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Historic Downtown Leesburg

I’ve highlighted a lot of communities and neighborhoods around Leesburg… but, "what about homes for sale in downtown Leesburg", you ask?! Well, before I jump into the types of homes for sale in downtown Leesburg, and their wide price ranges, let’s first talk about downtown Leesburg itself. (Or, if you want to skip this great write up of the downtown attractions, you can skip directly to the Real Estate section)

Why live near downtown Leesburg?

The number one draw for people to come to downtown Leesburg is…. drum roll please…  All the restaurants and shopping!  There are dozens and dozens and I’m not going to be able to name them all!  So, I hope nobody gets offended if I leave your favorite off this summary, but here goes my attempt at a brief "walking review" just by taking a stroll southbound on King Street one block

Map of downtown Leesburg restaurants

Let’s start at Rebellion Bourbon Bar!  Being at the corner of Market and King Street, some would call this intersection the very center of town.

A recent addition to the downtown area, Rebellion features a fantastic menu, and their bourbon selection is ENORMOUS!  They have also started adding live music during the week!  They have two levels, with a “speak easy” section up stairs and even offer a private VIP membership area where you can smoke cigars.

The Wine Kitchen

Moving south towards Loudoun Street, you'll find this cute little restaurant, which also happens to be one of my favorite places to eat.  I love meeting friends and clients here for lunch during the week too!

In addition to having great food, they have a constantly rotating wine selection.  I highly recommend getting a wine flight as they have these funny little write up cards to go with each wine.   I don't know who comes up with these write ups, but they're awesome!!  The wine Kitchen is not very big, so you might want to call ahead and make a reservation on the weekend.


Right across the street from the Wine Kitchen is Tarbender's Lounge, owned by my friend, Paul Zangos  (aka Paul Tarbender)!!  It's a very 1920s vibe.

Paul Zangos (aka Paul Tarbender)

It’s kind of a hidden little Speak Easy that you have to enter through a secret door disguised as a phone booth.  I’m serious!  Check out the video I did three years ago highlighting Tarbender’s here, which includes walking through the secret phone booth door!    And Tarbender's often has a jazz musician on the weekends too!

King Street Oyster Bar

Couldn’t get a reservation at the Wine Kitchen? No worries, the Oyster Bar has you covered!   Don't worry, they don't just serve oysters!  The Oyster Bar has a great menu with lots of variety, the food is delicious and the drinks are top notch!  If you want to hide, the Oyster Bar has one or two tables on the back deck that can only be accessed by walking through part of the kitchen!  But, if you want to be "seen" you might get lucky and get a window table where you can watch everybody walk by.

Black Hoof Brewing Company

Directly across from the Oyster Bar, this place seems to be packed every time I walk by no matter what time of day!

Black Hoof Street View
Black Hoof allows pets... all kinds of pets!

If you are looking for good brews and good times, you’ll find them at Black Hoof apparently!   But, I’ll be honest, I have not actually visited yet.  But it’s so crowded all the time… it must be good!  And you can bring your pet... ANY pet!!!!  LOL


Aptly named as you enter through a tiny little side alleyway that leads to their alcove seating and the main entrance.  This place is super cute.  And they’ve recently expanded their back patio and deck seating where you’ll find the place packed on warm days.  The food is good, the atmosphere is unique, and sometimes they have a live acoustic musician on the weekend!

Echelon Wine Bar

One of my new favorite places to eat and drink in downtown Leesburg... if you thought finding the entrance to Tarbender’s was hard, wait til you see this one.  The front door is just a plain looking door, so if you aren't looking UP as you walk along the sidewalk, you'll completely miss the sign for it.  Below you can see the narrow stairs that lead down to it from the door.  Inside it's gorgeous!  And don't let the pictures fool you, I like to think it’s a secret, but the place is usually packed!   They have an enormous wine cellar and all their food is like artwork!

Senor Ramon's Taqueria

Catty corner to Delirium, this is easily a top 3 taco place in all Loudoun county.  It has kind of an industrial vibe and almost feels like fast food (they do serve it up pretty quickly).  It’s not very “bar” like, though they do make great margaritas!  And the tacos are amazing!   If you don’t want to pay a ton of money for some great tacos, this is it!  And they have some "interesting" ingredients here for the more adventurous types, including beef tongue!

Black Walnut Brewery

If Black Hoof Brewery was too crowded, or just isn’t your scene, you can head just one block past Loudoun Street to find Black Walnut Brewery.  Black Hoof and Black Walnut are VERY different places.  Black Walnut Brewery is super laid back and are constantly changing up their craft beers.   Inside is cozy, but they have a great outdoor area with fire pits to chill out also.  In the warmer months, they will have live music for everybody to enjoy.  Very dog friendly also!  If you just want to chill out and have a beer (or two), this is the place.  I should mention that neither brewery is really a "restaurant".  They have some food, but you might consider getting Senor Ramon's to go and bring it down to enjoy with a beer!

Schmidt's BBQ

If, instead, you turn left and go east on Loudoun Street, you’ll find some great BBQ.  It's a great stop for lunch, and on the weekend's the place can get packed as they often feature live bands during the warmer months!  Be sure to check their schedule online to see who's playing!

Dynasty Brewing and Loudoun Brewing Company

There are no lack of Brewing companies in downtown Leesburg.  And on this journey, go just one block past Schmidt’s BBQ, and you’ll find Dynasty Brewing on your right, another very cool and laid back local brewer.    I have to give a shout out to Loudoun Brewing Company also, which is on the other side of downtown Leesburg, a little farther away, but is owned by my friend Phil Fust.  Great beer and people!  Like the other breweries, these are not really "restaurants", so you should check if they are having music and/or a food truck that weekend.  Both often do!

Market Station

And, finally, keep going just a few more yards east on Loudoun Street and you’ll make it to Market Station, home of Fireworks Pizza, Los Tios Mexican Grill and one of my favorite fine dining restaurants, Tuscarora Mill, locally known simply as “Tuskies”.  The bar at Tuskie’s is great, and the menu is delicious. My husband and I often go here and just sit in the bar area, rather than the main dining section, just for the vibe.

My daughter actually worked here through high school as a hostess, so we have a special affinity for this place.  And here's a little money saver tip… they sell $100 gift cards at Costco for only $80!!

MacDowell's Beach

And lastly, right across the street from Tuskies is MacDowell’s Brew Kitchen, now more commonly known as MacDowell’s Beach!  In the summer, the Beach is the place to be for live music, tasty beverages and "beach" food.  Grab a burger and a beer, hang out with friends (or make new ones), and enjoy the show!!

MacDowell's Beach has music

Take off your shoes and bury your toes in the sand as you jam out to some of the best local musicians and bands in the area!  On a Saturday or  Sunday afternoon you might hear the soothing sound of island steel drums or lone acoustic musician.  While on a Friday or Saturday night jam out and dance on the beach until the sound ordinance kicks in at 10pm!  They also have a large indoor area for when they have bands going to midnight or the whether turns ugly!

More than restaurants

I know I’ve literally just named over a dozen restaurants… and there are literally a dozen more I didn’t get a chance to name!  And dotted in between all these restaurants are cute shops like Very Virginia, The Resourceful Woman, The Lucky Knot and so many others!!!

And, of course, I have to mention Tally Ho.  The former local theater, Tally Ho has been transformed into a live performance venue where nationally touring bands come and perform.   You would be amazed at how AWESOME some of these nationally touring tribute bands are.  For example, “The Four Horsemen” is the number one Metallica tribute band in the country, performing almost a hundred shows a year across the United States.

Tally Ho bands

For $20-$40 you can get a near front row, album quality, performance of your favorite songs that will sound like the real deal!!!    Considering how expensive concert tickets have become, this is a GREAT way to rock out to your favorite songs performed live without breaking the bank!  


They also sometimes have some "up and coming" original bands that are making a name for themselves, and occasionally DC Improv hosts rising professional comedians here!  It’s worth checking the schedule for the next month to see if they have something coming you like!

Downtown Leesburg Big EVENTS

Downtown Leesburg is also home to a LOT of special events where they close the streets down.  In warm months, the town shuts down King Street between Loudoun and Market Street for “Sidewalk dining” on Friday evenings from 5-9pm.  It’s a great opportunity to walk around outside with a drink and eat outside and mingle with folks.

And they also have planned “events” like the Leesburg classic car show or the Leesburg Flower & Garden Festival, which lasts all weekend.  You can find the full list here. If you missed it this year, here’s a short drone video of the Flower & Garden Festival from this April!  I’m hoping to do a full write up on it in my blog section before the 2024 Festival!

Need more? What else could possibly be downtown!?!?   Well, it is also the center of government for Loudoun County!   So, if you’re a lawyer, there’s certainly a lot of appeal to living close to where you work!  But, I love that right across from the courthouse is a biker bar called Downtown Saloon with a sign that says, “Better Off Here Than Across The Street”… and also happens to be right next to our local tattoo parlor.   Gotta love it!

Onto the Real Estate!!

Oh my gosh, that was a lot of information!  But, now that we’ve got that out of the way, let’s talk about some of the homes for sale in downtown Leesburg!!  Finally!!!


If you're looking for homes for sale in downtown Leesburg, you’ve got TWO Options!

Option 1: Historic Leesburg Homes

As I illustrated above, the section of King Street between Market and Loudoun Street sort of defines downtown Leesburg.  But parallel and adjacent to those streets, you have a lot of narrow, one way streets that are lined with historic homes.

Here’s a great example of a 4,900 sqft home on Cornwall Street that sold at 2.1M!  Originally built somewhere around the year 1760, this home literally pre-dates the United States of America!!!  And even though it’s just one block from Market Street, it actually sits on half an acre!

11 Cornwall Street Historic Home Front
11 Cornwall Street Historic Home Back

Prices can vary greatly here… just a few houses down, on the same street, this home sold for $995K in July.

Originally built in 1769, and at 3,800 square feet, this home has seen a LOT of renovations over the years.  But you’re still owning a piece of history! Check out the wood ceilings and stone walls in the picture below!

11 Cornwall Street Historic Home Basement

Not EVERY home in downtown Leesburg is "historic" technically.  A few hundred yards in the other direction, and you’ll find homes like this 2,100 sqft stone house built in 1953, that sold for $737K.

If you’re interested in finding a “historic” home for sale in downtown Leesburg here, let me know and I can put together a custom search for you.  There are a lot of factors that go into finding a historic home and I’d love to work with you on it.  Or, if you’re thinking of selling your home in downtown Leesburg, give me a call, I’d love to help you maximize your home sale!

Option 2:  Something a little newer..

If we venture just a few blocks south on King Street, right along the W&OD trail, they have actually built a brand new condo complex called King Street Station.  These are super luxury, modern one and two bedroom condos finished in 2020.  Here’s an example of a 1,750 sqft, two bedroom condo, that sold in 2024 for over $900K!!  However, prices definitely vary.  A one bedroom sold in 2023 in the mid $400s.

But, if you can walk just a little bit farther away, just south of Market Station (near the Tuscarora Mill & MacDowell’s Beach area) there is a new 3 & 4 bedroom townhome community called Crescent Place.  It's still very walkable to downtown and you get a lot more for your money here, in my opinion.  At the end of last year (2023) three bedroom townhomes with almost 2,000 sqft of living space were selling for under $700K.  And four bedroom townhomes with 2,800 sqft of living space were selling for under $800K.

Another great thing about being in downtown Leesburg is your proximity to the W&OD Bike Trail.  If you haven’t checked out my posts on why the W&OD is so awesome, check it out here!   And both of these newer developments are literally right next to the trail.   Crescent Place also has some cute shops as part of the development including a bike shop!

And as I mentioned before, there are a LOT of neighborhoods just outside the downtown area.  The previous neighborhood I lived in was Old Waterford Knoll and my house was just under a mile to downtown Leesburg.  So when looking for homes for sale in downtown Leesburg, it might be wise to broaden the aperture a little just to see what's nearby.  Old Waterford Knoll is just one example... you can also checkout the VERY large neighborhood of Exeter, which is also very close to downtown Leesburg.  Send me a message and I can help!


As a 20+ year Loudoun resident, I know this area well, and as a top producing Real Estate agent, I know how to best market your property and maximize the sale of your home.  You deserve to work with the best!  If you are thinking of buying or selling in this area, give me a call!  I’d love to put all my knowledge, resources and energy to work for you!  I’m definitely always up for getting together at any of the great restaurants downtown to discuss!

Tarbender's Lounge

Right across the street from the Wine Kitchen is Tarbender’s Lounge, owned by my friend, Paul Zangos  (aka Paul Tarbender)!!  It's a very 1920s vibe.

Places to Live in Historic Leesburg
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