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$2,390,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,072 Sq. Ft.
  • 1.94 Acres
  • 2 Car Garage
  • Updated 5 days ago
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Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

Full Property Details for 55 Winterset Dr

General

  • Price: $2,390,000
  • HOA FEE: $6/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,655 (2026)
  • Status: Active
  • Type: Single Family
  • Source: MLSPin
  • MLS ID: 73548377
  • Updated: 8/22/2026
  • Added to Site: 48 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Bathroom
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Fireplace(s): Family Room, Living Room, Bedroom
  • Appliances: Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
  • Flooring: Tile, Carpet, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Main - Full Baths: 3
  • Main - 1/2 Baths: 1
  • Bathroom 1: First
  • Bathroom 2: First
  • Bathroom 3: Second

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Yes, Main, First
  • Bedroom 2: Walk-In Closet(s), Closet, Wall-to-Wall Carpet, Second
  • Bedroom 3: Closet, Wall-to-Wall Carpet, Second
  • Bedroom 4: Closet, Wall-to-Wall Carpet, Basement

Other Rooms

  • Living Room: Cathedral Ceiling(s), Ceiling Fan(s), Beamed Ceilings, Hardwood Flooring, French Doors, Exterior Deck, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled, Main, First
  • Family Room: Cathedral Ceiling(s), Beamed Ceilings, Hardwood Flooring, Picture Window(s), Balcony/Deck, French Doors, Exterior Deck, Exterior Access, Open Floorplan, Recessed Lighting, First
  • Kitchen: Hardwood Flooring, Picture Window(s), Stone/Granite/Solid Countertops, Kitchen Island, Exterior Deck, Exterior Access, Open Floorplan, Recessed Lighting, First
  • Dining Room: Hardwood Flooring, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Sconce, Main, First
  • Laundry: First Floor, Gas Dryer Hookup

Additional Information

  • Year Round: Yes
  • Security/Safety: Security System

Exterior

  • Exterior Features: Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
  • Color: Shingle

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 14
  • Parking Features: Attached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street

Location

  • County: Barnstable
  • Subdivision: Great Hill
  • Driving Directions: Old Queen Anne Road to Winterset Drive, house located at the end on the left.

School Information

  • Elementary School: Chatham
  • Middle School: Chatham
  • High School: Monomoy

Community

  • Association: Yes

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ductless
  • Cooling Zones: 6
  • Heating Type: Baseboard, Natural Gas
  • Heating Fuel: Baseboard, Natural Gas
  • Heating Zones: 5

Utilities

  • Sewer: Private Sewer
  • Water: Public
  • Utility Description: Connection for Gas Range, Connection for Gas Dryer, Outdoor Gas Grill Hookup

Structural Information

  • Architectural Style: Cape, Contemporary
  • Exterior Const.: Frame
  • Basement: Yes
  • Basement Desc.: Full, Finished, Walk-Out Access, Interior Entry, Garage Access
  • Roof: Shingle
  • Drive-In Doors: Insulated Doors, French Doors
  • Square Feet: 4,072
  • Sq. Ft. Source: Public Records
  • Year Built: 1970

Lot Features

  • Lot Size (Acres): 1.94
  • Lot Dimensions: 1.94
  • Frontage: Public
  • Lot Features: Corner Lot

Water Features

  • Water Front Desc.: Lake/Pond, 0 to 1/10 Mile To Beach, Beach Ownership(Private)

Financial Considerations

  • Price Per Sq. Ft.: $586.94
  • Association Fee: $75
  • Assoc Fee Freq.: Annually
  • Tax Amount: $5,655
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: Home is being offered fully furnished if buyer preference.
  • Property ID: 2260871
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 55 Winterset Dr —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 55 Winterset Dr

School District:Monomoy Regional School District
NameGradesDistance
Chatham Elementary School
147 Depot Road, Chatham, MA 02633
PK-41 mi
Monomoy Regional Middle School
425 Crowell Road, Chatham, MA 02633
5-71.4 mi
Monomoy Regional High School
75 Oak Street, Harwich, MA 02645
8-124.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 55 Winterset Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/11/2026
Listed
$2,390,000
35.03%
MLS
4/09/2023
Sold
$1,770,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 55 Winterset Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,180
3%
$1,492,700
6%
2024
$5,030
10%
$1,409,000
20%
2023
$4,566
16%
$1,176,800
39%
2022
$3,922
4%
$849,000
12%
2021
$3,779
5%
$758,800
1%
2020
$3,609
9%
$748,700
10%
2018
$3,314
—
$680,400
3%
2017
$3,323
1%
$660,700
1%
2016
$3,281
2%
$653,600
1%
2015
$3,223
-2%
$645,800
—
2014
$3,276
—
$644,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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55 Winterset Drive, Chatham, MA 02633 (MLS# 73548377) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 55 Winterset Drive is currently listed for $2,390,000 and was received on July 11, 2026. This property is listed by Janet Stuart from our Concord Office.Want to learn more about 55 Winterset Drive? Do you have questions about finding other Single Family real estate for sale in Chatham? You can browse all Chatham real estate or contact a Coldwell Banker agent to request more information.

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