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41 Watrous Point Rd, Old Saybrook
$3,750,000
6 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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
382 Maple Ave, Old Saybrook
$2,350,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
420 Maple Ave, Old Saybrook
$2,150,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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
11 Fencove Ct, Old Saybrook
$1,692,034
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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
CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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
4 Sheffield Cove Rd, Old Saybrook
$1,510,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
2 Old S Cove Rd, Old Saybrook
$1,475,000
3 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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
7 Ridge Rd, Old Saybrook
$1,440,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 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
446 Main St Unit 9, Old Saybrook
$1,420,000
2 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
108 Maple Ave, Old Saybrook
$1,200,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 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
10 Trolley Xing, Old Saybrook
$1,065,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24165029 MLS
Framed by professional landscape and stunning hardscape, this expansive shingle-style home is located equidistant to Essex and Old Saybrook Main Streets, five Connecticut River marinas and Saybrook Station. Incredible updates include the creation of a main level laundry/mudroom update, the addition of central air and more. Well designed and appointed spaces include a stunning open kitchen with top end appliances and three fireplaces in the formal living room, great room/kitchen and the primary bedroom. Gleaming pegged hardwood floors are found on the main floor and solid oak upstairs. This 3-4-bedroom home includes a 588 SF finished lower-level den and office doubling as a 4th bedroom. The bonus room with bar over the garage is perfect for game night, private (quiet) office or workout space! Outside an expansive patio with fire pit and Viking grilling center overlooks the grounds. Well set, immaculate and ready for summer in Saybrook! Just perfect.

10 Trolley Xing, Old Saybrook
95 Middletown Ave, Old Saybrook
$1,049,900
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
38 Jarvis Rd, Old Saybrook
$1,038,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24197776 MLS
Enjoy coastal living in the sought-after Knollwood Beach Association. This well-maintained, sun-filled home is just a short stroll from the beach, where beautiful shoreline walks, golf cart rides and a vibrant neighborhood setting are just moments from home. Offering a gracious sense of space, comfort and versatility, the home is equally suited for year-round living or a memorable coastal retreat. The bright, open floor plan is filled with natural light and designed for easy everyday living and entertaining. Two bedrooms on the main level provide the option for one-floor living, while two additional spacious bedrooms upstairs offer flexibility for family and guests. The kitchen features granite countertops and generous seating for meals and holidays, while plantation shutters add a timeless finishing touch throughout the home. A partially finished lower level provides additional flexible living space. Outside, a fully fenced yard and expansive patio create an inviting setting for summer gatherings, outdoor dining and relaxed evenings after a day at the beach. Knollwood Beach Association amenities include private beach access, clubhouse, tennis and basketball courts, all just moments from your doorstep. An exceptional opportunity to enjoy the quintessential Old Saybrook coastal lifestyle in one of the shoreline's most sought after communities. Conveniently located minutes from Main Street, shops, restaurants, Saybrook Point, golf, highways and the train.

38 Jarvis Rd, Old Saybrook
4 Fenwood Ln, Old Saybrook
$1,036,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24167269 MLS
Refined coastal retreat at 4 Fenwood Lane, in the Fenwood Beach Association of Old Saybrook, offering distant views of Long Island Sound and a seamless blend of luxury and shoreline living. This freshly painted, thoughtfully updated beach house is ideally located just one home from the main road, providing both convenience and a private setting. Enjoy deeded beach rights and a short walk to Fenwood Beach, with easy options to walk, bike, or take a golf cart to nearby destinations including Fenwick Golf Course. Designed for year-round or seasonal living, this well-appointed shoreline home also presents an exceptional opportunity as a weekend retreat or second home. The interior features new hardwood floors and a spacious light-filled layout. The chef's kitchen opens to expansive living and dining areas with a fireplace creating inviting gathering spaces. A sun-drenched sunroom captures natural light and distant water views, offering a relaxing setting throughout the Shoreline seasons. The private backyard and deck provide ideal outdoor entertaining space after a day at the beach. Turnkey and move-in ready for summer, this property is just minutes to Saybrook Point Marina and the Causeway, with convenient access to Liv's Oyster Bar, Pizza Works, Walt's, Sweet Luna's, and shopping on Main Street. Amtrak rail service from Old Saybrook offers direct access to New York City and Boston. Come live the dream on Old Saybrook shoreline, where every day feels like vacation.

4 Fenwood Ln, Old Saybrook
37 Mohican Rd, Old Saybrook
$1,030,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24170358 MLS
Nestled in the highly sought-after Cornfield Point Beach community, this beautifully maintained 3-bedroom, 2.5-bath residence offers an exceptional opportunity to enjoy coastal living just steps from the water. Blending timeless charm with thoughtful upgrades, this home is designed for both everyday comfort and effortless entertaining. At the heart of the home is a thoughtfully updated kitchen, featuring custom cabinetry, quality countertops, and a well-designed layout that maximizes both function and flow. Ample storage, generous prep space, and seamless connectivity to the main living areas make it ideal for everything from casual mornings to hosting gatherings. The main living area is warm and inviting, centered around a classic wood-burning fireplace that creates a cozy yet refined atmosphere. Custom millwork and cabinetry continue throughout the home, enhancing both style and practicality. The primary suite offers a private retreat, complemented by a well-appointed full bath with tasteful finishes and thoughtful design. Additional bathrooms are equally well maintained, including a convenient half bath on the finished lower level-perfect for guests while entertaining. Each space reflects a cohesive aesthetic with quality fixtures and clean, coastal-inspired finishes. The finished lower level significantly expands the home's versatility, featuring a custom bar area, built-in desk space ideal for a home office, and a comfortable lounge area for relaxing or entertaining.

37 Mohican Rd, Old Saybrook
96 Fenwood Dr, Old Saybrook
$1,030,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
37 Woodland Dr, Old Saybrook
$999,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
6 Trolley Xing, Old Saybrook
$995,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
12 Hill Rd, Old Saybrook
$991,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
28 Bellaire Dr, Old Saybrook
$982,500
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24188825 MLS
Welcome to the highly sought-after Cornfield Point Beach Association, where coastal charm meets effortless year-round living. This beautifully maintained cottage-style ranch offers the perfect seaside retreat for those seeking an upscale second home or an easy-to-maintain retirement residence in one of Old Saybrook's most desirable beach communities. The newer white kitchen opens to inviting living spaces highlighted by hardwood floors, classic wainscoting, custom built-ins, and a spacious living room with a fireplace. The home features three bedrooms, including a private primary suite with its own full bath, plus a second full guest bath. The spectacular four-season sunroom is filled with natural light and opens through sliders to a private rear patio, creating seamless indoor-outdoor living. Additional features include a welcoming front patio, outdoor shower, full basement, and storage shed. Enjoy all the benefits of year-round beach living while knowing the property also offers exceptional future potential. The owner has engineering reports and architectural plans available for those wishing to create a substantially larger custom home. Whether you're searching for a sophisticated shoreline getaway or the perfect place to enjoy retirement by the water, this exceptional Cornfield Point property offers a rare opportunity in one of Connecticut's premier beach associations.

28 Bellaire Dr, Old Saybrook
25 Sheffield St Unit 3, Old Saybrook
$969,000
2 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24203236 MLS ⋅ Village Center Residences BLDG.
Nestled in the vibrant center of downtown Old Saybrook, this contemporary end-unit townhouse-crafted in 2021-presents the ultimate blend of shoreline charm and modern ease. Moments from local boutiques, fine dining, the iconic Katharine Hepburn Cultural Arts Center, and pristine coastal beaches, the location is truly unmatched. Inside, sunlit open-concept living spaces are highlighted by rich hardwood floors, detailed trim work, and sweeping views toward Main Street. The gourmet kitchen serves as the home's centerpiece, boasting custom quartz counter seating, premium finishes, and seamless flow into the fireside living area. Step through to your private, fully enclosed back patio for peaceful outdoor dining and weekend gatherings. The main floor features a spacious primary retreat complete with soaring vaulted ceilings, a spa-inspired dual-vanity bath, and dedicated laundry facilities. Upward on the second tier, a second bedroom, dynamic open loft, full bathroom, and custom-organized walk-in storage offer total versatility. Downstairs, the finished lower level provides excellent bonus space, perfectly configured for a quiet home office, private gym, or media room.

25 Sheffield St Unit 3, Old Saybrook
28 Gates Rd, Old Saybrook
$960,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24184811 MLS
Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrook's most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic cottage offers timeless shoreline charm and standout curb appeal. The spacious enclosed front porch is the heart of the home, perfect for morning coffee, afternoon reading, and relaxing summer evenings. A cozy wood-burning fireplace adds warmth for cool nights by the shore. The expansive backyard is ideal for family gatherings, lawn games, and picnics, while your own "his and hers" beach sheds offer room for bikes, kayaks, beach gear, and more. The larger shed also includes a washer, dryer, refrigerator, and golf cart ramp. An outdoor shower makes rinsing off after beach days a breeze. Thoughtful updates including a new septic system (2019), new hot water heater (2021), new roof (2021), new refrigerator and microwave (2024), plus custom kitchen cabinetry and woodwork throughout. As a Cornfield Point resident, you'll enjoy private sandy and rocky beaches, a clubhouse, playground, basketball, tennis and pickleball courts, plus a full calendar of community events. Whether you're looking for the perfect summer getaway or a place to create lifelong family traditions, 28 Gates Road offers the entire package! Seasonal property. All furniture/TVs convey with sale.

28 Gates Rd, Old Saybrook
25 Sheffield St Unit 7, Old Saybrook
$960,000
2 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 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

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