299 Main St

Lakeville CT 06039

4916 sq. ft.

5.07 ac.

Single-Family

Last sold for $3,410,000

Thomas Callahan, last sold this property on 05 June 2026 after 267 days on market.

Overview

This 18th century American Georgian stands as one of Lakeville's finest historic properties, gracing over 5 pristine acres alongside Burton Brook. The distinguished residence perfectly balances preserved period authenticity with thoughtful modern updates, earning recognition in Luxe magazine and The Friends of the American Georgian Group-NYC tour. Original doorways, decorative trim, and historic fireplaces define the formal entertaining spaces, while a welcoming country kitchen with its own period fireplace anchors the casual living areas. The sophisticated blend of architectural heritage and contemporary comfort creates an exceptional living experience throughout. Four ensuite bedrooms and a primary suite with a separate dressing room provide generous accommodations. A thoughtful layout makes the residence ideal for hosting extended family and guests while maintaining privacy and convenience. Stone walls and mature landscaping embrace multiple outdoor living spaces, from intimate stone terraces to covered porches. The heated gunite pool and pool house with detached bathroom, three antique barns, and park-like setting complete this distinguished Litchfield County home.

Features

5 bedrooms

6 bathrooms

4916 sq. ft. floor area

5.07 ac. lot size

Single-Family

Estimated Value

We need at least 3 similar 5 bedroom single-family properties sold in Lakeville over the last 12 months.

Property history for 299 Main St

2026

Sold

$3,410,000

05 Jun 2026 by Thomas Callahan, of Elyse Harney Real Estate

2010

Sold

$1,750,000

24 Jun 2010 by Elyse Harney Morris, of Elyse Harney Real Estate

Happy sellers in Lakeville

We have insufficient information to provide an overview of customer satisfaction for Lakeville. Viewing the agent profiles, reviews and sales for Lakeville can provide insights for this location.