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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

505 MARTINGALE RIDGE DR, Middleburg, VA 20117
Open Sat 11AM-1PM
45

$2,950,000

4 Beds 5 Baths 3,993 SqFt

505 MARTINGALE RIDGE DR, Middleburg, VA 20117

MLS# VALO2097614

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
35159 ROSECROFT LN, Middleburg, VA 20117
New
47

$749,000

3 Beds 2 Baths 1,662 SqFt

35159 ROSECROFT LN, Middleburg, VA 20117

MLS# VALO2115226

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
23650 GRASTY PL, Middleburg, VA 20117
Active
74

$1,825,000

4 Beds 5 Baths 4,813 SqFt

23650 GRASTY PL, Middleburg, VA 20117

MLS# VALO2114762

Listed by Thomas and Talbot Estate Properties, Inc.

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)
21051 ST LOUIS RD, Middleburg, VA 20117
Active
102

$3,395,000

5 Beds 8 Baths 8,442 SqFt

21051 ST LOUIS RD, Middleburg, VA 20117

MLS# VALO2114338

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
100 FOX RUN TER, Middleburg, VA 20117
Active
14

$927,000

4 Beds 5 Baths 2,510 SqFt

100 FOX RUN TER, Middleburg, VA 20117

MLS# VALO2114368

Listed by Samson Properties

Bright MLS (BMLS)
Bright MLS (BMLS)
35571 MILLVILLE RD, Middleburg, VA 20117
Pending
50

$1,950,000

4 Beds 6 Baths 5,262 SqFt

35571 MILLVILLE RD, Middleburg, VA 20117

MLS# VALO2112484

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
37291 SEABISCUIT PARK PL, Middleburg, VA 20117
Price Dropped by $115K
89

$3,985,000

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)
17 STONEWALL CT, Middleburg, VA 20117
Under Contract
28

$449,900

2 Beds 2 Baths 1,200 SqFt

17 STONEWALL CT, Middleburg, VA 20117

MLS# VALO2111848

Listed by Ross Real Estate

Bright MLS (BMLS)
Bright MLS (BMLS)
1610 DELAPLANE GRADE RD, Upperville, VA 20184
Active
123

$11,200,000

4 Beds 4 Baths 365.60 Acres

1610 DELAPLANE GRADE RD, Upperville, VA 20184

MLS# VAFQ2019810

Listed by Hunt Country Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
21846 TRAPPE RD, Upperville, VA 20184
Pending
50

$19,800,000

11 Beds 13 Baths 17,000 SqFt

21846 TRAPPE RD, Upperville, VA 20184

MLS# VALO2111024

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
35162 NOTRE DAME LN, Middleburg, VA 20117
Active
68

$2,289,000

4 Beds 4 Baths 7,167 SqFt

35162 NOTRE DAME LN, Middleburg, VA 20117

MLS# VALO2111254

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
34642 ATOKA CHASE LN, Middleburg, VA 20117
Active
121

$4,395,000

5 Beds 4 Baths 3,344 SqFt

34642 ATOKA CHASE LN, Middleburg, VA 20117

MLS# VALO2110916

Listed by Douglas Elliman of Metro DC, LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
1610 DELAPLANE GRADE RD, Upperville, VA 20184
Active
123

$11,200,000

4 Beds 4 Baths 8,613 SqFt

1610 DELAPLANE GRADE RD, Upperville, VA 20184

MLS# VAFQ2019532

Listed by Hunt Country Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
208 CHESTNUT ST, Middleburg, VA 20117
Active
23

$1,100,000

2 Beds 2 Baths 2,522 SqFt

208 CHESTNUT ST, Middleburg, VA 20117

MLS# VALO2109210

Listed by Century 21 Redwood Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
606 MARTINGALE RIDGE DR, Middleburg, VA 20117
Active
43

$3,359,000

4 Beds 5 Baths 3,907 SqFt

606 MARTINGALE RIDGE DR, Middleburg, VA 20117

MLS# VALO2097580

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
38793 CHELTEN LN, Middleburg, VA 20117
Active
61

$5,500,000

5 Beds 10 Baths 16,667 SqFt

38793 CHELTEN LN, Middleburg, VA 20117

MLS# VALO2094274

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
2 STAGECOACH RIDGE LN, Middleburg, VA 20117
Under Contract
11

$3,375,000

4 Beds 4 Baths 1.49 Acres Lot

2 STAGECOACH RIDGE LN, Middleburg, VA 20117

MLS# VALO2095432

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
10157 JOHN S MOSBY HWY, Upperville, VA 20184
Active
80

$2,725,000

4 Beds 3 Baths 3,216 SqFt

10157 JOHN S MOSBY HWY, Upperville, VA 20184

MLS# VAFQ2016372

Listed by Thomas and Talbot Estate Properties, Inc.

Bright MLS (BMLS)
Bright MLS (BMLS)
601 MARTINGALE RIDGE DR, Middleburg, VA 20117
Pending
51

$3,750,000

4 Beds 7 Baths 6,110 SqFt

601 MARTINGALE RIDGE DR, Middleburg, VA 20117

MLS# VALO2092664

Listed by EXP Realty, LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
4 FOXTROT KNOLL LN, Middleburg, VA 20117
Active
45

$3,550,000

4 Beds 4 Baths 5,120 SqFt

4 FOXTROT KNOLL LN, Middleburg, VA 20117

MLS# VALO2087682

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
400 MARTINGALE RIDGE DR, Middleburg, VA 20117
Active
21

$2,700,000

2 Beds 2 Baths 3,963 SqFt

400 MARTINGALE RIDGE DR, Middleburg, VA 20117

MLS# VALO2087514

Listed by Corcoran McEnearney

Bright MLS (BMLS)
Bright MLS (BMLS)
110 N MADISON ST, Middleburg, VA 20117
Active
15

$3,200

3 Beds 2 Baths 1,575 SqFt

110 N MADISON ST, Middleburg, VA 20117

MLS# VALO2113736

Listed by LPT Realty, LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
6 PENDLETON ST, Middleburg, VA 20117
Active
77

$2,250,000

6 PENDLETON ST, Middleburg, VA 20117

MLS# VALO2112588

Listed by Thomas and Talbot Estate Properties, Inc.

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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