Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$5,950,000

179 Pineleigh Path, Osterville, MA 02655

5 Beds 5 Full Baths 3 Half Baths 8,740 Sq Ft 1.00 acres 3 Car Garage
MLS# 22602488 · Residential / (Single Family Residence)
Listed: 05/27/26 (listing data as of 07/30/26 at 3:57 pm)

About This Property

Set on the 14th fairway of the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. Thoughtfully designed living spaces feature soaring ceilings and a striking double-sided stone fireplace that creates a warm focal point between gathering areas. The kitchen is tailored for both everyday living and entertaining, offering professional-grade appliances, expansive stone countertops, and a custom mahogany butler's pantry that provides additional prep and serving space. A secluded primary suite enjoys its own dedicated wing on the first floor, complete with a luxurious bathroom, two walk-in closets, and French doors that open to a private patio overlooking the swimming pool and gardens. Outdoor amenities take full advantage of the private setting, with multiple covered porches and a heated Gunite pool with limestone surround, all positioned to capture views of the golf course.

Property Details

Property TypeResidential
(Single Family Residence)
StatusActive
MLS Number22602488
Year Built2006
Annual Taxes$37,014 (2026)
Total Assessment$5,443,300
Square Footage8,740
Price/Sq Ft$681/sq ft
Lot Size1.00 acres
Bedrooms5
Full Baths5
Half Baths3
Heat Source Forced Air, Propane
Add'l Heating Forced Air
Cooling A/C Central Air
Association Fee $4,620.00 (Annually)
Association Fee Includes Landscaping, Road Maintenance, Security
Garage Spaces3
Days on Market64
WaterfrontNo
Private PoolYes
Private Pool Description Gunite, Heated, In Ground
Miles to Beach.1 - .3
Fireplaces4
Lot Features Fenced/Enclosed, Golf Course Frontage, Level, Views, Wooded

Bedroom Details

Primary Bedroom

  • First Floor
  • Cathedral Ceiling
  • Office/Sitting Area
  • Private Full Bath
  • View
  • Walk-in Closet

Living Area Details

Kitchen

  • Pantry
  • Beamed Ceilings
  • Breakfast Bar
  • Built-Ins
  • Recessed Lighting
  • Upgraded Cabinets

Appliances

  • Dishwasher
  • Disposal
  • Freezer
  • Gas Range
  • Microwave
  • Range Hood
  • Refrigerator
  • Security System

Convenient To

  • Golf Course
  • House of Worship
  • Marina
  • School
  • Shopping
  • Convenient to Nantucket Sound
  • Convenient to Cotuit Bay
  • Convenient to West Bay

Exterior Features

  • Hot Tub
  • Private Yard
  • Underground Sprinkler System

Location

Nearby Listings

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Listing Courtesy of: Paul E Grover / Berkshire Hathaway HomeServices Robert Paul Properties
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 07/30/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.