Southold Homes with Sprinklers In Front Lot features

Welcome to Southold, New York, a charming coastal town nestled in the heart of Suffolk County. Known for its stunning landscapes, rich history, and vibrant community, Southold is not just a picturesque destination; it’s also home to an exceptional school district that prioritizes academic excellence and personal growth.

The Southold School District is renowned for its commitment to fostering a nurturing and engaging learning environment. With a strong emphasis on individualized education, the district caters to students from pre-kindergarten through high school, ensuring that each child receives the attention they deserve. Small class sizes, dedicated teachers, and a wide array of extracurricular activities make Southold schools a fantastic choice for families. The district consistently boasts impressive test scores and graduation rates, reflecting its dedication to preparing students for future success.

As you explore the real estate opportunities in Southold, you’ll discover homes that not only offer comfort and style but also feature convenient amenities like front lot sprinklers. These homes are designed with both aesthetics and practicality in mind, ensuring your lawn remains lush and vibrant throughout the seasons. Imagine coming home to a beautifully landscaped yard that requires minimal effort to maintain, allowing you more time to enjoy the stunning natural beauty that Southold has to offer.

Whether you’re drawn to the exceptional school district, the scenic surroundings, or the inviting community atmosphere, Southold is a place where families can thrive. Explore the available homes today and discover your dream abode in this idyllic corner of New York!

Newest Southold Homes with Sprinklers In Front Lot features

$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

$2,899,000

4 Beds ⋅ 3 Baths ⋅ 1005049 MLS

Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

405 Williamsburgh Drive, Southold

$1,750,000

3 Beds ⋅ 3 Baths ⋅ 951805 MLS

Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection, honoring the home’s original character while reflecting a level of care and stewardship that is exceptionally rare. From period details and time-honored construction methods, this residence stands as a living testament to Southold’s rich heritage. The interior offers a gracious and functional layout anchored by an enclosed brick porch, a large formal dining room, a newly renovated expansive eat-in kitchen, a classic parlor room, and a comfortable living room—all thoughtfully arranged for both elegant entertaining and everyday living. Adding to the home’s exceptional character are three stunning fireplaces, each serving as a striking focal point and a reminder of the home’s historic craftsmanship. The residence features three bedrooms and two and a half bathrooms. The first floor includes the primary bedroom and two full bathrooms, allowing for convenient main-level living, while the second floor offers two additional bedrooms and a half bath, providing privacy and flexibility for guests . Outside, the property includes a two-car detached garage and is set on a quiet, peaceful lot in close proximity to Southold Bay, offering the serenity of North Fork living with easy access to the water and surrounding natural beauty. With official historic status, this home carries both distinction and prestige—appealing to discerning buyers who value provenance, integrity, and timeless elegance. Opportunities to own a property of this caliber, condition, and historical significance are exceedingly rare. This is more than a home—it is the stewardship of a true legacy. Lastly, the final photos on this listing demonstrate the secret hatch in the floor and each person to visit between 1750-1800's carved their names into the china cabinet paneling. So interesting to explore all the names. ** NOTE: The legal address for this home is 3500. However, the number on the post outside the home is 3290. CPF Tax/The Peconic Bay Region Community Preservation Fund applies to this listing.**

3500 Pine Neck Road, Southold

$6,850,000

5 Beds ⋅ 5 Baths ⋅ 946886 MLS

Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum structural integrity, energy efficiency and elevated finishes throughout. The sleek open-concept design encompasses approximately 4,500 square feet of living space. The light-filled residence showcases curated architectural features, ranging from floor-to-ceiling glass, floating staircases, bluestone and covered patio, water-view balcony, and a walk-out lower terrace. The Modern custom kitchen is adorned with ceiling-high cabinetry, Thermador appliances, marble countertops and porcelain inlay backsplash. The adjoining great room is anchored by a stunning gas fireplace surrounded by textured porcelain and this main level also includes an office, dining room and junior en-suite offering private access to the water and soon to be built saline heated pool. An upper level primary en-suite includes a private balcony and three additional spacious bedrooms, luxury baths, laundry and unfinished bonus space. The lower level offers 2,000 square feet for new owners to reimagine and personalize. The offering is complete with Founders Landing Beach, wineries, farm to table dining and a vibrant North Fork atmosphere.

1750 Hobart Road, Southold

$2,799,000

8 Beds ⋅ 7 Baths ⋅ 859020 MLS

2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom estate, offering the rare opportunity to personalize your dream home to suit your lifestyle and taste. Whether your envisioning a peaceful year-round residence, a high-end vacation home or a lucrative investment property, this home offers it all. Your luxury escape awaits -custom build your forever home today! Photos shown are from an identical recently built house In Southold --- Easy To Preview.

1350 Hortons 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.