Old Saybrook Homes under $750,000

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Newest Old Saybrook Homes under $750,000

$625,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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

$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

$659,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$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

$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

$495,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$750,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200662 MLS ⋅ Sheltered Cove BLDG.

Spectacular North Cove unobstructed water views and downtown village living come together in this beautifully renovated townhouse-style condo, offering an exceptional opportunity for shoreline buyers seeking a turn-key home under $1 million. Enjoy captivating water views and wildlife from the open kitchen, dining and living areas, with a stylish renovated kitchen featuring a breakfast bar and wonderful natural light. The spacious two-bedroom layout includes a primary bedroom with its own full bath and spectacular views overlooking North Cove. With 2.5 baths, a wood-burning fireplace, central air, one-car garage and a dry full basement offering excellent potential for additional finished space, this home has everything you need for year-round or weekend living. Ideally located in the heart of the village, walk to downtown restaurants, shops and more, while the train station, golf course and town beach are just minutes away. The association also offers a large clubhouse with kitchen for gatherings and a wonderful in-ground pool. Best of all, enjoy spectacular shoreline views without the need for flood insurance. By appointment only.

100 Dudley Ave Unit F30, Old Saybrook

$750,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24200281 MLS

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

71 Knollwood Dr, Old Saybrook

$285,000

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

$515,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$649,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$675,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

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Old Saybrook Homes under $750,000

Newest Old Saybrook Homes under $750,000

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