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Tucked away on a tranquil, tree-lined lot in East Hampton’s coveted Northwest Woods, 44 Diane Drive offers a seamless blend of contemporary design and effortless indoor-outdoor living. Spanning 2,500 sq. ft., this light-filled 4-bedroom, 2.5-bathroom residence features soaring double-height ceilings, expansive glass windows, and open-concept living spaces centered around dual living areas and a cozy fireplace.
The modern chef’s kitchen flows directly into the dining and living spaces, creating an inviting layout for entertaining. Outdoors, a private backyard sanctuary awaits, complete with a heated pool, expansive sun deck, and mature landscaping.
Ideally located just minutes from East Hampton Village, Sag Harbor, harbor beaches, and local dining, this exceptional property is offered for flexible rental terms:
Year-Round Lease
Winter / Off-Season Rental
Summer 2027
Key Details:
Layout: 4 Bedrooms | 2.5 Bathrooms | 2,500 SF
Amenities: Heated Pool, Expansive Decking, Fireplace, Central Air
Location: Northwest Woods | Close to Villages & Harbor Beaches
Pricing, term details, or to arrange a private showing.
| Listed | August 31, 2026 |
| Days on Market | 2 |
| Last Updated | September 1, 2026 |
Full public sale/price history isn't available through our listing feed for this property.
Estimated effective monthly cost including any move-in incentives shown above. Use our Net Effective Rent Calculator for a full breakdown on this $8,000/mo rental.
Closed-sale data isn't available through our current listing feed for this neighborhood.




