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View All Latest Upperville 1500+ Sq. Ft. Properties for Sale
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
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
The simple pleasures of farmhouse living, in the heart of Upperville.<br><br> There is something wonderfully comforting about an old farmhouse—the wide-plank feel of hard...
- 3 Beds
- 2 Baths
- None Available SubDv.
- 20184 Zip Code
- ACTIVE Status
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
Nestled in the heart of historic Upperville, this charming farmhouse offers timeless character on a picturesque 1-acre lot. Featuring 3 bedrooms, 2.5 bathrooms, and over ...
- 3 Beds
- 3 Baths
- None Available SubDv.
- 20185 Zip Code
- ACTIVE Status
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
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
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
Price reduced! Don’t miss this charming house located on a side street in historic Upperville on almost ¾ of an acre! Tucked away from the main road is this fully renovat...
- 3 Beds
- 3 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
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
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
Welcome to 1154 Crofton Lane! Located in historic Upperville, Virginia - 3 bedroom, 3.5 bath home certain to impress. This modern Farmhouse sits on .66+/- acres showcasin...
- 3 Beds
- 4 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
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
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
Rare village offering with acreage and views! Tucked away on a quiet dead-end street on the southern edge of historic Upperville, this beautifully updated brick home offe...
- 4 Beds
- 2 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
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
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
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
Take a step back in time and own a piece of history. “The Armistead House” is a charming, historic brick home in the heart of Upperville, Virginia. Designated a Virginia ...
- 3 Beds
- 3 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
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
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
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
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
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
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
Price reduced! Enjoy a weekend retreat or full-time residence on almost an acre in the heart of the historic village of Upperville. Just minutes west of Middleburg, this ...
- 3 Beds
- 4 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
Tucked away on a quiet side street in the heart of historic Upperville, the delightful “Hatcher’s Cottage” has been thoughtfully and thoroughly renovated offering the rus...
- 3 Beds
- 3 Baths
- None Available SubDv.
- 20184 Zip Code
- CLOSED Status
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
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
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
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
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
1500+ Sq. Ft. Upperville Real Estate
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