Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,390,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,072 Sq. Ft.
  • 1.94 Acres
  • 2 Car Garage
  • Updated 1 day ago
See This Home
Save This Home
See This Home
Save This Home
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

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: 7/11/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Bathroom
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • 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, First
  • Bedroom 2: Second
  • Bedroom 3: Second
  • Bedroom 4: Basement

Other Rooms

  • Living Room: First
  • Family Room: First
  • Kitchen: First
  • Dining Room: First
  • Laundry: First Floor

Additional Information

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

Exterior

  • Exterior Features: Deck, Patio, Professional Landscaping
  • Color: Shingle

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 14
  • Parking Features: Under, 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: Ductless
  • Cooling Zones: 6
  • Heating Type: Baseboard, Natural Gas
  • Heating Fuel: Baseboard, Natural Gas
  • Heating Zones: 5

Utilities

  • Sewer: Private Sewer
  • Water: Public

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.: Potential to subdivide, buyer to do due diligence.
  • Property ID: 2260871
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 55 Winterset Dr —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

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.

Estimate the Cost for 55 Winterset Dr

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 55 Winterset Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

330 Champlain Rd, Chatham, MA 02633 - Photo 1 Just Listed
$2,199,000

330 Champlain Rd  Chatham, MA 02633

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,520
    Sq. Ft.
41 Court St, Chatham, MA 02650 - Photo 1
$2,295,000

41 Court St  Chatham, MA 02650

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 3,504
    Sq. Ft.
234 Round Cove Rd, Chatham, MA 02633 - Photo 1
$2,150,000

234 Round Cove Rd  Chatham, MA 02633

  • Single Family
  • Active
  • Updated 7 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,481
    Sq. Ft.
22 Winslow Dr, Orleans, MA 02653 - Photo 1
$2,150,000

22 Winslow Dr  Orleans, MA 02653

  • Single Family
  • Active
  • 5
    Beds
  • 5
    Total Baths
  • 4,091
    Sq. Ft.

Just Listed near 55 Winterset Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5 Rogers Way, Harwich, MA 02645 - Photo 1 Just Listed
$559,000
Open House

5 Rogers Way  Harwich, MA 02645

  • Single Family
  • Active
  • Updated 11 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,208
    Sq. Ft.
190 Belmont Rd, Harwich, MA 02645 - Photo 1 Just Listed
$1,295,000

190 Belmont Rd  Harwich, MA 02645

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,124
    Sq. Ft.
9 Bells Neck Rd, Harwich, MA 02671 - Photo 1 Just Listed
$290,000

9 Bells Neck Rd  #APT 5  Harwich, MA 02671

  • Condo
  • Active
  • Updated 4 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 460
    Sq. Ft.
216 Route 28, Harwich, MA 02645 - Photo 1 Just Listed
$2,000

216 Route 28  Harwich, MA 02645

  • Commercial Residential Facility
  • Active

Price Reduced near 55 Winterset Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1 Belmont Rd, Harwich, MA 02671 - Photo 1 Price Reduced
-$26,000 (-2.81%)
$899,000

1 Belmont Rd  #630  Harwich, MA 02671

  • Condo
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,860
    Sq. Ft.
22 Mandeville Rd, Harwich, MA 02671 - Photo 1 Price Reduced
-$10,000 (-1.19%)
$829,000

22 Mandeville Rd  Harwich, MA 02671

  • Single Family
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,134
    Sq. Ft.
8 Lakeway Ln, Harwich, MA 02645 - Photo 1 Price Reduced
-$20,100 (-2.18%)
$899,900

8 Lakeway Ln  Harwich, MA 02645

  • Single Family
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 2,118
    Sq. Ft.
13 Robert Ln, Harwich, MA 02671 - Photo 1 Price Reduced
-$45,000 (-5.66%)
$750,000

13 Robert Ln  Harwich, MA 02671

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,980
    Sq. Ft.

Recent Sales near 55 Winterset Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

55 Christopher Harding Ln, Chatham, MA 02633 - Photo 1 Sold
$2,150,000

55 Christopher Harding Ln  Chatham, MA 02633

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,510
    Sq. Ft.
101 Oyster Pond Furlong St, Chatham, MA 02633 - Photo 1 Sold
$2,650,000

101 Oyster Pond Furlong St  Chatham, MA 02633

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 2,057
    Sq. Ft.
8 Captains Walk, Chatham, MA 02650 - Photo 1 Sold
$2,595,000

8 Captains Walk  Chatham, MA 02650

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,479
    Sq. Ft.
8 Captains Walk, Chatham, MA 02633 - Photo 1 Sold
$2,595,000

8 Captains Walk  Chatham, MA 02633

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,479
    Sq. Ft.

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.

Tour this property