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Set on two private acres in one of East Orleans' most coveted Barley Neck neighborhoods, 30 Chestnut Road is an exceptional Cape Cod retreat where refined interiors, resort-style outdoor living, and deeded beach access come together beautifully. Designed for both effortless everyday living and memorable gatherings, the home features four bedrooms and 3.5 baths, including a luxurious first-floor primary suite. The open-concept floor plan is anchored by a beautifully appointed kitchen with a generous center island, high-end appliances, and a butler's pantry. The adjoining living room, with custom built-ins, a charming window seat, and wood-burning fireplace, offers a warm and inviting place to gather, while the four-season sunroom brings the outdoors in throughout the year. A spacious bonus room above the garage provides wonderful flexibility for overflow guests, a home office, or additional recreation space. Outside, the property is truly extraordinary. The pool area feels like a five-star private oasis, surrounded by mature landscaping and generous space for lounging, dining, and entertaining. A private path leads to the neighborhood's deeded beach, making days on the water an effortless part of life here. Adding even more possibility is a separate cottage with electricity and a full foundation, offering exciting potential for conversion to an accessory dwelling unit, subject to Town approvals. Private yet close to the beaches, boating, and village amenities that make East Orleans so special, 30 Chestnut Road offers the space, setting, amenities, and lifestyle today's discerning buyers seek. This is Cape Cod living at its finest..

More Info

Basic Information

  • Bedrooms4
  • Mls StatusNew
  • Bathroom4
  • Lot Features Cleared, Level
  • Parcel Number M:0057 B:0000 L:00480,2364643

Tax Information

  • Tax Assessed Value $2,017,100
  • Tax Year 2026
  • Taxes$12,324

Parking

  • Parking Spaces12
  • Covered Spaces 2
  • Garage YN Yes
  • Parking Features Attached, Garage Door Opener

Rooms

  • Bathrooms Total Decimal 3.5
  • Full Bath3
  • Half Baths1

Basic Information

  • List Price$3,000,000
  • MLS Number73587830
  • Modification Date10/07/2026
  • Property SubTypeSingle Family Residence

Location

  • Address30 Chestnut Drive
  • Building Number30
  • CountyBarnstable
  • StateMA
  • StreetChestnut Drive
  • TownOrleans
  • Zip02653

Building

  • Attached Garage YN Yes
  • BasementFull
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 1
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Property StyleCape
  • Rooms7
  • Year Built1998
  • Year Built Details Actual
  • Year Built Source Public Records

Property

  • Acreage2.1

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Baseboard, Oil
  • Sewer Private Sewer
  • Water Source Private

Property Information

  • Square Feet3,677
  • Building Area Source Public Records
  • Living Area 3,677
  • Lot Size Square Feet 91,345
  • Lot Size Units Acres

Water Body

  • Miles to Beach0.3
  • Waterfront Features 1/10 to 3/10 To Beach

Other

  • Date Listed10/07/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Daneen Law of Gibson Sotheby's International Realty

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