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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 Connally Dr, Old Saybrook
$699,000
3 Beds ⋅ 3 Baths ⋅ 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, 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

1 Briarcliffe Trl, Old Saybrook
$499,900
4 Beds ⋅ 2 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

6 Overlook Dr, Old Saybrook
$935,000
4 Beds ⋅ 4 Baths ⋅ 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

17 College St, Old Saybrook
$999,000
3 Beds ⋅ 3 Baths ⋅ 24208689 MLS
Discover the perfect blend of comfort, style, and convenience in this beautifully remodeled home. Tucked in a prime location just minutes from fine dining, shopping, the golf course, and the train station, this property offers unparalleled access to everything you need. Walking along the shore to Saybrook Point Inn and Saybrook Lighthouse. Step into the heart of the home: a chef's kitchen with high-end appliances, designed to make cooking and entertaining a breeze. Enjoy seasonal waterviews that bring a touch of tranquility to your everyday life. The lushly landscaped yard is an ideal setting for summer evenings-whether you're hosting friends, enjoying a quiet moment, or taking a dip in your very own swim spa. This home isn't just gorgeous; it's energy-efficient too, featuring solar panels that help reduce your carbon footprint and save on utility costs. With every inch thoughtfully updated, all that's left to do is move in and make it your own.

17 College St, Old Saybrook

5 Sand Creek Dr, Old Saybrook
$1,249,000
4 Beds ⋅ 3 Baths ⋅ 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

6 Nutmeg Cir, Old Saybrook
$749,000
3 Beds ⋅ 3 Baths ⋅ 24204473 MLS
This meticulously maintained hidden gem features an inviting open floor plan with a dramatic double-sided fireplace creating warmth and character between the main living areas. The living room is enhanced by beautiful built-ins and a charming reading nook, while the spacious kitchen features an expansive island, built in china cabinets with plenty of room for family gatherings, casual dining and entertaining. Just beyond, the sunroom with skylights is filled with natural light and provides a peaceful place to relax throughout the seasons. The recently updated bathrooms add a fresh, polished feel, while a new roof and a newer heating and cooling system installed has five mini-split units offering added comfort and peace of mind. The full basement is partially finished, providing flexible space for a home gym or casual hangout, while still offering excellent storage. Outdoors, this hidden gem continues to impress. A fenced in yard enhances privacy, along with an expansive deck and heated Gunite saltwater pool and surrounding entertaining areas create a wonderful setting for summer enjoyment. You are on vacation every day in your backyard! Backing directly to a nature preserve this home enjoys a natural peaceful setting and access to nearby trails and outdoor recreation. Ideally located just minutes from Old Saybrook's vibrant Main Street, shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living

6 Nutmeg Cir, 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

3 Anchorage Ln, Old Saybrook
$799,900
4 Beds ⋅ 3 Baths ⋅ 24205326 MLS
Welcome to 3 Anchorage Ln, a spacious colonial designed with the flexibility, comfort, and space to grow into for years to come. This 4-bedroom, 3-full-bath home offers 2,496 sqft with a thoughtful layout that works for everyday family life, entertaining, and working from home. The beautifully remodeled kitchen is the heart of the house, opening to the living and dining rooms and creating an inviting space for gatherings. The first floor offers a versatile den/family room, dedicated office space, full bath, and laundry room, providing plenty of options as your needs evolve. The office could easily serve as a first-floor bedroom, with the convenience of a full bathroom nearby. Upstairs, the spacious primary suite offers a private retreat with an en-suite bath and three closets, along with three additional bedrooms and another full bath. Major updates include a new oil boiler and water heater in 2024, oil tank in 2025, 200-amp electrical service, and central air. A 2-car garage and unfinished basement provide abundant storage. Enjoy the added benefit of deeded 10-foot access for convenient passenger loading and unloading, along with the opportunity to launch and enjoy kayaks. Set on a 0.25-acre lot, the home is close to Saybrook Point, marinas, waterfront dining, Harvey's Beach, Main Street shops, and all that makes Old Saybrook such a wonderful place to call home. A home with room to grow, spaces that adapt with you, and coastal amenities right nearby.

3 Anchorage Ln, Old Saybrook

25 Sunset Rd Unit 18, Old Saybrook
$749,900
2 Beds ⋅ 4 Baths ⋅ 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

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

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

100 Dudley Ave Unit F30, Old Saybrook
$750,000
2 Beds ⋅ 3 Baths ⋅ 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

71 Knollwood Dr, Old Saybrook
$750,000
3 Beds ⋅ 2 Baths ⋅ 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

43 Quarry St, 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

24 W Shore Dr, Old Saybrook
$1,225,000
3 Beds ⋅ 1 Baths ⋅ 24199561 MLS
Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield Point, one of Connecticut's most desirable beach communities. Ideally located just steps from the beach. This move-in-ready home offers the perfect combination of comfort, coastal living, and breathtaking water views. The home features 3 bedrooms and 1 full bath, along with a bright living room showcasing stunning water views. The kitchen is equipped with new appliances, while the convenient laundry area includes all appliances. Recent improvements include a new boiler and hot water heater, providing added comfort and peace of mind. Enjoy the coastal lifestyle from the enclosed breezeway, which offers beautiful water views, or relax on the remodeled upper deck-perfect for morning coffee, entertaining, or taking in the surrounding scenery. A spacious one-car garage provides excellent storage and convenience. As a member of the Cornfield Point Beach Association, you'll enjoy an array of amenities, including a private beach, basketball court, tennis court, clubhouse, and private boat ramp. Whether you're looking for a year-round residence, weekend getaway, or a place to enjoy the best of shoreline living, this community offers an exceptional lifestyle.

24 W Shore Dr, Old Saybrook

1324 Boston Post Rd, 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

11 Kitteridge Hill Rd, Old Saybrook
$699,000
3 Beds ⋅ 3 Baths ⋅ 24197434 MLS
Tucked away on a peaceful cul-de-sac off School House Road, this beautifully maintained Cape offers over 2,700 square feet of finished living space in one of Old Saybrook's most desirable locations. Directly across from The Preserve trail access and just moments from Clark Park, this home is perfectly positioned for those who appreciate nature, recreation, and privacy. The inviting main level features a spacious living room with gleaming hardwood floors and a classic wood-burning fireplace, a formal dining room, convenient half bath, and an updated kitchen with rich cherry cabinetry and granite countertops that flows seamlessly into a warm and welcoming family room with a Garrison wood-burning stove. Sliders open to a stunning cedar-paneled three-season room overlooking the private backyard, expansive deck, and patio-an ideal setting for relaxing or entertaining. Upstairs, the spacious primary suite offers a beautifully sized en-suite bath with custom shower, while two additional bedrooms and a second full bath provide plenty of room for family and guests. A fully finished lower level is the perfect space for an at home gym, office or family room! Thoughtful updates throughout, including Andersen replacement windows, newer garage doors, enhanced attic insulation, 200amp service and ice dam heating cables, provide lasting value and peace of mind. A rare opportunity to enjoy timeless charm, modern updates, and an exceptional location...truly move-in ready.

11 Kitteridge Hill Rd, Old Saybrook

8 Kenn Rd, Old Saybrook
$649,000
2 Beds ⋅ 2 Baths ⋅ 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

170 Old Post Rd, Old Saybrook
$900,000
3 Beds ⋅ 3 Baths ⋅ 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

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
$799,999
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

9 Old Colony Rd, Old Saybrook
$675,000
4 Beds ⋅ 2 Baths ⋅ 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

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

37 Woodland Dr, Old Saybrook
$999,000
3 Beds ⋅ 2 Baths ⋅ 24186222 MLS
Experience coastal luxury in this stunning 3-bedroom, 2-bathroom ranch style home nestled in Knollwood Beach. Set on a rare .33 acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring an expansive remodeled white kitchen with quartz counters, large center island. The family room boasts a dramatic fireplace, while a sunlit dining room/sunroom offers panoramic views of the marsh and Cove. A first-floor primary bedroom a two additional bedrooms, and 2 gorgeous full bathrooms. Additional features a patio and a large deck, new exterior vinyl siding with Azek trim, a 1000 sq ft basement for storage, central air, freshly painted exterior and main floor, remodelled baths, updated electrical, gutter guards and refinished flooring. Roof and septic are newer. No flood insurance needed. Appears to have room for a garage if needed. Enjoy beach rights and clubhouse access, tennis/pickleball courts and playground through the Knollwood Beach Association, a golf cart community, enhancing your coastal lifestyle in this exceptional home.

37 Woodland Dr, 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

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

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