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30 Chestnut Drive
Orleans MA 02653 US

$3,000,000

Active Listing ID 22605085
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5 bed
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3,677 square feet
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4.00 Bath (3 Full , 1 Half)
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Lot: 2.10 Acres
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Single Family Residence

$3,000,000

Active Listing ID 22605085
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30 Chestnut Drive 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..

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Property Features

  • Facts
  • Lot Size: 2.10 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Private Yard, Outdoor Shower
  • Floor Covering: Tile, Wood
  • Roof Type: Asphalt
  • Heating Fuels: Oil
  • Additional Features
  • Basement
  • Fireplace
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 3000000
  • unparsedaddress: 30 Chestnut Drive
  • postalcity: Orleans
  • stateorprovince: MA
  • country: US
  • postalcode: 02653
  • bathroomsfull: 3
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 2.1
  • lotsizeunits: Acres
  • lotsizearea: 2.1
  • livingarea: 3677
  • livingareaunits: Square Feet
  • latitude: 41.765966
  • longitude: -69.956587
  • listagentfullname: Daneen Law
  • listagentemail: daneen.law@gibsonsir.com
  • listagentkey: 3yd-CCIAORMA-U2064
  • listagentmlsid: U2064
  • listagentpreferredphone: 5082370977
  • listagentofficephone: 5082370977
  • listofficekey: 3yd-CCIAORMA-GSIR1
  • listofficemlsid: GSIR1
  • disclaimer: Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CCIAORMA
  • yearbuilt: 1998
  • listingcontractdate: 2026-10-07
  • countyorparish: Barnstable
  • parcelnumber: ORLE M:57 B: L:48-0
  • elementaryschooldistrict: Nauset
  • middleorjuniorschooldistrict: Nauset
  • highschooldistrict: Nauset
  • appliances: Water Heater
  • cooling: Central Air
  • constructionmaterials: Shingle Siding
  • flooring: Tile, Wood
  • heating: Oil
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Open
  • roof: Asphalt
  • waterfrontyn: False
  • franchiseaffiliation: None
  • exteriorfeatures: Private Yard, Outdoor Shower
  • architecturalstyle: Cape Cod
  • rooms: Basement, Bathroom 4, Bathroom 2, Bedroom 5, Bedroom 1, Bathroom 3, Bedroom 3, Bedroom 4, Bathroom 1, Bedroom 2
  • otherstructures: Outbuilding
  • patioandporchfeatures: Porch, Patio
  • basement: Full
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -69.95659, 41.765965
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Gibson Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"daneen.law@gibsonsir.com", "ListBrokerageCity":"Brewster", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Gibson Sotheby's International Realty", "ListBrokeragePhone":"(508) 896-5000", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"MA", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"2404 Main Street", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"6 Route 6A ", "ListOfficeAddress2":"", "ListOfficeBrokerMlsId":"GSIR1", "ListOfficeCity":"Orleans", "ListOfficeCountry":"US", "ListOfficeEmail":null, "ListOfficePostalCode":"02653", "ListOfficeStateOrProvince":"MA", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, Orleans, MA", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/30-Chestnut-Dr_Orleans_MA_02653_M32203-76696?f=listhub&s=CCIAORMA&m=22605085&c=rexren", "MLSModificationTimestamp":"2026-10-08 15:16:54", "Neighborhoods":[{"Description":null, "Name":"Orleans"}], "PostalCode":null, "RoomCount":7, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":12324, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/8/2026 5:34:31 PM GMT
Source Updated Date: 10/11/2026 12:52:36 AM GMT

Courtesy of: Daneen Law, Gibson Sotheby's International Realty, daneen.law@gibsonsir.com

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.