Greenport NY Real Estate & Homes for Sale

Direct beachfront property offering roughly 130 feet of unobstructed Long Island Sound views! Welcome to 29 West Shore Drive- a breathtaking westerly facing waterfront residence that promises magnificent sunsets, gentle seaside breezes and the picturesque lifestyle you've been dreaming of. For the first time in over 30 years this exquisite property is now available for sale, offering a unique opportunity to own a piece of paradise. Featuring 4 well-appointed bedrooms and 3 full bathrooms, this home is designed to accommodate and delight. Furthermore, you'll find a spacious living space with a stately stone fireplace that combines comfort with elegance, making it the perfect backdrop for creating lasting memories with loved ones. Through the living room French doors, enter a lovely sitting area with 180-degree views of ocean. The uniquely large, flat yard is perfect for gatherings or simply enjoying the peaceful ambiance of seaside living. This home is part of Cornfield Point Association - sandy beach, club house, basketball & tennis court & boat ramp. Easy access via I-95 and the train. Two hours from NY or Boston. Close to all amenities - restaurants, cafes, shopping, marinas, The Kate Theater & Fenwick Golf Course. Whether you're looking for a year-round home or a seasonal getaway, 29 West Shore Drive provides a rare blend of tranquility, beauty, and convenience in one of Old Saybrook's most sought-after locations. Don't miss the chance to make this dream home yours.

Nestled in the prestigious Cornfield Point Beach Association neighborhood, this upgraded ranch offers one-level living at its finest with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, central air, this home provides comfort and style. A spacious open plan living room welcomes you home with a wall of windows that flood the space with light and air; durable wood-look plank flooring offers easy maintenance. With vaulted ceilings, gas log fireplace, and ceramic tile flooring, your family room offers a cozy, inviting atmosphere. An immaculate updated kitchen with cherry cabinetry, breakfast bar island, stainless appliances, and granite counters is perfect for hosting. Spacious and light-filled, bedrooms feature updated carpeting and ample storage. A large driveway and detached garage provide plenty of off-street parking, while mature privacy hedging and greenspace creates an ideal space to relax with friends and family. HOA fees include trash, playground, tennis court & snow removal on the main road! Experience the incomparable quality of life Old Saybrook has to offer: blocks from the ocean, enjoy magnificent sunsets, local eateries, and beautiful nature preserves. With easy access to the train station for a quick commute into NYC, this home is perfect for year-round living, or seasonal enjoyment. Don't miss your opportunity to own this superlative one-level property; schedule your showing today!

INVESTMENT OPPORTUNITY - CORNFIELD POINT BEACH ASSOCIATION! This property presents a rare opportunity to own a versatile space that combines commercial and residential appeal. Whether you're seeking a lucrative investment, envisioning your own Airbnb, or own beach escape, this property offers endless possibilities. Situated in the sought-after Cornfield Point Beach Association, this property is at the entry of this very desirable beach community with many residents and guests driving by daily! The property boasts a flexible layout, featuring a spacious storefront ideal for retail, caf?, breakfast/lunch destination or ice cream! Additionally, there's a separate residential unit upstairs with 4 bedrooms, oversized deck, plenty of parking, full bath providing a rental opportunities. Maximize your investment with dual income streams. Whether you choose to lease out the storefront, rent the residential unit, or utilize both spaces for personal and commercial purposes, this property promises lucrative returns and financial flexibility. There is also the option of converting the storefront into 1-2 apartments. Walk or bike to Cornfield Point Beach/two town beaches, Main Street's shops, restaurants are a short drive/bike ride away, as are the Kate Cultural Arts Center, Fenwick Golf Course and Saybrook Point. Just a few hours from NYC or Boston, your private shoreline retreat is calling you. No flood insurance required.

Fantastic renovated Knollwood Beach home on .89 acre lot with views of South Cove and Beaman creek. Ez walk to beautiful beach and neighborhood access to Beaman Creek for kayaking. This lovely home enjoys both a first floor master suite and a gorgeous 2nd floor master suite with sitting room. The combination living room / dining room is spacious with vaulted ceilings and newer Windows taking in the lovely marsh and South Cove water-views! Love nature? The bird watching is incredible, and the amazing 4 season room is very large with a dining area and perfect for watching the sunsets! The second-floor addition and oversized one car garage were added in 2009. The 2nd floor interior balcony office has a stunning view of the Cove. The home has a finished lower level as well adding to the living area if needed.

A Fenwood Beach home on a beautiful level .50 acre lot! Totally rebuilt in 2014 Enjoy over 3200 sq. ft. of comfort. This stylish home boasts central air conditioning, a large "dream-like" Carrera marble white kitchen which opens to large great-room and dining-room. The kitchen has a large island that sits 6 comfortably, a large rear work area, a breakfast area, and all the bells and whistles. The Great-room includes a beach-stone fireplace, and French doors to a rear stamped concrete patio area. The open dining-room over-looks the lovely spacious back-yard. First floor also includes a charming foyer area, a front to back living-room (could be converted to a first floor master) and a mudroom with a half bathroom off kitchen area. The second level has 4 bedrooms in total consisting of the master-suite with large his & her closets with built-ins and a sitting area plus an office. The guest-bedroom has an en-suite bathroom, and two additional bedrooms share a 3rd full bathroom. The home has a large dry basement.The home has an outdoor shower, golf cart shed big enough for two carts, and a two car over-sized garage. Exterior is expensive maintenance - free cement board (Hardy board) siding. The Shed was remodeled recently with internet and electricity and used as a exercise room. Home has irrigation. Walking distance to Fenwood Association Beach. Steps to path leading to Fenwick golf course. Home is NOT in a flood zone.

This traditional Fenwick cedar shingle style home has spectacular water views of the Connecticut River and South Cove. It also enjoys Fenwick's unique lifestyle: beach, tennis courts, Yacht Club and famed golf course. The 2,634 home built in 2006 with the highest craftsmanship and state-of-the-art materials has wideboard floors throughout. The great room with a coffered ceiling has a wall of windows above the long banquette, a large beach stone fireplace and built-in cabinets. French doors on the main level open to a full width porch, which overlook the long water views and beautiful professionally landscaped gardens. The open kitchen is flooded with sunlight and is a chef's delight with all top of the line appliances. Rich mahogany cabinetry and marble counters and sit down island are custom made. The first floor 15x15 master suite has built-ins, and has access to the porch. A guest room/office off the kitchen has a beadboard ceiling, shiplap walls, and state-of-the-art Murphy bed built into custom cabinetry. Mudroom side entrance with outdoor shower, includes extra built-in cabinets, farm sink and washer/dryer. Two guest rooms on the second level, one with built-in beds have access to the balcony with views of the hydrangea border gardens and water. This beautiful dream home sits on a private .46 acre parcel and has full mechanicals including a full house generator. Located half way between New York and Boston and is only minutes to all major transportation.

Charming Colonial with something for everyone. Serene location on private street but only a short distance to the center of town. Beautiful living room with hardwood floors, raised panels and coffered ceiling along with built in bookcases. Large formal dining room with bay window offering an abundance of natural sunlight. The fully applianced country kitchen has a pantry and fireplace, recessed lighting and access to a glass sunroom with tile floor. Access to the deck and rear yard enhance the desirability of this room. Perfect room to sit and just relax or locate your piano here and make it a stunning music room. Upstairs you will find 3 spacious bedrooms and 2 full bathrooms. Primary bedroom includes a full bath with tub, two walk in closets and an atrium door to access the second sunroom with views of South Cove. New carpet in the primary bedroom, both walk in closets and the sunroom make this enclave a warm and cozy area to enjoy a good book or private office. Perfect size deck on the rear of the house with quick and easy access to the inground pool on those warm summer nights. Full basement, Oil forced hot air heat and Central Air. With the proximity to the town center you will be able to catch a show at "The Kate", hit the gym or use the pickleball courts for a quick game or just meander along visiting all of the great shops and restaurants on Main St. This house offers the complete package. Don't let this opportunity pass you by.

DIRECT WATERFRONT! Wake up every morning with an ocean breeze! This year round beach home features one floor living, open floor plan, 3 bedrooms, private beach at your door step, breathtaking water views from every window, granite countertops, completely updated and furnished, propane heat, central air, cathedral pine ceilings that accentuates the home, plenty of privacy with a fence, easily can fit 5 cars in the parking area, Saybrook Manor Association has two private beaches for residents only, a club house with many Summer activities including July 4th fireworks and extra parking if needed, right in front of the house there is a designated swimming area, fishing and crabbing to the right of the swimming area and during low tide you can walk the sand bar almost a mile, Spacious patio perfect for entertaining and relaxing while enjoying the spectacular views! Main Street's shops, restaurants are a short drive/bike ride away, as are the Kate Cultural Arts Center, Fenwick Golf Course and Saybrook Point. Just a few hours from NYC or Boston, your private shoreline retreat is calling you!

Impeccably maintained home with water views and beach access. This year round home comes fully-furnished and also includes all kitchen ware, bedding, pictures and more. The decor is sophisticated yet casual. Located in a peaceful beachfront neighborhood. Beautifully built by award winning Amity Construction & Design with gorgeous marble tiled bathrooms and a bright, open floor plan. The first level includes a quaint sitting area at the entrance with a double sided fireplace that opens to the living room, dining room, wonderful open kitchen with island for extra seating and a half bath with washer and dryer. One of the primary en suite bedrooms is also located on the main level. The second level houses a second primary bedroom en suite and two other bedrooms as well as one extra full bathroom. The third level has been completed to include the fifth bedroom and full bath as well as an entertaining area and balcony to view the fantastic Westbrook shoreline all the way to Old Saybrook. A dry lower level is ready to be finished as extra living or entertaining space. There is plenty of storage and parking for family and guests. This is a home to fall in love with!

Welcome! This charming four-bedroom, two-and-a-half bath home offers 2170 square feet of living space and is ideally located- close to schools, library, & community center! Only half a mile from the nearest boat launch and one-and-a-half miles from the beach. This diamond in the rough has a great location - close to shops, restaurants, cafes, and The Katharine Hepburn Cultural Arts Center. The updated bathrooms are beautifully done, complemented by a new front door for a welcoming entrance. Inside, a floor-to-ceiling wood burning fireplace graces the vaulted ceiling living room, creating a cozy atmosphere. Additional features include new kitchen floor, a newer laundry room, upgraded electrical panel, public water, central air, and septic system, making this home both comfortable and functional. Schedule your private tour now.

Welcome to your custom-built eco-friendly dream home nestled within the exclusive Chalker Beach Association, offering unparalleled vistas of the majestic Long Island Sound. Step into your 2000sqft. sanctuary, meticulously crafted to harmonize with its natural surroundings and cater to your every comfort. This enchanting abode boasts three spacious bedrooms and three full bathrooms, ensuring ample space for relaxation and rejuvenation. Conveniently located beneath your home lies private parking, ensuring effortless access and convenience for you and your guests. The first floor invites you into a serene retreat, featuring a lavishly appointed bedroom and bathroom, seamlessly integrated with an open-concept kitchen. Adorned with stainless steel appliances and an induction stovetop, the kitchen is a culinary haven where you can unleash your culinary creativity. Gather around the dining table, capable of hosting a summer soiree for ten, while you soak in the tranquil water views from the adjacent great room. Ascending to the second floor, you'll discover two additional bedrooms, and two luxurious full bathrooms. The crowning jewel of this level is yet another breathtaking great room, offering panoramic vistas that inspire the creation of cherished memories for years to come. Radiant in-floor heating throughout the home ensures warmth and comfort even during the coldest New England winters, enveloping you in a cozy embrace year-round.

If you are searching for an historic Main Street property, explore converting the iconic James Pharmacy building to a single-family residence. The property is currently a bed and breakfast and a main level bistro. Anna James, the first African American female pharmacist operated and resided at the pharmacy for decades. Her niece, noted novelist Anna Petry, was born here and assisted Miss James. The main floor restaurant retains the historic pharmacy built-ins and soda fountain. Arched glass windows offer Main Street views. Innkeeper quarters are on the main level. Extensive renovation and updates transformed the building to current standards while preserving its historic architecture. Four bedrooms include main level innkeeper quarters and three second floor bedrooms each with an ensuite bath and gas fireplace. There are two half baths on the main level. A full basement houses mechanicals and exceptional storage. All mechanicals are updated including oil heat, central air and the septic system. There is city water. Main Street restaurants, shops, The Kate arts center and Saybrook Station are all a short stroll. Also listed as commercial MLS ID 24006903.

"Experience unmatched convenience and ample parking with this stunning property boasting parking spaces for up to 9 cars on both sides of the house. Perfect for those who love to entertain or require space for multiple vehicles, this feature ensures hassle-free hosting and easy access for residents and guests alike. Whether you're hosting a gathering or simply returning home, never worry about parking again with this exceptional real estate offering. "Nestled along the serene coastline, this captivating 5-bedroom abode embodies the essence of coastal living at its finest. As you step through the front door, you are greeted by an inviting foyer that sets the tone for the rest of the residence. The spacious living area boasts a seamless flow, perfect for entertaining guests or simply unwinding with loved ones. Adorned with tasteful decor and premium finishes, this space serves as the heart of the home, where memories are made against the backdrop of the ocean's soothing melody. The outdoor bar is the heart of the space. Whether you're mixing up signature cocktails or pouring a cold beer, the bar provides the perfect backdrop for entertaining guests or enjoying a quiet moment.

You'll love this gorgeous spacious Ranch in the sought after Indian town Beach Association with a private marina, town hall, and three beautiful beaches. The stunning remodeled home features an open floor plan with a stunning kitchen, brand new stainless steel appliances and granite countertops You will enjoy cooking in this kitchen with plenty of natural sunlight coming in from the large window that overlooks a private fenced in backyard in addition to the great room with a cathedral skylight ceiling. Get ready to cozy up and enjoy the natural gas fireplace that features decorative glass doors and an oak mantle to "wow" your guests! The newly sanded hardwood floors throughout the house are easy to keep clean with a built-in central vacuum system. The two Full baths reflect today's modern trends with glass doors. The impressive master suite features a private bathroom, and large windows. The sitting area has an amazing view of the backyard with sliders to the deck. The insulated garage has a polyurea floor that is not only attractive but a great place to keep all your beach gear from a golf cart to jet skis, and beach chairs when taken in the sun. The mechanicals of the house featured ducted central air, tankless on-demand water heater, and Viessman natural gas boiler. Get ready to enjoy beach life at its finest in Old Saybrook in a walkable friendly community with plenty to do in a turnkey home. This home is a must see and will not last! Schedule your private tour today!

North Cove WATERFRONT home built in 1994 with private access to the cove. Wake up to unobstructed water-views and watch the boats pass by. Love sunsets? This quality construction home sits high on its manicured lot and enjoys beautiful views of the North Cove, wonderful breezes, bird watching and leisurely walks around the historic neighborhood and to Saybrook Point or lovely downtown Old Saybrook. Enjoy 2 fireplaces, one in Primary Suite, one in Livingroom, 2 ensuite bedrooms, hardwood floors throughout, oversized one car garage, a wonderful family room overlooking a private backyard with lovely gardens and a brick patio. Property includes the waterfront lot which protects your views and provides the access to North Cove.

Discover coastal living at its finest in Old Saybrook. Nestled in a peaceful neighborhood, yet close to all the essentials, this residence offers the ideal blend of tranquility and convenience. Enjoy leisurely strolls to nearby restaurants, beaches, and downtown attractions, making every day feel like a vacation. Experience the best of the Connecticut shoreline in this extraordinary property. Rest assured, this listing will exceed your expectations! This meticulously upgraded home boasts a newly designed kitchen featuring elegant white shaker style cabinets, an expansive island, sleek granite countertops, and stainless steel appliances. Step inside to find stained hardwood floors, beamed cathedral ceilings, and a captivating stone fireplace, creating a warm and inviting atmosphere. The updated bathrooms and generously sized bedrooms offer comfort, style and privacy. Entertain with ease in the recreation area on the lower level, complete with a separate laundry room and additional half bath for added convenience. Outside, enjoy the spacious backyard and oversized shed equipped with electricity, perfect for storage or a workshop. Experience sustainable living at its finest with this modernized home boasting upgraded insulation, windows, roof, siding, and solar panels.

Year Round Beach Home just across the street and steps from Long Island Sound and the beautiful Westbrook beaches. This remodeled home is between the public Westbrook Town Beach and the neighborhood-only Coral Sands Beach. Nestled in beach community and short walking distance to Pilots Point Marina. This comfortable home has many updates and makes a perfect home for anyone who desires to move to the shore! Sunny and bright home features open floor plan with Living Room/Kitchen sharing cathedral ceiling updated decor. Sunroom off living room currently serves as dining area with access to small deck to enjoy the view and peaceful setting. Larger deck with stairs to backyard and outdoor shower. Generous Primary Bedroom with walk in closet; laundry. Lovely Remodeled Full Bath has soaking/bubble tub and tiled shower.

Escape to the tranquility of seaside living with this charming and move-in ready 2-bedroom, 1-bath mobile home nestled in the heart of our highly sought-after beach community. Unwind in the comfort of two generously sized bedrooms, each offering ample natural light and cozy spaces to relax or enjoy the outdoors on the covered deck. Discover the convenience of living in a desirable beach community, where local shops, restaurants, and entertainment options are just moments away. This property is meticulously maintained and ready for you to move in. Whether you're seeking a permanent residence, a vacation getaway, or an investment opportunity, this mobile home is a rare gem. Buyer to do their own due diligence on financing, it may have to be a cash purchase.

Captivating sunsets, full moons, and sea air compliment the stunning unobstructed Sound views from this charming Victorian home. Loved year round and enhanced by the current owners so that one can enjoy an open floor plan, vaulted beamed ceilings, wood floors, chic KT w/ subzero frig and Viking range. The warmth and light from the south facing enclosed 3 season porch provides additional living area- cute spot for a futon or day bed! No HOA, an added perc to a waterfront home where the beach is within steps of your home and protected by town seawalls. West Beach is one of Westbrook's largest stretch of beaches, 5 minute walk to the fishing pier, concession stand, playground and supervised swimming. Local spa resorts and restaurants are in abundance nearby. Versatility abounds within the home, floor plan provided. Those with a creative eye will welcome the manageable size. This yard will blossom with perennials come spring and the trellis will fill with roses- a true New England welcome! Available immediately for you to plan your summer vacation or cozy up around the fireplace and enjoy the quiet balance of winter.

Waterfront on West Beach! You'll love this one-of-a-kind, newly renovated year-round home, located steps from the sand with breath-taking ocean front views! Located on the beautiful Connecticut shoreline overlooking Long Island Sound. This home is minutes away from restaurants, shops, marinas, and the train station, providing easy access to New York and Boston. This home is ideally situated to enjoy the beach lifestyle all year round! Significant remodel completed in 2018. All rooms have been freshly painted and decorated with soothing ocean and beach colors throughout. No need for any expensive remodeling, as all the work has been done. The only thing you will need to move in is your toothbrush! (And your beach towels and suntan lotion!) Features include: " A gourmet kitchen with top-of-the-line stainless steel appliances including a Chef's oven range/hood " A wood/gas burning stone fireplace " A downstairs primary bedroom with a spa-like ensuite bathroom, complete with a walk-in shower and tub " Upstairs bathroom completely remodeled including a newly restored claw foot tub " Screened in ocean front porch with new hickory floors " New French-style front door and newer windows offering dramatic panoramic ocean front views " The original floors have been stripped and refinished by hand " Programmable Schlage door lock system " Nest/Ring cameras " Tankless water heater " Central and mini split air conditioning and heating system " Views, views, views!

This absolutely charming, fully renovated, 4-bedroom, 2 full bath home is one not to be missed. You'll be amazed by the views of this never ending, beautiful, sandy beach, directly across the street, with beach rights. Enjoy relaxing on the large deck overlooking the marsh or taking an outside shower after a day at the beach. Living here is like going back in time, it's not uncommon to see a family of three generations strolling down the beach or playing board games at the kitchen table. Ride your bikes to Dairy Queen or hang out on the beach waiting for the ice cream truck to come to you. The water activities are endless! Inside the protection of Duck Island and the breakwater, you can enjoy paddle boarding, kayaking, water skiing, jet skiing, boating and more. Experience going to sailing camp at the nearby marina. Moor your boat out front or keep it at one of the many close by marinas. Don't miss another summer waiting to find that special house, you just did! House was built in 1935, was renovated in 2009 This three-season home can be purchased separately or with the .14-acre waterfront lot across the street. Please see MLS # 24006135 for pricing and information regarding the lot.

Owned by just two families over the past 74 years, this house makes you feel like you have arrived home. Easy sidewalk access to Main Street and the village center brings you to all the wonderful restaurants and shops, services, the town green, town hall, the Kate Theater, the library, parks, two schools and in the other direction, you can easily reach two shopping centers. Situated on just under a half acre with a large level yard, oversized 2 car carport to keep you and your vehicles dry and in front an enclosed front porch to enjoy. Inside you'll find the updated eat-in kitchen with built-in corner cabinet, formal dining room with picture window, spacious living room with fireplace and charming window seat. The first floor also has two bedrooms and a updated full bath with tile floor and custom details including arched doorways. The second floor features a large bedroom with custom built cabinetry, a cedar closet, newer full bath and walk-in attic storage. Even more living space in the fully heated basement where you'll find a finished bonus room, a workshop and the laundry room. The Buderus Boiler keeps you toasty warm and in the summer you can keep cool with a newer split air system. This is a special home in a great location and ready for new owners to move right in!

Welcome to 32 Indian Trail Westbrook, this direct waterfront home with engineered plans for new dock, home/lot has been recently approved for a 3 floor home. Build your shoreline dream home, walk out to your sail boat, all the while overlooking pilots point marina. If the project of a tear down, rebuild is not what your looking for, this property has been gutted down to studs and has the potential to be fixed into an adorable waterfront beach cottage. . One of CT's best beach neighborhoods ! Walk down to your beach association and soak up some sun on one of CT's most pristine and private sandy beaches. Stroll to several restaurants in walking distance or kayak over to Bills Seafood for live music, great food and a great time! Immerse yourself in one of CT shorelines best summer environments, and buy at a price to build exactly what you want your summer or full time home to be! Plans for home and dock are available upon request. Property is sold AS-IS

Boaters and water lovers please take note. "Sunset View" house (as the sign on the front of the house reads) has an identity problem. The sunsets are awesome beyond any doubt, but are they the main draw, or is it the mind-blowing deep water dock with a 20,000 lb. lift capable of raising a 40' boat five feet above mean high tide, plus two additional 1,500 lb. PWC lifts and a mooring? "Sunset View Dock House"? Come to think of it, every bit of this impeccably maintained waterfront home offers reasons for a new sign - "Sunset View Like New Dock House with All The Bells and Whistles". Tough to fit on one sign, but so true! This is the home of a renowned shoreline builder/yachtsman who just had to have a useful dock - a rare commodity along the CT shoreline. Originally renovated in 2009, a tasteful addition in 2017 allowed for four bedrooms (all with walk-in closets) plus a second level family room and a "crow's nest" office. The primary suite has a spacious balcony with unbelievable views of sunsets, Long Island Sound, Duck Island, your boat and water toys. Other amenities include a great room w/coffered ceiling, stone fireplace, wet bar, dining area, dream kitchen with Wolf & Subzero appliances, 3.1 baths, dry basement storage, whole house generator, electric dog fence, central audio and durable Hardie board siding. No flood insurance required. Located near restaurants, shopping, beaches, Clinton Country Club and the train station. Just two hours to NYC or Boston. Sign Up Now!

Live, or demolish & build here at 125 Shore Rd! This parcel, which is a total of 4 acres combined sits at the most photographed location for sunsets in town! Wide open views of LI sound, both Old Saybrook Lighthouses, and impressive optics over the marsh and Black Hall River! Currently, a 1,476 sq/ft Farmhouse Colonial home sits here. Enjoy this home as it stands with its updated interior including the maple shaker kitchen cabinets, granite countertops, SS appliances, and views from almost every room. THE MAIN ATTRACTION here is the potential to demolish & build the proposed home which is rendered that has the same style as the one two doors down (pictured.) Take note of the aerial photos that have been edited to visualize the opportunity. Take a look at those renderings too! Currently working on approvals, so now is a great time to get involved and claim your spot! Special model-home viewing option available! Proposed home will be approx. 3,000 sq/ft. Additional building options available, or perhaps you have your own plans; bring em'! They don't make land anymore, especially a spot like this! Stop getting a glimpse from only your car - it's time to enjoy the view from your couch, kitchen, shower or pool!