Old Saybrook CT Real Estate & Homes for Sale

Location, Location, Location! Experience the luxury of waterfront living in this prime first floor, one bedroom, one bath North Fork condo. This coastal panoramic beauty could be all yours plus a private sandy beach, private marina, community clubhouse, gym, 3 pickle ball courts, 2 tennis courts, 1 basketball court and in-ground pool all on 16 seaside acres. Conveniently located to golfing and to renowned Greenport...enjoy all the NoFo has to offer - vineyards, boating, fine dining, shopping and more!

LOOKING FOR PARADISE? Let me take you through this stunning waterfront condo in one of the most desirable spots on the North Fork, Greenport, with breathtaking views of the Peconic Bay and Shelter Island. This condo has an updated eat in kitchen, updated bathroom, a nice size living room, high ceilings, and windows that rain in tons of natural light throughout. On this 4 acre natural beachfront property, you can enjoy the convenience of having a newly redone tennis court, basketball court, and swing set, just a stone throw away. The property includes a large private storage unit for each condo which is great for storing all your outdoor gear and much more. It also has a common area which is inclusive of the deck, bathroom, rinse shower, a community kitchen, and sunbathing chairs to make your time at the private beach more relaxing and comfortable. The private dock gives you easy access to hop on your boat and explore the surrounding waters. Boat slips have a nominal fee of ONLY $700 FOR THE ENTIRE SEASON. Who says you just have to be on the water? You are not in the mood for water sports today? Then lets go golfing. Just minutes away is the beautiful Islands End Golf Course welcoming all. The always lively town of Greenport with its variety of bars, restaurants, and shops, brings a world of entertainment and is perfect for an evening or night out. This waterfront condo offers a perfect blend of serenity, accessibility, entertainment, and is a dream for anyone looking for the vacation lifestyle. Don't just imagine it, come out and see for yourself!

Adorable with room to grow! This complete renovation kept the character and opportunity to expand on this corner property to create your dream yard. Just blocks away from marina's, sandy beaches, tasting rooms and more. Extensive renovation in 2021 with windows, doors, roofing, siding, insulation, electric, plumbing as well as new baths and kitchen creates the perfectly crafted space with wood ceilings, original wood floors and more.

Renovated Greenport Village Farmhouse with custom woodwork details throughout! With a simplified way of living, the location is amazing and the spaces have been uniquely well designed to maximize the use of space and quality craftsmanship. The yard and hardscapes were installed with the designs of coastal village landscape architect offering low maintenance patio, grilling station and paper birch creating year round visual interest. The front porch is wrapped in red cedar and is so cute its the envy of the neighborhood. The interior offers custom kitchen cabinetry, main floor laundry and a full bath on both levels. On demand hot water recently installed for energy efficiency to keep you warm in the winter and energy efficient central air to keep the summer season cool and fresh! The marinas, waterfront dining, beaches, golf course, vineyard tasting rooms encompass this Farmhouse so there is no reason to be bored. The bus, train, ferry and Greenport Village shops and destinations create so many opportunities to explore al that the village living has to offer.

Quintessential 1920's farmhouse with many architectural details intact - pinewood floors, original hardware, glass-fronted built-in pantry, large front porch. Three light filled bedrooms, full bath and a half. Large property with ample room for pool & existing barn/garage with studio. Close to Village Center, "67 Steps Sound Beach", multiple local Vineyards & Farm stands. The property shines with authentic character.

Introducing 165 Angler Rd, a beautifully custom-designed,new construction home that fulfills every buyer's wish list. Positioned just steps from a pristine Bay beach and in close proximity to Greenport Village's vibrant waterfront district, this residence boasts a sophisticated spa-like heated in-ground pool with a stone patio surround and is incredibly well appointed, seamlessly blending traditional details with chic modern elements. With three floors of finished space including a fully finished basement hosting a home office, media room, and full bathroom, this home offers versatile living options. The main level features 9ft ceilings with a light-filled open Great Room, a first-floor bedroom and bathroom, while the third level features two guest bedrooms sharing a full bathroom and a generously sized primary bedroom with a private full bathroom and an oversized walk-in closet. The superb craftsmanship of this home is evident in the custom millwork, built-in shelving, rift and quartered hardwood floors, and upscale finishes. Equipped with dual-fiber-optic cable lines and Cat6 ethernet in all bedrooms and living spaces, this home provides an ideal work from home environment and remote monitoring capabilities for added convenience. The chef's kitchen is designed for culinary enthusiasts, featuring GE Cafe appliances, wall-to-wall stone counters, wine fridge, floating shelves, built-in wine storage, and a large center island, perfect for year-round entertaining. This exceptional Greenport residence offers the perfect blend of sophisticated finishes, modern amenities, and a prime location. Not to mention, you will enjoy world class vineyards, local breweries, hiking trails and many additional beach options between the Great Peconic Bay and LI Sound.

Swan Landing, a custom build by award-winning architecture firm, Shope Reno Wharton Associates, was created to exemplify luxury living at the highest caliber. Featured in Architectural Digest and House & Garden, at 23,000 +/- sq. ft. and situated on 5.3 pristine acres of land; this unparalleled estate embodies the essence of strategic architecture and design. The home features a deepwater dock, indoor pool, outdoor pool, beach, tennis court, English garden, guest house, greenhouse and much more.

Newly 2024 Renovated 4 Bedroom 3 Full Bath Ranch in Desirable Location of Greenport Harbor & Sandy Beach. Enter to Soaring Ceilings and Beautiful Wood Flooring. Featuring open concept Great Room complete with a stunning Quartz Top Center Island, Bar and Wine Refrigerator perfect for easy entertaining. Kitchen Features: Soft Close Cabinetry, Quartz Cabinets and New Appliances. Master Bedroom w/ New Master Bath, 3 Additional Bedrooms, 2 Additional New Bathrooms, Laundry Room. Garage -3 Car Deep. New Siding, Windows, Roofing, Gutters, Energy Efficient Electric Heat & CAC, Electric and All Exterior and Interior Doors. New Driveway, Front Walkway and Stoop. The area offers proximity to parks, vineyards, farms, beaches, restaurants, and night life. Whether you are looking for a seasonal retreat or a year-round residence, this property presents a great opportunity to live near the beach in a relaxing to key environment

Lovingly updated to enhance its 19th-century glory, this enchanting residence invites you to experience a blend of historic charm and modern comfort. Beyond its picturesque facade lies a beautifully renovated home boasting not only timeless elegance but also provides a separate studio space, offering endless possibilities for creativity or relaxation. Step into the lush oasis of the yard, where mature trees and vibrant plantings, including majestic rhododendrons, delicate dogwoods, blossoming crabapples, striking coral bark maples, and the subtle beauty of kerria, create a serene backdrop for outdoor gatherings or moments of quiet contemplation as well as providing room for a pool. Conveniently situated, this idyllic property offers easy access to all that Greenport Village has to offer, ensuring that every amenity, from quaint shops to renowned restaurants, is within reach.

**Exquisite Nantucket Style Cedar Shake Home with Breathtaking Waterviews** Perfectly situated on one of the most coveted streets in Greenport Village, this 3-bed, 5-bath home has a commanding presence and is positioned perfectly to enjoy wide views of Stirling & Greenport Harbor. Step inside to discover a thoughtfully designed "upside-down" layout that places the main living areas on the upper level, maximizing views of the surrounding waters and enhancing the feeling of openness and natural light. Meticulously crafted with attention to detail, this residence boasts white oak wood floors that exude timeless charm and vaulted ceilings anchored by wood beams for a touch of rustic elegance. The lower level features 2 en-suite bedrooms, a cozy den and laundry. Upstairs has an open floorplan featuring a gourmet eat-in-kitchen with high-end stainless steel appliances & a walk-in pantry, a dining room with water views in every direction, and a living room with a gas fireplace. Through sliding glass doors, step out to the mahogany waterside upper deck to soak in the maritime ambiance or enjoy al fresco dining with a view. Outside, the fully fenced grounds with mature & manicured landscaping create privacy for a peaceful outdoor retreat, all while the vibrant village life awaits just moments away. Ask about the dock slip available for rent. Come see for yourself! It'll be worth your time!

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 2 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan.

Legal 2 Family home in Greenport Village with excellent rental history and brand-new pool! Completely renovated down to the studs in 2022, this home has been redesigned with style and flair! Sexy, sleek design throughout with designer styled kitchens and baths. Generous living areas both inside and out. All new windows, plumbing, electric, insulation and more! The upstairs apartment enjoys a large trex deck overlooking the pool, while downstairs has sliders to a large, covered patio area. Extensive landscaping and landscape lighting gives this home a peaceful and tranquil vibe! Detached 1 car garage could easily be converted to pool house. Smart home (Nest) technology throughout for heating, fire/CO detectors and door locks. Less than .5 miles to the heart of Greenport village and all the best stores, restaurants, etc. Amazing opportunity for rental income of both units or utilize one apartment for personal use and rent the other!

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful residential streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry, and ground floor maritime space with a half bath. Four blocks from the center of the village's shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 10 features two bedrooms, two full baths, and one half-bath. Open-concept kitchen/dining/living room. 539 sq ft maritime space with an additional half bath. Sale is subject to the terms & conditions of an offering plan.

A distinctive and stylish offering in the heart of Greenport Village. This 4400 sq. ft. loft features 4 bedrooms across three floors of thoughtfully renovated living space and an adjacent 800 sq. ft. accessory building. Twelve oversized skylights flood the main floor with natural light, illuminating the interior and further highlighting the soaring ceilings. The open floor plan creates an inviting atmosphere and an exceptional entertaining space with a chef's kitchen that connects to a second floor outdoor deck. The third floor features lofted ceilings and a primary bedroom with walk in closet and luxurious full bathroom. The ground level offers the perfect blend of comfort and convenience with two bedrooms, two baths, home gym, den and laundry room. A well appointed courtyard connects the main house to the accessory building. With its unique blend of style, sophistication and functionality, all just a block from Village shops, restaurants, and the waterfront, 511 Carpenter offers an opportunity to embrace the quintessential Greenport lifestyle.

beautiful ,Vibrant Greenport Expansive Heated Pool, private parking,Deeded Boat slip INCLUDED. Can DOCK a 35 or larger foot sail boat . Sweeping views of of the Bay from front to rear of Condo.Wood burning Fireplace, Tennis courts, Water is included, most reasonable.Greenport electric. Trash removal, Snow removal, Grounds upkeep Insurance is included.FOR EXTERIOR OF COMPLEX. Sit and watch the children play at the sandy beach from your beautiful back deck.Barbecue and picnic by the water.Where else can you get a waterfront and a Dock for the low price and taxes. This is a Wonderful way to enjoy nature at its most inviting.Steps from Historic Greenport Village. Dine,shop,dance,antique, Close to Ferrys to Hamptons.Shelter Island,or Connecticut from Orient. less than 2 hours from Manhattan. GREAT.GREAT LOCATION.

Home Sweet Home. Neat and Tidy One Floor Living. New Roof. Nice Yard. Convenient Location. Near Shops, Restaurants and Transportation. 3 Bedrooms.

Welcome to 520 Madison Avenue! This 4 bedroom, 2.5 bathroom property is undergoing a complete and thoughtful renovation to like-new construction, offering modern luxury while maintaining traditional village charm. Step inside to discover a spacious great room featuring an island kitchen and dining area, highlighted by cathedral ceilings and abundant natural light. On chilly evenings, unwind by the gas fireplace in the living room, creating a cozy atmosphere. Retreat to the first-floor primary bedroom, boasting cathedral ceilings, a serene ensuite bathroom, and a generous walk-in closet. Upstairs, you'll find two additional bedrooms and a bathroom complete with a large soaking tub. Outside, your oasis awaits with a heated saltwater pool and expansive yard, bordered by protected lands for unparalleled tranquility. Enjoy complete privacy without worrying about peering neighbors - just chirping birds and fluttering butterflies. Located just a few blocks away from all the excitement the village has to offer, yet feeling worlds away in its peaceful setting, this property is truly one-of-a-kind. Don't miss out on the opportunity to own this exceptional residence, complete in time for Summer 2024! *Images shown are renderings. Actual finishes and details may vary. Additional photos coming soon..

Turn-key mixed use offering in the heart of Greenport Village. This space was completely overhauled in 2017 w/ all new HVAC, plumbing and electric. The property is located in the commercial retail district of the village and offers an array of uses, which include and not limited to accessory apartment, gallery, eating and drinking establishment, studio, event space, dry retail, professional office, etc.. The space is currently set up and CO'd as a restaurant and features a large bar, two bathrooms and an area that would be perfect for an open kitchen on the main floor. The second level is a lounge w/ additional half bathroom offering additional seating and views of Greenport shipyard and Greenport Harbor. The lower level consists a prep area, walk-in fridge, ample space for storage and a majority of the mechanicals. This is an investor opportunity or a great space for an end user operator in an ideal location 1 block from the center of the Village

Location, Location, Location is what this Greenport two story water view home is all about. Renovations had began but not finished, just waiting for you to make your own!

Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and granite countertops. Unwind in Your Private Backyard Paradise. Be captivated by the home's breathtaking gardens surrounding the inviting in-ground pool and hot tub. This fully renovated, turnkey oasis awaits you - move in and start relaxing today!

This one bedroom, second floor apartment in Driftwood Cove is perfect for a hassle free weekend getaway or easy year round living. Close to Greenport Village, Shelter Island Ferry and NYC train and bus stations. Can be rented after 1 year of ownership to year round residents. Maximum 2 person occupancy. Additionally Greenport will be investing in rebuilding the harbor bulkhead. Will not last!

Greenport, North Fork - Driftwood Cove Co-Op features affordable and comfortable living in park-like setting close to area amenities including Village of Greenport, area beaches, wineries, farmstands and more. Manicured property with mature plantings enhances this co-op with onsite parking, laundry and open space to enjoy yourself. Unit J71 is located on at an inner-corner with small front porch accessing the first-floor unit. Living room/kitchen open plan with bedroom and full bath. Greenport electric. Monthly charges cover water, landscaping, snow removal, etc. Subject to an offering plan. Presently rented. Don't miss this opportunity to own your own home. Priced to sell.

Design your paradise! Just over one acre of land to dream and create your ideal home. 60800 County Road 48, Greenport is conveniently located and abuts 53 acres of a nature preserve to deliver the ultimate privacy and serenity. Currently has two existing structures on the property, a residential home as well as a two car detached garage. Sold "As Is"

Located in a desirable area of Shelter Island known as Hay beach, This traditional home is ready for it's new owner. The home offers an open floor plan with vaulted ceilings, a chef's kitchen with a large island and dining area. The master suite offers substancial closets, double sinks with a large shower with a bench seat. The two additional bedrooms share a bathroom, the second floor has a private bedroom suite. The backyard has luscious landscaping, mahogany deck and a 18x36 gunite pool with patio. The added bonus is that this property has health dept approvals for a 2 bedroom accessory building.

Charming 3 bedroom 2.5 bath Cape with gated yard and heated pool in the heart of everything the North Fork of Long Island has to offer. Built in 2008, the house was refurbished with all new paint, carpets and appliances. Walk to the Fifth Street Beach and Playground which has BBQs, Picnic Tables, volleyball and basketball court. Make this your forever home or summer getaway where you can come in from NYC by the LIRR and walk with your wheelie right to your home away from home. Can also walk to town, harbor, restaurants and pubs. Stove top has gas for cooking. Huge Master Bedroom upstairs with Bedroom & attached full bath downstairs. Two zone central A/C. Unfinished basement with outside access has washer and dryer along with an extra refrigerator/freezer. The inground heated pool with new liner and pump makes staying at the house more fun than the beach. Summer Rentals fetch $5000 week. Furniture & accessories avail.