Upperville VA Real Estate & Homes for Sale

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 space with spectacular views of the iconic Blue Ridge Mountains. Originally built in 1997 by esteemed architect Errol Adels, the home finished a two-year renovation in late 2017 and continues to be well maintained. Inside, a magnificent great room includes the gourmet kitchen, dining room and two seating areas that overlook the terrace and swimming pool. Each of the homes five bedrooms - including two large ground level master suites - offer ensuite baths clad in floor to ceiling Carrara marble. Additional noteworthy features include 10' custom doors, custom oak cabinetry, Miele and Sub-Zero appliances, Italian marble countertops, Lefroy Brooks fixtures and sconces, 180-year-old reclaimed wide-plank flooring, and custom millwork throughout. The 1,225 sq foot guest house has a spacious entertaining space with a concealed full kitchen, large bedroom and ensuite bath. The pool, outdoor spaces and gardens are inviting and well proportioned. Tasteful decor. Completely private and in the middle of Virginia hunt country, Lily Pad is an ideal weekend or full-time residence.

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. 1700s 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.

Virginia s renowned â??Hunt Countryâ? 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 â??Walk Out Levelâ? 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.

Own a Slice of Hunt & Wine Country History - Where Storybook Charm Meets Timeless Tranquility Tucked atop a gentle knoll overlooking the babbling waters of Pantherskin Creek, this enchanting 1700s cottage is more than just a home-its an invitation to enjoy history, nature, and slow living. Major renovation in 2021. Set on 1.16 acres of serene Virginia countryside, this cottage features brick floors, original stone walls, beamed ceilings, and a wood-burning stove. Its the kind of space that feels straight out of The Holiday-cozy & brimming with character. The upper level features oak-clad, vaulted ceilings and fresh shiplap walls creating a light filled bedroom suite. This cottage has been meticulously updated with all-new Mechanical, Electrical, Plumbing, terracotta tile roof, and windows since 2022, blending modern convenience with the timeless charm. The newly installed septic system supports a 3-bedroom capacity, and the county has approved plans for a proposed 830 sq ft Accessory Dwelling Unit (ADU). Whether you envision expanding the main house, adding a guest cottage, or additional rental income, the possibilities are endless. Proximity to Middleburg, all of Virginias equestrian events and 30+ wineries makes this cottage an ideal location!

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 serene escape while remaining just minutes from Sky Meadows State Park, local breweries, and vineyards. Currently operating as a successful Airbnb, the property presents a flexible opportunity-whether you're seeking a private getaway, an income-producing investment, or a home designed for entertaining. With no HOA and surrounded by mature trees, you'll enjoy both seclusion and freedom. The location is ideal, situated just 2.5 miles from the Upperville Colt & Horse Show and 4.5 miles from the Middleburg Classic, with easy access to Middleburg, Delaplane, Bluemont, and major highways. Inside, the open-concept layout invites you into a stunning kitchen outfitted with granite countertops, stainless steel appliances, a spacious island, and a double oven-perfect for cooking and entertaining with ease. Two expansive owners suites, each with its own private en-suite bath, offer luxurious comfort and flexibility. A charming built-in shelving unit paired with a bay window creates a cozy space to relax and take in the views. The screened-in porch, complete with a stone fireplace, allows you to enjoy the beauty of every season in comfort. With four bedrooms, four and a half bathrooms, and a layout designed for entertaining both indoors and out, this home offers the perfect blend of modern amenities and rustic charm. Completely updated and equipped with HughesNet internet, staying connected is never an issue. The home can be sold fully furnished for an additional cost, making it truly turnkey. This is a rare gem in Virginia horse and wine country-dont miss your chance to own a slice of paradise.

Take a step back in time and own a piece of history. â??The Armistead Houseâ?? is a charming, historic brick home in the heart of Upperville, Virginia. Designated a Virginia Historic Landmark and on the National Register of Historic Places, it was built in 1823 by a doctor whose medical oï¬?ce was the small stone structure known today as the Upperville Library. Mr. Bowles Armistead purchased the home before the Civil War and since that time the Armistead House has been in their family for almost two centuries. In this first time oï¬?ering, you will have the opportunity to own a piece of history in the heart of beautiful Piedmont hunt country. The original 1823 colonial brick structure was enhanced in 1923 with an addition mirroring the original building. A first floor master addition was added in the 1970s. Enter the handsome front door of this beautiful brick home with dark green plantation shutters and original wavy glass windows to the foyer of the home, complete with ten foot ceilings, a coat closet and the original wood plank flooring with historic square cut nails. To the left of the foyer is a formal living room with a wood burning fireplace and to the right is the formal dining room with fireplace. All three rooms have doors leading out to a charming covered porch overlooking the yard with mature trees, boxwoods, peonies, and a stone retaining garden. The side door to the house is next to your private parking area which leads to the 1970's added mudroom/laundry room. There are multiple closet spaces and built-in bookshelves in the hallway for ample storage. There you will also find a first floor master bedroom with attached full bath. The galley style kitchen to the left has beautiful natural lighting with charming latch windows. Two additional bedrooms are found upstairs. One with a hallway full bathroom and original closed fireplace and mantel and the other with two large closets and dressing room with full bathroom. The second floor has access to the upper level screened in porch overlooking the backyard. This house comes complete with a full generator. The Armistead House is situated in the heart of historic Upperville nestled in between two historic churches - Upperville Baptist and Trinity Episcopal Church. Walk to church, the library, post oï¬?ce or dinner at Hunters Head Pub or simply enjoy the evening on your covered porch overlooking the gardens and rolling countryside beyond. Minutes from Middleburg, Virginia and an easy commute to Washington, D.C. and the surrounding airports.

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.