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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-3PM
45

$2,950,000

5 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)
1310 DELAPLANE GRADE RD, Upperville, VA 20184
Under Contract
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)
1150 POPLAR ROW, Upperville, VA 20184
Coming Soon
1

$950,000

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)
22202 NEWLIN MILL RD, Middleburg, VA 20117
New
37

$750,000

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)
34520 ATOKA CHASE LN, Middleburg, VA 20117
Active
100

$2,999,999

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)
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)
37143 ADAMS GREEN LN, Middleburg, VA 20117
Active
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
Active
63

$1,495,000

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)
38386 LITTLE RIVER TPKE, Middleburg, VA 20117
Active
92

$2,985,000

5 Beds 5 Baths 4,893 SqFt

38386 LITTLE RIVER TPKE, Middleburg, VA 20117

MLS# VALO2117342

Listed by MAXVALUE, REALTORS

Bright MLS (BMLS)
Bright MLS (BMLS)
22065 WHITETAIL RIDGE LN, Middleburg, VA 20117
Pending
61

$1,849,000

3 Beds 4 Baths 3,825 SqFt

22065 WHITETAIL RIDGE LN, Middleburg, VA 20117

MLS# VALO2125122

Listed by Washington Fine Properties, LLC

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

$1,300,000

4 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
Active
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)
33960 WELBOURNE RD, Upperville, VA 20184
Price Dropped by $50K
43

$548,000

3 Beds 1 Baths 1,405 SqFt

33960 WELBOURNE RD, Upperville, VA 20184

MLS# VALO2124666

Listed by Corcoran McEnearney

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)
12 STONEWALL CT, Middleburg, VA 20117
Price Dropped by $24K
32

$474,999

2 Beds 3 Baths 1,200 SqFt

12 STONEWALL CT, Middleburg, VA 20117

MLS# VALO2120882

Listed by Long & Foster Real Estate, Inc.

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 $10K
41

$459,000

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)
23650 GRASTY PL, Middleburg, VA 20117
Under Contract
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)

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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