Southold 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.

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!

Direct waterfront property with over 70 feet of Long Island Sound frontage and spectacular panoramic views. Completely renovated and expanded in 2015 this home is move-in ready, just in time to enjoy the summer! Boasting an open floor plan fit for today's lifestyle the home retains its original warmth and New England charm with hardwood floors, beadboard ceilings, extensive stone walls and traditional landscaping. A beautiful, large kitchen serves as the focal point of the first floor. It is an optimal gathering place complete with a fireplace, dining area and a sitting area, all surrounded by breathtaking water views. The oversized island with mahogany countertop pairs beautifuly with the leathered granite counters. From the kitchen, doors lead to a pristine stone patio with outdoor fireplace and built in grill area. An office and a mudroom with a full bath complete the first floor. The back staircase leads to the primary bedroom suite with access to a private deck,full bath, two walk-in closets and more breathtaking views. The main staircase leads to the second floor hallway with access to three additional bedrooms, a full bath, and a bonus/media room that sits over an ample two-car garage. This meticulously maintained year round home is close to the train station, shopping, restaurants and marinas. Enjoy daily sunrises and sunsets from this truly special property.

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.

"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.

Waterfront: unique opportunity to enter the Direct Waterfront market at a reasonable price point. This adorable 2 Bedroom Cape enjoys spectacular West facing Sunsets, Sandy Beach, Outdoor patio with retractable awning and outdoor shower. Features open floor plan, Floor to Ceiling windows, Stone face gas Fireplace and 1 Car garage. Enjoy swimming, fishing, kayaking, clamming and all water activities from this Cosey Beach front Gem. The opportunities here are endless. As is or bring your Architect to design your Dream Home. Convenient to Village, I 95, Yale, NYC, Boston and Bradley International Airport. A must see for the Waterford Enthusiast and Nature Lover.....

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.

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.

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.

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

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!

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!

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.

The Hammocks is an active 55+ community of 53 Individual Custom Built Homes. This large Greek Revival has the Primary Bedroom Suite on the main floor for easy one floor living. Beautifully designed kitchen offers double wall ovens and double sinks with French door walkouts to the patio. The adjoining family room with fireplace and cathedral ceilings offers a large area for gatherings. The double sided fireplace adds warmth to both the Living room and Dinning room in the cooler months. Finish it off with two large bedrooms and a full bath on the upper level and a finished room in the basement for added space. Great floor plan! This house also features custom interior Plantation shutters and a Generac whole house generator

Discover a masterpiece of contemporary architecture nestled along the picturesque Connecticut shoreline. This stunning home seamlessly blends modern sophistication with timeless elegance. As you approach down the private drive, the awe-inspiring design and meticulous attention to detail will captivate you. Step inside to a world of luxury where the main living areas enchant with their unique layout and retreat-like ambiance, offering endless possibilities for your lifestyle. Unwind in the indoor hot tub and sauna, bask in the expansive sunroom's serenity, or host gatherings in the sitting room, family room and two-story living room. The rich woodwork and oversized windows connect you harmoniously with the surrounding nature. This property has a notable history, previously owned by William D. Brohn, the renowned orchestrator behind musical scores for Miss Saigon, Ragtime and Wicked, offering inspiring spaces to nurture your craft. Outside, the enchanting grounds boast beautifully landscaped gardens, a gazebo and balconies with breathtaking views. Conveniently located near beaches, restaurants and shopping, this home is a must-see for those seeking the quintessential Connecticut lifestyle. Call today for your exclusive showing and experience the pinnacle of coastal living.

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!

Endless Views: Welcome to 34 Osprey Commons! Stately shingle home ideally situated on the most premium location in The Hammocks-the extraordinary 55+ community of 53 architecturally designed homes close to town, marinas and beach. Enjoy expansive panoramic views of the Hammock River Marsh, Long Island Sound and Clinton Harbor from every vantage point. Spectacular bird watching and wildlife surround this property. Gather with friends on the spacious bluestone patio for a front row seat to the summer fireworks and experience the most spectacular sunsets all year round. The exterior is classic New England architecture with a lovely porte-cochere, attached 2-car oversized garage, ample parking and private paving stone driveway. Enter into the formal foyer and notice the gleaming hardwood floors and 9-foot ceilings. Natural light permeates throughout this home. The first floor encompasses a lovely formal living room with see-through gas fireplace for cozy nights in as well as a light and bright open concept kitchen with granite countertops that opens to your dining room all with endless views. First floor bedroom with ensuite bath can be used as primary or for guests. An elevator brings you upstairs to another primary bedroom with private balcony, ensuite bath and more stunning views. Two additional bedrooms, bonus room and storage area complete the 2nd floor. Backyard is very private, and west side yard abuts open space making it feel more expansive. No flood insurance required.

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.

Super cute and ready for new owners, this home has been lovingly renovated over the past five years. Great location south of RTE 1; walk to shops and restaurants and a short drive to the wonderful Clinton Town Beach! Recent updates include new roof, gutters, windows, carpeting. Stunning new kitchen with beautiful tile floor and backsplash accents; stainless appliances, new slider to brand new back deck and lovely fenced yard. The living room has hardwood floors, new front door and pretty picture window ~ this home is loaded with light! There are two bedrooms on the first floor along with a full bath, and two bedrooms on the second floor plus full bath. There is a drive under garage with electric garage door opener, workshop and laundry area. Many mechanical updates - please see attachments for a comprehensive list. Clinton boasts many wonderful recreational opportunities, beaches, boating, antiquing, and award winning restaurants ~ come home to your shoreline getaway!

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.

Westbrook, known as a friendly port, offers multiple marinas and town beaches, a train station, and a medical clinic. Electric Boat is 35 mins on RT 95 N & Yale 40 mins 95 S. The property has been updated and remodeled, with a brand new roof, mechanics, and top-of-the-line construction. The open floor plan kitchen features a Viking stove, granite counters, and a center island. The primary bedroom suite has a full bathroom and two oversized California closets. The living room has a fireplace and patio. The area offers numerous activities, including restaurants, shopping, a pickle ball court, dog park, library, historical society, garden, club, fishing, kayaking, hiking trails, and bird sanctuary. A beautiful inground pool adds to this oasis.

Please no drive-by's without an appointment. The long driveway has gate with no place to turn-around unless the gate is open. Agent will meet you for appointments and will open the gate. You cannot see the home from the street. If you are looking for a historic 19th Century gem, this circa 1810 colonial is for you. Waterside Lane is one of the most desirable streets in Clinton and sits on a fully fenced .88-acre lot that is walking distance to Clinton town beach, marinas and town center. The kitchen has been updated with newer appliances and an efficient wood burning stove. There are six fireplaces and a gas insert in dining room. Four bedrooms, 1.5 baths and three additional small rooms on the second level which provide privacy and space. There is also a large walk-up attic. Special features include hand-painted wall murals, wide floorboards, beamed ceilings, built-in shelving and cabinetry which all add to this home's incredible character. Outside features include a large screened in porch overlooking a terraced patio and gardens. The 2-car detached garage and large lot provide plenty of space for parking. This historic home with its central location and character truly checks all the boxes.