Southold Homes with Part Wooded Lot features

Welcome to Southold, New York, a charming coastal town nestled in the heart of Suffolk County. Known for its picturesque landscapes, friendly community, and rich history, Southold is a haven for families seeking an idyllic lifestyle. One of the standout features of this area is its highly regarded school district, which is committed to nurturing the minds of its students. Southold School District prides itself on providing a comprehensive education with a strong emphasis on academic excellence, character development, and community involvement. With small class sizes and dedicated educators, children here receive personalized attention that fosters both learning and growth.

In addition to its educational offerings, Southold boasts a variety of homes that beautifully blend with the natural surroundings. Many properties feature part wooded lots, providing residents with a serene retreat right in their own backyards. Imagine waking up to the gentle rustle of leaves and the soft chirping of birds, all while enjoying the privacy and tranquility that a wooded lot offers. These homes are perfect for families who appreciate the outdoors, as they often come with ample space for gardening, outdoor activities, or simply enjoying the beauty of nature.

Living in Southold means embracing a lifestyle that balances small-town charm with modern conveniences. With beautiful beaches, local vineyards, and a vibrant community, you’ll find that Southold is not just a place to live, but a place to thrive. Discover your dream home in this enchanting town and experience all that Southold has to offer!

Newest Southold Homes with Part Wooded Lot features

$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

$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

$985,000

5 Beds ⋅ 2 Baths ⋅ 1017107 MLS

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

230 Booth Road, 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

$2,799,000

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

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