View All Latest Upperville 5+ Acre Properties for Sale

1610 Delaplane Grade Rd, Upperville image

1610 Delaplane Grade Rd, Upperville $10,950,000

Peace and Plenty at Bollingbrook, circa 1809, is a remarkable Virginia estate with breathtaking sunset views and a history reaching back to the earliest years of the Comm...

4 Beds
4 Baths
None Available SubDv.
20184 Zip Code
ACTIVE Status

1325 Rokeby Rd, Upperville $2,000,000

Set amidst the rolling landscapes of Virginia’s storied horse and hunt country, 1325 Rokeby Road presents a rare opportunity to experience the timeless elegance of the Up...

4 Beds
5 Baths
None Available SubDv.
20184 Zip Code
PENDING Status

1310 Delaplane Grade Rd, Upperville image

1310 Delaplane Grade Rd, Upperville $1,875,000

Just south of the charming village of Upperville, Stone Oaks is a beautifully maintained brick home privately situated on 14 acres with sweeping Blue Ridge Mountain views...

4 Beds
4 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

33195 Millville Rd, Upperville $2,125,000 ▼

New price - a significant price repositioning! Small Spring Farm is being offered for the first time in over 50 years. Nestled on 27 scenic acres just north of Upperville...

4 Beds
4 Baths
Upperville SubDv.
20184 Zip Code
ACTIVE Status

20532 Trappe Rd, Upperville $2,595,000

Located on prestigious Trappe Road amongst large estates, sweeping views and compelling history is this newly renovated property with so much to offer! It features a circ...

3 Beds
4 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

8555 John S Mosby Hwy, Upperville $1,800,000

A rare opportunity to purchase a move in ready equestrian facility in the heart of Piedmont Hunt Country. Desirably located on John Mosby Hwy. in the heart of Uppervil...

3 Beds
2 Baths
None Available SubDv.
20185 Zip Code
CLOSED Status

21846 Trappe Rd, Upperville $19,800,000

Set amid the picturesque countryside of Upperville, Virginia, Ayrshire Farm rises from the landscape with a presence that feels both timeless and stately. Encompassing 57...

11 Beds
13 Baths
Upperville SubDv.
20184 Zip Code
CLOSED Status

1610 Delaplane Grade Rd, Upperville $10,950,000 ▼

Peace and Plenty at Bollingbrook, circa 1809, is a remarkable Virginia estate with breathtaking sunset views and a history reaching back to the earliest years of the Comm...

4 Beds
4 Baths
None Available SubDv.
20184 Zip Code
ACTIVE Status

21281 Belle Grey Ln, Upperville $6,500,000

Welcome to 21281 Belle Grey Farm in beautiful Upperville Virginia, where you can enjoy breathtaking sunrises and sunsets on this spectacular 122-acre equestrian estate. T...

3 Beds
3 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

21281 Belle Grey Ln, Upperville $6,500,000

Welcome to 21281 Belle Grey Farm in beautiful Upperville Virginia, where you can enjoy breathtaking sunrises and sunsets on this spectacular 122-acre equestrian estate. T...

3 Beds
3 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

21515 Trappe Rd, Upperville — Llangollen $21,350,000

Landmark 1,100� acre estate in the heart of the Middleburg/Upperville hunt country. Steeped in history, Llangollen dates to 1795 and is anchored by a gorgeous 9-bedroom C...

9 Beds
11 Baths
None Available SubDv.
20185 Zip Code
CLOSED Status

21881 Willisville Rd, Upperville $2,495,000

Welcome to your own private retreat on 16 +/- Acres! This stunning property is nestled on 16+/- fully fenced acres, offering the perfect blend of luxury, comfort, and fu...

5 Beds
7 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

Welbourne, Upperville $925,000

Excellent Loudoun County location minutes to Upperville and Middleburg. Surrounded by large properties all mostly in conservation easement. Land is gently rolling, ston...

20184 Zip Code
CLOSED Status

1225 Dunvegan Dr, Upperville $1,295,000

Not often does a small farm come available on 13+ acres tucked between large farms in conservation easement in the Middleburg-Upperville area. Situated just East of the c...

3 Beds
3 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

33846 Foxlease Ln, Upperville $7,007,777

Littleton Farm comprises over 153 spectacular acres with a serene four-acre lake, two smaller ponds and Beaverdam Creek meandering through the property. Tucked in the sou...

7 Beds
8 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

33846 Foxlease Ln, Upperville $7,007,777

Littleton Farm comprises over 153 spectacular acres with a serene four-acre lake, two smaller ponds and Beaverdam Creek meandering through the property. Tucked in the sou...

7 Beds
8 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

1248 Delaplane Grade, Upperville $1,335,000

Discover Your Serene Retreat: A Prime Horse and Wine Country Property Welcome to your private haven nestled in the heart of horse and wine country, where charming meets...

2 Beds
2 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

21881 Willisville Rd, Upperville $2,600,000

Nestled in the picturesque countryside of Upperville, Virginia, 21881 Willisville Rd unveils a brand new architectural masterpiece, seamlessly blending modern luxury with...

5 Beds
7 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

7521 John S Mosby Hwy, Upperville $995,000

Hard to find, small property in the middle of horse and hunt country. Charming, well designed log home on 5 private acres between the villages of Middleburg and Uppervill...

3 Beds
2 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

9050 Hogan Ln, Upperville $1,225,000

Gorgeous mountain views and ultimate privacy await you at this beautifully remodeled farmhouse-style retreat. Nestled on 10 peaceful, wooded acres, this home offers a ser...

4 Beds
5 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

1388 Crenshaw Rd, Upperville $4,500,000

Set on an idyllic five-acre parcel and bordering a 400-acre private estate, this extraordinary Neoclassical Palladian villa offers nearly 6,000 sq feet of interior living...

5 Beds
7 Baths
None Available SubDv.
20184 Zip Code
CLOSED Status

10157 John S Mosby Hwy, Upperville image

10157 John S Mosby Hwy, Upperville $2,575,000 ▼

Welcome to Slate Hill, an exquisite country estate on almost 7+/- acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide...

4 Beds
3 Baths
None Available SubDv.
20184 Zip Code
ACTIVE Status

5+ Acres Upperville Real Estate

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