Sag Harbor Real Estate

Sag Harbor Real Estate

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Newest Listings in Sag Harbor

311 Main Street, Sag Harbor
$9,600,000
4 Beds ⋅ 6 Baths ⋅ 1058964 MLS
Set along the water on one of Sag Harbor Village's most storied streets, this exceptional Captain's Row estate unfolds across nearly .60 +/- acres of beautifully landscaped grounds. Built circa 1850, this beautifully restored and renovated Greek Revival Sag Harbor waterfront home sits directly on Main Street with frontage on Otter Pond and views toward Upper Sag Harbor Cove. Mature trees, rolling lawns, hydrangeas and established gardens surround the residence, pool and spa, and multiple structures, creating a private waterfront setting just moments from the center of the Village. Expanded with architect Anthony Vermandois, the 2,670 +/-SF residence offers four bedrooms, five full baths and one-half bath, complemented by a separate 406 +/-SF studio and a 157 +/-SF pool house. A gracious covered front porch welcomes you into the home, where original wide-plank wood floors, period architectural details and seven working fireplaces lend warmth and a sense of history throughout. The main level is designed for both everyday living and entertaining. At its heart is a generous chef's kitchen centered around a large island and an extraordinary open-hearth fireplace. Premium appliances include a Wolf range, Sub-Zero refrigeration and Bosch dishwashers, with three dishwashers throughout the home's kitchen and entertaining spaces. A secondary kitchen and butler's pantry are fully equipped with an additional refrigerator, dishwasher, sink, oven and cooktop, ideal for entertaining. A separate bar, conveniently positioned near the formal dining area, creates a natural flow for gatherings. A sitting room, additional dining area and light-filled sunroom overlooking the gardens and water create inviting spaces for gathering and relaxing. A full bath, powder room and dedicated first-floor laundry complete the main level. Upstairs, the primary suite overlooks Otter Pond, with a spacious bedroom, spa-like bath and private outdoor terrace. A separate sitting area with its own fireplace offers an intimate place to relax while enjoying the surrounding landscape and water views. Two additional en-suite bedrooms, each with its own fireplace, provide beautifully appointed guest accommodations, while a fourth bedroom completes the second floor. A second washer and dryer adds convenience. Above, a walk-up attic provides substantial additional storage, while the 1,136 +/- SF unfinished lower level offers further flexibility. The grounds are as distinctive as the residence itself. Mature specimen trees, abundant hydrangeas, established gardens and flowering plantings frame rolling lawns, while walking paths meander through the nearly .60 +/- acre property toward the water. The result is a park-like setting that feels remarkably removed from the activity of the Village. A 15' x 40' heated gunite pool and spa is surrounded by expansive bluestone patios with generous areas for lounging, dining and entertaining. The 157 +/-SF pool house, featuring 12' ceilings and a full bathroom, is complemented by a 221 +/-SF lighted, vaulted roofed seating area, creating an inviting setting for covered outdoor dining and entertaining overlooking the pool and gardens. A separate 406 +/- SF legal three-room studio adds another dimension to the estate and is approved and permitted as a bedroom, living room, full bath and kitchenette-equipped accessory dwelling unit (ADU), offering flexible space or additional living accommodations separate from the main residence. Currently configured as a single-family residence, the property is also zoned for two-family use, offering additional flexibility for future ownership. Multiple structures and generous on-site parking further distinguish the property within its Village setting. For all its privacy, the estate remains seamlessly connected to Sag Harbor life with Village restaurants, boutiques, galleries, marinas, the Hampton Jitney and bay beaches all just moments away.

311 Main Street, Sag Harbor

2136 Deerfield Road, Sag Harbor
$5,495,000
8 Beds ⋅ 9 Baths ⋅ 1057392 MLS
4.3 Acre Gated Compound in Sag Harbor Property Highlights at a Glance Residence: 8,750 ± sq. ft. main home featuring 8 bedrooms and 8.5 bathrooms. Grounds: 4 private acres with a regal double-gated brick and cobblestone circular driveway. Outdoor Oasis: 3,000 sq. ft. travertine stone patio surrounding a heated gunite pool and attached spa. Pool Pavilion: 1,700 sq. ft. newly renovated pavilion with 20 ft. cedar ceilings, wrap-around covered stone patios, a custom built-in bar, and an outdoor fire pit. Lower Level & Extras: 3,000 sq. ft. finished basement with marble floors, a gym area, and a 2-car detached garage with a loft/art studio. Architectural Elegance & Interior Finishes Step through the double front doors into a grand, double-height entry framed by soaring two-story windows. The interior showcases exquisite craftsmanship, including Brazilian cherry wide-plank floors, 7 ft. doors, and 10 ft. ceilings throughout. The Chef's Kitchen: A true modern masterpiece featuring a center island with a waterfall countertop, exclusive Miele and Viking appliances, and an informal breakfast area under a 25 ft. octagonal-pitched ceiling. Living & Dining: An open-plan great room with a striking stone fireplace flows seamlessly into the formal dining room, which also features a cozy fireplace. Main-Level Master Retreat: Enjoy vaulted ceilings, a private sitting area, spacious his-and-hers closets, and a spa-like bathroom complete with stone floors, 20 ft. ceilings, double-stacked windows, a soaking tub, and a seamless glass steam shower. Upper Level & Guest Spaces: Five additional en-suite bedrooms, a dedicated media room with reclining chairs and a drop-ceiling projection screen, a first-level maid's suite, a private den, and a separate office. An A-List Entertaining Oasis Designed for ultimate privacy and high-end hosting, walls of French glass doors open to a breathtaking outdoor setting. Whether you are hosting an intimate gathering on the covered stone patios, mixing drinks at the custom back-pool bar, or gathering around the fire pit under the stars, this property defines the pinnacle of Hamptons luxury. Ready to experience this breathtaking Sag Harbor compound for yourself?

2136 Deerfield Road, Sag Harbor

956 Millstone Road, Sag Harbor
$5,495,000
6 Beds ⋅ 5 Baths ⋅ 1053019 MLS
Masterfully Renovated & Perfected Sag Harbor Sanctuary Exclusively Offered at $5,495,000 A rare opportunity to own a special Hamptons home designed for effortless indoor-outdoor living. In a resort caliber setting for entertaining or quiet enjoyment. You won’t want to miss this special home located in Sag Harbor, just moments from the pristine ocean and bay beaches. Set on just under 2 acres, this impeccably renovated 6-bedroom, 4.5 bath residence offers approximately 4,000+ sq. ft. of living space, with the luxury of a lushly landscaped and beautifully designed yard, Every detail has been thoughtfully created from the beautifully designed interior to the inviting outdoor living space with an oversized inground pool, an outside bar and very large outdoor deck, outdoor shower, fish pond, fire pit area, and much more. All furniture on the back deck will be included in the sale. Whether enjoyed as a full-time residence, an elegant weekend escape, or a premier luxury rental investment, this turnkey property offers exceptional lifestyle appeal and outstanding income potential. Just recently totally redone interior is move-in ready and impeccably finished, this exceptional home embodies the very best of Hamptons luxury living. House includes a 3 car garage with lots of extras, and a lower level (partially finished) with a wine cellar, a laundry with top of the line commercial washer and dryer and a pool table. Once you get here you will not want to leave. Don’t miss this one. It has it all!

956 Millstone Road, Sag Harbor

16 Stock Farm Lane, Sag Harbor
$2,800,000
5 Beds ⋅ 5 Baths ⋅ 1049226 MLS
Saltbox on Almost 2 Acres in Sag Harbor Private Stock Farm Lane property of 1.86 acres is ready for a new owner's landscape design dreams to be created here. There are beautiful large oak trees and lots of room for planting flower gardens. Room for a pool house or art studio. Allowable lot coverage is at 12,000 sq ft. The current 2,800 sq. ft. Saltbox style home can easily be expanded. There is a charming wood burning fireplace in living room and open kitchen with upscale appliances. A first floor primary suite and additional powder room for guests plus 2 car attached garage. The second level has 3 bedrooms and 2 baths. The lower level has a den plus 5th bedroom and full bath. There is still plenty of storage and a laundry room. New HVAC system, new Nitrogen Septic System being installed and generator ensures a comfortable environment all year-round. The home's amenities extend beyond the walls. A 40-feet pool invites you to relax and unwind. Located in a private community, this home offers water access for kayaks, perfect for those who love spending time in nature .North Haven Community Tennis is at the other end of the street. The location is unbeatable, just a stone's throw away from the Shelter Island Ferry and the vibrant Sag Harbor shops, marinas, and nightlife. This property is more than just a home; it's a lifestyle. Experience the blend of Hampton's Style, and comfort at 16 Stock Farm Lane.

16 Stock Farm Lane, Sag Harbor

16 Barclay Drive, Sag Harbor
$6,600,000
4 Beds ⋅ 4 Baths ⋅ 1030939 MLS
West Banks Waterfront Community North Haven Surrounded by the natural beauty and tranquility of West Banks, a private waterfront community in North Haven , 16 Barclay dr is a well appointed modern traditional residence. This gated enclave is a true boaters paradise featuring a deep water dock , a private beach and the most glorious westerly sunsets in all the Hampton's. Sited on 1.72+/- acres and surrounded by a 20 acre reserve, this property offers elegant style and sophistication. The desirable floor plan offers 4200 square feet of beautiful living spaces, and an additional 2050 square feet of a lower level with high ceiling heights, just waiting to be finished. Upon arrival, the coastal light cascades through the double height ceiling living room and wall of glass windows overlooking this lush property. The first level offers a wonderful flow with a large eat in kitchen, granite counters and center island, offsetting all the amenities for entertaining one would appreciate. A formal dining room , office or family room anchor the living area's. A first level private and spacious primary suite with walk-in large closets, and a luxurious bath with jacuzzi tub is a great addition. The second level's open landing divides two wings, offering an en-suite second primary bedroom and bath with a spacious walk in closet and additional unfinished area's that can be reimagined as a sitting room or extra living space. There are 2 additional bedrooms on the opposite wing with a shared Jack and Jill bath completing the second level. Numerous unfinished area's across this level just waiting to be expanded and customized. Mature plantings and beautiful landscaping create a park like setting surrounding the sparkling salt water gunite pool and lovely patio's for lounging and entertaining . A two car over sized attached garage also is a wonderful addition. This two-story traditional residence provides a serene and beautiful Hampton's retreat in a uniquely private and rare setting. The expansive acreage gives room for this residence to be substantially increased in sq footage with additional living area's if desired. A live in community caretaker is part of this wonderful offering, and conveniently available for concierge needs. Additionally, community tennis and a designated mooring for the boating enthusiast enhances this coastal experience. The natural beauty and tranquility of North Haven, also offers "Love Lady Park" a new addition to this area, with walking trails and gathering area's for all season enjoyment. This exceptional North Haven, Sag Harbor property and lifestyle, is just 10 minutes to the Historic Sag Harbor Whaling Village with coastal waterfront dining and marina's. The iconic Bay Street Theater features high profile entertainment and the Historic Whaling museum, are just a few local favorites. This sought-after private community and the residence at 16 Barclay Drive present an opportunity to own a substantial Hamptons residence in a World Class location!

16 Barclay Drive, Sag Harbor

36 Breezy Drive, Sag Harbor
$2,695,950
4 Beds ⋅ 3 Baths ⋅ 1032956 MLS
Discover turnkey Hamptons living at 36 Breezy Drive, a completely renovated four-bedroom, three-bath residence offering approximately 2,578 square feet on a private 0.56-acre parcel minutes from Sag Harbor Village and Long Beach. Reimagined from top to bottom, the light-filled interior balances modern refinement with relaxed coastal style. Wide-plank wood flooring, contemporary lighting, crisp millwork and a sophisticated neutral palette unify a flexible floor plan designed for effortless everyday living and entertaining. The newly renovated kitchen anchors the home with custom white cabinetry, marble countertops and backsplash, stainless-steel appliances, generous storage and an oversized center island with seating. It flows naturally into multiple dining and living areas, where expansive windows, French doors and a brick fireplace create an inviting atmosphere for intimate evenings or larger gatherings. All three bathrooms have been beautifully updated with contemporary vanities, glass-enclosed showers, large-format stone-look tile and modern fixtures. Four well-proportioned bedrooms include an expansive upper-level primary retreat with a sitting area, workspace and treetop views. First-floor bedrooms provide added flexibility for guests, extended family or a private office. A spacious screened porch extends the living area outdoors, offering an ideal setting for summer dining and lounging. Beyond it, a fenced garden terrace, mature landscaping and a broad lawn create exceptional privacy. The detached two-car garage includes valuable upper-level bonus space, while a separate outbuilding offers even greater versatility. Set within a peaceful cul-de-sac neighborhood yet convenient to Sag Harbor’s celebrated shops, restaurants, marinas and beaches, this fully renovated residence presents a rare combination of turnkey comfort, adaptable space and effortless Hamptons living.

36 Breezy Drive, Sag Harbor

1350 Brick Kiln Road, Sag Harbor
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 1030014 MLS
RARE SAG HARBOR VILLAGE PARCEL: 0.66 Acres | Pool Site | Expansion & New Build Opportunity Under $1.6M Uncover an exceptional opportunity in one of the East End’s most coveted historic enclaves. Ideally situated less than a half-mile from the heart of vibrant Sag Harbor Village, 1350 Brick Kiln Road offers a rare combination of location, parcel scale, and extraordinary upside potential for development. Set on an expansive, sun-drenched 0.6-acre lot, this home features a versatile layout with 3 full bedrooms and 3 full bathrooms, seamlessly blending historic Sag Harbor character with modern comfort. Enjoy a direct sidewalk stroll straight into town to experience world-class dining, boutique shopping, and deep-water marinas. Just around the corner, enjoy immediate proximity to community parks featuring renovated tennis courts, a playground, and pickleball courts. Key Highlights: Unmatched Development Potential: A rare 0.6-acre parcel in the village area offering remarkable room for expansion, custom redevelopment, or creating a high-end luxury compound featuring a private pool, pool house, and outdoor entertainment oasis. 3 Full Bedrooms & 3 Full Bathrooms: Spanning 1,307 sq. ft. across two levels, the home offers comfortable living quarters with a main-level full bath, central air conditioning, classic hardwood floors, and a dedicated home office space. Garage & Extra Storage: Includes a detached 2-car garage alongside a partial basement for additional utility and storage needs. Prime Location: Minutes to Havens Beach and Foster Memorial Town Beach, with effortless access to the Hampton Jitney and Bridgehampton LIRR. Whether you choose to move right in, customize the existing home, or capitalize on its prime development potential to construct your dream Hamptons estate, this property represents one of the strongest investment values near Sag Harbor Village.

1350 Brick Kiln Road, Sag Harbor

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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.