$1,428,927Average Value$499Average Price per Sq Ft15Homes For Sale
Middleburg blends rustic warmth with upscale appeal
Lush, lavish and rustically elegant, Middleburg became known as the “Horse and Hunt Capital of the Nation” in the early 1900s and gained a reputation as a luxury retreat for the Washington elite in the ‘60s. But its auspicious beginnings actually date back to a stone tavern built in 1728. That tavern, the Red Fox Inn and Tavern, remains the oldest continuously operating inn in the United States and now serves as an iconic—and symbolic—landmark for the Town of Middleburg. Somphane Jones, a Realtor with Pearson Smith Realty and Loudoun County resident, describes Middleburg as, “a gorgeous, upscale place packed with understated luxury, but it’s more about the atmosphere. Take the Red Fox Inn. The food is phenomenal, but it’s so cozy and warm, that it transports you to another place. No matter when I’m there, it just feels like fall.”
Brick sidewalks add historic charm to Middleburg streets.
Middleburg attracts visitors with shops and historic charm.
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Home prices range widely, but all offer timeless appeal
The feeling that you can step into another time or place defines Middleburg so well. The homes themselves are like a choose-your-own-adventure book. For example, picture yourself downtown in a stately 1830 Federal-style brick manor house with five bedrooms, a broad circular driveway and an original stone smokehouse—the price tag is $1.7 million, but the experience is priceless. Or, for $500,000, write your story in a renovated two-bedroom cottage built in the late 1700s. If 1920s bungalows are your preferred genre, find one on a tree-lined block with three bedrooms and 2,000 square feet for $1.5 million. Want to spin a simple rural yarn? Head to the hills for a two-bedroom, 800-square-foot Cape Cod on a half-are for $425,000, or enjoy modern upgrades in a late 1800s farmhouse with three bedrooms and 1,500 square feet for $575,000. If your imagination is inspired by a historic horse farm anchored by a sprawling 1900 estate home with four bedrooms and more than 4,000 square feet, it’s yours for $3.4 million or more. You can tell equally tantalizing tales with a range of contemporary custom homes and planned communities offering a median list price of over $1 million.
Colonial Revival homes are common in Middleburg.
Stone cottage-style home adds charm to Middleburg.
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Loudon County Public Schools earn high remarks on Niche
Schools are also plentiful. Students can attend Loudoun County Public Schools like Banneker Elementary, which offers robust arts, music and gifted learning programs. Blue Ridge Middle School features more than 65 student clubs, and Loudoun Valley High School provides a Capstone program focused on post-secondary success. Each school receives an A-minus rating from Niche.
Loudoun County High School serves students in Middleburg.
Banneker Elementary has served Loudoun County for over 75 years.
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Middleburg has historic parks, pools and equestrian space
When school’s out, Middleburg provides the penultimate natural playgrounds. Visit Mickie Gordon Memorial Park, featuring 100 acres of sporting grounds, fishing ponds and picnic pavilions, or hike historic trails across open meadows and a 200-year-old bridge at the Battle of Uppersville Historic Park. Franklin Park offers 203 acres with athletic fields, a playground, fishing, equestrian facilities, picnic pavilions, a performing arts center and an outdoor pool. The historically elegant Middleburg Community Center also provides a pool, social events, classes and seasonal celebrations in town.
Purcellville Park's pavilion hosts community gatherings near Middleburg.
Middleburg offers parks for outdoor recreation.
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Downtown blends historic charm with shops and dining
Whatever your chosen adventure, historic downtown will play a leading role. Many buildings date from the late 1700s through the mid-1800s and announce themselves with bright awnings and decorative shingle signs. Jones calls downtown “the destination for eats and boutiques,” and it’s easy to see why. The commercial center buzzes with eclectic boutiques, high-end clothiers, equestrian shops and fine arts galleries. Dining options are everywhere. You can satisfy your seafood cravings at King Street Oyster Bar or dig into hearty pub fare at the Red Horse Tavern. Of course, you’ll need food for home, so Safeway provides your daily staples.
Locals browse boutiques in downtown Middleburg.
Red Fox Inn remains a landmark in Middleburg.
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Middleburg honors its equine roots with races and exhibits
For equestrian enthusiasts, Middleburg is nationally recognized for its annual events, including Christmas in Middleburg, where hounds lead horses and riders in full hunt regalia through town. You can also attend the Middleburg Spring Races or the Virginia Fall Races; catch America’s oldest horse show, the Upperville Horse and Colt Show; or explore the region's rich equine heritage at the National Sporting Library and Museum.
Luxury inns and scenic sips define Middleburg’s pampered side
And for those that like pampered play, wineries, breweries and luxury inns like the Salamander Resort and Spa or Good Stone Inn and Restaurant dot the countryside and provide breathtaking views and upscale experiences.
Greenhill Vineyards offers wine tasting near Middleburg.
King Street Oyster Bar serves seafood in Middleburg.
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Written By
Anna Strock
Photography Contributed By
David MacNeill
Video By
Alex Finneran
Interested in learning more about homes in this area?
Reach out to
Jecholia Jessee,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Middleburg, VA sell after 72 days on the market compared to the national average of 53 days. The median sale price for homes in Middleburg, VA over the last 12 months is $1,301,017, down 1% from the median home sale price over the previous 12 months.
Designed for both refined entertaining and privacy, this incomparable property captures the essence of Virginia's hunt country with dramatic Blue Ridge Mountain views, mature oak trees, and bold streams creating a private sanctuary. The entertainer's paradise unfolds across 10.76 acre and 7,172 square feet of elegant living space featuring exquisite craftsmanship and seamless indoor-outdoor flow.
Looking for a spot to build your dream home or hunt box in the heart of the village of Middleburg? There are very few building lots available so check out Lot B just off #4 Chestnut Street in town! This private .27 acre parcel is open and level, with a pipe stem driveway for easy access. Enjoy a short walk to downtown shops, restaurants, town pool, post office, grocery stores, library and more.
This idyllic property combines sophisticated modern design with practical luxury. Everything from the ground up on this historic property has been updated during a recently completed remodel. The home’s thoughtfully designed main level facilitates single-level living with an open plan living/dining room, kitchen, private primary bedroom with ensuite bathroom, a second full bathroom and a family
Conveniently located, this fully furnished condo in the Ridgeview section of the historic village of Middleburg is move-in ready. Bright and clean, this lower level 2 Bedroom/2 Bath condo has an open floor plan with a light filled living room that opens into the dining room and spacious kitchen. Relax on your covered back patio and enjoy the peacefulness of the woods that border the conservation
Custom Stone/Log Home available for rent on a private Middleburg Farm Setting. This custom home was built in 1984 with reclaimed ops from a log cabin dating to the 1800's. The 4BR 3.5 Bath home features cherry floors, custom millwork, cedar-lined closets, two fireplaces, a huge kitchen. The one-acre yard is included in the lease. VERY private with tranquil fields and woods. East of Middleburg it
Available Feb. 1, 2026. Fantastic Middleburg rental opportunity in a mid-town location just a short two block walk to Main St, Restaurants, Safeway, and shops. Fully renovated 3 bedroom, 2 full bathroom all brick home that backs to open meadows with gorgeous views of Salamander Resort and the surrounding countryside. Recent updates in 2025 include new paint, new recessed lighting, and new LVP
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
