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Middleburg + Upperville

NEIGHBORHOOD

Middleburg

A small community of around 700 people, Middleburg has much to offer. It's home to some of the largest estates in the region, including those built within the last few decades. An old community established in the 1700s, it's long been an area of importance within the region. Its Middleburg Historic District, which dates to the 1800s, is on the National Register of Historic Places. It's easy to find stately homes here, often with sprawling acreage, although many have seen significant renovations and upgrades, with some noted for their lavish gardens.

US 50 is the only real highway into the area, but it continues through Washington, D.C. The community is served by the Loudoun County Public School District and has a commercial district along the highway, with the Middleburg Community Center, several small restaurants, and shops in this area. The Red Horse Tavern, Brick and Mortar mercantile, and Red Bar Sushi are a few favorites. Toward the northern portion of the city is the Empower Adventures park, with its outdoor ziplines, eco-hikes, and rappelling. This area is densely forested.

View The Market Report

Available Homes in
Middleburg + Upperville

1150 POPLAR ROW, Upperville, VA 20184
Open Sun 1PM-3PM
80

$925,000

3 Beds 2 Baths 2,384 SqFt

1150 POPLAR ROW, Upperville, VA 20184

MLS# VAFQ2022412

Listed by Keller Williams Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
9027 JOHN S MOSBY HWY, Upperville, VA 20185
New
56

$899,000

3 Beds 3 Baths 2,432 SqFt

9027 JOHN S MOSBY HWY, Upperville, VA 20185

MLS# VAFQ2022772

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
107 WALNUT, Middleburg, VA 20117
New
34

$948,800

5 Beds 3 Baths 2,358 SqFt

107 WALNUT, Middleburg, VA 20117

MLS# VALO2129326

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
6428 JOHN S MOSBY HWY, Middleburg, VA 20117
Active
50

$795,000

4 Beds 3 Baths 2,608 SqFt

6428 JOHN S MOSBY HWY, Middleburg, VA 20117

MLS# VAFQ2022624

Listed by Sheridan-MacMahon Ltd.

Bright MLS (BMLS)
Bright MLS (BMLS)
36006 LITTLE RIVER TURNPIKE, Middleburg, VA 20117
Active
81

$1,395,000

3 Beds 3 Baths 2,792 SqFt

36006 LITTLE RIVER TURNPIKE, Middleburg, VA 20117

MLS# VALO2128060

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
1310 DELAPLANE GRADE RD, Upperville, VA 20184
Pending
97

$1,795,000

4 Beds 4 Baths 4,348 SqFt

1310 DELAPLANE GRADE RD, Upperville, VA 20184

MLS# VAFQ2021294

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
22202 NEWLIN MILL RD, Middleburg, VA 20117
Under Contract
37

$725,000

4 Beds 3 Baths 2,490 SqFt

22202 NEWLIN MILL RD, Middleburg, VA 20117

MLS# VALO2126344

Listed by Paul Wesley Real Estate

Bright MLS (BMLS)
Bright MLS (BMLS)
33195 MILLVILLE RD, Upperville, VA 20184
Active
76

$2,595,000

4 Beds 4 Baths 3,324 SqFt

33195 MILLVILLE RD, Upperville, VA 20184

MLS# VALO2124578

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
406 E WASHINGTON ST, Middleburg, VA 20117
Active
56

$1,950,000

3 Beds 2 Baths 3,956 SqFt

406 E WASHINGTON ST, Middleburg, VA 20117

MLS# VALO2126668

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
36190 TURKEY ROOST RD, Middleburg, VA 20117
Active
88

$2,850,000

4 Beds 5 Baths 4,499 SqFt

36190 TURKEY ROOST RD, Middleburg, VA 20117

MLS# VALO2126154

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
34520 ATOKA CHASE LN, Middleburg, VA 20117
Price Dropped by $299K
100

$2,700,000

3 Beds 3 Baths 2,946 SqFt

34520 ATOKA CHASE LN, Middleburg, VA 20117

MLS# VALO2126254

Listed by Washington Fine Properties, LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
37143 ADAMS GREEN LN, Middleburg, VA 20117
Under Contract
56

$1,525,000

4 Beds 5 Baths 3,365 SqFt

37143 ADAMS GREEN LN, Middleburg, VA 20117

MLS# VALO2126322

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
12 ORANGE DR, Middleburg, VA 20117
Price Dropped by $50K
63

$1,445,000

4 Beds 4 Baths 4,158 SqFt

12 ORANGE DR, Middleburg, VA 20117

MLS# VALO2125854

Listed by Hunt Country Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
23357 WILDWOOD LN, Middleburg, VA 20117
Pending
85

$1,300,000

3 Beds 4 Baths 3,250 SqFt

23357 WILDWOOD LN, Middleburg, VA 20117

MLS# VALO2121878

Listed by Pearson Smith Realty, LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
23084 AFFIRMED PARK CT, Middleburg, VA 20117
Under Contract
91

$2,845,000

4 Beds 5 Baths 6,142 SqFt

23084 AFFIRMED PARK CT, Middleburg, VA 20117

MLS# VALO2124228

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
23559 PARSONS RD, Middleburg, VA 20117
Active
75

$2,900,000

4 Beds 5 Baths 4,832 SqFt

23559 PARSONS RD, Middleburg, VA 20117

MLS# VALO2124276

Listed by Sheridan-MacMahon Ltd.

Bright MLS (BMLS)
Bright MLS (BMLS)
105 REED ST, Middleburg, VA 20117
Price Dropped by $125K
62

$1,975,000

4 Beds 5 Baths 4,489 SqFt

105 REED ST, Middleburg, VA 20117

MLS# VALO2120426

Listed by Sheridan-MacMahon Ltd.

Bright MLS (BMLS)
Bright MLS (BMLS)
700 W WASHINGTON ST, Middleburg, VA 20117
Price Dropped by $65K
61

$1,625,000

3 Beds 3 Baths 2,240 SqFt

700 W WASHINGTON ST, Middleburg, VA 20117

MLS# VALO2120098

Listed by Sheridan-MacMahon Ltd.

Bright MLS (BMLS)
Bright MLS (BMLS)
23333 FOUR CHIMNEYS LN, Middleburg, VA 20117
Active
46

$2,850,000

4 Beds 7 Baths 6,287 SqFt

23333 FOUR CHIMNEYS LN, Middleburg, VA 20117

MLS# VALO2118900

Listed by Hunt Country Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
22282 ST LOUIS RD, Middleburg, VA 20117
Price Dropped by $9K
41

$449,900

2 Beds 1 Baths 772 SqFt

22282 ST LOUIS RD, Middleburg, VA 20117

MLS# VALO2115404

Listed by On The Market Properties

Bright MLS (BMLS)
Bright MLS (BMLS)
22244 SAM FRED RD, Middleburg, VA 20117
Under Contract
51

$1,550,000

3 Beds 3 Baths 3,226 SqFt

22244 SAM FRED RD, Middleburg, VA 20117

MLS# VALO2116714

Listed by Keller Williams Realty/Lee Beaver & Assoc.

Bright MLS (BMLS)
Bright MLS (BMLS)
22244 SAM FRED RD, Middleburg, VA 20117
Under Contract
51

$1,550,000

3 Beds 3 Baths 18.20 Acres

22244 SAM FRED RD, Middleburg, VA 20117

MLS# VALO2116974

Listed by Keller Williams Realty/Lee Beaver & Assoc.

Bright MLS (BMLS)
Bright MLS (BMLS)
1 FOXTROT KNOLL LN, Middleburg, VA 20117
Active
127

$5,500,000

4 Beds 6 Baths 3,882 SqFt

1 FOXTROT KNOLL LN, Middleburg, VA 20117

MLS# VALO2114350

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
37291 SEABISCUIT PARK PL, Middleburg, VA 20117
Price Dropped by $110K
87

$3,875,000

5 Beds 7 Baths 8,199 SqFt

37291 SEABISCUIT PARK PL, Middleburg, VA 20117

MLS# VALO2111662

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)

Data provided by Bright MLS. Property information is for the users personal, non-commercial use. Information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties that appear on the website may no longer be for sale, and may be under contract or sold. ©2026 Bright MLS, All Rights Reserved. Information is reliable but not guaranteed.

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    © 2026 The Luxury Collective | Compass - All rights reserved | Privacy Policy | DMCA Policy | Powered by Blok.

    The Luxury Collective DC is a real estate team affiliated with COMPASS, a licensed real estate broker and abides by all applicable Equal Housing Opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Some or all of the listings may not belong to the firm whose website is being visited. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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