Winthrop Estate – An Elegant Home

Summary:

I’m Jamie, the proud steward of the timeless, beautiful Winthrop Estate, a restored 1920s mansion that blends historic charm with modern luxury. Perfect for groups, it features luxurious bedrooms, a chef’s kitchen, modern amenities & elegant gathering spaces– an ideal retreat for creating lasting memories.



Please note: By prior approval, we welcome special celebrations that include only resident guests, for up to 24. Events for more than 24 and outdoor amplified music are not permitted. Pre-wedding hair, makeup, photography, and special meals for resident guests are welcome.



The Space:

Thoughtfully renovated with modern touches, this jewel is set on 45 acres and offers the perfect blend of charm and convenience.



Location Highlights:

- Less than a mile from the center of Lenox, with its vibrant restaurants, cafes, bars, shops, and galleries.

- Within a mile of Kennedy Park, a 500-acre hardwood forest featuring 15 miles of groomed trails for hiking, cross-country skiing, and picnics.

- Just 1.5 miles from Tanglewood’s front gate.



Onsite Amenities:

- Grand Social Spaces:

- A purple-heartwood-paneled library.

- A plant-filled conservatory.

- Chef’s Kitchen, fully equipped

- Outdoor Features:

- BBQ grill, fire pit, and stove.

- Whiffle ball and lawn croquet.

- Acres of hiking trails.

- Recreation & Workspaces:

- Game room with ping pong, foosball, Legos, and board games.

- Dedicated workstation with an external monitor and powered standing desk.

- EV charger compatible with all vehicle types



Accommodations:

- 7 main bedrooms comfortably accommodate 14 guests.

- 5 additional standard bedrooms with a shared bathroom can host 10 more guests.

- Total capacity: 24 guests.

- A dining room with seating for up to 24 people.



Please note: By prior approval, the Winthrop Estate welcomes special celebrations for up to 24 guests only. These are limited in scope and must follow our house rules. Large events, parties, and amplified music are not permitted. Pre-wedding preparation such as hair, makeup, photography, and curated meals for resident guests are always welcome.



Enjoy the perfect mix of historic elegance and modern comfort at the Winthrop Estate.



Other Things to Note:

To ensure a seamless and secure experience, all guests will be screened prior to check-in and asked to sign a house rules agreement.



Please keep in mind that the Winthrop Estate is nestled in the scenic countryside of Lenox. While we strive to maintain a clean and comfortable environment, the natural surroundings may include occasional encounters with flies and other wildlife. This is part of the charm of country living, and we appreciate your understanding.



We look forward to hosting you at the Winthrop Estate!



Interaction with Guests:

Once you have made your booking, we will give you our contact information and you can reach us before and during your stay. We are happy to share local information and house history.