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958 Middlesex Tpke, Old Saybrook
$3,200
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24217798 MLS
Annual Unfurnished Rental in a Prime Location Between Old Saybrook and Essex This spacious and versatile property offers 3 bedrooms and 2 full baths, with 1,826 square feet of main-level living plus an additional 1,120 square feet of finished lower level, complete with a full bath-ideal for extended living, recreation, or workspace. Zoned for both residential and commercial use, this property presents a unique opportunity for a variety of lifestyles, including work-from-home or small business potential. Set well back from the road on 1.2 level acres, the home provides privacy and generous parking, including a 2-car garage and ample additional spaces. Inside, you'll find warmth and character throughout, with hardwood floors and an inviting, open layout. The centrally located kitchen flows easily into the family and dining areas, highlighted by a cozy fireplace. An enclosed porch offers the perfect spot for year-round enjoyment. A flexible spacious room off the kitchen is ideal for a home office, playroom, or additional living space, with convenient access to the attached garage, a three-season porch, and the backyard. Professionally maintained and well managed. A rare rental opportunity offering space, flexibility, and an exceptional shoreline location.

958 Middlesex Tpke, Old Saybrook
7 Toms Rd, Old Saybrook
$1,200,000
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24216468 MLS
2 Plots sold together- 7 & 18 Toms Rd. Rare opportunity to own a slice of CT shoreline! Tucked away at the end of a private road, this charming seasonal waterfront cottage offers water on 2 sides, water views on 3, private beach, backyard dock & breathtaking sunsets. Cherished by the same family for generations, this special coastal retreat captures everything there is to love about beach living. Recently refreshed with new flooring, new granite counters, new hot water heater and electrical updates. The cottage features an inviting open floor plan, flexible sleeping accommodations with convenient convertible beds & a spectacular enclosed front porch where you can relax, entertain & take in the waterfront scenery. Spend your days swimming, kayaking, paddleboarding, or simply enjoying the sand & sea breeze. An outdoor shower makes rinsing off after a day at the beach a breeze. The property includes both front & back lots, offering a unique waterfront setting with room to enjoy the outdoors. Conveniently located near Harvey's Beach & all that Old Saybrook has to offer, this property presents an incredible opportunity for a personal summer getaway, a family retreat, or a seasonal rental investment. Currently winterized & ready for its next chapter, this is your chance to create lasting shoreline memories in a truly special location. Come experience the sunsets, salty air, and laid-back beach lifestyle.

7 Toms Rd, Old Saybrook
2 Hawk Brk, Old Saybrook
$900,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24215827 MLS
Very private location yet close to major commuter routes, this wonderfully maintained Colonial has large living spaces inside & out! Entry foyer w/2 oversized closets, tile flr and access to huge 2 car garage. The 1st flr features a huge eat-in kitchen w/rich cherry cabinetry, center island w/downdraft range, tile & hdwd floors, spacious pantry closet & access to the 16.5x24 back deck perfect for relaxing & dining. The formal DR is perfect for that special meal and the formal living rm has a cozy wood burning brick fireplace & hearth-both rooms have gleaming hardwood flrs. The 19.5x24 ft family room is a breathtaking space featuring soaring vaulted ceiling, hdwood flrs w/walnut inlay, oversized Palladian window & rear bay window. A full bath rounds out flr 1. The 2nd flr features a Master Suite comprised of huge BR, laundry room, full bath w/soaking tub and bidet, dressing area w/ample closets & spacious sitting rm. The remainder of the 2nd flr features 2 more well-proportioned BRs accompanied by a full bath w/tub-shower combo & tile flr. There is a full walkout basement w/partially finished 19.5x25 room w/French doors leading directly to the backyard. There is also an enormous walk up attic with soaring ceilings that will hold all your treasures or could be finished for even more living space. Oil hot water heat & a 2 zone central air conditioning system will keep you comfy all year. There is a Central Vac & whole house generator so you always have peace of mind. Come see

2 Hawk Brk, Old Saybrook
14 Cinnamon Rdg, Old Saybrook
$625,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24217273 MLS
Photos uploaded!! Available to be shown 10/31 --- NEW LISTING in beautiful Cinnamon Ridge! This OH-SO charming cape set on a picturesque, very private 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
11 Kitteridge Hill Rd, Old Saybrook
$679,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
121 Bokum Rd, Old Saybrook
$574,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24212897 MLS
Escape to your own private country retreat along the beautiful Connecticut shoreline! Nestled on over two acres of gorgeous, level land, this newly renovated 1,100-square-foot home offers a rare opportunity to enjoy the serenity of country living with all the conveniences of Old Saybrook just minutes away. Imagine creating magnificent gardens, hosting summer gatherings and picnics on the expansive lawn, or simply relaxing with your favorite book surrounded by nature. There's plenty of room for pets to play, outdoor hobbies, and perhaps even a horse, subject to town approval. The beautifully refreshed home offers comfortable, easy living, whether as a full-time residence, charming weekend escape, or potential income-producing Airbnb. With over two acres of usable land, the possibilities for creating your own personal sanctuary are truly exciting. Enjoy peaceful mornings, star-filled evenings, and the luxury of space and privacy, all within easy reach of beautiful beaches, marinas, waterfront dining, boutique shopping, and Amtrak service connecting to New York and Boston. Perfect for those seeking a relaxed lifestyle away from the hustle and bustle, this special property offers the best of country and coastal living. A wonderful opportunity to enjoy the shoreline on your own terms!

121 Bokum Rd, Old Saybrook
12 Drummers Trl, Old Saybrook
$995,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24211855 MLS
LONG ISLAND SOUND VIEWS,2.02 PRIVATE ACRES & EXCEPTIONAL CONDITION!Perched on a sunny hilltop, this beautifully maintained Colonial Contemporary offers approximately 3,300 sq. ft. of thoughtfully designed living space, coastal breezes and a fabulous open floor plan. The heart of the home is the impressive chef's kitchen featuring a large granite island, commercial-size side-by-side Sub-Zero refrigerator/freezer, Thermador double convection ovens, 6-burner gas cooktop with custom-paneled hood and Bosch dishwasher. The kitchen opens seamlessly to the dining area and spacious family room with gas fireplace-perfect for entertaining or simply enjoying the view. Vaulted ceilings, beautiful hardwood floors, a dramatic foyer and French doors leading to a private deck add to the bright, open feel. A rare floor plan offers BOTH first- and second-floor primary bedroom suites! Four bedrooms and 3 1/2 baths, with every bedroom enjoying direct access to a bathroom, provide wonderful flexibility for family, guests or multi-generational living. Additional highlights include first-floor laundry; central air; 2-zone gas heat; oversized 2-car garage; front porch; spacious, dry, partially finished basement; generator; basketball court; and lighted pea-stone driveway. Set on 2.2 secluded acres, yet close to beaches and everything that makes Old Saybrook and the Connecticut shoreline so special.This beautifully maintained home presents an exceptional opportunity to enjoy coastal living at its best

12 Drummers Trl, Old Saybrook
1 Briarcliffe Trl, Old Saybrook
$485,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
6 Overlook Dr, Old Saybrook
$935,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24207853 MLS
Step into this farmhouse with a bright, open and inviting floor plan. A welcoming grand foyer sets the tone, leading into sun-filled living spaces accented by hardwood floors, skylights and abundant windows throughout. The stunning wraparound deck is a true focal point of the home, offering the perfect setting for entertaining, relaxing or simply enjoying the peaceful surroundings. The main level features a spacious first-floor primary suite with a walk-in closet, laundry and a renovated bathroom. Upstairs, a loft overlooks the living space and is complemented by generously sized bedrooms and beautifully updated bathroom with heated floor. The full walkout basement provides excellent storage and additional possibilities.This home offers convenient access to the restaurants, shops, beaches, highways and train station. Enjoy all that Old Saybrook has to offer while coming home to a property that feels warm, distinctive and made for both entertaining and relaxing. Deferred maintenance needed. Professional photos coming.

6 Overlook Dr, Old Saybrook
5 Sand Creek Dr, Old Saybrook
$995,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205576 MLS
Welcome to 5 Sand Creek Drive, a truly unique coastal contemporary in Old Saybrook, beautifully positioned to capture stunning marsh and water views. Filled with natural light and designed around its exceptional setting, this distinctive home offers an open floor plan, brand-new windows throughout, and wonderful spaces for both everyday living and entertaining. The dramatic living room is a standout, featuring a vaulted ceiling and stunning stone wood-burning fireplace that creates a warm and inviting focal point. A separate den offers another comfortable gathering space with a gas log stove, while the open layout allows the main living areas to flow seamlessly together. The first floor provides exceptional flexibility with a spacious primary suite, plus a second first-floor bedroom and an additional full bath-ideal for guests, extended family, or one-level living. Upstairs, a loft-style second level offers three additional bedrooms, a full bath, and a bonus room, providing plenty of space for family, guests, a home office, or recreation. Outdoor living is just as special. Step onto the deck and take in the peaceful marsh and water views or follow the exterior spiral staircase to the widow's-walk-style upper deck, where the elevated vantage point showcases the surrounding coastal landscape. A 3-car attached garage provides generous parking and storage, while the home's contemporary architecture beautifully complements its shoreline setting.

5 Sand Creek Dr, Old Saybrook
47 Maple Ave, Old Saybrook
$475,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24206696 MLS
Welcome to 47 Maple Ave., a charming 1958 ranch offering comfortable one-level living in a desirable Old Saybrook location. This three-bedroom, one-and-a-half-bath home features hardwood flooring throughout and a classic, easy-flowing floor plan. A full basement provides plenty of additional storage and possibilities. Step outside to a large deck overlooking the fenced yard-perfect for outdoor dining, entertaining, gardening or simply relaxing. Best of all, enjoy the convenience of being within walking distance to town, with Old Saybrook's shops, restaurants, cafes and local amenities close by. A wonderful opportunity to enjoy shoreline living with the charm, convenience and potential of a classic New England ranch.

47 Maple Ave, Old Saybrook
25 Sunset Rd Unit 18, Old Saybrook
$669,900
2 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
61 Springbrook Rd, Old Saybrook
$480,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204068 MLS
Great investment opportunity in Old Saybrook! Create a two family home by dividing this into two apartments. OR need an in-law suite? This home has that possibility!!! The town of Old Saybrook is very open to ADUs(additional dwelling unit), 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 or future bedroom complete with a large walk in closet, a full bath and a laundry room. Full sized windows and two exterior doors- this is a true walk out basement but doesn't feel like a basement at all! A large two car detached garage with a large loft above would be great for a home office, gym or studio or maybe even another apartment. Come take a look and jump on this opportunity!

61 Springbrook Rd, Old Saybrook
43 Quarry St, Old Saybrook
$285,000
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
170 Old Post Rd, Old Saybrook
$900,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192820 MLS
Discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. Perfect for multi-generational living. The Bushnell-Dickinson House retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil molding, 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 cottage, complete with a full kitchen and laundry. This offers wonderful flexibility: for visitors, an in-law suite, private studio, or Air B&B. This building is not included in the listing square footage or room count. An attractive 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. The custom-built garden shed with running water is a gardener's dream. 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 shopping, restaurants, beaches, Main street events, and the train station. It is almost equal distance to Boston and New York. Enjoy peaceful coastal living on your own private estate-like property.

170 Old Post Rd, Old Saybrook
30 Riverside Ave, Old Saybrook
$6,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191885 MLS
RARE Opportunity to experience a slice of waterfront life on the New England shoreline in quintessential Old Saybrook, CT! This stunning beach-style cape home sits at the mouth of the Connecticut River to Long Island Sound and offers sweeping waterfront views from almost every window! With 3,392 sq ft of tastefully updated space, this home is perfect for entertaining or enjoying it however you see fit. An open floor plan welcomes you on all 3 floors of the home. Completely updated throughout, the kitchen offers modern amenities with state-of-the-art appliances, including a wine fridge, granite countertops, and custom cabinetry. Vaulted ceilings in the living room help you take in the stunning water view and the natural light that spills in from every angle. And a fireplace is available for cozy New England nights. With 3 large bedrooms, including a primary bedroom with an en-suite bath and walk-in closet, and 3.5 bathrooms, you will never want to leave this oasis! 2 potential office spaces are available to work from home in, utilizing either of the bonus spaces this home has: a family room and rec room! Hardwood floors, central air, newer windows and views you'll never forget! This home is situated at the end of a cul-de-sac and is a two-minute walk to Oak Leaf Marina. Minutes from Rt 9 and Rt 95; close to New Haven and under 2 hours to New York City! Make this rental opportunity yours today!

30 Riverside Ave, Old Saybrook
12 Rocky Point Rd, 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

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