The Plains, Virginia | 435 acres | $19,600,000 2227 Penny Lane, The Plains VA 20198
MLS #VAFQ2010208
For more information please contact John Coles jcoles@thomasandtalbot.com (540) 270-0094


Oakendale Farm, ca. 1938 is the epitome of an exquisite Virginia hunt county estate. Located within minutes of Middleburg, Virginia, its 435 acres are in prime Orange County Hunt territory with potential for incredible ride-out. From the Manor house to the meticulously manicured gardens, grounds, dependencies, and the hundreds of acres of surrounding pastures with protected view-sheds, Oakendale is in a class of its own.


The entrance to the estate is from a quiet country road, 5 minutes south of historic Middleburg. Once inside the gates, the first drive to the left leads to the courtyard of the manor house, a second courtyard with private office and guest house, and a third courtyard which features the custom greenhouse and, the oversized and heated 5 bay garage with a spacious second floor entertainment room. Next to the garage is a 105k generator which provides back-up power to the manor house and most of the other buildings in these courtyards.


MANOR HOUSE: Designed by renowned architect, William Lawrence Bottomley and constructed by master builder, W. J. Hanback, the Colonial Revival stone manor house is sited perfectly to enjoy the commanding views of the estate and surrounding countryside from the Bull Run to the Blue Ridge Mountains.


One enters the foyer (15' x 14'), to its beautiful, curved staircase, and wide board walnut flooring which carries throughout the formal living areas. To the right of the foyer, wide steps lead down into the anteroom, which creates a lovely entry into the gracious Living Room (36' x 18'6") with walk-in bay window and French doors to the back gardens. Just beyond the walk-in bay window a garden was created to frame the magnificent views to the Blue Ridge Mountains.


Once again from the foyer, a hallway leads into the very handsome paneled library (16' x 16'), with fireplace, French doors opening to gardens and a curved reading nook surrounded by windows. The hallway then leads to the elegant stone terrace with seating walls surrounded by boxwood gardens designed to draw attention to the expansive and protected views. From the terrace one has access to the pool (60' x 40'), and pool house with covered terrace, grill, wet bar, showers and changing rooms.


Returning to the home, the next room from the foyer is the formal dining room (20' x 18') sized for grand dining, as well as an intimate dining area for 4 surrounded by windows, once again designed for the views. Just beyond the dining room is a very private garden room perfect for taking afternoon tea.


Once again from the foyer, the room to the left of the front door houses 2 coat closets and leads to the elevator and the butler's pantry. From here one enters the Kitchen (20' x 17'), which features a 6 burner Viking Range with Viking Hood. The workspace is open to the light filled Breakfast Room (12'6" x 9') surrounded by windows. Beyond the kitchen is the laundry area, steps to both the upper and lower levels and a side door, which leads to the courtyard shared by the 2-story office and guest house.


The second level of the manor house offers a magnificent primary suite complete with bedroom (21' x 17'), private porch for breathing in the glorious views, sitting room (20' x 16'), exercise room/dressing room (12' x 9') and 2 full baths. The remainder of the second level offers: bedroom #2 (17' x 16') with private bath, bedroom #3 (15' x 10') with private bath and a separate suite with 2 bedrooms (11' x 9' & 12' x 8'), full bath and sitting room with kitchenette. This suite also has access to the back stairwell.


Oakendale Farm consists of 2 tax parcels, one with 333 acres and the second with 102 acres, both parcels are protected by an easement with the Virginia Outdoors Foundation.


The manor house and other structures of Oakendale are made even more wonderful surrounded by its exceptional land with spring-fed ponds, fenced pastures and extraordinary ride-out. It has been said that Oakendale can best be experienced from the back of a horse.



  • 2-story office with porch
  • Guest house with terrace
  • Farm manager's house
  • 5+ car garage with grand party room
  • 8 stall courtyard barn with double wash stall, office, laundry and one bedroom apartment
  • Barn for 2 horse trailers
  • Equipment barn with 8 bays (3 climate controlled)
  • Bank barn and Creamery
  • Exquisite greenhouse
  • Pool (60' x 40'), pool house with terrace, showers and changing rooms
  • 105k generator
  • Historic Log Cabin located on the adjacent 102 Acre parcel


The Plains, Virginia | 435 acres | $19,600,000 Get Directions | MLS #VAFQ2010208
For more information please contact John Coles jcoles@thomasandtalbot.com
Offer subject to errors, omissions, prior sale, change of price or withdrawal without notice.
Information contained herein is deemed reliable but is not so warranted nor is it otherwise guaranteed.