55 Winterset Dr Chatham, MA 02633
North Chatham NeighborhoodEstimated payment $13,601/month
Highlights
- Community Beach Access
- 1.94 Acre Lot
- Cathedral Ceiling
- Chatham Elementary School Rated A-
- Deck
- Wood Flooring
About This Home
Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private 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, 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. Home is being offered fully furnished if desired.
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,655
Year Built
- Built in 1970
Lot Details
- 1.94 Acre Lot
- Corner Lot
HOA Fees
- $6 Monthly HOA Fees
Parking
- 2 Car Garage
- Off-Street Parking
Home Design
- Shingle Roof
- Asphalt Roof
- Shingle Siding
Interior Spaces
- 4,066 Sq Ft Home
- 3-Story Property
- Central Vacuum
- Cathedral Ceiling
- 4 Fireplaces
- Finished Basement
- Basement Fills Entire Space Under The House
Flooring
- Wood
- Carpet
Bedrooms and Bathrooms
- 4 Bedrooms
Outdoor Features
- Deck
- Patio
Utilities
- Central Air
- Heating Available
- Well
- Water Heater
Listing and Financial Details
- Assessor Parcel Number CHAT M:0011G B:0074 L:H108-0
Community Details
Overview
- Great Hills Subdivision
Recreation
- Community Beach Access
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $5,180 | $1,492,700 | $359,400 | $1,133,300 |
| 2024 | $5,030 | $1,409,000 | $339,100 | $1,069,900 |
| 2023 | $4,566 | $1,176,800 | $296,100 | $880,700 |
| 2022 | $3,922 | $849,000 | $296,100 | $552,900 |
| 2021 | $3,779 | $758,800 | $255,700 | $503,100 |
| 2020 | $3,609 | $748,700 | $244,000 | $504,700 |
| 2019 | $3,528 | $727,400 | $216,100 | $511,300 |
| 2018 | $3,314 | $680,400 | $216,100 | $464,300 |
| 2017 | $3,323 | $660,700 | $209,700 | $451,000 |
| 2016 | $3,281 | $653,600 | $205,700 | $447,900 |
| 2015 | $3,223 | $645,800 | $210,900 | $434,900 |
| 2014 | $3,276 | $644,900 | $210,900 | $434,000 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/12/2026 07/12/26 | For Sale | $2,390,000 | +35.0% | $588 / Sq Ft | |
| 04/10/2023 04/10/23 | Sold | $1,770,000 | -1.4% | $435 / Sq Ft | View Prior Sale |
| 03/12/2023 03/12/23 | Pending | -- | -- | -- | |
| 03/10/2023 03/10/23 | For Sale | $1,795,000 | -- | $441 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | $1,770,000 | None Available | |
| Personal Reps Deed | -- | None Available | |
| Personal Reps Deed | -- | None Available | |
| Personal Reps Deed | -- | None Available | |
| Deed | $955,000 | -- | |
| Deed | $260,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $1,416,000 | New Conventional | |
| Previous Owner | $400,000 | Credit Line Revolving | |
| Previous Owner | $750,000 | No Value Available | |
| Closed | $400,000 | No Value Available |
Source: Cape Cod & Islands Association of REALTORS®
MLS Number: 22603375
APN: CHAT-000011G-000074-H000108
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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. includes 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. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026 © Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
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