Southold Homes with Pool

Welcome to Southold, NY – a charming gem nestled in the heart of Suffolk County, where the beauty of the North Fork meets the allure of coastal living. Renowned for its picturesque landscapes and vibrant community, Southold is not just a destination; it's a lifestyle. One of the standout features of this enchanting town is its highly regarded school district, known for its commitment to academic excellence and holistic development. Southold School District prides itself on small class sizes, dedicated educators, and a strong sense of community, ensuring that every student receives personalized attention and support. Families are drawn here not just for the quality education but also for the nurturing environment that fosters growth and creativity.

In addition to its educational offerings, Southold boasts an array of stunning homes, many of which come complete with private pools. Imagine basking in the sun on warm summer days, entertaining friends and family, or enjoying serene evenings under the stars—all from the comfort of your own backyard oasis. Homes with pools in Southold provide the perfect blend of relaxation and recreation, allowing residents to unwind in style while enjoying the natural beauty of their surroundings.

Whether you’re seeking a seasonal retreat or a permanent residence, Southold offers a unique blend of tranquility and community spirit. With its excellent schools and beautiful homes with pools, this area is perfect for families and individuals alike who want to embrace the quintessential New York lifestyle. Come discover the charm of Southold and find your dream home today!

Newest Southold Homes with Pool

$3,250,000

5 Beds ⋅ 5 Baths ⋅ 1048014 MLS

Known as The Old King Farmhouse and Owl Hollow, this historic 1.05± acre compound is one of Peconic’s most distinctive properties, pairing a beautifully preserved c.1860 Italianate Victorian residence with a remarkably purpose-built artist’s studio in the heart of the North Fork. Rich in history and thoughtfully stewarded over time, the approximately 3,260-square-foot residence offers four bedrooms and two-and-a-half baths while preserving many of its original architectural details, including period fireplaces, wide-plank wood floors, oversized windows, and graciously proportioned rooms filled with natural light. The interiors strike a rare balance between historic character and understated elegance, allowing the home’s craftsmanship and surrounding landscape to take center stage. Across the grounds, Owl Hollow serves as an extraordinary extension of the property. The approximately 1,200-square-foot studio is defined by soaring timber trusses, dramatic north-facing windows, a wood-burning fireplace, and its own Certificate of Occupancy, offering exceptional flexibility as an artist’s studio, creative workspace, guest retreat, entertaining pavilion, or wellness space. Set among mature specimen trees, clipped hedges, perennial gardens, and a fenced vegetable garden, the grounds unfold as a series of outdoor rooms centered around a heated 18’ x 36’ saltwater pool. A rare pre-existing, non-conforming wattle-and-daub stable offers additional storage or future possibilities, while separate driveways, updated utilities, new septic systems, rental permits, and separate Certificates of Occupancy further enhance the property’s versatility. Both the residence and studio have an established history as luxury rentals. Located in the bucolic hamlet of Peconic, moments from renowned vineyards, farm stands, beaches, and marinas, The Old King Farmhouse and Owl Hollow represent an increasingly rare opportunity to own a historic North Fork compound where architecture, landscape, and creative living exist in perfect harmony.

1200 Indian Neck Lane, Peconic

$2,950,000

4 Beds ⋅ 4 Baths ⋅ 963793 MLS

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location. Held in the same family for more than 50 years, the over 4000-square-foot home is set on two private acres overlooking the natural beauty of Great Pond. Expansive light-filled rooms, walls of glass and bold architectural lines create a residence that feels as compelling today as it was when first conceived. Mature landscaping, an inground pool, abundant wildlife and magnificent sunsets all contribute to the architectural composition. These features enhance the sense of retreat and home, while two beautiful Long Island Sound beaches—Kenney’s and McCabe’s—are just moments away. A true North Fork treasure, equal parts architectural time capsule and North Fork, grab this opportunity before it's gone.

9305 Soundview Avenue, Southold

$3,295,000

4 Beds ⋅ 5 Baths ⋅ 1039113 MLS

New Construction Luxury Southold Home underway set to be complete September 2026. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100 SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant front wrap-around-porch, heated saltwater 18x36 pool, and both first and second level primary bedrooms with ensuite baths and walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson Windows, Kitchen-Aid Appliances and Quartz Countertops, Wide Plank Natural White Oak Floors, Gas Fireplace, Custom Glass Shower Doors throughout, and more. Full Finished Basement with 9.5’ ceilings, Outside basement entrance, full bathroom, built in wine fridge, and custom glass doors leading to your Gym and Custom Cedar Sauna. Enjoy exclusive Southold Park District rights—offering access to private beaches, kayak launches, and Founders Landing—while being just minutes from stunning Long Island Sound beaches, scenic Sound View Dunes, world-class vineyards, farm stands, and charming village dining.

390 Wildberry Lane, Southold

$2,200,000

3 Beds ⋅ 3 Baths ⋅ 1038709 MLS

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

225 Lakeside Drive S, Southold

$2,695,000

3 Beds ⋅ 2 Baths ⋅ 1036373 MLS

Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted for horses. While perfect as-is, its use could easily extend beyond equestrian purposes and be reimagined to suit your needs. A heated pool overlooking the vineyards rounds out the grounds, offering the perfect spot for entertaining or unwinding. Located less than a mile from bay beaches and the restaurants and shops of Southold Hamlet, putting amenities and everyday convenience equally within reach. This is a rare opportunity to own a classic North Fork property that balances open land, everyday comfort, and easy access to it all.

2850 Main Bayview Road, Southold

$2,795,000

4 Beds ⋅ 5 Baths ⋅ 1036799 MLS

The Laurel Collection by MarrCon is an exclusive enclave of eight newly constructed luxury homes ideally located in the heart of Southold. With only 3 residences remaining, this limited offering presents a rare opportunity to enjoy exceptional new construction in one of the North Fork’s most desirable locations. 1475 Laurel Avenue showcases The Laurel Model, the largest model within the collection, offering approximately 4,375 square feet of beautifully designed living space set on .80 acres. The property is complete with a 20' x 40' heated saltwater gunite pool with an automatic cover, surrounded by an expansive Napa Stone marble patio. There is also ample room to create a pool house or outdoor kitchen. Backing to preserved land that can never be developed, the property offers lasting privacy and a peaceful, serene setting. Inside, nine-foot ceilings span both the first and second floors, complemented by vaulted and coffered ceiling details and 8½-inch white oak flooring throughout. The first floor features two bedrooms, including a luxurious primary suite with a generous walk-in closet and private access to the masonry patio, backyard, pool and gardens. The dramatic great room is anchored by a 46-inch linear gas fireplace and flows seamlessly into the beautifully appointed chef’s kitchen, featuring custom inset cabinetry, marble countertops, high-end GE Monogram appliances and a wet bar. The first floor also includes an office or flexible-use space complete with a wall of windows, built-in shelving and a wine refrigerator. Upstairs, two additional ensuite bedrooms feature beautifully finished baths with large-format tile and custom vanities. A spacious family room and oversized laundry room with custom cabinetry and a sink complete the second level, along with an additional stackable washer and dryer for added convenience. The lower level offers tremendous potential for additional living and entertaining space and can be finished to suit, with nine-foot ceilings, an egress window and walkout access already in place. Perfectly positioned to enjoy everything the North Fork has to offer, The Laurel Collection is just moments from beautiful beaches, wineries, farm stands and the charming villages of Southold and Greenport.

1475 Laurel Avenue, Southold

$2,895,000

5 Beds ⋅ 6 Baths ⋅ 1037213 MLS

North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, 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 spectacular 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 both as a private retreat while still 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 16x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

1135 Wildberry Lane, Southold

$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

$1,395,000

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

$1,549,999

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. New, New New, Priced to Sell. Present all offers, seller negotiable.

3715 Hortons Lane, 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

Start Your Search

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.