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65 Knollwood Dr, Old Saybrook
$925,000
3 Beds ⋅ 3 Baths ⋅ 24191006 MLS
The best of both worlds-enjoy the tranquility of a peaceful setting while being just a short stroll to the beach. Beautifully updated and impeccably maintained, this year-round home offers the perfect blend of coastal charm and modern comfort. A welcoming front porch invites you inside where you'll find beautifully renovated kitchen and baths as well as quality finishes throughout. You'll love the four-season sunroom, with French doors and a wall of windows offering marsh views and spectacular sunsets year-round. Some recent updates include a newly added one-car garage, windows, siding, roof, rear deck, electrical panel, A/C, and sprinkler system. A deck off the living room and sunroom provides the perfect place to relax, entertain, or simply enjoy the peaceful surroundings. The full walkout lower level offers flexibility with an additional bedroom, family room, full bath and separate laundry room. Easy access to Beamon's Creek where you can launch a kayak and explore South Cove. The Knollwood Beach Association includes a private beach, clubhouse, tennis/pickleball, basketball court, a playground and the charm of a golf cart-friendly community. Low-maintenance and truly move-in ready, this exceptional shoreline home offers a lifestyle that's hard to beat.

65 Knollwood Dr, Old Saybrook

119 Great Hammock Rd, Old Saybrook
$775,000
3 Beds ⋅ 2 Baths ⋅ 24189317 MLS
Every Day a Getaway! Some properties ask you to choose between full-time living & vacation living. Not this one. Set in the heart of Old Saybrook, this fully furnished 7-room Cape Cod delivers the ease of a residence with the spirit of a seasonal retreat - and comes with a private guest house. The main home offers 3 bdrms,, 2 baths & includes a coveted 1st fl bdrm for single-level living. A large eat-in kitchen flows into an adjacent family room, while a formal living room provides a more refined space for entertaining. The recently added sunroom is the standout: bright, expansive, and framed by multiple sliders & abundant windows that draw the outdoors in. Upstairs, the primary BR is a retreat unto itself - generously sized, with ample closets, a sitting area, and direct access to a personal balcony. Morning coffee or an evening glass of wine feels different from up here. Guests get a private 500-sq. ft guest house with a kitchenette, full bath, & living room. A spiral staircase leads to a large bdrm loft with its own small balcony. The location does the rest of the work. O S's Main St.- with its restaurants & shops - is close by, Fenwick Golf Course is minutes away for golfers. Harvey's Beach sits just 0.4 miles away, with OS's town beach just 0.2 miles beyond. For commuters, I-95 and Route 9 are both nearby, and Amtrak puts Boston and New York City within 2.5 hours. A home, a vacation, and a place for the people you love to visit - all in one address.

119 Great Hammock Rd, 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

25 River Ave, Old Saybrook
$800,000
2 Beds ⋅ 1 Baths ⋅ 24183581 MLS
Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants, shopping, and all that Old Saybrook has to offer. The inviting outdoor spaces include a spacious patio, firepit area, beautiful gardens, and plenty of room to entertain family and friends. A detached shed provides additional storage, while ample parking accommodates guests with ease. A special feature of this property is access to private beach parking, making your beach days effortless. Boaters will appreciate the opportunity for a boat slip, subject to availability-simply inquire for details. Spend your days strolling to the beach, enjoying nearby boating and fishing, or taking a golf cart ride through one of Old Saybrook's most beloved shoreline neighborhoods. Whether you're looking for a year-round residence, weekend retreat, or investment opportunity, this home offers the very best of Connecticut shoreline living. Relax, entertain, and enjoy the peaceful coastal surroundings while being just minutes from everything Old Saybrook has to offer. A rare opportunity to own in one of Old Saybrook's most sought-after beach communities.

25 River Ave, Old Saybrook

26 Willard Ave, Old Saybrook
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 24182151 MLS
A rare opportunity to enjoy shoreline living while generating rental income! This beautifully remodeled Old Saybrook property features a detached garage with a one-bedroom, one-bath accessory apartment above-ideal for rental income, extended family, guests, or an au pair. Located in one of Old Saybrook's desirable beach communities, you're just minutes from the water, marinas, beaches, restaurants, and all the Connecticut shoreline has to offer. The main home is a beautifully updated split-level ranch combining modern finishes, flexible living space, and an exceptional outdoor setting. Step inside to an inviting open-concept floor plan filled with natural light, featuring gleaming hardwood floors, a center island, ample dining space, and a cozy gas fireplace that serves as the focal point of the main living area. The thoughtfully designed kitchen is perfect for everyday living and entertaining, with easy access to the rear deck and backyard. Upstairs are three spacious bedrooms, including an oversized primary suite with convenient laundry facilities and generous closet space. A full bath serves the additional bedrooms. The fully finished walkout LL offers incredible versatility with a large family room, media room, additional finished space, a second full bath, and a second laundry area-ideal for guests, recreation, home offices, or multi-generational living. A pellet stove provides an additional heat source. Recent improvements include a brand-new septic system and driveway.

26 Willard Ave, Old Saybrook

1445 Boston Post Rd, Old Saybrook
$12,000,000
4 Beds ⋅ 1 Baths ⋅ 24183764 MLS
A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a local treasure for generations. The improvements require significant modernization and renovation, presenting an ideal opportunity for someone seeking to preserve and enhance a historic property. Whether envisioned as a private estate, hospitality-related use, office, wellness concept, or other permitted use, the property offers exceptional potential for those with a vision for restoration and stewardship. Ideally situated on Boston Post Road with convenient access to Interstate 95, Route 9, shoreline beaches, marinas, shopping, and restaurants, the property benefits from excellent visibility and accessibility within one of Connecticut's most desirable shoreline communities. This offering is subject to the property's historic designation and must be purchased together with the adjoining Bushnell Farm land parcel (MLS #24183765). The combined offering presents a truly unique opportunity to preserve, restore, and shape the future of one of the Connecticut shoreline's most recognizable historic properties.

1445 Boston Post Rd, Old Saybrook

11 Cambridge Ct E, Old Saybrook
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 24178785 MLS
DISTINCTIVE COASTAL LIVING | OLD SAYBROOK - Sweeping salt marsh vistas, water views and exceptional privacy create a memorable setting for this thoughtfully updated home. Set on 1.6 beautifully landscaped acres at the end of a quiet cul-de-sac, the property offers inviting interiors, a saltwater pool and a separate studio, bringing together the space to entertain, unwind and pursue creative interests. Panoramic windows frame autumn's coastal colors, while open living and dining spaces welcome holiday gatherings and relaxed evenings at home. Refinished hardwood floors, high-end kitchen appliances, hand-painted tilework and custom linen curtains add warmth and distinctive detail. Outdoors, an oversized saltwater pool, newly laid Techo-Bloc paver patio and multilevel AZEK decking create a resort-style setting for outdoor dining, relaxation and entertaining. Professional landscaping, mature trees and a koi pond enhance the grounds. A refurbished freestanding studio provides a special space apart from the main residence. Significant improvements include the roof, electric heat pump HVAC system and updated pool systems. Minutes from beaches, Saybrook Point Marina, restaurants and shops, this exceptional home combines everyday convenience with the peaceful seclusion of a personal retreat. A beautiful place to come home to, year-round.

11 Cambridge Ct E, 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

12 Rocky Point Rd, Old Saybrook
$5,900,000
4 Beds ⋅ 4 Baths ⋅ 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

11 River Edge Rd, Old Saybrook
$6,600,000
6 Beds ⋅ 4 Baths ⋅ 24151590 MLS
Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 7,239 square feet, including 1,500 finished square feet on the lower level including an ensuite bedroom and recreational room with French doors opening to the expansive back yard. This residence combines timeless architectural sophistication with the serene beauty of nature. Leave the world behind as you travel up the winding driveway that sets this home back from the road for ultimate privacy. The exterior is a master class in curb appeal, featuring a three-car garage and a porte cochere, all framed by lush landscaping and your own private pond and a dock. Step through the front door into a soaring cathedral ceiling foyer. As the heart of the home, this space is open to the floor above and finished with exquisite marble flooring, offering a regal welcome to guests. The floor plan is defined by wide-open spaces that flow seamlessly from one room to the next, making it as ideal for grand-scale entertaining as it is for quiet relaxation. With six spacious bedrooms, there is ample room for family, guests. There is also a home office and a sun room both overlooking the Connecticut River. Embrace the river breeze from your choice of outdoor vantage points: This isn't just a home; it's a lifestyle.

11 River Edge Rd, Old Saybrook

18 Old S Cove Rd, Old Saybrook
$849,950
4 Beds ⋅ 3 Baths ⋅ 24163559 MLS
*Refreshed & Newly Priced* 4-BEDROOM COASTAL RANCH- FEATURING TWO PRIVATE SUITES on .42 Acre - ONLY 100 yds FROM THE WATER! Nestled in the heart of Old Saybrook's highly coveted South Cove- approximately 100 yards from the water's edge, this beautifully refreshed 4-bedroom coastal ranch blends move-in comfort with an expansive 0.42-acre (18,295 SF) water-view lot- an oversized property that promotes privacy, an expansive yard for pets, and endless freedom for outdoor entertaining, gardens, or custom outdoor living features. This unique coastal property, grounded in a sophisticated New England palette of warm architectural whites and serene mineral tones, welcomes you with an abundance of natural light and open floor plan designed for entertaining- Large front living room with hardwood floors and original stone fireplace that flows seamlessly into the inviting eat-in kitchen anchored by charcoal cabinetry and brushed nickel hardware- further sweeping into the sun-drenched family room where French doors lead to the rear covered porch overlooking the spacious yard and tranquil marsh scenery. The highly adaptable multi-wing floor plan is designed for modern living, boasting two entirely independent private suites with dedicated exterior entrances- flexible for guests, a wellness retreat, studio, or a quiet client-facing office overlooking the landscape. Flex spaces like these are among the most desired features in today's market, and this home provides two!

18 Old S Cove Rd, Old Saybrook

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