View All Latest Upperville 3500+ Sq. Ft. 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

9016 John S Mosby Hwy, Upperville $1,550,000

European-Inspired Architectural Gem in Virginia Horse Country! Just eight miles from Middleburg and approximately one hour from Washington, DC, this exceptional 3,800-squ...

3 Beds
2 Baths
None Available SubDv.
20184 Zip Code
ACTIVE 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

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

1143 Crofton Ln, Upperville $1,248,000

Nestled in both Fauquier & Loudoun County, this expansive modern Farmhouse is a newly constructed gem in historic Upperville, boasting breathtaking western Blue Ridge mou...

6 Beds
6 Baths
None Available SubDv.
20184 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

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

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

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

1129 Delaplane Grade Rd, Upperville image

1129 Delaplane Grade Rd, Upperville $2,710,000

Hidden behind a privet hedge, adjacent to the village of Upperville, Alston House ( 1129 and 1131 Delaplane Grade Rd) offers privacy and gracious living on two level lots...

5 Beds
5 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

3500+ Sq. Ft. Upperville Real Estate

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