Greenport NY Real Estate & Homes for Rent

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. The Perimeter Of The Gorgeous Backyard Is Completely Fenced-In. Kick Back And Savor The Beauty From Your Very Own Screened Porch. Beloved Greenport Village Is Merely A Stones Throw Away. 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

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. The Perimeter Of The Gorgeous Backyard Is Completely Fenced-In. Kick Back And Savor The Beauty From Your Very Own Screened Porch. Beloved Greenport Village Is Merely A Stones Throw Away. 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

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

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

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!

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

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!

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).

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

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.

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.

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)

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.

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.