Upperville

Upperville, Virginia, situated in Fauquier County, is a charming small town renowned for its scenic countryside, historic structures, and vibrant equestrian community. Home to the prestigious Upperville Colt & Horse Show, the oldest horse show in the United States, Upperville embodies a rich heritage and a deep connection to equestrian traditions. Located in the heart of Virginia Hunt Country, Upperville was established in 1797 by Josephus Carr and continues to be celebrated as one of America’s most esteemed equestrian communities. Despite its small size, Upperville holds a significant place in Mid-Atlantic and Virginia Hunt Country lore, with a legacy of iconic traditions that have shaped the town’s identity over the years. The town boasts a wealth of historic landmarks, including the iconic Trinity Episcopal Church, designed in the French medieval parish style by H. Page Cross and donated by philanthropist Paul Mellon in the 1950s. Upperville is also home to a number of renowned country homes and estates, such as Sandy Lerner’s Ayrshire Farm and Paul and Bunny Mellon’s Oak Spring Farm estate, alongside charming 19th-century-style brick, wood, and log residences lining its main thoroughfare. For outdoor enthusiasts, Sky Meadows State Park offers a gateway to the Appalachian Trail and breathtaking views of the Blue Ridge Mountains, spanning over 1,000 acres of protected parkland. Upperville’s blend of history, natural beauty, and equestrian culture makes it a captivating destination for visitors and a cherished community for residents alike.

5 Results

$11,200,000

1610 DELAPLANE GRADE RD
UPPERVILLE, VA 20184

4
Beds

3 | 1
Baths

8,613
SqFt

(99)

Virtual Tour

#VAFQ2019532 | House

$2,625,000

10157 JOHN S MOSBY HWY
UPPERVILLE, VA 20184

4
Beds

2 | 1
Baths

3,216
SqFt

(80)

Virtual Tour

#VAFQ2016372 | House

$2,595,000

33195 MILLVILLE RD
UPPERVILLE, VA 20184

4
Beds

4
Baths

3,324
SqFt

(76)

Virtual Tour

#VALO2124578 | House

$925,000

1150 POPLAR ROW
UPPERVILLE, VA 20184

3
Beds

2
Baths

2,384
SqFt

(80)

#VAFQ2022412 | House

$899,000

9027 JOHN S MOSBY HWY
UPPERVILLE, VA 20185

3
Beds

2 | 1
Baths

2,432
SqFt

(56)

#VAFQ2022772 | House

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