luxury real estate for rent Greenport, United States

Looking for a resort like retreat just outside of bustling Greenport Village? Look no further! This 6 bedroom, 4.5 bathroom stunner offers everything you could ask for and more. From 3 en-suite bedrooms to an open floor-plan with high-end appliances and a killer in-ground pool/hot tub combo, this property serves as the ideal summer rental. This rare offering is also just a short walk to a sugar sand bay beach, close proximity to Islands End Golf Course, local wineries, farm stands and much more!, Additional information: Appearance:Pristine,Interior Features:Guest Quarters

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards. Permit# 0026.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away.The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692. Showings begin March 1, 2025.

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June 1 - 28 $25,000; June 29 - July 18 $33,000; July (2 weeks) $24,000; Sept 4 - Oct 2 $30,000. Permit #1230.

Mid-Century Contemporary with views of Long Island Sound in a private community with association beach across the road. Cathedral ceilings & large windows add to the bright & open feeling of the communal area. Water view deck for relaxing and entertaining. 1000 sf of living area plus 800 sf walk-out basement converted to a fully renovated recreation room/office with recessed lighting, new furniture, renovated bathroom, and laundry. Offered June $8,000; Sept 3-29 $ 6,500; Oct $5,500. Permit# 0368.

Come enjoy this newly renovated summer home, situated on 2/3 of an acre and located in the Silver Beach vicinity. Close to many beautiful beaches and blocks away to gorgeous sunsets. This home is a wonderful rental with an eat-in-kitchen, living / dining room, bedroom en-suite with shower and 2 bedrooms with hall tub/shower. The dining area has sliding doors that lead to the yard with privacy and brick patio with seating and a gas grill. Spend your summer on Shelter Island and make wonderful memories. Off Season $3,500, June -$8,000 , July $12,000 , August $12,000, July/Aug. $20,000 , MD-LD-$28,000

Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located .6 miles from coveted Wades Beach and Mashomack Preserve. This secluded property feels like a private sanctuary, surrounded by lush greenery, blooming trees, and vibrant summer flowers. The open-concept living-dining-kitchen area is perfect for entertaining, with a spacious layout that seamlessly flows onto a wrap around deck overlooking the fenced in yard. The house has a mirror image layout for the lower and upper floors, two bedrooms and one bath upstairs and the same setup on the lower level with each its own entry. Access to Coecles Harbor Marina pool. Seasonal Rates: May $7,500 , June $10K , July $15K , Aug-LD $17,500 , May-LD $45,000 , MD-LD $40,000

Enjoy living in the crown jewel of Orient Village, the Shaw House built in 1730. Restored & meticulously maintained with original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. 2 large decks span the back of the house overlooking Orient Harbor & Yacht Club. Offered Dec 2024 $6,000. 2025 prices: Jan $5,000; Feb $5,000; March $5,000; Apr $5,000; May $10,000; June $15,000; Sept $15,000; Oct $8,000; Nov $8,000; Dec $6,000. Permit #0293., Additional information: Appearance:excellent

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; June $11,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000; Dec $10,000. Permit# 1020.

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16x32 heated pool, newly renovated chef's kitchen & baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to association Willow Terrace bay beach. Embrace the North Fork lifestyle. Offered June $25,000; July $55,000. Permit #0516.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; May $10,000; June $16,000; July $25,000; Aug $25,000. Permit #0827.

Spacious home with wrap-around screened porch, living room, formal dining room, eat-in kitchen, den, 3 bedrooms, 2 full baths. Original details. Set on a large parcel in the heart of Orient Village. Bike or stroll to the yacht club, bay beaches, Village Lane shops and Poquatuck field. Offered Aug $16,500. Permit #0506.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered July $10,000; Aug $10,000; Sept 3-Oct 1 $7,000. Permit #0091.

Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished with master bedroom with full bath plus 2 additional bedrooms & full bath, large gourmet kitchen, den, spacious living room/dining room/common space opening to wrap-around deck overlooking pool. Walk to Village, Latham's farm stand. Aug $xx,000.

2025 Rates: June $30,000, July $60,000, July-August $125,000 and August-Labor Day $65,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef's kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it's own full bath. Additional features include a full house generator, alarm system, and two smart tv's. This home is close proximity to Wades Beach and Mashomack Preserve.