Southold NY Real Estate & Homes for Rent

Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day.

Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day.

Direct waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including 2023 new chef's kitchen with waterviews over the hedges, renovated powder room, screened in front porch and lovely back deck with large and private garden and vineyard views. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront, private sandy beach and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork all close by and easy to reach. Southold Town Rental Permit 0631

Direct waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including 2023 new chef's kitchen with waterviews over the hedges, renovated powder room, screened in front porch and lovely back deck with large and private garden and vineyard views. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront, private sandy beach and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork all close by and easy to reach. Southold Town Rental Permit 0631

Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don't miss out on this great rental! Southold Town Rental Permit #1096

Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don't miss out on this great rental! Southold Town Rental Permit #1096

Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don't miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.

Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don't miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.

Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful hardwood doors and floors throughout. Additionally, residents have full access to the clubhouse and inground pool. This condo is the perfect blend of modern comfort, convenient amenities with close proximity to beautiful North Fork beaches. Permit #1106

Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful hardwood doors and floors throughout. Additionally, residents have full access to the clubhouse and inground pool. This condo is the perfect blend of modern comfort, convenient amenities with close proximity to beautiful North Fork beaches. Permit #1106

Welcome to your perfect summer getaway nestled in the heart of North Fork wine country. This recently renovated Southold rental offers the epitome of luxury and comfort, greeting you with a bright and airy living space, adorned with top-of-the-line appliances, furnishings and tasteful decor. The open-concept layout seamlessly connects the living area to the fully equipped kitchen, boasting state-of-the-art appliances that make cooking a joy. Whether you're preparing a gourmet meal or simply brewing your morning coffee, you'll appreciate the convenience and style of these modern amenities. With three cozy bedrooms and two pristine bathrooms, there's ample space for the whole family or friends to unwind and recharge after a day of exploring. Outside, a spacious yard beckons you to soak up the summer sun or savor al fresco dining amid the lush greenery of the landscaped garden. Whether you're hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. As if that weren't enough, this summer rental includes all utilities, so you can relax and enjoy your stay without worrying about additional costs. The only thing you'll need to arrange is housekeeping, required every two weeks to maintain the pristine condition of this exquisite retreat. Don't miss your chance to experience the best of Southold living in this impeccably designed summer rental (Southold Town rental permit #1074)

Welcome to your perfect summer getaway nestled in the heart of North Fork wine country. This recently renovated Southold rental offers the epitome of luxury and comfort, greeting you with a bright and airy living space, adorned with top-of-the-line appliances, furnishings and tasteful decor. The open-concept layout seamlessly connects the living area to the fully equipped kitchen, boasting state-of-the-art appliances that make cooking a joy. Whether you're preparing a gourmet meal or simply brewing your morning coffee, you'll appreciate the convenience and style of these modern amenities. With three cozy bedrooms and two pristine bathrooms, there's ample space for the whole family or friends to unwind and recharge after a day of exploring. Outside, a spacious yard beckons you to soak up the summer sun or savor al fresco dining amid the lush greenery of the landscaped garden. Whether you're hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. As if that weren't enough, this summer rental includes all utilities, so you can relax and enjoy your stay without worrying about additional costs. The only thing you'll need to arrange is housekeeping, required every two weeks to maintain the pristine condition of this exquisite retreat. Don't miss your chance to experience the best of Southold living in this impeccably designed summer rental (Southold Town rental permit #1074)

New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer's Delight! Dogs allowed up to 10 lbs. Tenant pays utilities and pool care.

New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer's Delight! Dogs allowed up to 10 lbs. Tenant pays utilities and pool care.

Stunning new construction with 110' of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom stainless hood, wine cooler and an oversized custom island with a built in microwave. 2 primary bedrooms one located on 1st floor with radiant heated floors in the bathroom, marble shower, free standing soaking tub, double custom vanity and a custom walk-in closet with illuminated hanging rods. Finished mud room & laundry room, powder room with gorgeous marble floors. Second floor features 3 bedrooms including another primary suite, full bath, a great room w/ a color changing LED fireplace. Full basement with BR&BA. This is a must see! Available July: $50K and Aug-Labor Day: $50K. Permit #: 1101

Stunning new construction with 110' of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom stainless hood, wine cooler and an oversized custom island with a built in microwave. 2 primary bedrooms one located on 1st floor with radiant heated floors in the bathroom, marble shower, free standing soaking tub, double custom vanity and a custom walk-in closet with illuminated hanging rods. Finished mud room & laundry room, powder room with gorgeous marble floors. Second floor features 3 bedrooms including another primary suite, full bath, a great room w/ a color changing LED fireplace. Full basement with BR&BA. This is a must see! Available July: $50K and Aug-Labor Day: $50K. Permit #: 1101

Beautifully decorated, charming 4 bedroom, 2 bath home with custom details throughout. Complete with an outdoor shower, enjoy the tranquil setting relaxing on the patio or in the luxurious sauna. Revel in the great location conveniently located near sandy beaches, wineries, restaurants, and public transportation. Available for August. Rental Permit #0639.

Beautifully decorated, charming 4 bedroom, 2 bath home with custom details throughout. Complete with an outdoor shower, enjoy the tranquil setting relaxing on the patio or in the luxurious sauna. Revel in the great location conveniently located near sandy beaches, wineries, restaurants, and public transportation. Available for August. Rental Permit #0639.

55 And Over Community Co-Op Available For Rent. 1 Bedroom Ground Floor Unit On The North Fork. Located In The Lovely Town Of Southold With Nearby Shopping, Restaurants , And Transportation. Parking Available.

55 And Over Community Co-Op Available For Rent. 1 Bedroom Ground Floor Unit On The North Fork. Located In The Lovely Town Of Southold With Nearby Shopping, Restaurants , And Transportation. Parking Available.

Summer Beckons At This Spacious Retreat In A Private, Park-Like Setting In A Very Desirable Cul-de-Sac Community Of Southold. Featuring Large Gunite Swimming Pool, Deeded Beach, Multiple Bedrooms, Large Sun-Drenched Living Areas That Open To Backyard. Rental Available First 2 Weeks Of August. Come And Get It. Permit#0848

Summer Beckons At This Spacious Retreat In A Private, Park-Like Setting In A Very Desirable Cul-de-Sac Community Of Southold. Featuring Large Gunite Swimming Pool, Deeded Beach, Multiple Bedrooms, Large Sun-Drenched Living Areas That Open To Backyard. Rental Available First 2 Weeks Of August. Come And Get It. Permit#0848

Treasure the memories made during the Summer of '24 at this chic waterview home overlooking Corey Creek. Completely redesigned and renovated in 2017-2018, this four bedroom, four bath (plus outdoor shower) open floor plan post-Modern boasts nearly every amenity. Located off the beaten path in quiet Laughing Waters, this home includes beach rights at the community's private beach. Listed price is per week. Southold Town requires a minimum occupancy of two weeks. Permit # 0971.

Treasure the memories made during the Summer of '24 at this chic waterview home overlooking Corey Creek. Completely redesigned and renovated in 2017-2018, this four bedroom, four bath (plus outdoor shower) open floor plan post-Modern boasts nearly every amenity. Located off the beaten path in quiet Laughing Waters, this home includes beach rights at the community's private beach. Listed price is per week. Southold Town requires a minimum occupancy of two weeks. Permit # 0971.

Escape to this idyllic waterfront haven. This summer retreat includes 3-bedrooms and 3-bathrooms, blending luxury and comfort seamlessly. Enjoy modern amenities including a fully equipped Chefs kitchen, and an open concept living space with floor to ceiling windows. Kayak, or Paddle Board from your private dock to the local sandy beach. The property also features a generous outdoor space, perfect for relaxation and entertaining and a Tesla charging station adding additional convenience. Don't miss the opportunity to make this waterfront sanctuary your summer getaway!