1419 Chesapeake St

Charlottesville VA 22902

3372 sq. ft.

0.27 ac.

Single-Family

Last sold for $507,055

Rick Matley, last sold this property on 10 September 2026 after 56 days on market.

Overview

Step into the timeless charm of this 1932 Craftsman bungalow in the sought-after Woolen Mills neighborhood. Rich hardwood floors, beautiful wood trim, 9' ceilings and classic architectural details blend seamlessly with an updated kitchen and bath, offering the perfect balance of historic character and modern convenience. Replacement thermal windows enhance comfort and efficiency. Designed for easy one-level living, the home features 2 BRs and 1 beautifully updated bath. The full unfinished basement includes a professionally installed dry basement system and offers excellent potential for addt'l finished living space. A walk-up attic provides an exciting opportunity to create a spacious primary suite with an addt'l bath. Set on an oversized quarter-acre-plus lot, the property offers room to garden, play, & grow. Relax on the inviting covered front porch overlooking the neighborhood or enjoy the privacy of the covered rear porch and beautifully landscaped backyard featuring established perennials, flowering shrubs, and ornamental trees. Off-street parking, a detached garage or large storage building, and a whole-house generator complete this exceptional property. A rare opportunity to own a classic Craftsman in a great neighborhood.

Features

2 bedrooms

1 bathroom

1 carspace

1 garage space

3372 sq. ft. floor area

0.27 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in Charlottesville over the last 12 months, the estimated median property value of 1419 Chesapeake St is $371.5k.

Median value

$371.5k

Estimated value range

$209k - $550k

Median days on market

Estimated value trend

-15%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Charlottesville. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1419 Chesapeake St

2026

Sold

$507,055

10 Sep 2026 by Rick Matley, of NEST REALTY GROUP

2019

Sold

$385,000

07 Jun 2019 by Roger Voisinet, of REMAX Realty Specialists | Charlottesville

2017

Sold

$353,900

10 Apr 2017 by Roger Voisinet, of REMAX Realty Specialists | Charlottesville

Happy sellers in Charlottesville

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