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.

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

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

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.

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.

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.

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!

Immacualte 5 bedroom, 4 bath pool home only two houses away from Goose Creek. Lush landscaping and heated in-ground pool recently added. Three levels of living with bedrooms on each floor. Perfect home for entertaining. Fully finished lower level opens to pool. Main level has a screened porch and bbq porch that overlook the pool Enjoy the outdoors in the pool, on the newly built social area, or from the outdoor dining area. Truly a special jewel for the month of August-LD.

Tranquil farm setting in the heart of North Fork, close to all. Centrally located to all the North Fork has to offer, but tucked away on quiet block surrounded by farms. Enjoy our newly furnished home with 5 beds, 2 baths, and an in-ground saltwater pool. Wake up and sip coffee on your front porch & enjoy the serene views with farm animals roaming in the background. 2 mins drive to Southold town. 4 mins drive to Horton Point lighthouse or Mcbain beach. 10 mins to Greenport Village.

Ideal summer getaway in the heart of the North Fork with 5 bed and 4.5 baths. The home sits on a shy half acre complete with accessory office/gym structure, inground gunite pool and has incredible views of the neighboring North Fork vineyard. The first floor features an open floor plan with a large eat-in kitchen, dining area, living room and family room. There are four bedrooms in the main portion of home and an accessory attached apartment with an additional bedroom, family room and kitchenette. Enjoy close proximity to downtown Southold, beaches and wineries. Renovated top to bottom in 2021. June- 25K, July 35K.

Adorable ranch across from the water in Laughing Waters Community. Association beach available to tenants. Enjoy a summer vacation in this 2 bdr,1 bth ranch with porch/den, kit, Lr and patio. Garage/ shed not included in lease. Swim, kayak , relax in this special place.

Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23,000. Full Month of July: $50,000. First two weeks of August (8/1-8/15): $25,000.

This home at 4845 South Harbor Road, Southold, is a truly unique and meticulously renovated craftsman cottage that is comfortable and charming. You are steps away from one of the finest beaches on the North Fork, South Harbor beach. Popular wineries Croteaux and Mattabella are down the street, and Greenport Village is ten-minute drive. The house has a lovely wraparound porch plus a screened in porch. The backyard has a spacious back patio, gas grill, and dining table with chairs. This is really a fantastic location to enjoy the North Fork! RP# 0424

Public Remarks:If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny's Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025 - JULY & AUGUST ARE NO LONGER AVAILABLE .

This updated and well maintained home and pool is poised on a sprawling three private acres and a true getaway! Boasting four large bedrooms, 3 full recently renovated bathrooms. Backyard oasis with playset and lush lawn. Located less than two miles to Southold's favorite Cedar Beach and Goose Creek Beach, just over one mile to Croteaux Vineyards- plenty of other wineries, organic farms and restaurants nearby! The space features a first floor living room area with high ceilings and access to an outside wrap around deck which overlooks pool area. Modern Chef's Kitchen, Dining Area, Bedroom 1, Master Bedroom with a CAL king bed and Bath and access to the Garage. Downstairs has a fun Bar Room with direct access to the Pool, Bedroom 2 has a king bed, Bathroom down the hall, the Laundry Room with Washer/Dryer and another Living Room area with a piano, TV and games. Upstairs, Bedroom 3 has a full over full bunk bed with trundle, daybed and crib if needed. Bedroom 4 has a king bed. You will make wonderful summer memories in this home! Rental Permit #0362

Founders Village 55+ community - one of the most sought after condo communities in Village of Southold. Great location in the condo complex with more grounds and open space. 2 bedrooms, 2 baths, fireplace in living room, washer/dryer on first floor. Plenty of storage space in the basement. Easy walk to town, shopping and public transportation. Pool and Club House. Walk to summer concerts on the Square on Main Street, library, grocery, and lots of restaurants, shops, post office, and public transportation close by - every thing you need!

Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season.

Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It's The Perfect Summer Getaway. Call Today To Schedule Your Private Tour.

Experience refined living in the exquisite 3 bedroom 3 bath home available to rent for the summer season. This charming residence is in the heart of Southold where beach and town access is most convenient. Delight in the spacious grounds surrounding this property tucked up on a meandering hill providing a serene, private retreat. The backyard is fenced and pets are welcome. Step inside to discover a modern chic interior, perfectly curated for comfort and style. The spacious grand primary en-suite bedroom is complete with a new spa-appointed bathroom, vaulted ceilings, and walls of windows. There is also another en-suite bedroom equally appointed with great light and plenty of closet space. The third bedroom is on the main level with easy access to the living quarters. The home is complete with a beautiful kitchen that leads out to a large deck for entertaining, a comfortable and spacious living space, and a formal dining room. The lower level has laundry and a small recreation space. Goose Creek Beach is within a mile. Come enjoy the East End!

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023