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Land with Home for Sale in Orleans, Massachusetts

30 Chestnut Dr, Orleans, MA 02653

$3,000,000
2.1 acres
Active sale
ago
Est $17,481/mo

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..

3,677
Sq feet
5
Beds
3
Full baths
1
1/2 bath
1998
Built

Location

Street address
30 Chestnut Dr
Zip code
02653
Community
Orleans
School district
Nauset
Elevation
26 feet
Coordinates
41.766, -69.9566

Directions

Main Street to Barley Neck Road to Nichols Road to Chestnut Drive. GPS may take your down Old Field so you may want to follow these directions

Property details

Acreage
2.1 acres
Zoning
R
MLS #
CCIAOR 22605085
Posted

Property taxes

2026
$12,324

Parcels

  • ORLE M:57 B: L:48-0

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Exterior

Parking
Open
Pool
Patio, Porch
Structures
Outbuilding
Features
Outdoor Shower, Private Yard

Structure

Style
Cape Cod
Stories
2
Basement
Full
Water
Well
Sewer
Septic Tank
Heating
Oil
Cooling
Central Air
Materials
Shingle Siding
Roof
Asphalt

Interior

Room Count
7
Rooms
Basement, Bathroom x 4, Bedroom x 5
Flooring
Tile, Wood
Fireplaces
Yes
Appliances
Water Heater

Listing history

DateEventPriceChangeSource
Oct 7, 2026New listing$3,000,000—CCIAOR
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This 2.1-acre property is located at 30 Chestnut Dr in Orleans, MA 02653. The property is available for sale, priced at $3,000,000. It has a 3,677 square foot 5-bedroom, 3.5-bath house built in 1998.

Listed by Gibson Sotheby's International Realty, (508) 896-5000

Checked 2 hours agoUpdated Source

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