680 Falmouth Rd.
Rte. 28 Mashpee, MA 02649

Phone:

508-989-1943


$6,250,000
15 Windy Hill Way
Chatham, MA 02633
MLS# 22601111
5 beds  |  6 baths  |  5620 sqft


IMG_6805-2-Edit
  1 / 90  
IMG_6805-2-Edit IMG_6921-2-Edit IMG_6802-2-Edit IMG_6924-2-Edit-Edit IMG_6919-2-Edit IMG_6839-2-Edit IMG_6840-2-Edit IMG_6809-2-Edit IMG_6818-2-Edit IMG_6811-2-Edit IMG_6820-2-Edit IMG_6518-Edit IMG_6525-Edit IMG_6507-Edit IMG_6504-Edit IMG_6513-Edit IMG_6536-Edit IMG_6542-Edit IMG_6548-Edit IMG_6630-Edit IMG_6587-Edit IMG_6572-Edit IMG_6594-Edit IMG_6601-Edit IMG_6604-Edit IMG_6775-Edit IMG_6619-Edit IMG_6625-Edit IMG_6612-Edit IMG_6614-Edit IMG_6617-Edit IMG_6770-Edit IMG_6635-Edit IMG_6947-Edit IMG_6940-Edit IMG_6956-Edit IMG_6740-Edit IMG_6964-Edit IMG_6763-Edit IMG_6962-Edit IMG_0593 IMG_0591 IMG_6755-Edit IMG_6720-Edit IMG_6725-Edit IMG_6679-Edit IMG_6687-Edit IMG_6690-Edit IMG_6657-Edit IMG_6662-Edit IMG_6668-Edit IMG_6991-Edit IMG_6970-Edit IMG_6986-Edit IMG_6718-Edit IMG_6767-Edit IMG_6769-Edit IMG_6780-Edit IMG_6784-Edit IMG_6788-Edit IMG_6799-2-Edit IMG_6827-2-Edit IMG_6822-2-Edit IMG_6844-2-Edit IMG_0590 IMG_6841-2-Edit IMG_6842-2-Edit IMG_6897-2-Edit IMG_6894-2-Edit IMG_6927-2-Edit IMG_6905-2-Edit IMG_6911-2-Edit IMG_6901-2-Edit IMG_6914-2-Edit IMG_7009-Edit IMG_7003-Edit IMG_7001-Edit-3 IMG_7005-Edit IMG_7007-Edit IMG_0578 IMG_0579 IMG_0581 IMG_0583 Photo_6553685_DJI_85_jpg_4251764_0_20255 Windy Hill2 15 Windy Hill1 Photo_6553690_DJI_90_jpg_4968841_0_20255 Project 293 - Ground Floor Project 293 - 2nd Floor Project 293 - Basement • Level 1

Property Description
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.

Details
Maps
Documents
Contract Info
List Price/SqFt: 1112.1
Status: Active
Original List Price: 6250000
List Price: $6,250,000
Current Price: $6,250,000
List Date: 2026-04-01
Legal and Taxes
Town: Chatham
Village: Chatham
Estimated Annual Taxes: 23421
Building Assessments: 5070200
Other Assessments: 55700
Total Assessment: 6596800
Land Court Cert #: (178561)
Underground Fuel Tank: No
Flood Ins Required: No
Lead Base Paint: No
Asbestos: No
Mass Use Code: 101 - Residential, single family
Nitrogen Sensitive Area: Yes
Street #: 15
Street Name: Windy Hill
Street Suffix: Way
County: Barnstable
State: MA
Zip Code: 02633
Tax ID: CHAT M:12A B:004B L:C8
Tax Year: 2026
General Property Info
Region: Lower Cape
School District: Monomoy
Zoning: R40
Property Sub-Type: Single Family Residence
Renovated: Yes
Year Renovated: 2015
Renovated Comments: Finished Basement. New Furnace 2025
Stories: 2
Total Rooms: 13
Field Card SqFt: 4514
Additional Finished Space: 1106
Additional SqFt Source: Public Records
Basement: Yes
Baths - Half: 1
Private Dock: No
Private Pool: Yes
Lot Size SqFt: 40473
Leased Land: No
Lot Size Source: Assessor
Acres: 0.93
Garage: Yes
# of Cars: 2
# of Parking Spaces: 5
Year Round: Yes
Golf Course Front: No
Golf Course View: No
Waterfront: No
Waterview: No
Miles to Beach: .1 - .3
Mi. to Beach Comments: Private access to Stage Harbor
Fireplace: Yes
# Fireplaces: 2
Warranty Available: No
Property Includes Recording Devices: No
Year Built: 2007
Total Finished Space: 5620
Bedrooms - Total: 5
Baths - Full: 5
Baths - Total: 6
Remarks & Misc
Public Remarks: 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.
Directions to Property: Stage Harbor Road to Champlain Road to Windy Hill Way #15.
Street Description
Paved: 1
Private: 1
Special Listing Cond
None: 1
Lot Features
Gentle Sloping: 1
Interior Lot: 1
Level: 1
Sloped: 1
Views: 1
Year Built Desc
Actual: 1
Basement Description
Finished: 1
Full: 1
Garage Access: 1
Interior Access: 1
Walk-Out Access: 1
Parking Features
Driveway: 1
Gravel: 1
Architectural Style
Cape Cod: 1
Shingle: 1
Garage Description
Attached: 1
Direct Access: 1
Garage Door Opener: 1
Baths Per Level
Basement Baths: 1
Baths - Level 1: 1
Baths - Level 2: 4
Neighborhood Amen
Beach Access: 1
Deeded Beach Rights: 1
Foundation Details
Poured: 1
Convenient To
Golf Course: 1
In Town Location: 1
Major Highway: 1
Marina: 1
Medical Facility: 1
Public Tennis: 1
School: 1
Shopping: 1
Convenient to Water Body 1: Stage Harbor
Convenient to Water Body 2: Oyster Pond
Convenient to Water Body 3: Nantucket Sound
Floors
Carpet: 1
Tile: 1
Wood: 1
Sewer
Septic Tank: Title V Grade Level
Fencing
Partial: 1
Roof Description
Pitched: 1
Wood: 1
Siding Description
Shingle: 1
Primary Bedroom
Primary Bedroom: 1
Primary Bedroom Level: Second Floor
Balcony: 1
Closet: 1
Flooring: Wood
Private Full Bath: 1
Recessed Lighting: 1
Heating
Forced Air: 1
Bedroom 2
Bedroom 2: 1
Bedroom 2 Level: Second Floor
Closet: 1
Flooring: Wood
Recessed Lighting: 1
Cooling
Central Air: 1
Bedroom 3
Bedroom 3: 1
Bedroom 3 Level: Second Floor
Closet: 1
Flooring: Wood
Recessed Lighting: 1
Fuel Type
Natural Gas: 1
Bedroom 4
Bedroom 4: 1
Bedroom 4 Level: Second Floor
Balcony: 1
Closet: 1
Flooring: Wood
Private Full Bath: 1
Recessed Lighting: 1
Water
Public: 1
Hot Water
Water Heater: 1
Foyer
Foyer: 1
Foyer Level: First Floor
Flooring: Wood
Recessed Lighting: 1
Hot Water Source
Electric: 1
Laundry Room
Laundry Room: 1
Laundry Room Level: Second Floor
Flooring: Wood
Recessed Lighting: 1
Living Room
Living Room: 1
Living Room Level: First Floor
Fireplace: Gas
Flooring: Wood
Recessed Lighting: 1
Dining Room
Dining Room: 1
Dining Room Level: First Floor
Bay/Bow Windows: 1
Flooring: Wood
Recessed Lighting: 1
Kitchen
Pantry: 1
Kitchen: 1
Kitchen Level: First Floor
Breakfast Nook: 1
Built-Ins: 1
Countertops: Granite
Flooring: Wood
Kitchen Island: 1
Private Half Bath: 1
Recessed Lighting: 1
Other Structures
Pool House: 1
Other Room 1
Room Type: Bedroom 5
Level: Second Floor
Exterior Features
Hot Tub: 1
Outdoor Shower: 1
Private Yard: 1
Underground Sprinkler System: 1
Other Room 2
Room Type: Family Room
Level: First Floor
Other Room 3
Room Type: Family Room
Level: Basement
Other Room 4
Room Type: Home Office
Level: Second Floor
Appliances
Dishwasher: 1
Electric Dryer: 1
Gas Range: 1
Range Hood: 1
Refrigerator: 1
Washer: 1
Interior Features
Central Vacuum: 1
Hot Tubs/Spa: 1
HU Cable TV: 1
Recessed Lighting: 1
Walk-In Closet(s): 1
Patio And Porch Features
Deck: 1
Patio: 1
Porch: 1
Private Pool Description
Covered: 1
In Ground: 1
Vinyl: 1
DPR Eligibility
DPR Eligible: No
Property Features
Street Description: Paved; Private
Special Listing Cond: None
Architectural Style: Cape Cod; Shingle
Year Built Desc: Actual
Basement Description: Finished; Full; Garage Access; Interior Access; Walk-Out Access
Foundation Details: Poured
Lot Features: Gentle Sloping; Interior Lot; Level; Sloped; Views
Neighborhood Amen: Beach Access; Deeded Beach Rights
Garage Description: Attached; Direct Access; Garage Door Opener
Parking Features: Driveway; Gravel
Convenient To: Golf Course; In Town Location; Major Highway; Marina; Medical Facility; Public Tennis; School; Shopping
Primary Bedroom: Primary Bedroom; Balcony; Closet; Private Full Bath; Recessed Lighting
Bedroom 2: Bedroom 2; Closet; Recessed Lighting
Bedroom 3: Bedroom 3; Closet; Recessed Lighting
Bedroom 4: Bedroom 4; Balcony; Closet; Private Full Bath; Recessed Lighting
Foyer: Foyer; Recessed Lighting
Laundry Room: Laundry Room; Recessed Lighting
Living Room: Living Room; Recessed Lighting
Dining Room: Dining Room; Bay/Bow Windows; Recessed Lighting
Kitchen: Kitchen; Breakfast Nook; Built-Ins; Kitchen Island; Pantry; Private Half Bath; Recessed Lighting
Appliances: Dishwasher; Electric Dryer; Gas Range; Range Hood; Refrigerator; Washer
Floors: Carpet; Tile; Wood
Interior Features: Central Vacuum; Hot Tubs/Spa; HU Cable TV; Recessed Lighting; Walk-In Closet(s)
Patio And Porch Features: Deck; Patio; Porch
Private Pool Description: Covered; In Ground; Vinyl
Other Structures: Pool House
Exterior Features: Hot Tub; Outdoor Shower; Private Yard; Underground Sprinkler System
Fencing: Partial
Roof Description: Pitched; Wood
Siding Description: Shingle
Heating: Forced Air
Cooling: Central Air
Fuel Type: Natural Gas
Water: Public
Hot Water: Water Heater
Hot Water Source: Electric

IDX
Listing Office: John C Ricotta & Assoc.
Listing Agent: Timothy P Bailey

Last Updated: April - 08 - 2026

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS, Inc include the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS, Inc shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 02/14/2017. All properties are subject to prior sale, changes, or withdrawal. Copyright 2020© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved