55 Winterset Dr Chatham, MA 02633
North Chatham NeighborhoodEstimated payment $12,840/month
Total Views
21,320
4
Beds
3.5
Baths
4,072
Sq Ft
$564
Price per Sq Ft
Highlights
- Property is near a marina
- 1.94 Acre Lot
- Cathedral Ceiling
- Chatham Elementary School Rated A-
- Deck
- Wood Flooring
About This Home
Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,179
Year Built
- Built in 1970 | Remodeled
Lot Details
- 1.94 Acre Lot
- Near Conservation Area
- Fenced
- Cleared Lot
- Garden
- Property is zoned R60
Parking
- 2 Car Attached Garage
- Basement Garage
- Open Parking
Home Design
- Flat Roof Shape
- Block Foundation
- Slab Foundation
- Pitched Roof
- Asphalt Roof
- Shingle Siding
Interior Spaces
- 4,072 Sq Ft Home
- 2-Story Property
- Beamed Ceilings
- Cathedral Ceiling
- 4 Fireplaces
- Wood Burning Fireplace
- Bay Window
- French Doors
- Mud Room
- Dining Room
Kitchen
- Gas Range
- Microwave
- Dishwasher
- Kitchen Island
Flooring
- Wood
- Carpet
- Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- Primary Bedroom on Main
- Cedar Closet
- Linen Closet
- Walk-In Closet
- Primary Bathroom is a Full Bathroom
Laundry
- Laundry Room
- Stacked Washer and Dryer
Finished Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
Outdoor Features
- Property is near a marina
- Deck
- Patio
- Porch
Location
- Property is near a golf course
Utilities
- Cooling Available
- Hot Water Heating System
- Gas Water Heater
- Private Sewer
Listing and Financial Details
- Assessor Parcel Number 11G74H108
Community Details
Overview
- Property has a Home Owners Association
- Great Hills Estates Subdivision
Recreation
- Bike Trail
Map
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Home Values in the Area
Average Home Value in this Area
Tax History
| 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 |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 08/27/2025 08/27/25 | Price Changed | $2,295,000 | -4.2% | $564 / Sq Ft |
| 08/14/2025 08/14/25 | Price Changed | $2,395,000 | -2.0% | $588 / Sq Ft |
| 08/01/2025 08/01/25 | Price Changed | $2,445,000 | -2.0% | $600 / Sq Ft |
| 05/06/2025 05/06/25 | For Sale | $2,495,000 | +41.0% | $613 / Sq Ft |
| 04/10/2023 04/10/23 | Sold | $1,770,000 | -1.4% | $435 / Sq Ft |
| 03/12/2023 03/12/23 | Pending | -- | -- | -- |
| 03/10/2023 03/10/23 | For Sale | $1,795,000 | -- | $441 / Sq Ft |
Source: Cape Cod & Islands Association of REALTORS®
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Personal Reps Deed | -- | None Available | |
| Personal Reps Deed | -- | None Available | |
| Personal Reps Deed | -- | None Available | |
| Deed | $955,000 | -- | |
| Deed | $260,000 | -- | |
| Deed | $955,000 | -- | |
| Deed | $260,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $1,416,000 | Stand Alone Refi Refinance Of Original Loan | |
| Previous Owner | $400,000 | Credit Line Revolving | |
| Previous Owner | $750,000 | No Value Available | |
| Previous Owner | $400,000 | No Value Available | |
| Previous Owner | $668,500 | Purchase Money Mortgage | |
| Previous Owner | $240,000 | Purchase Money Mortgage |
Source: Public Records
About the Listing Agent
Tara's Other Listings
Source: Cape Cod & Islands Association of REALTORS®
MLS Number: 22502257
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 2025 © Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
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