$10,000 Closing Credit¹
#22500960, Lori L Fanning Smith, Listing Office: Compass Massachusetts, LLC
$2,495,000 List price
55 Winterset Dr Chatham, MA 02633
$10,000
Closing credit¹
4 beds
3 full, 1 partial
1.9 acres
House
Property details
About 55 Winterset Dr
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 & 2 walk-in closets, 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.
Highlights
Home typeSingle Family Residence
HeatingHot Water, Other
StatusActive
BasementYes
Lot size1.94 Acres
Year built1970
ParkingBasement, Attached
MLS #22502257
Attached garage2 spaces
FireplaceWood Burning
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 3
- Appliances: Dishwasher, Washer, Refrigerator, Microwave, Gas Water Heater
- Basement: Yes
- Flooring Type: Hardwood, Carpet, Tile, Other
- Interior: Recessed Lighting, Pantry, Walk-in Closet(s)
- Fireplace: Wood Burning
- Total Bedroom Count: 4
- Garage Space: 2 spaces
- Attached Garage: Yes
- Parking: Basement, Attached
- Exterior: Garden, Fence
- Heating: Hot Water, Other
- List Price: $2,495,000
- Annual Tax Amount: $5,030
- Tax Year: 2024
- Lot: On Golf Course, Near Golf Course, Cleared
- Directions: Rte. 28 to Old Queen Anne Rd. to Winterset Drive, to upper driveway on left off Cul d Sac.
- Year Built: 1970
- Stories: 2
- Lot Size: 1.94 Acres
- MLS Number: 22502257
- MLS Name: CapeCod
- Office Name: Bayview Real Estate
- Office Phone: (508) 362-8543
- Office Email: jeanschiffmann@yahoo.com
- Listing Agent: Tara J Schiffmann
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by other brokerage firms are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing broker nor this broker shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. 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.
Copyright 2025© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/19/2025, 3:15:37 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
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$2,495,000
55 Winterset Dr
$10,000
closing credit¹
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Seller rebate
0.5% sale price²
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Apr 10, 2023 | Home Sold | $1,770,000 |
| Aug 29, 2003 | Home Sold | $955,000 |
| Jun 07, 1999 | Home Sold | $260,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $1,409,000 | $5,030 |
| 2023 | $1,176,800 | $4,566 |
| 2022 | $849,000 | $3,922 |
| 2021 | $758,800 | $3,779 |
| 2020 | $748,700 | $3,609 |
| 2018 | $680,400 | $3,314 |
| 2017 | $660,700 | $3,323 |
History based on county public records data.
Nearby schools
5
Chatham Elementary School
Public District PK-4
1.0 mi
•147 Depot Rd
5
Harwich Elementary School
Public District PK-4
5.5 mi
•263 South St
9
Orleans Elementary School
Public District KG-5
6.1 mi
•46 Eldredge Pkwy
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $67,285. The majority of Chatham, MA residents have income between $35k-100k annually. Residents typically live in single, no kids family. The most common level of education of people living in this area is post secondary degree.
How much money do the neighbors make?
23%
<35k
46%
35k-100k
22%
100k-200k
9%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
56%
Single, No Kids
7%
Single, with Kids
29%
Married, No Kids
8%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
9%
<11 yrs old
6%
12-17 yrs old
11%
18-34 yrs old
39%
35-64 yrs old
35%
65+ yrs old
What do the neighbors do for fun?
PGA/LPGA
Skiing/snowboarding
Figure Skating
Where do the neighbors shop?
Stein Mart
BJs Wholesale Club
Kmart
Where do the neighbors go to eat?
Bob Evans
Panera
Cracker Barrel
What do the neighbors drive?
Lincoln
Infiniti
Buick
What do the neighbors listen to?
News/Talk/Information
Adult Hits- Adult Standards
All data provided by Home Junction and Claritas
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Frequently asked questions
About 55 Winterset Dr
The listing price of 55 Winterset Dr property is $2,495,000.
The property 55 Winterset Dr is a house located in Chatham, Massachusetts, 02633.
Active Listing: 55 Winterset Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 55 Winterset Dr are: Chatham Elementary School (GreatSchools Rating 5/10), Harwich Elementary School (GreatSchools Rating 5/10), Orleans Elementary School (GreatSchools Rating 9/10), Monomoy Regional Middle School (GreatSchools Rating 6/10), Cape Cod Lighthouse Charter School (GreatSchools Rating 6/10), Nauset Regional Middle School (GreatSchools Rating 4/10), Monomoy Regional High School (GreatSchools Rating 6/10), Cape Cod Region Vocational Technical (GreatSchools Rating 7/10), Dennis Yarmouth Regional High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2024 is $5,030 (source: MLS/based on county public records data).
The last sale was on April 10, 2023 for $1,770,000 (source: MLS/tax record).
The property at 55 Winterset Dr has 4 bedrooms and 3 full and 1 half bathrooms.
The year of construction for 55 Winterset Dr is 1970.
This home is located at 55 Winterset Dr in Chatham, MA and zip code 02633. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since May 14, 2025 and is currently priced at $2,495,000.
In April 2025, from all listings sold in Chatham, MA there were more than 0 sold above asking price, over 6 sold below and more than 2 were sold right at the asked price. Between March and April 2025, Chatham, MA real estate market has seen increase in the number of listings by 6.7%. Listings spent 57 days on the market in April 2025, and had a median list price of $1,212,500 during the same period.
From Rocket Homes Real Estate and based on county public records data.