Upperville VA Real Estate & Homes for Sale

8 Properties Found

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Beds:
4
Baths:
4.00
Sq.Ft.:
8,613
Status:
Active
MLS#:
VAFQ2019810
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
365.6 Acres
Year built:
1809
Courtesy: Hunt Country Sotheby's International Realty 540-687-8500
View additional info

ADDITIONAL INFORMATION

Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom and a stroll on the wrap around balcony. Of course, a luxurious bath leading to an expansive closet of 27 ft. x 18ft. outfits the suite. In addition, there are two, luxurious bedrooms with fireplaces and private baths, a back staircase, full basement, a three-car garage, and a lovely mudroom entry to the Kitchen with enclosed porch. The Pool House flanks a saltwater pool with a wide lounging ledge and overlooks the Blue Ridge displaying spectacular sunset views! Among the pristinely manicured grounds is the notable 250-year-old Cedar of Lebanon tree, largest in Virginia. Preserved in Easement with the Land Trust of Virginia and in the Piedmont Hunt territory, this 365-acre retreat offers unparalleled tranquility and privacy for All to enjoy!

Beds:
4
Baths:
4.00
Sq.Ft.:
8,613
Status:
Active
MLS#:
VAFQ2019532
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
365.6 Acres
Year built:
1809
Courtesy: Hunt Country Sotheby's International Realty 540-687-8500
View additional info

ADDITIONAL INFORMATION

Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom and a stroll on the wrap around balcony. Of course, a luxurious bath leading to an expansive closet of 27 ft. x 18ft. outfits the suite. In addition, there are two, luxurious bedrooms with fireplaces and private baths, a back staircase, full basement, a three-car garage, and a lovely mudroom entry to the Kitchen with enclosed porch. The Pool House flanks a saltwater pool with a wide lounging ledge and overlooks the Blue Ridge displaying spectacular sunset views! Among the pristinely manicured grounds is the notable 250-year-old Cedar of Lebanon tree, largest in Virginia. Preserved in Easement with the Land Trust of Virginia and in the Piedmont Hunt territory, this 365-acre retreat offers unparalleled tranquility and privacy for All to enjoy!

Beds:
4
Baths:
4.00
Sq.Ft.:
8,613
Status:
Active
MLS#:
VAFQ2019810
Type:
Single Family-Detached
Lot size:
365.6 Acres
Year built:
1809
A broker reciprocity listing Courtesy: Hunt Country Sotheby's International Realty 540-687-8500
View additional info

ADDITIONAL INFORMATION

Beds:
4
Baths:
4.00
Sq.Ft.:
8,613
Status:
Active
MLS#:
VAFQ2019532
Type:
Single Family-Detached
Lot size:
365.6 Acres
Year built:
1809
A broker reciprocity listing Courtesy: Hunt Country Sotheby's International Realty 540-687-8500
View additional info

ADDITIONAL INFORMATION

Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom

Beds:
4
Baths:
3.00
Sq.Ft.:
3,216
Status:
Active
MLS#:
VAFQ2016372
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
7.57 Acres
Year built:
1820
Courtesy: Thomas and Talbot Estate Properties, Inc. 540-687-6500
View additional info

ADDITIONAL INFORMATION

Welcome to Slate Hill, an exquisite country estate on almost 10 acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700’s property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing the natural light to flood in, 9ft ceiling beams, and the original fireplace mantle. The master bedroom has a fireplace, cedar closets and a luxury bath with custom slate shower walls and Hansgrohe Raindance showerhead and fittings. Of the three guest bedrooms, one includes an en-suite bathroom and two walk-in wardrobes. Other features include new standing seam metal roofs on the main house and cabin, a new two-zone HVAC system, and a new washing machine and dryer (2024). A large stone patio is reached through the kithcen. Extensive mature landscaping and gardens surround the house. George Washington's original log cabin has been fully restored with a repointed chimney & two fireplaces, a loft bedroom and new full bath. Horse amenities include a center aisle barn by renowned builders King Construction (2021), with four oversized stalls, tack room, bathroom, wash stall and feed/laundry room. A breezeway with carriage doors provides beautiful airflow and views. Behind the barn, are four fenced paddocks and a 120x70 EquiSand riding arena that suits all riding disciplines.

Beds:
7
Baths:
8.00
Sq.Ft.:
8,246
Status:
Active
MLS#:
VAFQ2016146
Type:
Residential
Subdivision:
Greystone
Lot size:
51.77 Acres
Year built:
1994
Courtesy: Thomas and Talbot Estate Properties, Inc. 540-687-6500
View additional info

ADDITIONAL INFORMATION

Virginia’ s renowned “Hunt Country” provides the fabulous setting for this exquisite country estate, encompassing over 51.7 acres of verdant pastures, lush woodlands. and towering trees. A long and picturesque driveway, alongside a sparkling, meandering stream, winds through the woods and leads to the entrance of this stunning three level English manor home. Boasting a total of 7 spacious Bedrooms, 7 ½ Baths, and over 6,935 square feet of spectacular living space, this stately home is private, secluded and ideally located in prestigious Greystone. The historic villages of Upperville and Middleburg are just minutes away, offering fine shops, wonderful restaurants, bucolic vineyards, sporting clubs and excellent schools. The breathtaking views of the magnificent Blue Ridge Mountains serve as a backdrop and create a simply magical setting. Upon entering the main residence, the extraordinary architectural design and uncompromising quality of workmanship is immediately evident. The dramatic Center Hall offers a warm and gracious reception and extends to the rear façade, with French doors accessing an absolutely gorgeous courtyard. A beautiful gunite Pool, bordered by field stone terraces and brilliant gardens, create a magical and serene setting. Showcasing some of the outstanding features of this impeccable property are spacious rooms, 11’ high ceilings, vaulted and beamed ceilings, multiple French doors and walls of windows, bathing the rooms in natural sunlight. The Main House features handsome crown moldings, gleaming hardwood floors, and three beautiful wood burning fireplaces, adding warmth and charm to the ambiance of the rooms. The Kitchen, which is highlighted by premium appliances (Viking and SubZero), opens to the Great Room. The Primary Bedroom was completely remodeled, and the luxurious Bath includes heated flooring, stone counter tops and a fantastic soaking tub. The second level features three spacious Bedrooms, one of which is currently used as an additional office. Two more lovely, tiled full Bathrooms are located here. The stunning lower “Walk Out Level” is ideal for many uses. There is an additional Bedroom, a crafts room, a Family Room and two additional full Baths. A fabulous new wing / Pool House/ Guest Quarters, was added to the main residence. It greatly expanded the living space and includes a gorgeous Great Room, a paneled Library, a second Kitchen, two additional Bedrooms and two additional full Baths, plus a wonderful, screened Porch, overlooking the Pool and courtyard. This entire wing is tastefully designed and beautifully appointed, creating a marvelous area for the enjoyment of both family and friends. This wing is perfect as an in-law suite, guest suite, private office or separate living quarters for extended family. Huge windows grace every wall and capture scenic vistas of the open fields and paddock, perfect for the equestrian, with a four-board fenced paddock and run-in shed. Westfield is a splendid country estate, beautifully appointed and built with extraordinary quality, offering the utmost in a gracious and luxurious lifestyle. Highlights of Westfield: Whole House Generator / Heated gunite inground pool / Pool and cover completely rebuilt in 2021 / Exterior of stucco and stone / Wood and tiled flooring / 11-foot-high ceilings, vaulted, coffered and tray ceilings / Three bay attached garage / Beautiful stone fountain serves as centerpiece of the courtyard / An addition of a new wing overlooking the Pool and courtyard / Mature Orchard includes: Peaches, Apples & Plums / Shooting Range for Target practice/Window treatments in Living Room, Foyer, Kitchen, new in 2023/Water treatment system was upgraded and replaced in April 2025/Home Alarm System was fully replaced in 2024/Whole House Sound System upgraded in early 2023/Pool Heater replaced in 2024/Pool and Automatic Cover completely rebuilt in 2021/Pool motor replaced in April 2025.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,216
Status:
Active
MLS#:
VAFQ2016372
Type:
Single Family-Detached
Lot size:
7.57 Acres
Year built:
1820
A broker reciprocity listing Courtesy: Thomas and Talbot Estate Properties, Inc. 540-687-6500
View additional info

ADDITIONAL INFORMATION

Welcome to Slate Hill, an exquisite country estate on almost 10 acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700's property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing the natural light to flood in, 9ft ceiling beams, and the origin

Beds:
2
Baths:
2.00
Sq.Ft.:
2,367
Status:
Active
MLS#:
VAFQ2014722
Type:
Residential
Subdivision:
None Available
Lot size:
0.84 Acres
Year built:
1900
Courtesy: Corcoran McEnearney 703-436-0077
View additional info

ADDITIONAL INFORMATION

Opportunity to to own a charming historic church building in the heart of Upperville. A perfect location and opportunity to live in the heart of the historic village of Upperville just west of Middleburg. The church and the studio have been both renovated and connected to offer more living space and a seamless home in excellent condition. Beautiful Mountain views from the large back yard. Close to Sky Meadows State Park, the Appalachian Trail and many local Vineyards.

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1–8 of 8 properties displayed
Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.
Andrea D. Conner, License 225222413, Xome Inc., License 226024700, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Information is provided by Charlottesville Area Association of Realtors®. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interestedin purchasing. Copyright © 2026 Charlottesville Area Association of Realtors®. All rights reserved.




Upperville Real Estate

Upperville is located in Virginia. Upperville, Virginia has a population of 118. Upperville is more family-centric than the surrounding county with 100% of the households containing married families with children. The county average for households married with children is 35.08%.

The median household income in Upperville, Virginia is $78,987. The median household income for the surrounding county is $111,368 compared to the national median of $69,021. The median age of people living in Upperville is 59.3 years.

Upperville Weather

The average high temperature in July is 86.6 degrees, with an average low temperature in January of 23.3 degrees. The average rainfall is approximately 43.7 inches per year, with 19.1 inches of snow per year.

Upperville Map

Upperville Real Estate Market Conditions

  • Median sales price

    $3,817,500
    8.1%
    change since last quarter
  • # Active listings

    10
    30-day change

Upperville Schools and Demographics

Education near Upperville, VA

City County
High School Graduates 100 92.84
College Degree - 2 year 26.09 7.66
College Degree - 4 year 48.91 37.7
Graduate Degree 11.96 10.53
Expenditures per Student 13,767 13,767
Students per Teacher 13 13

Elementary Schools near Upperville, VA

Grades Students P/T Ratio ZIP
Banneker Elementary School PK - 05 157 17.8 20117
Boyce Elementary School KG - 05 319 14.3 22620
Claude Thompson Elementary School PK - 05 296 16.4 20115
Middleburg Community Charter KG - 05 114 22.8 20117
Round Hill Elementary School PK - 05 553 17.5 20141
W.G. Coleman Elementary PK - 05 346 15.7 20115

Middle Schools near Upperville, VA

Grades Students P/T Ratio ZIP
Marshall Middle School 06 - 08 471 10.9 20115
Middleburg Elementary School PK - 05 61 10.7 20117

Ungraded Schools near Upperville, VA

Grades Students P/T Ratio ZIP
ALC At Burke UG - UG 0 20115

Demographics near Upperville, VA

City County
Neighborhood Type Suburban
Population 118 72,416
Population Density 279 112
Median Age 59.3 40.9
People per Household 1.7 2.8
Median Household Income 78,987 111,368
Average Income per Capita 46,383 49,440

Real estate near Upperville