Southold Homes with Pool

Welcome to Southold, New York – a hidden gem nestled in the heart of Suffolk County on the picturesque North Fork of Long Island. This charming town is renowned for its serene landscapes, rich history, and vibrant community atmosphere, making it a perfect destination for those seeking a tranquil lifestyle. With its stunning waterfront views, lush vineyards, and beautiful beaches, Southold offers a unique blend of rural charm and coastal elegance.

One of the most sought-after features in Southold’s real estate market is homes with pools. Imagine stepping into your own private oasis, where you can unwind under the sun or host memorable gatherings with family and friends. These homes with pools provide the perfect backdrop for summer barbecues, lazy afternoons, and refreshing dips after a long day. Whether you prefer a sleek modern design or a classic, rustic feel, Southold boasts a variety of properties that cater to your unique tastes and lifestyle.

Beyond the allure of your own pool, Southold offers a plethora of outdoor activities, from exploring the scenic trails of the local parks to indulging in the bountiful farms and vineyards that populate the area. With a close-knit community and a wealth of recreational options, you’ll find that Southold is not just a place to live, but a place to thrive.

Discover your dream home in Southold, where every day feels like a vacation, and the joys of poolside living await you. Embrace the opportunity to create lasting memories in this idyllic corner of New York!

Newest Southold Homes with Pool

$3,675,000

5 Beds ⋅ 6 Baths ⋅ 1031351 MLS

Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany front door and decking, solid wood closet systems, bespoke pantry shelving, and a handmade stone mantle and hearth. This lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with Bertazzoni and Bosch appliances, extra large island and breakfast nook, formal dining room with Butler's pantry, first floor junior primary ensuite, and library. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym, additional bedrooms or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork.

150 Deer Run, Southold

$2,695,000

5 Beds ⋅ 4 Baths ⋅ 1031524 MLS

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

605 Cedar Drive, Southold

$1,475,000

4 Beds ⋅ 4 Baths ⋅ 1024798 MLS

Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed for relaxed year-round or seasonal enjoyment. Outdoor amenities include a new heated 16 x 32 inground saltwater pool, hot tub, outdoor shower, and gracious covered porches at both the front and rear of the home. Classic Craftsman details enhance the curb appeal, including Arts & Crafts-style columns on river rock bases, double-dipped cedar shingles, a custom garage door, and a signature Craftsman front door. Inside, the main level offers an inviting open layout with wood floors throughout. The spacious living room features a wood-burning fireplace, while the eat-in kitchen, dining room, and window-filled den provide warm, functional spaces for everyday living and entertaining. Both the kitchen and den open directly to the rear covered porches, creating an easy flow for indoor-outdoor living. The first floor also includes two bedrooms, one full bath, one half bath, and a mudroom/laundry room. Distinctive interior details include oak trim around the windows and doors, as well as a beautiful staircase with a one-of-a-kind custom newel post. Upstairs, the primary suite serves as a private retreat with a generous sitting and office area, two-sided gas fireplace, sauna, and a fabulous tiled bath with spacious walk-in shower. A newly added junior primary suite, completed in 2026, adds comfort, privacy, and flexibility for guests or extended stays. Just a few doors from the edge of charming Southold Village, the Southold Historical Society and close to Founders Landing Bay Beach and Park, this exceptional home offers easy access to the marina, restaurants, shops, wineries and NYC transportation. This is a rare Southold Village offering with remarkable character, amenities, and the superior North Fork location you have been looking for.

425 Maple Lane, Southold

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 1016523 MLS

Southold – Goose Creek- Located along a quiet private lane leading to Goose Creek Beach, this beautifully crafted and completely renovated cedar shingled two story home offers the perfect blend of charm, privacy, and North Fork living. The first floor features an open, sun filled layout highlighted by a spacious living room with a wood burning stove, a bright and airy kitchen with an expansive dining area framed by walls of windows, and a dining area with doors opening to the pool and patio. A first floor sitting room with an adjacent full bath provides a flexible space that can be easily converted into a first floor primary en-suite. Upstairs, the generous primary en-suite offers creek views, accompanied by two additional guest bedrooms and a full guest bath. Privacy surrounds the heated saltwater in ground pool and patio, creating a peaceful retreat for relaxation or entertaining. This exceptional property captures the essence of the North Fork lifestyle — a short stroll to beautiful Goose Creek Bay beach, yet tucked away in a quiet, coveted location. With creek access you can launch a kayak or paddleboard and enjoy the serene waters of Goose Creek. f you are interested in a "real" North Fork experience, this house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

1195 Goose Creek Lane, Southold

$2,795,000

4 Beds ⋅ 5 Baths ⋅ 999394 MLS

Welcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart of the North Fork's Town of Southold. This home is situated on .80 acres & boasts 4,327 SF of living space with 4 bedrooms and 4.5 baths and combines clean lines of modern design with the allure of North Fork chic. This home comes with Authentic Western Red Cedar Shingle siding and a stucco accented stair tower that makes the grand foyer rise into the second story. There are 9ft high ceilings on the first and second floors in addition to vaulted and coffered ceiling details with 8-1/2” white oak floors throughout. Enjoy two bedrooms on the first-floor which includes a primary bedroom with a generous walk-in closet and private access to the masonry patio opening to the backyard pool and garden. The great room contains a 46” linear gas fireplace and is open to the well-appointed kitchen which includes custom inset cabinets, marble countertops and high-end GE Monogram appliances with a wet bar. The second floor has two bedrooms both ensuite with large tile and custom vanities. The second floor also contains a beautiful family room and a large laundry room with custom cabinetry and a sink. The basement can be finished to suit which includes 9’ ceilings. Enjoy the incredible entertainment ready backyard featuring a 20X40’ heated gunite saltwater pool, including automatic pool cover with a Napa Stone marble patio. The secluded backyard includes custom designed landscaping and masonry by our Landscape Architect.

1475 Laurel Avenue, Southold

$1,599,999

4 Beds ⋅ 4 Baths ⋅ 998241 MLS

Designer Modern Farm Ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living Room, Dining Room and Kitchen, Gorgeous Kitchen with quartz countertops, Stainless Steel Appliances, built in Wine Cooler, New Windows throughout, New Interior Doors, New Exterior Doors, Custom Closets, New flooring, updated Designer Baths, New Boiler, New Well Pump, New Hot Water Heater. Spectacular 20x40 Inground Saltwater Pool with Cambridge Paver Patio. Covered Front Porch overlooking Farm Views. Access Resident Only Town Beaches, Boat Ramps and Parks with Town Permit. Close to McCabe Beach for Incredible Sunset Views. Marina, Airstrip and Trails nearby. Farm animals permitted. Possible Sub-division. New, New New, Priced to Sell.

3715 Hortons Lane, Southold

$1,049,000

4 Beds ⋅ 3 Baths ⋅ 942546 MLS

Welcome to this charming residence nestled in the heart of Southold. This gem boasts 4 spacious bedrooms, 2 full bathrooms, along with an additional half bath for your convenience. Step inside to be greeted by a formal dining room, perfect for hosting memorable gatherings. The primary bathroom offers a private sanctuary, while the walk-through kitchen is equipped with stainless steel appliances including a dishwasher, oven, range, and refrigerator, ready to inspire your culinary creativity. Experience the warmth of this gem with cozy carpeting, elegant hardwood, and a welcoming fireplace, not to mention the indoor hot tub. The property also features a partial basement, providing extra space for your needs. As part of the Goose Neck Homeowners Association, enjoy access to a deeded private beach, boat dock, and 5 water access points around the penninsula, adding to the exceptional lifestyle this home offers. This delightful gem is located in a vibrant community, teeming with local amenities to explore and enjoy. From the bustling local markets to the serene parks, there's something for everyone. This is not just a house, it is a sanctuary, which you can call home. So stop, take a look, and imagine the possibilities... Your next chapter starts here!

5045 Main Bayview Road, Southold

$3,450,000

5 Beds ⋅ 4 Baths ⋅ 995842 MLS

Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set on nearly a full acre, the property is an entertainer’s dream with a heated saltwater pool, outdoor shower, and a screened-in porch ideal for summer evenings. The home also boasts a 3-car garage, whole-house sound system, security system, elevator, and a full irrigation system that keeps the grounds lush and green. Gorgeous landscaping with landscape lighting throughout. High-end construction materials and thoughtful design elevate the entire living experience, with 8-foot ceilings in the basement offering the perfect opportunity to create a media room or home gym. Enjoy spectacular sunsets, unbeatable beach access, and the potential to easily add a pool house—water and electric are already in place. This is coastal living at its finest.

790 N Sea Drive, Southold

$2,250,000

4 Beds ⋅ 5 Baths ⋅ 990099 MLS

Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom and three second-floor ensuite guest rooms. The interior is designed for both comfort and entertaining, with a two-sided gas fireplace, quartz kitchen countertops, Bosch and XO appliances, dimmer lighting throughout, electric shades in key living areas, ceiling fans in all bedrooms, and a first-floor laundry room. Home includes 7 built-in TVs, a 98-inch Sony screen and home theater with blackout shades, creating an impressive entertainment space. Since purchasing, the owner has elevated the property, including full front and rear landscaping, new lawns, extensive plantings, 73 trees, a new front walkway and steps, a rear sprinkler system, outdoor accent lighting, and a limestone patio surrounding the pool. The exterior is anchored by an 18x36 gated heated saltwater pool with a 500-gallon inground propane tank for the pool heater, a rear porch, dog run, retaining wall, and roof deck with water views. Additional features include a Sonos music system inside and out, alarm system, 2-car attached garage with shelving, additional refrigerator, and electric car hookup. Ideally located in Southold, this move-in-ready home combines new construction ease with substantial post-purchase improvements already completed.

1665 Glenn Road, Southold

$2,895,000

5 Beds ⋅ 6 Baths ⋅ 990263 MLS

North Fork living, refined. Welcome to Wildberry. A newly constructed residence where design, light, and landscape converge - set against sweeping, sunset vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its surroundings. Luxury finishes have been selected and wired for full smart home capability. Intuitively designed for both everyday living and elevated entertaining. Offering 5 bedrooms and 5 full bathrooms and one half bathroom, the layout balances scale and comfort, providing a private retreat while accommodating guests with ease. Featuring two primary en-suite bedrooms on both the first and second floors, three guest bedrooms and a full cabana-style bathroom in the walk-out basement for pool party guests. Salt water pool is 18x36 and surrounded by patio with outdoor kitchen. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork. Home is expected to be completed July 2026, photo is artist rendering, landscape design is rendering not actual, additional photography and information coming soon.

1135 Wildberry Lane, Southold

$1,445,000

3 Beds ⋅ 2 Baths ⋅ 975344 MLS

Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen includes modern appliances and ample counter space. Large windows provide natural light and water views, with direct access to the rear deck. The outdoor space includes a spacious deck with room for seating and dining, along with a gas grill setup. The dock provides convenient access for boating, kayaking, and other activities. The home includes three bedrooms and two bathrooms, offering flexible space for a variety of living arrangements. Additional features include well-maintained interiors and updated elements throughout. Conveniently located near local wineries, restaurants, and shops, with access to all that the North Fork has to offer.

470 Windy Point Lane, Southold

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 953464 MLS

The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the community. New Construction Package – $1,400,000 In partnership with respected local builder, this option delivers a thoughtfully designed 2,215 sq ft home that blends timeless details with coastal luxury. Plans include 4 bedrooms, 3 full baths with 9 foot ceilings throughout, creating an airy and elegant space. The first floor of the home features an open-concept kitchen, living, and dining perfect for hosting and easy flow of day-to-day living. Walk up the front porch and enter the front door to a spacious living room accompanied by a warm fireplace for those cooler nights. As you continue you’ll pass through the dining area with floor-to-ceiling doors that look out over the backyard. Enter the brand-new chef’s kitchen featuring a large kitchen island, stainless steel appliances, and beautiful walk-in pantry! The main floor also features a full bath and bedroom, perfect for guests or single-floor living. Upstairs, you’ll find 3 additional bedrooms — 2 that share the full bath in the hall, and a primary bedroom with walk-in-closet and en suite bathroom. Laundry is a breeze with a washer-dryer on the second floor! Outdoors, appreciate the intentional details designed with North Fork living in mind. The detached garage features a beautifully integrated pool cabana, accessed by a man door. Designed to suit outdoor entertaining and living, the cabana comes equipped with an island bar top, sink, half bath, and space for a grill — the perfect spot to entertain or wind down after a day at the beach with family or guests. At 500 Summer Lane, you’re less than 1.5 miles from some of Southold’s best gems like Croteaux Vineyard, Goose Creek Beach, Sophie’s Restaurant, and local farm/flower stands. A little further you’ll find the charming Southold Town, Cedar Beach, endless vineyards, Greenport Harbor Brewery, and so much more. The North Fork is Calling Your Name!

500 Summer Lane, Southold

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.