30 Chestnut Dr Orleans, MA $ 3,000,000
30 Chestnut Dr
$ 3,000,000
Recently Listed
Share Save

30 Chestnut Dr

Orleans, MA, 02653
$ 3,000,000
Bedrooms5 Baths3.1 Sq 3,677

Monthly Estimate*

$ 20,720

30 Chestnut Dr, Orleans, MA 02653 - Image 1
30 Chestnut Dr, Orleans, MA 02653 - Image 2
30 Chestnut Dr, Orleans, MA 02653 - Image 3
30 Chestnut Dr, Orleans, MA 02653 - Image 4
30 Chestnut Dr, Orleans, MA 02653 - Image 5
30 Chestnut Dr, Orleans, MA 02653 - Image 6
30 Chestnut Dr, Orleans, MA 02653 - Image 7
30 Chestnut Dr, Orleans, MA 02653 - Image 8
30 Chestnut Dr, Orleans, MA 02653 - Image 9
30 Chestnut Dr, Orleans, MA 02653 - Image 10
30 Chestnut Dr, Orleans, MA 02653 - Image 11
30 Chestnut Dr, Orleans, MA 02653 - Image 12
30 Chestnut Dr, Orleans, MA 02653 - Image 13
30 Chestnut Dr, Orleans, MA 02653 - Image 14
30 Chestnut Dr, Orleans, MA 02653 - Image 15
30 Chestnut Dr, Orleans, MA 02653 - Image 16
30 Chestnut Dr, Orleans, MA 02653 - Image 17
30 Chestnut Dr, Orleans, MA 02653 - Image 18
30 Chestnut Dr, Orleans, MA 02653 - Image 19
30 Chestnut Dr, Orleans, MA 02653 - Image 20
30 Chestnut Dr, Orleans, MA 02653 - Image 21
30 Chestnut Dr, Orleans, MA 02653 - Image 22
30 Chestnut Dr, Orleans, MA 02653 - Image 23
30 Chestnut Dr, Orleans, MA 02653 - Image 24
30 Chestnut Dr, Orleans, MA 02653 - Image 25
30 Chestnut Dr, Orleans, MA 02653 - Image 26
30 Chestnut Dr, Orleans, MA 02653 - Image 27
30 Chestnut Dr, Orleans, MA 02653 - Image 28
30 Chestnut Dr, Orleans, MA 02653 - Image 29
30 Chestnut Dr, Orleans, MA 02653 - Image 30
30 Chestnut Dr, Orleans, MA 02653 - Image 31
30 Chestnut Dr, Orleans, MA 02653 - Image 32
30 Chestnut Dr, Orleans, MA 02653 - Image 33
30 Chestnut Dr, Orleans, MA 02653 - Image 34
30 Chestnut Dr, Orleans, MA 02653 - Image 35
30 Chestnut Dr, Orleans, MA 02653 - Image 36
30 Chestnut Dr, Orleans, MA 02653 - Image 37
30 Chestnut Dr, Orleans, MA 02653 - Image 38
30 Chestnut Dr, Orleans, MA 02653 - Image 39
30 Chestnut Dr, Orleans, MA 02653 - Image 40
30 Chestnut Dr, Orleans, MA 02653 - Image 41
30 Chestnut Dr, Orleans, MA 02653 - Image 42
View a Virtual Tour

Single Family Home for sale in Orleans, MA

for $3,000,000 with 5 bedrooms and 3 full baths, 1 half bath. This 3,677 square foot home was built in 1998 on a lot size of 2.1.

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..

See more

Single Family Active

Price

$ 3,000,000

Bedrooms

5

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 12,324

Style

Cape

Lot Size

2.1

Year Built

1998

Town/City

Orleans

County/Region

Barnstable

MLS | Web ID

73587830

List By
Daneen Law

Listing Agent

Gibson Sotheby's International Realty

Broker

Affordability Calculator

$21,747
Per Month
95%
5%
0%
Monthly Principal & Interest
$20,720
Monthly Property Taxes
$1,027
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby

Neighborhood & Schools

MLS Property Information Network, Inc rules require that you sign in here to see more detail on this property.
Pricing History
DatePricePrice ChangeDescription
10/7/2026$3,000,000 Listed Price

Map


See all

30 Chestnut Dr, Orleans, MA, 02653 is a Single Family Home for sale at $3,000,000 with 3,677 sqft and a lot size of 2.1. 30 Chestnut Dr has 5 bedrooms, 3.1 baths, and was built in 1998. The property's zip code is 02653 which is in Orleans, MA