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2577 Pennybaker Ln, 
Keswick, VA 22947

$1,945,000


5

Beds


4

Baths


3,559

Sq Ft


Single Family

Active

Listed by

Rebecca White

Loring Woodriff Real Estate Associates

434-977-4005

Last updated:

October 29, 2026, 03:22 PM

MLS#

683546

Source:

CHARLOTTESVILLE

About This Home

2577 Pennybaker Ln

Set atop a prominent ridge in the Southwest Mountains, this estate parcel offers staggering year round views over 5 counties from 2 building sites. A house once existed at the most elevated building site (890ft in elevation), as evidenced by mature boxwoods and huge trees. While you build, live in a wonderful 2 bedroom cottage recently, cleverly converted from a barn that also enjoys staggering views. Or live in another charming, c.1800's residence on the property that is nestled in amongst mature trees and more massive boxwoods, overlooking pastoral and pond views. While the views grab you 1st, features of the land itself hold your attention, like the numerous large trees that dot the open meadows. A Virginia Frame barn provides workshop, machinery storage & livestock or equestrian potential. Bordered by land in conservation easement, absolute serenity and seclusion for decades to come are all but guaranteed. Panoramic, year-round views stretching from Wintergreen to Madison County. Just 15 minutes from town or CHO airport, all roads are paved to this property.

Home Facts

Single Family

4 Baths

5 Bedrooms

Built in 1800

Subdivision & Development:

NONE

Price Summary

1,945,000

$546 per Sq. Ft.

MLS #:

683546

Last Updated:

October 29, 2026, 03:22 PM

Added:

1 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

3,559 Sq. Ft.


Structure

Structure

Building Area:

3,559 Sq. Ft.

Year Built:

1800


Lot

Lot Size (Sq. Ft):

3,665,138


Finances & Disclosures

Finances

Price:

$1,945,000

Price per Sq. Ft:

$546 per Sq. Ft.

Source:CHARLOTTESVILLE
“Based on information submitted to the MLS GRID as of October 29, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.” "Listings courtesy of APPLICABLE MLS as distributed by MLS GRID.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.