# 55 Winterset Drive, Chatham, MA 02633

> **TL;DR:** 4bd/4ba single family, $2,295,000 ($564/sqft), built 1970, 4,066 sqft.
> Fireplace, Hardwood, A/C, 2-car garage. Est. $12,349/mo. Listed 111 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $2,295,000 |
| Price/sqft | $564 |
| Bedrooms | 4 |
| Bathrooms | 3 full, 1 half |
| Square Feet | 4,066 |
| Year Built | 1970 |
| Lot Size | 84,506 sqft (1.94 acres) |
| Stories | 3 |
| Garage | 2-car |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 111 |

## Why This Home Stands Out

- **Hardwood Floors** - Hardwood flooring listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $11,605 |
| Estimated Insurance | $669 |
| HOA | $75 |
| **Total** | **$12,349** |

## Key Amenities

- Fireplace
- Hardwood
- A/C
- 2-car garage

## Property Highlights

- Built in 1970
- 1.94 acre lot
- 3 stories
- 14 parking spaces
- Fireplace

## Description

### Agent Description
Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

## Location

- **Address:** 55 Winterset Drive, Chatham, MA 02633
- **County:** Barnstable
- **Neighborhood:** Great Hills
- **Coordinates:** 41.694159, -69.977027
- **Google Maps:** https://www.google.com/maps?q=41.694159,-69.977027

## Listing Agent

- **Name:** Janet Stuart
- **Brokerage:** Coldwell Banker Realty
- **Broker Phone:** (508) 962-6990
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/55-Winterset-Dr_Chatham_MA_02633_M40761-41651?f=listhub&s=CCIAORMA&m=22603375&c=propsimple)

## Photos

![55 Winterset Drive - Photo 1](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f237045678r.jpg)

![55 Winterset Drive - Photo 2](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2917876509r.jpg)

![55 Winterset Drive - Photo 3](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3538620409r.jpg)

![55 Winterset Drive - Photo 4](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1878643108r.jpg)

![55 Winterset Drive - Photo 5](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1342733569r.jpg)

![55 Winterset Drive - Photo 6](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1553429372r.jpg)

![55 Winterset Drive - Photo 7](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3434899927r.jpg)

![55 Winterset Drive - Photo 8](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f63883313r.jpg)

![55 Winterset Drive - Photo 9](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2174895276r.jpg)

![55 Winterset Drive - Photo 10](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1283510956r.jpg)

![55 Winterset Drive - Photo 11](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f117083441r.jpg)

![55 Winterset Drive - Photo 12](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1374264460r.jpg)

![55 Winterset Drive - Photo 13](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1657900411r.jpg)

![55 Winterset Drive - Photo 14](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2934150851r.jpg)

![55 Winterset Drive - Photo 15](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1423660469r.jpg)

![55 Winterset Drive - Photo 16](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3521429517r.jpg)

![55 Winterset Drive - Photo 17](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3645073738r.jpg)

![55 Winterset Drive - Photo 18](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1688099534r.jpg)

![55 Winterset Drive - Photo 19](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1590828162r.jpg)

![55 Winterset Drive - Photo 20](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2220746502r.jpg)

![55 Winterset Drive - Photo 21](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1675326447r.jpg)

![55 Winterset Drive - Photo 22](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f790610656r.jpg)

![55 Winterset Drive - Photo 23](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3088222138r.jpg)

![55 Winterset Drive - Photo 24](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f916276938r.jpg)

![55 Winterset Drive - Photo 25](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1040544617r.jpg)

![55 Winterset Drive - Photo 26](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f518242539r.jpg)

![55 Winterset Drive - Photo 27](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3896028210r.jpg)

![55 Winterset Drive - Photo 28](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2553500745r.jpg)

![55 Winterset Drive - Photo 29](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2974178959r.jpg)

![55 Winterset Drive - Photo 30](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3111230434r.jpg)

![55 Winterset Drive - Photo 31](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3667623141r.jpg)

![55 Winterset Drive - Photo 32](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2113814136r.jpg)

![55 Winterset Drive - Photo 33](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f142770822r.jpg)

![55 Winterset Drive - Photo 34](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f225846152r.jpg)

![55 Winterset Drive - Photo 35](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1180922777r.jpg)

![55 Winterset Drive - Photo 36](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2865583395r.jpg)

![55 Winterset Drive - Photo 37](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1948053564r.jpg)

![55 Winterset Drive - Photo 38](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f522477250r.jpg)

![55 Winterset Drive - Photo 39](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f4037818179r.jpg)

---

**MLS#:** 22603375 | **Updated:** 2026-10-27
**Source:** listhub

*Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-33d01212a1de4f80a65335f39a042747)

---

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      },
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      },
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        "@type": "PropertyValue",
        "name": "Property Subtype",
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      }
    ]
  },
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    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-33d01212a1de4f80a65335f39a042747#offer",
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    "price": 2295000,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
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    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-33d01212a1de4f80a65335f39a042747#agent",
    "name": "Janet Stuart",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-33d01212a1de4f80a65335f39a042747#brokerage",
      "name": "Coldwell Banker Realty",
      "telephone": "(508) 962-6990"
    }
  }
}
```