Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$5,850,000

15 Windy Hill Way, Chatham, MA 02633

5 Beds 5 Full Baths 1 Half Baths 5,620 Sq Ft 0.93 acres 2 Car Garage
MLS# 22601111 · Residential / (Single Family Residence)
Listed: 04/01/26 (listing data as of 07/30/26 at 3:05 pm)

About This Property

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

Property Details

Property TypeResidential
(Single Family Residence)
StatusActive
MLS Number22601111
Year Built2007
Annual Taxes$23,421 (2026)
Total Assessment$6,596,800
Square Footage5,620
Price/Sq Ft$1041/sq ft
Additional Finished Space1,106 sqft
Lot Size0.93 acres
Bedrooms5
Full Baths5
Half Baths1
RenovatedYes
Year Renovated2015
Heat Source Forced Air, Natural Gas
Add'l Heating Forced Air
Cooling A/C Central Air
Garage Spaces2
Days on Market120
WaterfrontNo
Private PoolYes
Private Pool Description Covered, In Ground, Vinyl
Miles to Beach.1 - .3
Fireplaces2
Lot Features Gentle Sloping, Interior Lot, Level, Sloped, Views

Bedroom Details

Primary Bedroom

  • Second Floor
  • Balcony
  • Closet
  • Wood Flooring
  • Private Full Bath
  • Recessed Lighting

Bedroom 2

  • Second Floor
  • Closet
  • Wood Flooring
  • Recessed Lighting

Bedroom 3

  • Second Floor
  • Closet
  • Wood Flooring
  • Recessed Lighting

Bedroom 4

  • Second Floor
  • Balcony
  • Closet
  • Wood Flooring
  • Private Full Bath
  • Recessed Lighting

Living Area Details

Living Room

  • First Floor
  • Gas Fireplace
  • Wood Flooring
  • Recessed Lighting

Dining Room

  • First Floor
  • Bay/Bow Windows
  • Wood Flooring
  • Recessed Lighting

Kitchen

  • Pantry
  • First Floor
  • Breakfast Nook
  • Built-Ins
  • Wood Flooring
  • Private Half Bath
  • Recessed Lighting

Appliances

  • Dishwasher
  • Electric Dryer
  • Gas Range
  • Range Hood
  • Refrigerator
  • Washer

Bedroom 5

  • Second Floor

Family Room

  • First Floor

Family Room

  • Basement

Laundry Room

  • Second Floor
  • Wood Flooring
  • Recessed Lighting

Convenient To

  • Golf Course
  • In Town Location
  • Major Highway
  • Marina
  • Medical Facility
  • Public Tennis
  • School
  • Shopping
  • Convenient to Stage Harbor
  • Convenient to Oyster Pond
  • Convenient to Nantucket Sound

Exterior Features

  • Hot Tub
  • Outdoor Shower
  • Private Yard
  • Underground Sprinkler System

Interior Features

  • Central Vacuum
  • Hot Tubs/Spa
  • HU Cable TV
  • Recessed Lighting
  • Walk-In Closet(s)

Location

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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.