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138 N Cove Rd, Old Saybrook
$2,000,000
4 Beds ⋅ 4 Baths ⋅ 24199659 MLS
A Rare Coastal Opportunity Awaits! Set in the highly sought-after North Cove Historic District of Old Saybrook, this grand colonial offers something truly special: a coveted prime coastal location, spectacular water views, and incredible potential to create the home you've always envisioned. Originally built in 1930 and expanded in 1987, this property has the character, scale, and bones of a remarkable coastal residence-but today, it's ready for a new vision. With water views from nearly every room, spacious living areas, French doors leading out to a large deck, beautiful bay windows, a brick fireplace, a first-floor primary suite, four bedrooms, three and a half baths, a two-car garage with loft space, and an exceptional setting-there is truly so much to work with. The existing layout provides a strong foundation for someone looking to renovate, reimagine, and create a truly spectacular coastal retreat in one of Connecticut shoreline's most desirable neighborhoods. Located within walking distance of local restaurants, shops, beaches, and everything else that Main Street has to offer. Property being sold in "as is".

138 N Cove Rd, Old Saybrook

22 Fenwood Dr, Old Saybrook
$1,777,000
3 Beds ⋅ 4 Baths ⋅ 24213563 MLS
***HIGHEST AND BEST DUE BY MONDAY 10/26 by 5PM**** Beautifully maintained Cape in the sought after Fenwood Beach community, offering ocean views and a short walk to the community's private beach. Enjoy the best of shoreline living with timeless charm, spacious interiors, and versatile living spaces. Cherry hardwood floors, a custom kitchen with breakfast nook opening to the backyard entertaining patio, formal dining room, living room with fireplace, and a cozy family room create a warm, inviting atmosphere. First-floor bedroom w/full bath and convenient laundry room add flexibility. Upstairs the primary suite features a walk-in closet, full bath w/soaking tub and separate walk-in shower, and private balcony with awning and ocean views. The family den offers its own fireplace and balcony access, creating an ideal second gathering space. Room to grow and space for everyone! A versatile bonus room, accessible from both levels, offers options for a home office, playroom, added bedroom or hobby space. Along with the upstairs den and separate exercise room, these flexible areas adapt to a growing family, remote work, guests, and changing needs. Enjoy a three-season enclosed porch, abundant closets, walk-up attic, and spacious two-bay garage with extra storage. Professionally landscaped grounds feature an irrigation system and patio for outdoor entertaining. Experience the charm of Old Saybrook, beautiful ocean views, and private beach access.

22 Fenwood Dr, Old Saybrook

96 Ayers Point Rd, Old Saybrook
$1,029,000
4 Beds ⋅ 3 Baths ⋅ 24188114 MLS
Exceptional value in Old Saybrook! If you have been searching for a private coastal home with water views, a pool and space to make your own, 96 Ayers Point Road deserves a second look. Set against panoramic marsh and Connecticut River views, this 4/5-bedroom home offers an increasingly rare combination of privacy, resort-style living and NO flood insurance required. Enjoy an in-ground gunite pool, expansive wraparound deck, walls of glass, unforgettable sunsets and abundant wildlife. The flexible floor plan offers the option of a first- or second-floor primary suite, multiple fireplaces and a vaulted main-level room ideal for a family room, office, studio or guest suite. The updated eat-in kitchen features new quartz countertops, a 6-burner gas cooktop and French doors opening directly to the deck for effortless indoor-outdoor entertaining. Rich Saltillo terracotta tile adds warmth and character throughout. The walkout lower level offers additional recreation, fitness or living potential. Recent improvements include a NEW ROOF, fresh interior paint and central A/C just over one year old. A 2-car oversized garage completes the property. Yes, there are areas ready for your personal updates, but the setting, views, privacy and lifestyle are already here. Minutes to Safe Harbor Saybrook Marina, Connecticut River boating, beaches, restaurants and downtown Old Saybrook. A compelling opportunity to own a distinctive water-view property on the Connecticut shoreline.

96 Ayers Point Rd, Old Saybrook

30 Neptune Dr, Old Saybrook
$899,000
4 Beds ⋅ 2 Baths ⋅ 24190267 MLS
Live every day like you're on vacation in sought-after Knollwood Beach! Lovingly enjoyed by the same family for nearly 50 years, this attractive four-bedroom, one-and-a-half-bath home offers a wonderful opportunity to become part of one of Old Saybrook's most desirable beach communities. Inside, the comfortable floor plan features a welcoming living room with built-in bookcases, and a cozy fireplace that add warmth and character. Sunlight pours into the adjoining sunroom, offering a peaceful retreat overlooking the outdoors. The inviting kitchen is filled with natural light and has been meticulously maintained, featuring warm wood cabinetry, stainless steel appliances, and Corian countertops. A welcoming breakfast nook at one end provides a comfortable spot for morning coffee or casual meals, while the adjoining first-floor laundry room adds everyday convenience and valuable storage. Just off the kitchen, the sun-filled dining room offers a comfortable setting for entertaining and gathering. Updates include a newer roof and heated bathroom floor, irrigation system and vinyl siding. Wood floors lie beneath much of the existing carpeting-ready to be revealed. A brick driveway and walkway wind toward the side entrance, setting a welcoming tone from the moment you arrive. The detached one-car garage and shed adds valuable storage for bikes, beach chairs, umbrellas, and all the essentials for a day by the water. No flood insurance.

30 Neptune Dr, Old Saybrook

86 Fenwood Dr, Old Saybrook
$859,900
2 Beds ⋅ 3 Baths ⋅ 24211563 MLS
Your Beach Retreat Awaits! Completely renovated and thoughtfully redesigned, 86 Fenwood Drive offers the perfect opportunity for a year-round residence or summer getaway. Ideally located just minutes from the kayak launch, cove, and beach, this charming home sits on a beautifully landscaped, level lot filled with mature plantings and inviting outdoor spaces. Step inside to discover a stunning custom kitchen featuring GE Cafe appliances, white shaker cabinetry, quartz countertops, and character-grade flooring that flows throughout the home. The bright and welcoming front living room is anchored by a cozy wood-burning fireplace, creating the perfect gathering space. At the rear of the home, the spacious family room showcases soaring ceilings, exposed beams, shiplap accents, and an abundance of windows overlooking the backyard. This versatile space could easily be converted into an additional bedroom if desired. Adjacent to the family room is a beautifully updated full bath featuring a new vanity with marble top and a stylish tiled shower. Convenient first-floor laundry is located just off the hallway leading to the bedroom wing. Both bedrooms offer generous proportions, while the primary suite boasts an oversized walk-in closet and a luxurious en-suite bath complete with heated floors, a soaking tub, updated vanity, and a large walk-in shower. The updates continue throughout the property, including a new propane tank, new septic tank, central air condition

86 Fenwood Dr, Old Saybrook

5 Tudor Ct E, Old Saybrook
$795,000
3 Beds ⋅ 1 Baths ⋅ 24204260 MLS
Spectacular South Cove views, deeded beach rights to Cornfield Point Beach and remarkably low taxes make this nicely updated shoreline home an exceptional opportunity! Set on a beautiful half-acre lot, this spacious split-level offers 3-4 bedrooms, a versatile floor plan and wonderful water views that bring the coastal setting right into your everyday life. Inside you'll find hardwood floors, double oven, a fireplace for cozy evenings and air conditioning for summer comfort. The flexible layout provides plenty of room for family and guests, a home office or additional living space. A 2-car garage offers excellent parking and storage, while major improvements in 2021 including a newer roof , heating system and septic system add peace of mind. Plus a new oil tank in 2026. Enjoy the generous half-acre setting and beautiful views of South Cove, or take advantage of your deeded beach access and embrace the shoreline lifestyle. Whether you're looking for a year-round residence, weekend escape or summer retreat, this property offers the hard-to-find combination of water views, beach rights, an updated home, 2-car garage and sizable lot. With annual property taxes just under $5,000, this is an outstanding value for coastal living!

5 Tudor Ct E, Old Saybrook

Old Saybrook
$780,000
3 Beds ⋅ 2 Baths ⋅ 24208703 MLS ⋅ Banbury Crossing BLDG.
Welcome to Banbury Crossing of Old Saybrook. One of the few condominium associations locally that have free standing units, no common or shared walls. It gets better...it is a ranch unit with everything on one floor with easy access from driveway or attached 2 car garage. 3 Bedrooms offers flexibility for guests or perfect space for in home office or sitting room to read or watch TV. Current owner added a beautiful sunroom with all glass walls to view the mesmerizing serene setting and flower gardens. Two decks, one off the sunroom and a deck off the primary bedroom with a seperate access to deck. Both decks are connected by a patio which will enhance your connection with nature as you enjoy your first cup of coffee. Open floor plan with cathedral ceiling in living room and bay window along with gas fireplace. Fully applianced kitchen including trash compactor. Short distance to village, shopping, Katherine Hepburn Cultural Arts Center & Saybrook Pt. Nearby library and also nearby pickle ball courts for the sports enthusiaists. This condominium checks all the boxes.

Old Saybrook

6 Willard St, Old Saybrook
$699,900
3 Beds ⋅ 2 Baths ⋅ 24202240 MLS
Spacious ranch with an impressive second-story primary suite, set in Old Saybrook's desirable Saybrook Point area and close to some of the town's best-loved destinations. Stroll to Main Street for restaurants, boutique shopping and a show at The Kate, or head toward Saybrook Point and the nearby marinas. The town beach is just minutes away. Inside, hardwood floors and abundant natural light welcome you into the main living area, where a pellet stove creates a warm focal point. The kitchen and dining area flow easily into the living room, while a first-floor office with sliders to the patio provides flexible space for working from home, a den or exercise. Two bedrooms and a full bath complete the main level. Upstairs, the spacious private primary suite features 9+ foot ceilings, a walk-in closet, laundry hookup and space for a full en-suite bath. The double vanity and toilet are already installed, with the shower roughed in and ready for the next owner to complete. Outside, enjoy a level .29-acre lot enclosed by 6-foot vinyl fencing, along with a large Klotter Farms shed for additional storage. The oversized 29' x 24' attached garage is another standout, offering exceptional room for vehicles, a golf cart, workshop, lawn equipment and storage. Enjoy central air, public water, 200-amps and a septic system installed in 2023. This is a fantastic opportunity to enjoy the OS lifestyle with Main Street, Saybrook Point, marinas, beaches, dining, and shopping all nearby.

6 Willard St, Old Saybrook

121 Bokum Rd, Old Saybrook
$574,000
1 Beds ⋅ 1 Baths ⋅ 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

369 Boston Post Rd, Old Saybrook
$499,995
2 Baths ⋅ 24124701 MLS
PRICED REDUCED .... This is the perfect commercial property, with mixed use and a great business opportunity, close to the center of Old Saybrook! Great opportunity for owner occupied or numerous business opportunities for rental space; Professional Offices, Law Office, Hair Salons, Nail Salon, Massage Studio, Therapist, etc... close to town and local businesses. Great investment opportunity collect rent and run your own business as an owner occupied property on the main level and collect rent from residential tenants upstairs. Lots of private off street parking paved driveway, great traffic count easy access to 95S, 95N and Rt9. Newer hot water heater, newer windows, public water, siding with a nice lawn for great curb appeal this property has a sign with electrical for great visibility for your business. Nothing to do, but put your personal touches on this property with a front entry area, numerous offices on the main level and multiple egress within the property that allows this property to be a perfect fit for any business! SCHEDULE YOUR PRIVATE TOUR! SHOWN BY APPOINTMENT ONLY NO DRIVE BY'S PLEASE! AS IS / WHERE AS

369 Boston Post Rd, Old Saybrook

50 Dudley Ave, Old Saybrook
$495,000
4 Beds ⋅ 3 Baths ⋅ 24215261 MLS
Enjoy the best of Old Saybrook living with this charming ranch ideally situated within walking distance to Main Street's wonderful restaurants, shops, and local attractions, and walking distance to seee beautiful water views. Offering easy one-floor living, spacious living areas, hardwood floors, and a full basement with partially finished space, this home is filled with possibilities! A lovely private backyard provides the perfect setting for relaxation or entertaining. Bring your personal style and vision to make this home your own. Whether you're looking for a year-round residence or a shoreline retreat, this is a wonderful opportunity to enjoy the Old Saybrook lifestyle in a fantastic, walkable location. Convenient to beaches, shopping, the train station, and major highways!

50 Dudley Ave, Old Saybrook

47 Maple Ave, 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

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