Old Saybrook Homes under $600,000

Welcome to Old Saybrook, Connecticut—a picturesque coastal town nestled at the mouth of the Connecticut River. Known for its rich maritime history and stunning natural beauty, Old Saybrook is a charming blend of quaint New England character and vibrant community life. With its scenic waterfront, historic landmarks, and welcoming atmosphere, it’s no wonder that families and individuals alike are drawn to this delightful town.

Old Saybrook boasts an array of recreational opportunities, from serene beaches to lush parks, making it a perfect spot for outdoor enthusiasts. Take a leisurely stroll along the shoreline, enjoy a picnic at one of the town’s beautiful parks, or explore the local shops and eateries that line the charming Main Street. The town is also home to cultural treasures, including the iconic Katharine Hepburn Cultural Arts Center, which hosts a variety of performances and events throughout the year.

For those seeking a place to call home, Old Saybrook offers a variety of housing options, including charming single-family homes, cozy cottages, and modern residences—all available for under $600,000. This makes it an attractive destination for first-time homebuyers, young professionals, and families looking to settle in a community that values both tradition and progress.

With its stunning landscapes, vibrant community spirit, and accessible housing market, Old Saybrook is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting town today, and embrace the lifestyle that Old Saybrook has to offer!

Newest Old Saybrook Homes under $600,000

$499,900

4 Beds ⋅ 1 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

$475,000

3 Beds ⋅ 2 Baths ⋅ 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

$525,000

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

$499,999

3 Beds ⋅ 1 Baths ⋅ 24202909 MLS

This Bright, freshly Painted, 1951 3 bedroom Ranch is located on Schoolhouse Road in Old Saybrook, Connecticut with quintessential New England charm, public beaches and parks, major access to interstate and state highways, commuter rails and long distance railways, and public transportation a short walk away. The property is situated on a .87 acre level lot, and has a two Car detached, oversized garage with a lean two shed. The basement includes a workshop area and porcelain wash sink, plenty of storage to boot. Please schedule your appointment today using Showtime!

35 School House Rd, 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

$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

$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

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