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100 Sheffield St Unit A2, Old Saybrook
$625,000
2 Beds ⋅ 3 Baths ⋅ 24179634 MLS ⋅ The Cove BLDG.
Nestled within The Cove, a serene community on Old Saybrook's storied North Cove, this beautifully appointed townhouse offers the quintessential Connecticut shoreline lifestyle, where the Connecticut River meets the estuary and the ever-changing, breathtaking natural backdrop is your constant companion. The welcoming foyer has abundant closet space and a convenient half bath. The kitchen with granite counters and breakfast bar, dining room, and living room all share gorgeous cove views. The dining room flows naturally into the light-filled living room, appointed with built-in shelves and sliders that open to a private patio, making indoor-outdoor living effortless. Upstairs, two ensuite bedrooms provide comfort and privacy. The primary suite is a true retreat, with sliders to a private deck where captivating cove views greet you the moment you open your eyes, and a full bath with walk-in shower. The second bedroom features a walk-in closet and its own full bath with tub/shower. A designated laundry room completes this level. The finished lower level is ideal as a recreation room, home office, or media room--alongside a large storage room housing a brand new furnace and on-demand hot water heater. Launch your kayak directly on the river and paddle out to the protected cove. Kayaks can be stored in your garage, attached shed, or on town racks conveniently located at the end of Sheffield Street. Saybrook Point, The Kate theater, fine dining, and Main Street are all minutes away.

100 Sheffield St Unit A2, Old Saybrook
207 School House Rd, Old Saybrook
$615,000
4 Beds ⋅ 2 Baths ⋅ 24193207 MLS
A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwood floors, and central air conditioning. Step inside to a welcoming living room featuring a classic wood-burning fireplace and oversized windows that fill the space with natural light while overlooking the beautifully landscaped front gardens. The eat-in kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive dining room-an ideal layout for holiday gatherings, dinner parties, and everyday entertaining. One of the home's standout features is the 280-square-foot, four-season sunporch, offering beautiful views of the private backyard and providing the perfect space to relax year-round. It is important to note the this sq. footage is not included in the Tax Record totals for the home. Situated on a picturesque 1.1-acre lot, this property also includes a partially finished basement with plenty of room for storage as well as an attached two-car garage. The home is freshly painted throughout with newly refinished hardwood floors, offering a bright, move-in-ready interior while providing the perfect canvas to make it your own. Offering space, quality, and exceptional care in a sought-after setting, this is a home you'll be proud to call your own.

207 School House Rd, Old Saybrook
22 Beaver Dam Trl, Old Saybrook
$625,000
4 Beds ⋅ 3 Baths ⋅ 24188934 MLS
Welcome to this classic home with a picturesque setting that is on a generous, level lot, the expansive backyard provides the perfect setting for outdoor entertaining, family gatherings, gardening, or simply relaxing and enjoying the outdoors. The backyard abuts the Old Saybrook preserve offering a private wooded backdrop with access to walking and hiking trails - an ideal setting! This home features four spacious bedrooms, hardwood floors throughout, a welcoming family room, a formal living room, and a dining room ideal for everyday living or holiday celebrations. The kitchen offers granite countertops, stainless steel appliances, and ample space for preparing meals and gathering with family and friends. Additional features include a Buderus furnace, updated electrical, generator ready, full basement offering abundant storage, a two-car garage, and in an area that is ideal for walking and biking. Conveniently located just minutes from two town beaches, marinas, restaurants, shopping, parks, and highways, this home offers the perfect combination of comfort, convenience, and location. Whether you're looking for your forever home or a place to enjoy all that the Connecticut shoreline has to offer, this Old Saybrook gem is ready to welcome its next owners!

22 Beaver Dam Trl, Old Saybrook
2 Half Penny Ln, Old Saybrook
$580,000
3 Beds ⋅ 2 Baths ⋅ 24192318 MLS
This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endless potential, this well-maintained home features one bedroom and a full bath on the main level and 3 additional bedrooms upstairs. An inviting open floor plan where the kitchen flows seamlessly into the dining area and family room. The kitchen has granite counter tops, island and double ovens. A cozy living room with a classic fireplace creating the perfect gathering space. Hardwood floors throughout, while the sunroom provides a bright retreat for reading or relaxing. The fully finished basement offers flexible living space ideal for a family room, home office, gym, or playroom. A spacious private yard includes a shed and outdoor shower set on a corner lot is perfect for outdoor barbecues or Summer evenings. Generator ready. Move right in and enjoy its charm while adding your own personal touches over time. Ideally located just minutes from Old Saybrook's vibrant Main Street, boutique shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living! Come make this home your own!

2 Half Penny Ln, Old Saybrook
9 Farview Ave, Old Saybrook
$500,000
3 Beds ⋅ 1 Baths ⋅ 24184175 MLS
Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing, and enjoying warm summer evenings. This home invites morning walks and evening strolls to Harvey's Beach, Saybrook town beach, Trask Park with a splash pad, and the shops and restaurants along Main Street. Whether you're heading out for dinner, catching the train, or enjoying a beach day, everything you love about Old Saybrook is right at your fingertips. A rare opportunity to own a lovingly cared for home in one of the shoreline's most sought-after areas-perfect as a year-round residence, weekend escape or investment. Come take a look!

9 Farview Ave, Old Saybrook
92 Bokum Rd, Old Saybrook
$525,000
2 Beds ⋅ 2 Baths ⋅ 24164864 MLS
A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and updated plumbing and septic, it offers modern peace of mind while preserving its timeless character. Rich in personality, the home evokes the romance of a countryside Tuscan Villa, from its ivy draped exterior to the layered, designer interiors originally re envisioned by Charles Spada in the 1990s. The private backyard is a tranquil escape, featuring exquisite stonework and curated plantings meant for quiet moments or intimate gatherings. Ideally situated just moments from boutique shopping, galleries, dining, Old Saybrook Town Beach, and the Katharine Hepburn Cultural Arts Center, this exceptional home offers both lifestyle and convenience. Featured in House Beautiful and Home Decorating Ideas, it is a true one of a kind residence ready to be enjoyed immediately, with furnishings available for purchase if desired.

92 Bokum Rd, Old Saybrook
21 Baum Ave, Old Saybrook
$600,000
2 Beds ⋅ 2 Baths ⋅ 24190986 MLS
Backyard goals? Achieved. Welcome to your own private oasis in the heart of Old Saybrook! Surrounded by low-maintenance vinyl fencing, lush lawn complete w/irrigation, this incredible outdoor space was made for summer--backyard BBQs, morning coffee under the pergola, & relaxing with family & friends. A spacious patio sets the stage for effortless entertaining, while the oversized shed provides exceptional storage for beach gear, bikes, lawn equipment, & more. Step inside & you'll find a beautifully maintained 2-bed, 2-full bath home that's just as inviting as the backyard, creating the perfect blend of warmth, character, and comfort. With hardwood floors throughout, a renovated kitchen, & energy-efficient mini-split systems, the layout is made for a weekend retreat or year-round escape. Perfectly situated just mins from downtown Old Saybrook, you'll enjoy convenient access to charming boutiques, local restaurants, marinas, golf courses, fitness studios, & public beaches-making it easy to embrace the best of CT's shoreline lifestyle. Whether you're hosting parties, unwinding after a day by the water, or exploring everything Old Saybrook has to offer, this thoughtfully updated, move-in-ready home delivers the perfect combination of comfort, convenience, and coastal charm. Looking for an investment? Its desirable location & turnkey appeal make it an ideal candidate for an Instagram-worthy vacation getaway/short-term rental to add to your portfolio. Don't let this one sail away!

21 Baum Ave, Old Saybrook
13-A Cove St, Old Saybrook
$717,500
2 Beds ⋅ 1 Baths ⋅ 24180696 MLS
Saybrook Point! Welcome to the coastal lifestyle you've been dreaming of! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is just steps away. Set on a generous sized lot this home is move-in ready filled with natural sunlight and thoughtfully updated throughout creating a bright welcoming interior which includes a 3-season sunroom where you can slow down and enjoy the coastal air and a full basement. With engineered plans already in place for future expansion, the possibilities are endless - whether you are looking for a year round residence, weekend getaway, or investment in one of shoreline's most coveted locations. Close to highways, trains and amenities. This is truly a hidden gem in the heart of Old Saybrook where every day feels like vacation!

13-A Cove St, Old Saybrook
25 Sunset Rd Unit 3, Old Saybrook
$685,000
2 Beds ⋅ 3 Baths ⋅ 24182248 MLS ⋅ Oyster River Landing BLDG.
Looking for a home that feels like vacation every day? Carefree coastal living can be yours at this stylish townhouse at the Oyster River Landing condos. With just 20 homes, residents enjoy beautiful grounds, sunsets, and a pool overlooking the private boat basin on the Oyster River. This leads out to Long Island Sound and is excellent for fishing, kayaking, and paddle boarding. As you enter the home, your eyes are drawn to the large sliders that open to a serene private patio and gardens. This townhouse has been extensively updated throughout. (list provided) The new teak wood floors add a nautical flair. The morning sun shines in the kitchen, with stainless-steel appliances, teak floor and a breakfast bar. The primary bedroom has an ensuite bath that has been extensively updated. Two closets have been fitted with custom closet systems. A second bedroom also has an ensuite bathroom, with tub, and two custom closet systems. The laundry is conveniently located between the two bedrooms. There is an unfinished lower level that provides an opportunity to expand about 700 sq ft of living space. The owners have a professional design available. The location of this condo is ideal, with just a walk or short ride to the town beach, Main St shops, restaurants, the town green activities, and the popular Katharine Hepburn theatre. The Saybrook Point resort and Fenwick golf course are also nearby. Come see why Oyster River Landing is called "Old Saybrook's best kept secret"!

25 Sunset Rd Unit 3, Old Saybrook
25 Sheffield St Unit 7, Old Saybrook
$960,000
2 Beds ⋅ 4 Baths ⋅ 24171224 MLS ⋅ Saybrook Village BLDG.
Step into refined, effortless living in this beautifully appointed luxury condo featuring 2 bedrooms, 2 full baths and 2 half baths. A charming entry welcomes you with a thoughtfully designed garden with roses, lilacs and a variety of other plantings setting a warm and inviting tone. Designed with an open floor plan and soaring cathedral ceilings, the space is filled with natural light and an airy, elegant feel. Rich hardwood floors flow throughout the main living areas, complemented by a cozy gas fireplace that creates the perfect focal point for relaxing or entertaining. The updated kitchen is both stylish and functional, offering corian countertops, stainless steel appliances, a 5 burner gas cook top and seamless connectivity to the dining and living spaces. Sliders lead out to a private patio, ideal for morning coffee or evening gatherings. The first-floor primary suite provides comfort and convenience with a full bath, walk in closet and easy one-level living, while the upper level includes the second bedroom, loft that is being used as an office and additional full bath offering flexibility for guests or a home office. The partially finished lower level includes a sewing room and half bath with plenty of storage space. Ideally situated in a prime location, just steps to Main Street with it's charming shops and restaurants and minutes to local beaches and marinas, this home offers the perfect blend of luxury, convenience and coastal lifestyle living.

25 Sheffield St Unit 7, Old Saybrook
420 Maple Ave, Old Saybrook
$2,150,000
3 Beds ⋅ 3 Baths ⋅ 24183797 MLS
Welcome to a coastal sanctuary where changing, panoramic views of the Long Island Sound greet you from almost every room. Situated directly across from the shore with no homes across the street to block your view, this remarkable year-round residence offers a permanent, front-row seat to the water. Enjoy all the benefits of an unobstructed marine horizon and instant beach access, completely free from the requirement of flood insurance. Inside, an incredible open floor plan boasts generous, light-filled spaces throughout. The seamless living and dining area is warmed by a cozy propane fireplace and flows effortlessly into a fully heated and cooled front porch-the ultimate sun-soaked perch for watching the waves. Brand-new windows throughout perfectly frame the water vistas, leading you to the heart of the home: a delightful eat-in kitchen just steps from a oversized side deck designed for effortless indoor-outdoor entertaining and more views. Upstairs, beautiful historic fir floors sweep through the three spacious bedrooms, including a primary suite that serves as a private oasis, hosting its own unique, glassed-bookcase sitting room overlooking the Sound. Two full baths complete the second level. Every coastal convenience has been thoughtfully considered, including an attached two-car garage, a partial basement for mechanicals, a built-in sprinkler system, a storage shed equipped with electricity, and an outdoor hot/cold shower for rinsing off after a day in the sand....

420 Maple Ave, Old Saybrook
4 Beach Rd, Old Saybrook
$1,600,000
3 Beds ⋅ 3 Baths ⋅ 24176301 MLS
DEEDED BEACH RIGHTS TO CORNFIELD POINT! One of Old Saybrook's most sought after beach communities! Enjoy beach days, sunset strolls, and the relaxed charm of shoreline living. This impeccably maintained Nantucket-style reverse floor plan home promotes scenic views from upper level main living space with private primary ensuite and 1st floor indoor/outdoor entertainment suite below offering timeless coastal charm and thoughtfully designed living spaces with breathtaking, expansive marsh views, features a spectacular, fully renovated chef's kitchen featuring premium appliances, Thermadore oven, a wine chiller, ice maker, breakfast bar, and an impressive oversized leathered quartzite stone island! An inviting living room with a wood-burning fireplace, which offers warmth and character, and a deck seamlessly extending from the kitchen features remote controlled retractable screens and integrated LED rail lighting, offering the flexibility of an open-air retreat or fully screened outdoor living space. Equipped with a premium partial Lutron smart lighting system and integrated Sonos 5-zone sound system. Every detail has been thoughtfully curated with high-end finishes and exceptional craftsmanship throughout. The primary suite includes a renovated bathroom with walk-in shower and installed California Closets.

4 Beach Rd, Old Saybrook
41 Watrous Point Rd, Old Saybrook
$3,750,000
6 Beds ⋅ 5 Baths ⋅ 24162782 MLS
Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and wildlife lovers alike. The dual shoreline offers the river side with tidal rhythms and sweeping panoramas stretching from Essex Harbor north to Old Lyme across the water, then south toward Long Island Sound. The marsh side along Turtle Creek hums with avian life-majestic Bald Eagles perch in the trees while Herons, Egrets, Osprey, and migrating songbirds create a symphony that changes with the seasons. Two private docks provide endless boating possibilities: launch from the deep-water river dock for open-water adventure, or drift into the tranquil creek for kayaking and wildlife observation. Inside, 5,536 square feet of light-drenched living space unfolds with effortless grace. The architecture celebrates both gathering and solitude-a chef's kitchen designed for culinary artistry flows seamlessly to indoor and outdoor dining areas, while five fireplaces anchor intimate retreats throughout.

41 Watrous Point Rd, Old Saybrook
120 Sandy Point Rd Unit 120, Old Saybrook
$615,000
2 Beds ⋅ 3 Baths ⋅ 24129742 MLS ⋅ Summerwood Condo BLDG.
Move right into this beautifully renovated 1,557 sq. ft. townhouse condominium in the highly desirable Summerwood on the Sound! This turnkey home offers 2 bedrooms plus a spacious third-floor loft-perfect for a home office or 3rd bedroom. Thoughtfully updated throughout, the home features hardwood flooring on all three levels, 2 1/2 beautifully renovated bathrooms, Andersen Windows, a Bosch High-Efficiency heat pump (2024), and a Rheem 50-gallon hot water heater (2024), new roof 2019. The open and inviting floor plan is filled with abundant natural light and features a cozy fireplace in the living room, creating the perfect space for relaxing or entertaining. The updated kitchen offers granite countertops, stainless steel appliances, and an ideal layout for everyday living and hosting family and friends. Enjoy seamless indoor-outdoor living with a private deck off the dining room. Summerwood on the Sound offers exceptional resort-style amenities including a private beach, paddle board/canoe racks, swimming pool, tennis courts, and pickleball courts. Located just minutes from downtown Old Saybrook, marinas, shopping, and dining, this meticulously maintained home offers the perfect blend of luxury, comfort, and low-maintenance coastal living. Nothing to do but move in and enjoy!

120 Sandy Point Rd Unit 120, Old Saybrook
2 Cinnamon Way, Old Saybrook
$704,000
3 Beds ⋅ 3 Baths ⋅ 24177176 MLS
Surrounded by a peaceful preserve with beautiful views, this light filled custom contemporary Colonial offers a rare blend of privacy, flexibility, and classic Old Saybrook charm. Step through the new custom front door into an open, airy layout where natural light pours through new windows and skylights, setting a warm tone from the moment you enter. The stylish kitchen features stainless steel appliances, a new backsplash, updated lighting, and an easy flow into the beautiful family room with vaulted ceilings, a fireplace, and double sliders leading to the expansive back deck. Morning coffee here feels special, with birdsong, wooded views, and the protected preserve as your backdrop, while fall evenings around the firepit create the kind of outdoor living people remember. The floor plan offers wonderful versatility with the option for a main level or upper level primary suite, including a first floor bedroom with full bath and deck access. Major exterior updates from 2023 to present include a new roof, siding, gutters, garage doors, skylights, front lawn, landscaping, exterior lighting, pergolas, and refreshed decking, while interior improvements include fresh paint, smooth ceilings in most rooms, custom first floor doors, renovated baths, new stair railing, hardware, and appliances. A walk out basement, 2 car garage, newer 4 zone Buderus furnace, and first floor mini splits add comfort and function. Close to Old Saybrook's historic Main Street and restaurants.

2 Cinnamon Way, Old Saybrook
208 Ingham Hill Rd, Old Saybrook
$615,000
3 Beds ⋅ 3 Baths ⋅ 24183646 MLS
Location & Potential! Spacious Cape Cod in serene setting on over 2 acres close to town & shopping. With some cosmetic TLC you can turn this into a beautiful house that you will be proud to make home. Newer roof, partially finished basement with seperate heating zone. Fully applianced kitchen with newer refrigerator. First floor laundry and beautiful sunroom. House being sold "As Is". Please - Do not pull into driveway without appointment.

208 Ingham Hill Rd, Old Saybrook
43 Indianola Dr, Old Saybrook
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 24168965 MLS
Enjoy coastal living at its finest in the coveted Cornfield Point community. This custom-built home offers nearly 3,000 square feet of thoughtfully designed space, featuring 4 bedrooms, 3 full baths, and a versatile main-level office, den, or media room to suit your lifestyle. Step outside to a spacious deck where you can take in serene marsh and water views of Cornfield Point Beach, with a retractable awning providing the perfect shade for sunny afternoons. Inside, the main level boasts an open floor plan with gleaming hardwood floors, custom wood paneling, a cozy gas fireplace, and expansive Thermopane windows that fill the home with natural light. Upstairs, you'll find four generously sized bedrooms, all with hardwood flooring, along with a convenient walk-up attic for additional storage or future expansion. The newly renovated primary suite bathroom features a dual-sink vanity and a beautifully appointed walk-in shower, creating a spa-like retreat. Cornfield Point offers an exceptional lifestyle with access to a pristine sandy beach, private boat launch, tennis and pickleball courts, a clubhouse, and a playground. The community is known for its vibrant social calendar and welcoming atmosphere, and its golf cart-friendly streets make getting around both easy and enjoyable. Nearby, you'll find Fenwick Golf Course, along with a variety of local dining, shopping, marinas, and cultural attractions, including the renowned Katharine Hepburn Cultural Arts Center.

43 Indianola Dr, Old Saybrook
95 Middletown Ave, Old Saybrook
$1,049,900
4 Beds ⋅ 2 Baths ⋅ 24176978 MLS
95 Middletown Avenue offers a rare opportunity to enjoy four season living in the heart of Saybrook Manor, one of Old Saybrook's most sought after shoreline communities. Renovated in 2022 with thoughtful attention to comfort and design, this beautifully updated home combines timeless coastal character with modern amenities and sweeping views of the Oyster River & Long Island Sound. With approx. 1,600 sq ft. of living space, the home features a reverse floor plan designed to maximize natural light and take advantage of the water views. The main living spaces feel bright and open, w/ hardwood floors, updated finishes, and open layout. A spacious deck with full panoramic views provides the perfect setting for morning coffee, outdoor dining, or relaxing while overlooking the water & shoreline. The home includes four bedrooms and two full bathrooms, offering flexibility for guests, remote work, or year round living. The updated kitchen opens comfortably into the living/dining areas, creating an inviting atmosphere. Modern conveniences including central air and mini split. The property includes a rare two car garage along w/ 400 square foot barn full of charm and potential perfect for a studio, workshop, gym, storage. An outdoor shower after a day at the beach. Residents enjoy a private beach exclusive to the community steps away! This home does not require flood ins adding long term value. Just minutes from marinas, restaurants, shopping the location is best CT shoreline living.

95 Middletown Ave, Old Saybrook
96 Fenwood Dr, Old Saybrook
$1,030,000
3 Beds ⋅ 3 Baths ⋅ 24125643 MLS
Located on a corner lot in the District of Fenwood with views of the water, this house has all of the comforts of home. The entire house has been refitted with all new heating and air conditioning. The spacious main level entry offers the living room, family room with a fireplace, formal dining room, full bath, and kitchen. The kitchen is complete with an island breakfast bar, and wet bar where the view of the cove is evident of the peaceful neighborhood. Upstairs are the 3 generous bedrooms one of which is the master suite. Pass by the full hallway bath and enter the great room with the second fireplace. This room can be utilized as an office, recreation room, or even sleeping quarters. The large double level patio is accessible from both the dining room, and family room. It is very quiet, and has great natural cover from the elements. Enjoy a cup of coffee and meals here as well as access to the outdoor shower, and storage shed. The attached 2 bay garage has plenty of storage for the outdoorsman or the handyman, and enters into the family room. Access to the private Fenwood beach is walkable and included in the HOA. The home is minutes from the village of Old Saybrook, and all of its marine amenities. The salt life awaits you at 96 Fenwood Drive!

96 Fenwood Dr, Old Saybrook
6 Trolley Xing, Old Saybrook
$995,000
3 Beds ⋅ 3 Baths ⋅ 24177743 MLS
Quintessential New England Gambrel Colonial with a dramatic sunroom addition and a brand new roof! Sited in a quiet cul-de-sac neighborhood, the gorgeous one acre grounds include numerous mature flowering trees and shrubs, as well as a pine tree perimeter for privacy. The original part of the 1st floor of the home includes a front to back living room with bookshelves, a formal dining room, a powder room and a cozy family room with fireplace. Completing the 1st floor is a large sunroom with a vaulted ceiling and built-ins. The upper level includes a primary bedroom with adjacent bath and 2 other bedrooms which share a bath with recent upgrades. The finished lower level has a recreation room with a fireplace with electric insert, a sauna and work room. From the main level the sunroom transitions to the beautifully landscaped and inviting deck, patio and recently added inground pool. In the 3 years of ownership, all lighting has been updated, new flooring, some mechanicals, new heating & AC, all wall coverings, new roof, pool added, updated bathrooms and the list goes on and on. It is a short drive to the historic downtowns of Old Saybrook and Essex, as well as the access to the train station and highways. Historic Old Saybrook is known for it's marinas, beaches, shops, first-class restaurants, and The Katharine Hepburn Cultural Arts Center.

6 Trolley Xing, Old Saybrook
5 Woodland Dr, Old Saybrook
$1,470,000
3 Beds ⋅ 3 Baths ⋅ 24163052 MLS
Rare opportunity to enjoy sweeping views of Long Island Sound from a quiet street just off Maple Avenue in sought-after Knollwood Beach. This beautifully renovated 3-bedroom, 3-bath coastal retreat, just one street from the water, offers unobstructed views and is ideal as a year-round home or second getaway. The bright, open floor plan is designed to capture the scenery, with an oversized living/dining area featuring hardwood floors, a custom stone propane fireplace, and a wall of south-facing windows. An oversized one-car garage, mudroom, and laundry area welcome you inside. The custom white kitchen features quartzite countertops, porcelain farm sink, stainless appliances, and a Bosch propane range-perfect for entertaining. The first floor also offers an updated full bath and flexible bedroom or office. Upstairs, the primary suite boasts cathedral ceilings, a custom bath with dual sinks, tiled shower, and generous closets. A third bedroom, remodeled full bath, and family room with French doors lead to a covered deck with panoramic water views. The partially finished lower level provides additional living space and storage. Features include dual street access, ample parking, whole-house generator, alarm system with cameras, fenced yard with mature landscaping, and new Mitsubishi split HVAC (2024). Meticulously maintained and not in a flood zone-an exceptional shoreline opportunity.

5 Woodland Dr, Old Saybrook
34 Sunset Ave, Old Saybrook
$400,000
2 Beds ⋅ 1 Baths ⋅ 24185319 MLS
Charming Custom Cottage in Old Saybrook - Welcome to this adorable 750-square-foot home nestled in the heart of Old Saybrook. Thoughtfully designed and full of character, this cozy retreat offers the perfect blend of timeless charm and modern comfort. Step inside to discover beautifully crafted custom wainscoting that adds warmth, elegance, and distinctive New England style throughout the living spaces. Natural light fills the home, creating a bright and inviting atmosphere that feels both spacious and welcoming. The efficient floor plan maximizes every square foot, featuring comfortable living areas, a well-appointed kitchen, and charming details that make this home truly special. Whether you're looking for a year-round residence, weekend getaway, or downsizing opportunity, this property offers easy living without sacrificing character. Outside, enjoy a manageable yard with space for relaxing, gardening, or entertaining. This adorable home was freshly painted inside and out, brand new carpeting and fresh stone on the driveway. Located just minutes from beaches, marinas, restaurants, and shopping, you'll experience all the coastal charm that Old Saybrook has to offer.

34 Sunset Ave, Old Saybrook
60 Ingham Hill Rd, Old Saybrook
$685,000
24072144 MLS
Picturesque waterfront 8.1-acre lot on the tranquil Oyster River in historic Old Saybrook. 1,400 feet of river frontage leading to Long Island Sound. Currently set as farmland, this could be a home run for builders sensitive to the needs of the land. With its beauty, you have 50-plus feet of road frontage and large footprint within the 50-foot tidal wetlands setback. I-95 is easily accessible, and development would be just minutes away from our town's beautiful beaches and charming Main Street. Whether you wish to continue meeting the demand for organic foods or embrace the seaside's organic growth, this is it.

60 Ingham Hill Rd, Old Saybrook
44 Coulter St, Old Saybrook
$531,000
3 Beds ⋅ 1 Baths ⋅ 24183873 MLS
Located in one of Connecticut's most desirable shoreline communities, this 3-bedroom ranch offers an incredible opportunity to create the home of your dreams. Just steps from downtown Old Saybrook and just up the street from one of the best scenic views in town. You'll enjoy easy access to shops, restaurants, marinas, beaches, and all the coastal charm this beloved town has to offer. The seller has already completed some of the preparation work, including carpet removal to reveal hardwood floors, wallpaper removal, and fresh interior paint throughout. This solid home is ready for your finishing touches and personal vision. The spacious, level lot features a lovely backyard with garden potential, while the full basement offers endless possibilities for expansion into a family room, recreation area, home office, or additional living space. A fireplace adds character and warmth, creating the perfect focal point for future gatherings. If you are someone looking to customize a home in a premier shoreline location, this property is filled with potential and opportunity. Don't miss your chance to own in the picturesque town of Old Saybrook, known for its beautiful beaches, vibrant downtown, and exceptional coastal lifestyle.

44 Coulter St, Old Saybrook
29 Old Post Rd, Old Saybrook
$750,000
3 Beds ⋅ 3 Baths ⋅ 24181692 MLS
Welcome to Crow's Nest, where classic New England country living meets direct waterfront luxury on the scenic Oyster River. Steeped in history, this enchanting historic farmhouse Circa 1850, is perfectly positioned along the west banks of the Oyster River, offering breathtaking water views from almost every single room. The character-rich interior features 3 bedrooms & 2.5 baths, offering cozy, sun-drenched spaces primed for your personal touch. For those with a vision, these charming spaces are ready to expand, with incredible potential to further enhance the elevated river vistas with slight modifications. A Rare, Multi-Parcel Investment Opportunity Uniquely spanning two separate parcels, this property offers unmatched flexibility and value. The home sits on one parcel, while the spectacular waterfront assets sit on a separate deeded parcel, meaning the dock parcel possesses the rare capability of being sold separately in the future if desired. The Crown Jewel: A fully permitted 325-foot private dock-standing proud as one of the absolute largest private docks in all of Old Saybrook. Bring your boats, jet skis, and kayaks! The Boathouse: An oversized 2-car detached garage offers the ultimate storage solution for all your water toys and gear. Enjoy close proximity to downtown Old Saybrook, yet remain tucked away in your own private waterfront enclave. Sit on your massive private dock, watch the wildlife pass you by & experience the pure freedom of waterfront.

29 Old Post Rd, Old Saybrook
30 Sunset Ave, Old Saybrook
$395,000
4 Beds ⋅ 1 Baths ⋅ 24180469 MLS
Welcome to this cozy, charming, cape style home located in the shoreline community of Old Saybrook. This property is situated just moments away from nearby beaches, marinas, restaurants and shopping. This four-bedroom cape is updated with town records and features a finished basement with plenty of entertaining space. Additionally, you can step outside and enjoy a lovely deck that is perfect for family gatherings. This is an Estate Sale subject to probate approval. House sold "AS IS:

30 Sunset Ave, Old Saybrook
175 N Cove Rd, Old Saybrook
$3,400,000
4 Beds ⋅ 5 Baths ⋅ 24166649 MLS
An exceptional offering in the heart of North Cove, this storied estate presents a rare convergence of history, scale, and coastal prestige in Old Saybrook. Set on over an acre of beautifully sited grounds with direct water access and a private dock, the property offers a lifestyle that is both tranquil and connected, just moments from the Cove, local marinas, and the village center. The setting is quintessential shoreline New England: open, peaceful, and deeply tied to the surrounding water. The residence itself spans over 3,500 square feet, offering generous living spaces, multiple bedrooms, and a layout that reflects its centuries-old origins while accommodating modern living. Its scale and presence are immediately apparent, with architectural details and craftsmanship that speak to its early 18th-century roots and long-standing role in the community. Serving as the historic "Black Horse Tavern" in the early 18th century, the home carries a meaningful legacy within North Cove's maritime history. Today, it stands as a residence of enduring character, offering the opportunity to thoughtfully preserve and enhance a truly distinctive property within the parameters that protect its historic significance. Properties of this caliber, where setting, scale, waterfront access, and provenance align, rarely come to market. This is a chance to own a significant piece of Old Saybrook's shoreline heritage in one of its most sought-after locations.

175 N Cove Rd, Old Saybrook
39 Middletown Ave, Old Saybrook
$385,000
4 Beds ⋅ 1 Baths ⋅ 24157756 MLS
Charming and beautifully updated 4 bedroom partially furnished Seasonal Cottage in desireable Saybrook Manor beach community. This home offers the perfect blend of character and modern improvements with vaulted ceilings and exposed beams. The completely remodeled kitchen features Corian countertops, a classic farmhouse sink, skylight for natural light and matching rolling kitchen cart for added prep and storage space. The renovated bathroom includes a luxurious rainfall shower head for a spa-like feel. The bright dining room is enhanced by a large new slider that opens to a spacious stone patio-ideal for indoor/outdoor living. The Living room has a skylight offering warmth and brightness for your gatherings. Enjoy summer evenings around the fire pit or rinse off in the outdoor shower with both hot and cold water after a day at the beach and enjoy dining under the pergula watching the sunset. Additional updates include new windows, new plumbing, and updated electrical, offering peace of mind for years to come. A perfect coastal-style retreat with thoughtful upgrades inside and out. Square footage does not include enclosed porch (an additional 140 sq ft). 2 short blocks from the Private community beach easily accessed with the included Golf Cart.

39 Middletown Ave, Old Saybrook
12 Hill Rd, Old Saybrook
$991,000
3 Beds ⋅ 3 Baths ⋅ 24147505 MLS
Welcome to Otter Cove Estates, located in Old Saybrook Ct. Live in the established area of residential homes that offer large lots of 2 acres at the mouth of the Ct River. This home offers 3 bedrooms with Master suite on the first floor with ensuite. Open floor plan large kitchen, built in newer appliances subzero built in fridge, Electrolux double ovens, Bosch dishwasher and newer microwave. Corian counter and breakfast bar. Family room adjoins with large fireplace, sky light, beautiful beams and display cubby for treasures. Dining room with window seat and wanes coating details. Hardwood floors, carpeted bedrooms. 2 bedrooms upstairs with full bath. central air and central vac. Bonus rooms over garage for media, family or storage. Yard has beautiful stone wall outside deck 18x23 with seating and planters. Large 2 bay garage with 9 ft door for large vehicles. Extra storage room that could be turned to 3rd smaller bay. Marinas from Saybrook Point to Ferry Rd for boating, fishing recreational use. Walking trails on Turtle Creek preserve. Kayak launch at river access. Close to town and Essex.Ease to I95, Rt 9 between Boston and NY. An everchanging seasonal landscape with deer, osprey, otters and more. Old Saybrook offers Main Street with local shops and dining strolling for coffee or a bite to eat. Historic town, mini golf, 9 hole golf course the Katherine Hepburn Cultural Arts building with events and pickle ball courts. Music on the green in the summer for the public.

12 Hill Rd, Old Saybrook
13 Briarwood Dr, Old Saybrook
$653,000
3 Beds ⋅ 2 Baths ⋅ 24182033 MLS
MAKE THIS HOUSE A HOME!! Investors, DIY buyers take note of this opportunity. A true fixer-upper being sold as-is. A sweet ranch with views of the marsh, Back River and Plum Bank out to Long Island Sound. 3 br, 1 1/2 bth set on .52 acres. Boarders open space with deeded beach rights to Cornfield Point Beach Enjoy spectacular sunsets and salt marsh views from your back porch Cozy fireplace in living room for cool nights, 1 car detached garage and a partially finished basement for additional space. Located just off the 3-mile shoreline walking, biking, running loop. Public beaches, golf, restaurants, shopping and marinas also nearby. Low taxes, rail service available to Boston and NYC

13 Briarwood Dr, Old Saybrook

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