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Single family home for sale at 30 Chestnut Dr, Orleans, MA 02653 | MLS# 73587830 | Listing updated on 2026-10-08
Photo 1 of Single family home for sale at 30 Chestnut Dr, Orleans, MA 02653 | MLS# 73587830 | Listing updated on 2026-10-08
Photo 2 of Single family home for sale at 30 Chestnut Dr, Orleans, MA 02653 | MLS# 73587830 | Listing updated on 2026-10-08
Photo 3 of Single family home for sale at 30 Chestnut Dr, Orleans, MA 02653 | MLS# 73587830 | Listing updated on 2026-10-08
Photo 4 of Single family home for sale at 30 Chestnut Dr, Orleans, MA 02653 | MLS# 73587830 | Listing updated on 2026-10-08
38+
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Street View

$3,000,000

Monthly Est:$14,932

  • Beds Icon5 Beds
  • Beds Icon
    4 Baths
  • Beds Icon3,677sqft

30 Chestnut Dr, Orleans, MA 02653

$14,932/moEst:

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  • Single Family Residence

  • Built in 1998

  • $-- HOA

  • 2.1 acres lot

  • $816/sq.ft

Description

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..

  • Houzeo last checked: 4 minutes ago
  • Listing updated: October 8, 2026 at 3:17 pm
  • Listing Provided by: Daneen Law (508) 237-0977 | Gibson Sotheby's International Realty (508) 255-6000
  • Source: MLS Property Information Network-MA | MLS#: 73587830 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Barnstable County

  • City

    Orleans

  • Neighborhood

    --

  • Year Built

    1998

  • HOA Fees

    -

  • Finished Area

    3,677 sqft

  • Lot Size

    2.1 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73587830

  • MLS Status

    New

  • Days on Market

    1

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 4

Interior

  • Sewer

    Private Sewer

  • Cooling

    Central Air

  • Heating

    Baseboard, Oil

Construction

  • Year Built

    Year Built: 1998

  • Home type

    Single Family Residence

  • Architectural Style

    Cape

  • Foundation Details

    Concrete Perimeter

Utilities & Energy

  • Water Source

    Private

  • Parking Features

    Attached, Garage Door Opener

  • Basement

    Full

Other Features

  • Lot Features

    Cleared, Level

Price History

DateEventPrice

10/07/2026

Source: mls_logoCape Cod And Islands MLS-MA #22605085

Listed for Sale

$3,000,000 +200.30%

$816/sqft

09/16/2010

Source: mls_logoCape Cod And Islands MLS-MA #20907184

Listing Removed

$999,000

$272/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 08, 2026, 06:30PM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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