo
$140,000
24206910 MLS
Tina Perma Beauty Spa is a turnkey, fully equipped beauty studio in the heart of Old Saybrook's Main Street corridor in one of the most affluent shoreline markets in the Northeast. Established in 2020, the studio has built a loyal repeat clientele across permanent makeup, laser treatments, lash and brow services, waxing, and full nail care. What makes this offering unusual is the combination of three things a buyer rarely finds together: demonstrated growth, an exceptionally low fixed cost base, and clear untapped pricing capacity. Revenue climbed 26% in 2025 while occupancy cost held at roughly $800 per month - under 9% of gross revenue. The result is a discretionary earnings margin near 50% on a business that has never carried a marketing budget above $2,300 a year. The studio conveys fully equipped, including two commercial laser platforms, an established website and social presence, and a client database with booking system. A qualified buyer steps into an operating business with revenue on day one.

15 N Main St, Old Saybrook
123 Elm St Unit 15, 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

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