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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
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
6 Point Rd, Old Saybrook
$2,970,000
3 Beds ⋅ 3 Baths ⋅ 24162977 MLS
Direct waterfront with phenomenal views! Perched on a bluff with 62 feet of shoreline frontage, this Nantucket-inspired residence provides an unparalleled, panoramic vantage point of Long Island Sound and the coastline. Perfectly positioned to capture the essence of being on the water, this home maximizes water views from every room and boasts magnificent sunrises and sunsets. Tucked away on a quiet, dead-end street in highly coveted Cornfield Point, you'll enjoy privacy paired with Association perks - sandy beach, kayak racks, boat launch, tennis & basketball courts, playground and clubhouse. The 2,363 square feet of living space is drenched in sunlight, featuring an open floor plan designed to bring the outside in. Upstairs is dedicated to an incredible primary suite with floor-to-ceiling windows that frame breathtaking vistas. A desirable first-floor bedroom suite offers the ease of one-level living. The kitchen, dining area and living room flow seamlessly connecting to a waterside patio - perfect for entertaining, alfresco dining and savoring morning coffee to the sound of the waves. Move-in ready and no flood insurance required. The professionally landscaped .20-acres includes a one-car garage with walk-up storage. Two hours from New York or Boston. Near amenities - shopping, restaurants, marinas, health clubs, golf and the cultural charm of "The Kate". Properties on Point Road rarely hit the market! Don't miss the opportunity to live like you're on vacation year-round.

6 Point Rd, Old Saybrook
382 Maple Ave, Old Saybrook
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 24161079 MLS
Wake up to sweeping views of Long Island Sound in this beautifully rebuilt Knollwood Beach home, designed for effortless coastal living. Recently renovated, this light-filled residence offers an open, flowing layout ideal for entertaining or relaxing by the shore. The recently renovated white kitchen features leathered granite counters, and stainless steel appliances, seamlessly connecting to the main living areas. A desirable first-floor master suite provides comfort and convenience, complemented by 2.1 well-appointed baths. Upstairs, a spacious family room opens to a covered terrace with breathtaking water views-perfect for morning coffee or evening sunsets. The finished lower level adds flexible space for guests, hobbies, or a media room. Outdoor living shines with a private backyard, expansive patio, and outdoor kitchen-ideal for summer gatherings. A large detached garage offers additional storage for beach gear and more. Energy-efficient living is enhanced with fully paid solar, while a newer 1,250-gallon septic system with new leach field provides peace of mind. Located outside the flood zone and part of the sought-after Knollwood Beach Association, residents enjoy a private sandy beach, clubhouse, kayak launch, tennis courts, and more. A rare opportunity for the discerning second-home buyer or retiree seeking the best of shoreline living.

382 Maple Ave, Old Saybrook
372 Maple Ave, Old Saybrook
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 24134739 MLS
Most beach homes ask you to choose: location or amenities, space or style, primary home or vacation retreat. This one says "why not both?" Perfectly positioned just 50 steps from Knollwood Beach, this spacious 3-bedroom 3-bath sanctuary delivers the rare combination of prime beach access and every amenity you'd expect from a year-round residence. A stress free move-in is possible here, as this residence is offered fully furnished.* Start your morning with coffee in the primary suite, with a balcony overlooking the ocean. Work from your spacious private home office with inspiring views. Prepare dinner in a gourmet kitchen designed for serious cooking. End your evening soaking in the hot tub under the stars, taking in panoramic ocean vistas. When it's time to unwind, choose your pleasure: a private sauna for relaxation, a freshly renovated home theater with surround sound for entertainment, or simply the comfort of thoughtfully designed living spaces enhanced by custom built-ins. Resort style amenities include several outdoor living areas to have a lively gathering or a serene quiet moment, ample closet and storage space including a butler's pantry/laundry room combo that ensures there's a space for everything, and private parking- a rare beach find. Enjoy the practical luxuries that make beach living effortless with plenty of room to truly live-not just visit. *some staging items including bedding do not convey

372 Maple Ave, 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
8 Owaneco Trl, Old Saybrook
$1,950,000
4 Beds ⋅ 4 Baths ⋅ 24176745 MLS
Welcome to this stunning gray shingle, Nantucket-style Cape Cod nestled in the sought-after Indiantown neighborhood of Old Saybrook - less than a quarter mile to the beach and a Private Marina! Offering over 2,800 square feet of beautifully appointed living space, this exceptional home was effectively built in 2018 and presents in excellent condition throughout. The open-concept floor plan seamlessly connects the chef's kitchen, great room, and dining room - perfect for everyday living and effortless entertaining. Gorgeous interior finishes elevate every space, combining coastal charm with modern sophistication. Step outside to the covered deck and enjoy the serene, sun-drenched backyard - a rare triple lot offering space, privacy, and room to breathe. Four spacious bedrooms and three and a half baths provide comfortable accommodations for family and guests alike. Propane heat and central air ensure year-round comfort. The two-car attached garage adds everyday convenience and includes an elevator and full house generator. A separate, detached 2-car garage offers exceptional flexibility - ideal for a workshop, or additional storage. This is coastal Connecticut living at its finest. Indiantown's beach rights, private marina, neighborhood character, and two private beaches make this a truly rare opportunity. Don't miss it!

8 Owaneco Trl, Old Saybrook
12 Toms Rd, Old Saybrook
$1,849,000
3 Beds ⋅ 2 Baths ⋅ 24162292 MLS
Overlooking its own private sandy beach with breathtaking water views in every direction, this beautifully renovated 1,652 sq ft year-round beach home offers the perfect blend of comfort and coastal luxury. Ideal for a second-home buyer or those looking to downsize in style, this property delivers an exceptional shoreline lifestyle.The home features a bright, open-concept layout with great flow, highlighted by hardwood floors on the main level and a spacious living area that captures sweeping views of Long Island Sound. A first-floor bedroom and full bath provide easy one-level living, while two additional upper-level bedrooms and a second full bath offer comfortable space for family and guests. Step out onto the expansive deck just off the main living area and take in stunning sunrises and sunsets over the water. Whether entertaining or relaxing, the views are simply unforgettable. Enjoy direct access to your own private beach, plus a shared dock on Back River-perfect for kayaking or small boating enthusiasts. Additional features include a large storage shed and ample parking for up to 8 cars. Turnkey and in excellent condition, this is a rare opportunity to own a private waterfront retreat designed for easy, year-round coastal living.

12 Toms 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
35 Research Pkwy, Old Saybrook
$1,750,000
3 Baths ⋅ 24151097 MLS
Well-Maintained Light Industrial-Warehouse-Office property located on 2.96 Acres. Easy access location......close to Old Saybrook, CT Center and Conveniently Located near I-95 and Route 9 entrance ramps. Entire 31,414 SF available. Presently Tenant-occupied and moving. Very Flexible use with easy floor plan changes/configurations.......Present set-up; Office & Light Industrial (7,000 sf) and Warehouse (17,000 sf) on the First Floor. The second floor has (7,000 SF office/storage space) which has 2 access points to the 1st floor Warehouse area. There are 4 loading dock areas w/6 OH Doors 4 doors are 8x8, plus a 10x12 & one at 12x20. There are 500 feet of road frontage on Research Parkway with 70 parking spaces surrounding the front and sides and back of the building along with additional space for several trucks.

35 Research Pkwy, Old Saybrook
5 Oakwood Rd, Old Saybrook
$1,700,000
3 Beds ⋅ 2 Baths ⋅ 24101504 MLS
This spacious Knollwood Beach home is only ONE house from Long Island Sound featuring sweeping water views. Step into timeless elegance with this stunning home where classic craftsmanship meets modern convenience. The first floor features a gourmet kitchen and dining area complete with granite countertops, a center island with canopy, and high-end appliances. Original wainscoting ceilings and two handcrafted light fixtures add warmth and charm. The upper and lower foyers showcase exquisite tin ceilings and a striking chandelier, while the cozy family room offers washed cedar walls and serene water views. The living room is adorned with custom cherry display shelves, a built-in bench, intricate dentil and crown moldings, and a granite and marble wood-burning fireplace. A Lennox-style chandelier, recessed lighting, and gleaming hardwood floors flow throughout the main level. Upstairs, the expansive primary bedroom boasts custom built-ins, original wainscoting ceiling, and an architecturally designed balcony with breathtaking views of Long Island Sound, complemented by custom window treatments. The luxurious en-suite bath features a Jacuzzi tub, double vanity, built-in cabinetry, laundry area, and spacious closets. Outside, the home's unique character continues with a ship-outline etched into the wood shingles, beautifully manicured floral gardens, and an impressive pressed concrete driveway. Additional features include a sprinkler system, invisible fencing, and heated garage

5 Oakwood Rd, Old Saybrook
11 Fencove Ct, Old Saybrook
$1,692,034
4 Beds ⋅ 3 Baths ⋅ 24199678 MLS
Meticulously maintained and beautifully updated, this exceptional home offers refined coastal living in the desirable Fenwood Beach Association. Fully rebuilt and redesigned in 2008. Privately situated on a cul-de-sac with partial water views, the home showcases quality craftsmanship throughout, including hardwood floors and a stunning renovated kitchen featuring custom cabinetry, granite countertops, a generous center island including a renovated eating area with plenty of sunshine overlooking the backyard. The inviting main level offers wonderful spaces for both everyday living and entertaining, including a gracious dining room, living room with gas fireplace, family room with built-ins and charming reading nook. Upstairs, primary bedroom with luxurious fully renovated bathroom and oversized walk in closet. An additional three spacious bedrooms are complemented by a family room with built-ins and renovated bathroom. Additional improvements include a renovated half bath and laundry room, generator ready and multi room full house audio including outside, and new garage doors. Outdoors, enjoy a private patio with partial water views - an ideal setting for entertaining or relaxing after a day at the beach. Fenwood's kayak/paddle board launch is a minute away while the beach is a short stroll to enjoy the sunset. Close to golf, Saybrook Point, the causeway, two town beaches, Main Street restaurants and shops!

11 Fencove Ct, Old Saybrook
5 Cove Lndg, Old Saybrook
$1,648,000
3 Beds ⋅ 3 Baths ⋅ 24185125 MLS
Nestled within an enclave of distinguished homes in the heart of Old Saybrook, this exceptional residence captures sweeping water views and breathtaking morning sunrises, offering a rare blend of sophistication, and timeless coastal charm. From the moment you enter this light filled home, exceptional craftsmanship and design are evident. Custom millwork defines each space, while rich wood flooring throughout creates warmth and seamless flow from room to room. Newly installed Pella Windows and Doors enhance both beauty and energy efficiency. At the heart of the home lies a beautifully appointed gourmet kitchen, masterfully renovated for both culinary excellence and everyday living. A generous center island anchors the space, complemented by exquisite, honed marble countertops. Premium appliances-including a Sub-Zero refrigerator and professional six-burner gas range are paired with a classic farmhouse sink, bespoke built-ins, and French doors leading to the terrace. The home offers both refined and casual living spaces from the elegant Living-room, centered on a fireplace with French doors leading a covered porch, a formal dining room that's perfect for entertaining and a more casual family room. The luxurious primary suite serves as a private retreat, complete with its own private balcony. Finishing off the second floor are two more spacious bedrooms, each with water-views. Every detail has been thoughtfully curated into one exceptional Package.

5 Cove Lndg, Old Saybrook
101-A Sequassen Ave, Old Saybrook
$1,615,000
24175708 MLS
Design the life you've imagined. Whether it's a shingle-style summer escape or a modern coastal masterpiece, this lot is the foundation positioned to capture the essence of the shoreline, this parcel is defined by its views of the sparkling Long Island Sound. Whether you are watching the sunrise over the water or enjoying the salt-scented evening breeze, the location provides the best of coastal living. - .45 Acres: A perfectly sized, level lot ready for your architectural vision; Fully Approved: this lot is ready for your dream build. Living in the Borough is more than just owning a home; it's joining a community steeped in tradition and leisure. Residents enjoy world-class amenities just steps from their front door: Golf: Play a round on the historic, beautifully maintained nine-hole golf course. Refine your game on the private Borough tennis courts. Come build your dream home.

101-A Sequassen 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
104 Knollwood Dr, Old Saybrook
$1,600,000
3 Beds ⋅ 2 Baths ⋅ 24153235 MLS
Knollwood Beach waterfront on South Cove with amazing views! Privately situated on a large .37 acre lot directly on the South Cove! Nicely restored and oozing with charm! Kayak out to the Long Island Sound from your backyard or just sit in the family room and enjoy beautiful sunsets over the water! A bird lovers paradise and plenty of fun with Knollwood Beach Association amenities including a sandy beach with raft, tennis Pickle Ball, club house, guest parking lot and kayak stand. Great investment opportunity as well.

104 Knollwood Dr, Old Saybrook
81 Coulter St Unit 4, Old Saybrook
$1,526,000
2 Beds ⋅ 3 Baths ⋅ 24113976 MLS ⋅ North Cove Crossing BLDG.
Beautifully appointed home with a captivating panoramic water view of North Cove and CT River. Free standing 2400+ square foot home in a small over 55 community of 16 luxury residences. This Nantucket style 2 story home was upgraded with wonderful amenities and tasteful touches inside. A designer kitchen was added with center island, granite counters and custom cabinetry. The addition of raised paneling and crown moldings are found thru out the home and gleaming wood floors on the main level. A formal dining room is spacious with new bow windows and features an open concept design into the living room with fireplace. A wall of glass doors for easy access to a large outdoor patio surrounded by lush landscaping and an electric awning to be enjoyed thru out the summer. Back inside you will find a remodeled powder room and a separate laundry room. A large open foyer with vaulted ceiling and wide staircase brings you up to the 2nd level or take the elevator! Upstairs you will find a guest bedroom, full bath, office and Primary suite. The Primary includes a sitting area, his and her walk-in closets and a renovated lavish bathroom with radiant heated floors. The convenient In-town location allows you to walk or bike to shopping, restaurants, train and more. A rare offering in a wonderful small seaside town. Super Stunning!

81 Coulter St Unit 4, Old Saybrook
4 Sheffield Cove Rd, Old Saybrook
$1,510,000
3 Beds ⋅ 3 Baths ⋅ 24166936 MLS
Coastal Living with Water Views Set on a private cul-de-sac overlooking South Cove, this 2,821 sq ft home offers water views from nearly every room. Sun-filled open floor plan with vaulted ceilings and skylights create a bright, airy feel throughout. The spacious kitchen features a 10' island and seamless flow to the main living and dining areas-ideal for everyday living and entertaining. The first-floor primary suite includes a spa-like bath with jetted tub, oversized glass shower, and an expansive walk-in closet with private sauna. Two upstairs bedrooms capture elevated water views. Outdoor living is equally impressive with a 31' deck, arched awnings, hot tub, outdoor shower, and professionally landscaped, fully fenced grounds with underground irrigation. Ideally located just a short walk to the Connecticut River, marinas, Main Street, and Katharine Hepburn Cultural Arts Center ("The Kate"), and minutes to Fenwick Golf Course, town beaches, and the Old Saybrook train station. Convenient access to both New York and Boston. Homeowner flood insurance: $1,181/year.

4 Sheffield Cove Rd, Old Saybrook
66 Pennywise Ln, Old Saybrook
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 24128259 MLS
In the heart of Saybrook Village, this completely restored and remodeled vintage home blends modern convenience with timeless character, ideal for the discerning over-55 buyer who values both history and comfort or multi-generational buyers. The gourmet eat-in kitchen is a showpiece, with exposed beams, custom cabinetry, granite counters, a large island and vaulted ceilings, flowing seamlessly into the inviting living and den areas. French doors open from the living room to a private rear sitting porch, while a wood-burning fireplace enhances its warmth. Two gracious primary bedroom suites-one on the first floor-each feature fireplaces, elegant full baths and abundant closet space, providing flexibility and privacy. The upper level offers two additional bedrooms, one with its own fireplace, a full bath, and a balcony overlooking the main stairway. Throughout the home, wide-plank hickory hardwood floors, five fireplaces, and custom millwork highlight its craftsmanship. Modern upgrades include new Andersen windows, Therma-Tru doors, spray foam insulation, a high-efficiency 5-zone hydro-air system, on-demand hot water, natural gas service, and a new 1500-gallon septic system. A spacious mudroom with exterior access, dual laundry areas, and thoughtful design make daily living easy. Completing this exceptional property is a newly built oversized barn garage with workshop and finished living space, offering endless possibilities. Not in flood zone. Professional Photos to come!

66 Pennywise Ln, Old Saybrook
2 Old S Cove Rd, Old Saybrook
$1,475,000
3 Beds ⋅ 4 Baths ⋅ 24185199 MLS
Welcome to one of Old Saybrook's most compelling brand-new luxury opportunities. Built by one of Connecticut's premier shoreline designers and builders, this exceptional coastal residence showcases a level of craftsmanship, architectural detail, and thoughtful design rarely found in today's market. Summer is in full swing, and with immediate occupancy and flexible closing arrangements available for qualified buyers, you can still enjoy the very best of the season at Saybrook Point. Perfectly positioned in the heart of this renowned waterfront community, the home offers something increasingly difficult to find along the Connecticut shoreline: brand-new luxury construction, timeless coastal architecture, and an unmatched waterfront lifestyle all without the maintenance, uncertainty, and costly renovations often associated with older shoreline homes. Designed for both everyday living and effortless entertaining, the residence is filled with natural light, soaring ceilings, expansive walls of glass, and carefully curated finishes throughout. The open-concept floor plan flows seamlessly from elegant living spaces into a spectacular chef's kitchen, creating the perfect setting for everything from intimate evenings to holiday gatherings and summer weekends with family and friends.

2 Old S Cove Rd, 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
30 Watrous Point Rd, Old Saybrook
$1,450,000
4 Beds ⋅ 5 Baths ⋅ 24107646 MLS
Framed by mature landscape and extensive hardscape, welcome to this private Watrous Point country home. Find a gracious, barrel-vaulted entry and a gallery-style foyer flanked by the library. Built to entertain, a solid cherry kitchen commands an 8-burner Wolf range, two Gaggenau convection ovens, warming drawers, dual Subzeros and a dream pantry. One of two fieldstone fireplaces anchors the dining area. A beverage center with wine cooler/icemaker bridges space to the great room - a soaring space with floor to ceiling fieldstone fireplace. Completing the utility spaces are the laundry, mud and powder rooms. The main level primary bedroom offers custom closets and a full bath. Upstairs, architectural angles provide interest and loft in all three bedrooms, all with seldom found ensuite baths and custom closets. The finished lower-level bonus room and half bath have a separate heating zone. There is extensive storage. Outside, find a gunite, heated pool with spa and a pool house. The heated woodshop offers many possibilities. Extensive updates include geothermal heating, Rinnai propane hot water heater, pool and pool house, woodshop, roof 2023, exterior paint 2024. Equidistant to Essex and Old Saybrook Main Streets, this quiet retreat is a stone's throw to all lower Connecticut River valley gems. Three acres provides privacy not maintenance. Enjoy meandering, country roads for walking and nearby Turtle Creek Preserve. Just 6 minutes to the train and 2 hours from NY and Boston.

30 Watrous Point Rd, Old Saybrook
7 Ridge Rd, Old Saybrook
$1,440,000
4 Beds ⋅ 4 Baths ⋅ 24163608 MLS
Cornfield Point, Old Saybrook - Coastal Living at Its Best! Steps to the beach with sparkling water views and stunning sunsets, this beautifully updated home blends timeless charm with modern upgrades. Originally built in 1926, it features an open layout perfect for entertaining. Imagine hearing the waves crash while dining on your brand new deck! The living room boasts the original Cornfield Point stone fireplace and exposed beams. The bright, sun-filled kitchen with newer appliances flows seamlessly into the dining area-all highlighted by gleaming hardwood floors. Upstairs, find an en-suite bedroom, two additional bedrooms, a full bath, and laundry, plus a separate primary suite accessed by a second staircase-four bedrooms in total. A large addition offers a family room with sliders to a gorgeous new patio, a private office, and half bath. Outside, enjoy professionally landscaped grounds, a brand new roof, and a new outdoor shower-perfect after a day at the beach. Located in the coveted Cornfield Point Beach Association, residents enjoy private beach access, clubhouse, tennis courts, playground, basketball court, and boat ramp. Whether for year-round living or a seaside escape, this exceptional home is ready for your next chapter of coastal memories.

7 Ridge Rd, Old Saybrook
24 Church St, Old Saybrook
$1,425,000
3 Beds ⋅ 3 Baths ⋅ 24155662 MLS
RARELY AVAILABLE NEW CONSTRUCTION IN NORTH COVE! This modern farmhouse-style Cape, built in 2023 in sought after North Cove, offers over 2,500 sq ft of bright, open living space. The high-end kitchen features a large center island, pantry, quartz countertops, and GE Cafe appliances including a duel fuel oven/stove. The layout includes 3 bedrooms and 3 full baths, with the flexibility to create a first-floor primary suite/4th bedroom with a large walk-in closet (currently used as an exercise room). Enjoy the quintessential Old Saybrook lifestyle with a short stroll to watch the sailboats or play some minigolf at Saybrook Point. Or maybe take your stroll to Main Street's coffee shops, restaurants, or to catch a show at The KATE. Enjoy summertime fun entertaining your guests on the large paver patio. Modern efficiencies include a new 2000-gallon geomatrix septic system (2023), a high efficiency heating/cooling heat pump system (not electric baseboard radiators), an underground sprinkler system and a propane fireplace. A perfect turnkey home in a premier walk-to-town location. Don't hesitate to embrace the rare peace of mind that comes with new construction while enjoying the coastal lifestyle of historic North Cove!

24 Church St, Old Saybrook
446 Main St Unit 9, Old Saybrook
$1,420,000
2 Beds ⋅ 3 Baths ⋅ 24171024 MLS ⋅ North Cove Landing BLDG.
Nestled along the serene shores of North Cove, this exceptional 2,300+ square foot detached shingle-style condo perfectly blends coastal elegance with unmatched privacy. Opportunities like this are rare, as high-end, detached units in this coveted waterfront location seldom become available on the market. The interior showcases a sophisticated open layout featuring a custom chef's kitchen, hardwood flooring, a formal dining area, and a light-filled living room anchored by a warm gas fireplace and rich hardwood flooring. Designed for ultimate comfort, the home boasts two spacious primary bedroom suites and a convenient half-bath, complemented by a dedicated office nook and a large, flex room upstairs. Practicality meets luxury with a separate laundry and mudroom located just off the attached two-car garage. Outside, a private mahogany deck offers a front-row seat to breathtaking water views, The lifestyle here is further enhanced by community amenities, including an inviting inground pool and a charming pool house for summer relaxation. Ideally situated for those who love the shoreline, this retreat is located less than one mile from the vibrant shops and restaurants of Main Street Old Saybrook and the iconic Saybrook Point.

446 Main St Unit 9, Old Saybrook
105 Fenwood Dr, Old Saybrook
$1,305,000
4 Beds ⋅ 2 Baths ⋅ 24149726 MLS
Welcome to 105 Fenwood Drive, nestled in the peaceful and picturesque community of Fenwood Beach Association. Experience waterfront living surrounded by natural beauty-where ospreys, great blue herons, and wintering bald eagles soar above thriving estuarine wetlands. Enjoy a short walk to the beach or an evening stroll to the causeway to watch the sunset. This golf cart friendly neighborhood offers a private beach rights and plenty of summer activities for residents to enjoy. For outdoor enthusiasts, launch a kayak or paddleboard right from the cove, or play a round at the nearby Fenwick Golf Course. Inside, this tastefully remodeled ranch showcases panoramic views of South Cove through a stunning wall of picture windows. Set on one of the most desirable lots in the neighborhood, this home offers comfortable year round coastal living in a serene setting that's truly one of a kind.

105 Fenwood Dr, Old Saybrook
108 Maple Ave, Old Saybrook
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24203677 MLS
Contemporary coastal elegance meets remarkable privacy along South Cove in Old Saybrook. Set well back from the road on 1.8 acres, this distinctive 3,188-square-foot cedar-sided residence captures sweeping water views from nearly every room. Originally built in 1965 and completely rebuilt in 1991, the home was thoughtfully designed to embrace its spectacular setting, with vaulted ceilings, expansive windows, and seamless connections to the outdoors. The living room features custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a vaulted family room and opens to a 300-square-foot enclosed porch-an inviting space for entertaining or relaxing. The main-level primary suite is a private retreat with vaulted ceilings, deck access, water views, dual bathrooms, and an impressive 120-square-foot walk-in closet. A formal dining room, additional bedroom, and separate laundry room complete the first floor. Upstairs, two bedrooms share a Jack-and-Jill bath. With 1.8 private acres and 278 feet of frontage along South Cove, this property offers a rare blend of waterfront, space, and seclusion. Whether enjoyed as a year-round residence or treasured coastal retreat, this is a setting that simply cannot be replicated.

108 Maple Ave, Old Saybrook
25 Maplewood Rd, Old Saybrook
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24123630 MLS
Knollwood Beach Association NEW Construction! Experience three levels of sun-filled coastal elegance in this tastefully designed home offering space and flexibility for modern living. The open floor plan flows with light-colored hardwoods throughout, anchored by a designer white kitchen on the main level, while a walk-out lower level with its own kitchenette provides the perfect setting for guests, an in-law, or extended family. With four spacious bedrooms and 3.1 luxurious baths featuring stunning fixtures, every detail reflects thoughtful craftsmanship. High ceilings, recessed lighting, and expansive windows create an airy sophistication, while outdoor living is elevated with a terrace off the living room and a private patio for entertaining. Year-round comfort comes with central air and city water, but the true allure is being just steps from the private beach. Knollwood Beach Association amenities enrich daily life with a kayak stand, pickleball, tennis, basketball, and a playscape-ideal for both children and grandchildren. Whether gathering family for holidays, enjoying weekends by the water, or entertaining in style, this is the rare blend of luxury, community, and coastal charm. Not in flood zone.

25 Maplewood Rd, Old Saybrook
26 Meadowood Ln, Old Saybrook
$1,169,000
3 Beds ⋅ 3 Baths ⋅ 24132080 MLS
No Flood Insurance Required! Built in 2025, this brand-new Old Saybrook Colonial blends architectural elegance, energy efficiency, and modern coastal living all outside the flood zone. Just moments from Town Beach, Fenwick Golf Course, Saybrook Point Marina, and downtown Main Street, this location offers the perfect balance of convenience and serenity. Inside, sun-filled red oak floors, impact-rated windows, and arched transitions define a timeless open floor plan. The chef's kitchen impresses with a 6-burner gas range, Carrera marble waterfall island, walk-in pantry, and custom cabinetry. Sliding doors open to a spacious Azek deck with unobstructed marsh and water views of Hagar Creek and Long Island Sound ideal for entertaining or quiet mornings. Upstairs, the primary suite is a private retreat with a sitting area, walk-in closet, deck access, and a spa-style bath wrapped in Carrera marble and porcelain. Built with James Hardie siding, tankless hot water, and passive solar design, this home offers lasting beauty and sustainability. Experience Old Saybrook's coastal lifestyle in a rare new-construction home where every detail reflects craftsmanship, comfort, and peace of mind. With more New Yorkers escaping the city grind, Old Saybrook has become a top choice, 4 minutes from the Amtrak station offering direct access to NYC and Boston.

26 Meadowood Ln, Old Saybrook
11 Trolley Xing, Old Saybrook
$1,100,000
5 Beds ⋅ 5 Baths ⋅ 24133796 MLS
Discover the best of Connecticut shoreline living at 11 Trolley Crossing in Old Saybrook-a private 3+ acre compound blending classic Colonial architecture with modern luxury. Designed for those who value space, comfort, and connection, this 3,600 sq ft residence invites you to experience an exceptional lifestyle surrounded by nature and minutes from the coast. A covered front porch opens to expansive, light-filled rooms where timeless craftsmanship meets everyday convenience. The kitchen fireplace creates a welcoming centerpiece for gatherings, while a second fireplace in the living room adds warmth and style. The first-floor primary suite allows for true one-level living, complemented by four additional bedrooms upstairs. The walk-out lower level features a third fireplace, half bath, and flexible space ideal for an in-law, recreation room, guest suite, or studio. Step outside to your own resort-style oasis an in-ground pool, pool house with full bathroom, and extensive stone patio designed for entertaining and relaxation. A heated, oversized 30x20 outbuilding offers additional garage or workshop space, joined by a detached three-car garage. The fenced yard and stone wall surround enhance privacy in a serene natural setting close to beaches, marinas, golf, and Old Saybrook's vibrant Main Street.Luxury, space, and versatility combine at 11 Trolley Crossing a property that invites you to visit, explore, and stay. Easy commute on Amtrak to New York City. Only 2hrs door - door

11 Trolley Xing, Old Saybrook

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