Southold Homes with Near Shops Lot features

Welcome to Southold, New York—a charming coastal town nestled in the heart of Long Island's North Fork. Known for its picturesque landscapes, vibrant vineyards, and rich maritime heritage, Southold offers a unique blend of rural tranquility and modern convenience. With its stunning waterfront views and lush greenery, it's no wonder that this idyllic town has become a sought-after destination for homebuyers looking for a peaceful retreat.

One of the standout features of Southold is its proximity to local shops and amenities. Residents enjoy easy access to a variety of boutique stores, artisanal markets, and delightful eateries that reflect the town's charming character. Whether you're in the mood for a leisurely afternoon of shopping or a quick bite at a local café, everything you need is just a stone's throw away.

The homes in Southold are as diverse as its residents, with options ranging from cozy cottages to spacious family residences, all set against the backdrop of the town's natural beauty. Many properties boast generous lots, providing ample space for gardens, outdoor entertaining, or simply enjoying the serene surroundings. Imagine sipping your morning coffee on a sun-drenched patio, or hosting friends for a barbecue in your expansive backyard.

With its combination of stunning scenery, friendly community, and vibrant local culture, Southold is more than just a place to live—it's a lifestyle. Embrace the charm and warmth of this remarkable town, and discover the perfect home that suits your dreams and aspirations. Welcome to Southold, where your ideal coastal living experience awaits!

Newest Southold Homes with Near Shops Lot features

$939,000

3 Beds ⋅ 4 Baths ⋅ 997034 MLS

Location!Location!Location! Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly 1 acre of meticulously landscaped property on a quiet dead end street, this exceptional custom built home is located just moments away from the historic village of Southold and the very best of the North Fork! Just a mile from the beach and steps away from Long Island's renowned wineries & Farmstands. Built by the homeowner with an uncompromising commitment to quality and craftsmanship, this 3 bedroom, 3.5 bathroom residence offers approximately 2,950 square feet of thoughtfully designed living space. Soaring cathedral ceilings, skylights, custom crown molding, solid wood doors and gleaming hardwood floors are just some of the details that distinguish this home. A stunning chef's kitchen was designed with custom cabinetry, granite counters and new stainless steel appliances, flowing naturally into spacious living and entertaining areas. The luxurious primary suite features a vaulted ceiling and spa inspired new bathroom creating a serene atmosphere to unwind at the end of the day. Adding versatility is a fully finished basement with a separate entrance and spacious living quarters ideal for extended family or those seeking additional flexibility. Outside, the property truly comes alive. Lush landscaping surrounds sitting areas, a vibrant vegetable garden, in-ground sprinklers and a charming permitted cottage. A wood-burning pizza oven creates a natural gathering place for entertaining, while multiple matching sheds, a 2-car garage and an expansive driveway accommodating up to 10 vehicles provide remarkable functionality. Every aspect of this property reflects thoughtful design and pride of ownership, from it's superior construction to it's beautifully maintained grounds. With acclaimed farm stands, wineries, beaches, restaurants and timeless character of Southold Village and the North Fork all close by, this is more than a home, it's an opportunity to embrace the lifestyle that makes this area so desirable. A rare combination of craftmanship, privacy, flexibility and location.....595 Greenfields Lane is a property that truly deserves to be experienced. Come see for yourself what makes this Southold home so special!

595 Greenfields Lane, 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

$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

$799,000

817145 MLS

Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life; You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom Conventional Septic System, (I/A NOT REQD.) Making It Ready For Your Grand Vision. Whether You're Looking To Build A Sprawling Family Estate, A Charming Vineyard Retreat, Or Anything In Between, The Possibilities Are Endless. Truly "Shovel Ready" Embrace The Tranquility Of Country Living With All The Benefits Of Being Near The Heart Of The North Fork’s Sought-After Attractions. Don’t Miss This Rare Opportunity To Create Your Own Slice Of Paradise!

1350 Hortons Lane, Southold

$1,249,000

3 Beds ⋅ 2 Baths ⋅ L3590177 MLS

Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the 'tower' of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!

2055 Boisseau Avenue, 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.