Greenport NY Real Estate & Homes for Rent

Look No Further! Adorable 4 Bedroom Rental In Historic Greenport Village. Easily Access All The Amenities That Village Life Has To Offer, Restaurants, Shops, Beaches, Wineries, Museums, And More!

Welcome to the stunning & newly renovated 485 Sutton Place in Greenport. This magnificent home seamlessly blends comfort, style and luxury living. The home provides a bright & airy feel throughout amongst its two levels of living. The first floor provides two spacious bedrooms and a full bathroom along with a bonus room with kitchenette that leads directly out to the backyard. Make your way to the second floor where you are welcomed by high ceilings and open concept living. A stylish living room with fireplace opens to the eat-in-kitchen and dining room with direct access to the balcony for alfresco dining. Completing the second level is a modern full bathroom, sizable bedroom, and an en-suite bedroom with a half bath. Kick back, relax and unwind in the private and spacious backyard that flaunts a new in-ground heated 18x36 saltwater pool with bluestone coping. The adjacent patio offers ample space for dining and provides shade to escape the summer heat. A dedicated fire pit area is the perfect space to cozy up on summer nights, toast to memories and treat yourself to delicious s'mores. Located on the North Fork of Long Island, this home's prime location provides convenient access to all the magnificent amenities the coveted town of Greenport has to offer and is less than a mile away to Greenport Village. For the wine aficionados, spend your day at the nearby Kontokosta Winery, a waterfront winery perched atop bluff that overlooks the Long Island Sound. Looking for a beach day? You have the option to spend your summer days at two nearby beaches, one private and one public. Experience the ultimate summer getaway on the North Fork.

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located seasonal offering. This charming and updated victorian home provides convenient access to all Greenport Village has to offer. You will enjoy water-views from almost every room, beach access right across the street, walking distance to all restaurant and shops. The interior is incredibly well appointed with a formal living room, media room, formal dining room, updated kitchen, bedroom, full bathroom and laundry on the main level. The 3 additional bedrooms on the second floor are all ensuite. Additionally, there is a large open air porch looking directly out to Greenport Harbor, along with an enclosed porch off of the media room. Jump on this fantastic offering before it's too late.

Looking for a truly unique place to live and enjoy Historic Greenport Maritime Village? This is the place for you! Ideally located in the center of the Village, close to shops, restaurants, bars, galleries and more! The rental, an old Carraige House, was gut renovated in 2006. The owner successfully & artistically designed the space to incorporate an industrial/maritime/NYC loft vibe. This 1-bedroom apartment has an additional den/office/art studio & storage. Private outdoor area too! A true MUST SEE! Photos depict the apartment furnished, not all furniture is still there. Can be offered "lightly furnished" or unfurnished - the choice is yours. (Southold Town Permit #: 22-133).

2024 Rates: June $5,000/week or $20K/month; July $6,750/week or $27,000/month; A1-LD $7,125/week or $28,500/month. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

Beautiful and completely renovated and tastefully furnished Greenport seasonal rental. 3 bedrooms, 1 bath home, on a large double lot, ideally located just around the corner from a beautiful bay beach and less than 2 miles to a nearby farm stand, winery and Historic Greenport Maritime Village. Enjoy a welcoming front porch, large yard, outdoor shower, Sonos outdoor sound system, high end finishes and appliances (subzero fridge, wolf oven/range), central air conditioning, wood floors & granite countertops. (Southold Town Rental Permit #1025) Southold Town Rental Rules, 2 week minimum applies.

Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for remote work and has a third private waterside balcony-prime indoor/outdoor summer living just a mile from Greenport Village's shops and restaurants. Personal property manager to address any tenant needs. Hamptons luxury with North Fork vibes.

Experience serenity at this stylishly renovated and tastefully adorned cape in the heart of Greenport village. This expansive residence offers three bedrooms, including a master suite with a private bath, two additional bathrooms, and a convenient home office. The main floor embraces an open-concept design, featuring light-filled dining and living areas, along with a well-appointed kitchen boasting stainless steel appliances. The fenced-in yard creates a tranquil space for stargazing after a day of summer adventures. Just steps away from Greenport Village's restaurants, shops, the Shelter Island Ferry, train, and Jitney bus, and a short distance to popular 67 Steps Beach, this is the perfect location for your unforgettable Greenport summer getaway.

Spend your summer enjoying all the North Fork has to offer at this Greenport waterfront home with dock and community bay beach. Completely updated with high end touches throughout including chef's custom kitchen with island, 3 bedrooms (2 are en-suite), 4 full bathrooms, expansive waterfront deck, and a lower level entertainment lounge. The perfect place to relax and unwind. Permit# 0955.

Welcome To Your Greenport Summer Retreat! This Colonial Stunner Has Just Been Completely Renovated To A Very High Standard. This Gem Boasts White Oak Hardwood Floors Throughout, Three Bedrooms, Two Full Bathrooms, Primary Is En-Suite With A Very Large Walk In Closet, A Quaint Gourmet Eat In Kitchen With Stainless Steel Appliances, A Beautiful Den That Could Also Be Utilized As A Workout Area Or Home Office, Large Dining Room Drenched In Natural Light, The Laundry Is Neatly Stacked & Tucked Away. This Beauty Sits On A Wonderful Mature Half Acre, Perfect For Entertaining Guests Or Getting Away From It All And Immersing Yourself In North Fork Peace And Nature. Be Part Of Everything The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Organic Produce & A Burgeoning Wine Country. Southold Town Rental Permit #1072. July: $15,000. August: $20,000. July/August: $35,000. August to LD: $23,000

Newly renovated 3 bedroom apartment in the heart of downtown Greenport. All the conveniences of living in the village, tucked away on a quiet street, just yards away from the main commercial district. The first level features a large kitchen that opens up to a living room filled with natural light and a updated half bath. The 2nd level features 3 bedrooms and a large updated full bath. Enjoy views of the shipyard and bay beyond. Don't miss this rare village gem!

Fabulous Water Front .condo.Deep water Dock. Pool Tennis.Vibrant Greenport Town

Greenport-Immaculate and spacious home. A welcoming front porch leads to the sunny Living room and dining room. A fully equipped gourmet kitchen with Thermador appliances with sliding doors to back deck, family room with vaulted ceilings also has access to large back deck, there is another den/office, a full bathroom with shower and laundry all on the first floor. The second floor there are two en-suite bedrooms and two additional bedrooms and full bath. Large manicured yard with deck and patio landscaped for privacy. Close to beaches, farm stands, Southold Fish Market, wineries and Greenport Village. Spend this summer in Greenport in this wonderful home. July Rented from July 20-August 3. Available June $15,000/month, June 20-July 20 for $20,000, August 3-LD $20,000, 2 or 3 weeks in July or August $7500/week and Off season $5000/week (2 week Minimum) #0744

2024 Rates: June $17,500, July $23,500, A1-LD $25,000 Welcome to 155 Caiola Ct, located in the desirable seaside community of Rock Cove Estates. This beautifully appointed home offers ideal amenities, beach access and location that one would desire from a Summer retreat. The interior features an inviting foyer leading into an formal dining room, open living room and eat-in-chef's kitchen. Additionally the main level offers a laundry off of the mud-room, sprawling first floor primary en-suite bedroom and home office. The second level features two guest bedrooms that share a full bathroom and a junior en-suite with private bathroom. The grounds are lush, full of mature plantings and showcases a large wood deck overlooking an impressive free-form in-ground swimming pool that basks all day in the summer sun. Additionally, you will enjoy private beach access just a short walk from the house, easy access into Greenport Village and a centralized launching point to enjoy world class vineyard, farm stands, fishing, hiking and so much more that the North Fork has to offer. Book your summer retreat now before this gem slips away!

This unique home has a style all its own. Stylish & chic, an impeccably restored historic Saltbox. It boasts an updated kitchen and bathrooms that a queen would admire. Enjoy its warm & open floor plan, calming fireplaces in common room/bedroom and kitchen. Walk on original wide floorboards from the 19th century & enjoy the lush decor and comfortable furniture from 20th century. Short distance to Greenport amenities, walking distance to beach. House Incl. Prius/smart car charger. Rental Permit #0722

Permit #22-161. Enjoy summer from this newly renovated waterfront condo with the option to bring a boat and enjoy your own deeded slip with access to Peconic Bay! If you aren't into boating, you can still enjoy the serene water views of the bay and Shelter Island from this gorgeous, ground-floor unit with 2 bedrooms and 2 baths, a living room with a wood-burning fireplace, and a stunning eat-in kitchen! Other amenities include a heated swimming pool, private beach, private tennis courts, back patio with grill, deeded parking spot & guest partking and only 2 blocks away from all the amazing restaurants and shops in Greenport Village! Utilities included. This is a can't miss opportunity to enjoy all Greenport and the North Fork has to offer!

Charming, clean, freshly painted and tastefully decorated, 3 bedroom,1 bath, Greenport bungalow. The enclosed sun-porch is a great extra space to relax on rainy days too. The location~ Just a couple of blocks from a beautiful Bay Beach with boat ramp and amenities. Just down the block from Portobello's Restaurant, Billy's By The Bay and Kontokosta Vineyard. Close to Village shops, bars, restaurants, farmstands, winery, galleries, museums and more. The well-equipped house is so inviting, just unpack and unwind! (Southold Town Permit #1012. Per Southold town, maximum occupancy: 5).

Greenport village 5 bedrooms, 2 baths with sweeping Water Views, adjacent to 6th St bay beach & park. Architect-designed & decorated interiors, chef's kitchen, 2nd floor sundeck and large yard with garden & outdoor dining area. Huge water-facing sun porch with wall of windows looking out on the bay. Short distance to farmers markets, wineries, shopping, LIRR & Jitney. RP# 22-298

Charming, Furnished 2nd Floor Greenport Village One Bedroom Apartment. Convenient to All. Nice Beach at the End of the Street. Winter 2024 $2,600 Per Month; Summer 2024, Memorial Day to Labor Day $10,000; June $3,500; July $3,500; August to Labor Day $3,500.

So Very Close to a Beautiful Bay Beach! 3 Bedrooms/2 Baths. Central Air Conditioning. 2 Large Decks. Nice Yard! Summer 2024 - June $7,500 or August-LD $12,000. Permit #0497.

Enjoy the stunning views of Shelter Island from your private deck and upstairs balcony. This Luxurious Bayfront Condo even includes a Deepwater Dock! Fully furnished and equipped for all your vacation needs. A beautiful Village beach and park is across the street and the unit is just a short distance to shops, galleries, bars and restaurants in Historic Greenport Village. Nearby ferry, bus and train offer easy access to Shelter Island, the Hampton's or NYC. Make your 2024 vacation plans amazing and make them now! (Southold Town Rental Permit #1026)

Pleasantly Updated Open Floor Plan Ranch with Vaulted Ceiling and Separate Den with Fireplace and TV. 3 Bedrooms, 2 Baths. Central Airconditioning. A Nice Deck, Heated Inground Pool, Outdoor Kitchen (with fridge and grill) and a Memorable Community Long Island Sound Beach Nearby to Enjoy. Summer 2024 - $4,900 Weekly with Two Week Minimum; June $18,000; Off Season (January to Mid-May) $3,500 Per Month. Permit # 0796.

Summer 2024. Luxurious Modern Home with Heated Inground Pool in Private Community with Memorable Bay Beach 3 Blocks Away. Short Distance to Golf and Greenport Village. Summer 2024 - June $20,000; July $35,000. Off Season (January to May) - $10,000 per month (single to multiple months considered). Permit # 0634.

2024 Rates: June $20K, July $35K Luxurious living in Greenport's private Rock Cove Estates. A stone's throw away to the deed private beach on the Long Island Sound. Highly desirable area where you can enjoy summer walks, lazy days at the beach or gorgeous sunsets. Create memories to last a lifetime in this beautifully decorated home. Close to Greenport Village, restaurants, shopping, wineries, and recreational activities.

Summer 2024 Rates: June 27-July 11 $15K, Sept4-Oct4 $5K/week: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.