Leesburg Historical Real Estate

COMING SOON! Great opportunity in a highly desirable in-town location. This distinctive Victorian home offers tremendous character and potential and is ready for its next chapter. The property needs significant renovation and is being offered strictly AS-IS. An excellent opportunity for an investor, renovator or buyer looking for a substantial project in a location that is difficult to replicate. Cash offers strongly preferred. Additional information will be available when the property becomes Active.

724 Valley View Ave Sw, Leesburg

Listing courtesy of Realty ONE Group Capital. Contact:

$995,000

4 Beds ⋅ 4 Baths

No HOA. A storybook setting, a charming 1941 stone Colonial, and panoramic views overlooking historic Leesburg make this 2.58-acre property truly special. With its timeless architecture, inviting cottage charm, and distinctive character that simply cannot be replicated in new construction, this lovely home offers a rare blend of classic appeal and modern convenience, less than five minutes by car from downtown Leesburg. Set on a rise, the property features a circular driveway, beautiful landscaping, and a welcoming stone walkway leading to the front entry. Inside, hardwood floors and classic architectural details set the tone. Located at the rear of the home, the classic living room features a wood-burning fireplace, a bay window with a charming seating nook, and breathtaking panoramic views. The nicely updated kitchen features cherry cabinetry, granite countertops, and French doors opening to the deck, where the expansive vistas take center stage. Just off the kitchen's dining area, the family room features a striking stone wall and another set of double doors leading to the deck, creating a wonderful connection between indoor and outdoor living. A main level study features built in bookshelves, a powder room and a door to a beautiful stone terrace overlooking the surrounding landscape and views. A handy mud room is located on the main level with a side door for everyday use. Upstairs, three spacious bedrooms feature hardwood floors and lovely views. The primary bedroom enjoys an updated 2026 bath featuring and panoramic views. Two additional generously sized bedrooms share and nicely updated hall bath. The lower level features a recreation room with fireplace, an additional flex room with full bath and two utility rooms. The walk-out lower level opens to the level rear yard, offering ample room for play and outdoor enjoyment. Three 2- car detached garages provide exceptional versatility: an oversized garage with room for up to four vehicles and additional storage above, a second two-car garage conveniently located near the house, and a third garage ideal for gardening equipment, yard tools, and recreational toys. Beautiful landscaping and distinctive stonework enhance the property's appeal. Less than five minutes by car to historic downtown Leesburg, very close to the Dulles Greenway, and less than 30 minutes to Dulles International Airport, the location is as convenient as it is picturesque. Golf enthusiasts will appreciate being less than a two-minute drive from Beacon Hill's newly reopened golf course, where memberships are available, while equestrians will enjoy the proximity to Clairvaux LLC, an A-rated show barn in neighboring Beacon Hill. With public sewer and a private well, this remarkable property offers a wonderful blend of charm, privacy, and convenience. Whether envisioned as the perfect weekend retreat for enjoying all that Loudoun County has to offer, from dining, golf, and vineyards to equestrian events and shopping, or as a year-round home in which to create lasting memories, this is a rare opportunity to own a truly distinctive property. Charming, memorable, and one of a kind!

41025 Leesburg Overlook Ln, Leesburg

Listing courtesy of On The Market Properties. Contact:

$575,000

Northern Loudoun County is a beautiful area of rolling hills, mountain views, and historic places. All-brick ranch house on a scenic highway with the opportunity for a roadside farm stand or food truck. Almost 2 acres of land with a pond and a seasonal stream. No HOA. Zoned AR-1. New roof. Newly remodeled kitchen with white cabinets and a farmhouse sink. Genuine hardwood floors. New paint throughout. Shop in Leesburg or the Lovettsville Co-op Market. Explore Lucketts Antiques for charming, unique finds. Nearby Lovettsville has great cafes, restaurants, and shops, not to mention the annual Oktoberfest held in late September. Also close, historic Waterford (a National Historic Landmark) is a charming, well-preserved 18th and 19th-century village that hosts the fantastic Waterford Fair each year in October. Cross over the Potomac River to visit Frederick, Harper’s Ferry, or Brunswick. A commuter train to Washington, D.C. is available from Point of Rocks, MD (only 3 miles away). Point of Rocks also has a boat launch on the Potomac River and the C&O Canal towpath, a walking & bike path that goes all the way to Georgetown. This is a great place to relax and enjoy all four seasons. Listen to spring peeper frogs sing next to your pond and watch daffodils pop up around your yard. In summer, watch hummingbirds and butterflies while enjoying a cup of coffee on the back porch. Visit your raised-bed garden to snack on fresh cherry tomatoes. In fall, harvest from your paw paw and fig trees and watch the leaves on the mountainside change color. When the weather gets chilly, sit by your campfire or in front of your wood-burning stove. Love where you live!

12831 James Monroe Hwy, Leesburg

Listing courtesy of Corcoran McEnearney. Contact:

$975,000

Your Own Private Retreat on Nearly 7 Acres in Leesburg! Imagine starting your morning with coffee overlooking your own peaceful stretch of Loudoun County countryside, spending the afternoon working on a project in your detached garage, and ending the day enjoying the quiet of your surroundings all just minutes from downtown Leesburg. 2 miles to Walmart Compass Creek Shopping. Welcome to 19347 Hundred Acres Lane, where 6.77 acres of privacy and possibility meet the convenience of an exceptional location. With over 3,300 square feet of living space, this home offers a comfortable, versatile layout designed for everyday living and entertaining. One of the home's standout features is the main-level primary suite with its own private sitting room, creating a relaxing retreat within the home. The first floor also features a spacious kitchen with a center island and stainless steel appliances, offering plenty of room for preparing meals and gathering. A dedicated home office, family room, separate living and dining rooms, and conveniently located laundry room provide a wonderful balance of everyday comfort and entertaining space. Upstairs, two additional bedrooms and a full bathroom offer plenty of flexibility. Fresh paint and new carpet in 2026 give the home a fresh, inviting feel, while a new water heater rounds out the recent improvements. Beyond the home, the property offers something increasingly difficult to find room to truly spread out. Whether enjoying a quiet evening on the multi-level deck, spending time outdoors, or tackling projects in the detached three-car garage with electricity, there's space to enjoy life at your own pace. The garage provides excellent versatility for vehicles, equipment, storage, or a workshop, adding both function and flexibility to this acreage property. And while the setting feels removed from the everyday hustle, you're just minutes from historic downtown Leesburg, where locally owned restaurants, charming shops, breweries, and community events create an inviting small-town atmosphere. Convenient access to the Dulles Greenway keeps the rest of Northern Virginia within easy reach. Nearly seven acres. A main-level primary suite. A detached three-car garage with electricity. And a location that brings it all together. At 19347 Hundred Acres Lane, it's not just about having more space it's about having more opportunities to enjoy it. Come experience the setting, explore the property, and see what makes this Leesburg retreat so special.

19347 Hundred Acres Ln, Leesburg

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$475,000

4 Beds ⋅ 3 Baths

A great opportunity to own one of the larger townhomes in Virginia Knolls, this is a 4-bedroom, 3-full bathroom townhome and offering more than 1,450 square feet of above-grade living space. This move-in-ready home features fresh paint, brand-new carpeting, and professional cleaning throughout. The main level offers a spacious living room and dining/family room with a sliding glass door leading to the fully fenced backyard—ideal for outdoor enjoyment, entertaining, or relaxing. Ideally situated near the cul-de-sac, this home offers added privacy and a peaceful setting. Virginia Knolls provides convenient access to Route 7, Route 15, the Dulles Greenway, and all that historic downtown Leesburg has to offer, with Dulles International Airport just 20 minutes away. A wonderful opportunity to make this spacious townhome your own!

336 Roanoke Dr Se, Leesburg

Listing courtesy of Keller Williams Realty Dulles. Contact:

$100,000

2 Beds ⋅ 1 Baths

Investor and builder opportunity in Leesburg, Maurice River Township, with the expensive site work already done. A new septic system about a year old and sized for a five-bedroom home, plus a new well about a year old, serve a 0.31-acre wooded lot at the end of a quiet dead-end street off Route 47. The existing structure is a single-wide mobile home with a large addition and is offered strictly as-is for its land and infrastructure value: it has a broken floor, structural and framing issues, loose walls, a roof at the end of its life and likely mold, and it should be treated as a teardown. Bring your plans for a replacement manufactured home or a new build and let the new well and septic carry the project Buyer to verify zoning,permits and rebuild requirements with Maurice River Township. Showings are by confirmed appointment only and a signed hold harmless agreement is required before entry; the property is not safe to walk without caution. Priced at land value with the site work done. Bring your offer.

21 Cain Ave, Leesburg

Listing courtesy of Keller Williams Realty - Moorestown. Contact:

$1,875,000

4 Beds ⋅ 2 Baths

Welcome to a remarkable 227-acre property in the Lucketts area of Leesburg, offering a rare combination of country living, existing improvements, agricultural possibilities, and room to explore a thoughtful vision for the land. Natural light fills the residence, creating bright, inviting spaces for relaxing and gathering. The welcoming front porch offers a place to enjoy morning coffee and the surrounding countryside, while the kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Comfortable bedrooms provide space to unwind, and the basement offers additional flexibility for recreation, hobbies, storage, or working from home. Beyond the residence, the property's conservation framework preserves a range of possibilities, subject to applicable easements, approvals, and county requirements. Potential uses may include agricultural activities such as growing grapes, operating the existing residence as a short-term rental, constructing one additional residence within the designated area, and certain temporary or seasonal gatherings. An existing permitted barn or outbuilding may offer opportunities for compatible activities conducted within the structure without material exterior changes. Events involving 100 or more guests may be considered through the Land Trust's written approval process. The property is not currently approved as a full winery or permanent wedding venue. Buyers interested in pursuing a vineyard, short-term rental experience, private gatherings, or other compatible concepts should review the governing conservation documents and consult the Land Trust and Loudoun County regarding permitted uses and required approvals. The surrounding Lucketts area offers access to distinctive northern Loudoun destinations, including Red Rock Wilderness Overlook Regional Park, Temple Hall Farm Regional Park, the Potomac River corridor, local wineries, The Old Lucketts Store, and the dining, shopping, and services of downtown Leesburg. With 227 acres, an existing residence, additional dwelling potential, and agricultural possibilities within its conservation framework, this property presents an opportunity to explore a distinctive vision for land and lifestyle in northern Loudoun County. Photos may be virtually staged

43086 Lucketts Rd, Leesburg

Listing courtesy of Keller Williams Realty. Contact:

$950,000

4 Beds ⋅ 2 Baths

This charming Cape Cod-style home, built in 1950, offers 1,638 sq. ft. of living space on a generous 0.99-acre corner lot in the desirable Leesburg neighborhood. The interior features a cozy kitchen with table space, perfect for casual dining, and a welcoming living area highlighted by a wood-burning fireplace. With four bedrooms and two full bathrooms, this home provides ample space for relaxation and comfort. Enjoy outdoor living with a wrap-around porch and deck, ideal for entertaining or unwinding. Additional exterior features include secure storage options and outbuildings, enhancing functionality. The property is conveniently located near public transportation, commuter lots, and an airport, ensuring easy access to the surrounding area Local amenities, including parks and shopping, are just a short drive away, making this home a perfect blend of tranquility and convenience. Off-street parking is available for added convenience. For investors and developers, this property is Zoned R-6 (Moderate Density Residential) within the Town of Leesburg. R-6 zoning permits single-family detached homes, duplexes and cluster development by right, subject to applicable Town requirements. Approximately 0.99-acre parcel offers potential redevelopment opportunities given its size and Leesburg location. Buyers and developers should independently verify allowable density, subdivision potential, rezoning opportunities and intended use with the Town of Leesburg. Property is being marketed for its existing residential use as well as its potential redevelopment opportunities.

130 Ne Fort Evans Rd Ne, Leesburg

Listing courtesy of Keller Williams Realty. Contact:

$1,092,500

5 Beds ⋅ 3 Baths

PRICE IMPROVEMENT! Welcome to Hiddenhollow! This incredible Folk Victorian Farmhouse retreat nestled away at the quiet end of Hiddenhollow Lane. Masterfully restored and meticulously updated over recent years this historic estate pairs timeless charm with contemporary refinement. Detailed with dedication to old and new craftsmanship that promises to captivate! The Estate & Grounds- Secluded on 11.3 private acres of Virginia countryside, the property is a true sanctuary. The expansive grounds feature a private, Bluegill-stocked pond, winding woodland trails, a vegetable garden, a chicken coop, a shed and a secure fenced space within. Zoned AR-1 with no HOA, covenants, or restrictive bylaws, the acreage offers uncompromised freedom. It can be suited for equestrian use, hobby farming, and/or adding custom ancillary structures. To note, exterior electrical for E/V charging, camper, a yurt, guest utility, the options are open! The Residence- Originally constructed in 1870, a restored Civil War era farmhouse boasting nearly 3,000 square feet of warm and welcoming space! This generous 5-bedroom (including a versatile main level suite bedroom) and 2.5 baths. Unbeatable charm such as the stunning staircase and banister, custom walnut bookcases in the library and original (refinished) rustic heart-pine wood floors! While the home proudly preserves its romantic heritage, a comprehensive overhaul of structural elements, mechanical systems, and aesthetic finishes and furnishings ensures absolute modern comfort mixed with the interiors balance of mid-century with vintage accents. Location & Lifestyle- Positioned in the heart of Loudoun County's renowned wine country, the estate sits just 15 minutes from historic downtown Leesburg, 5 miles from the commuter-friendly MARC train, and under an hour from the Washington, D.C. line. Surrounded by premier wineries, artisanal craft breweries, cideries, and championship golf courses, Walnut Hill is more than a home—it is a lifestyle ready to be inherited. Simply pack your bags and step into your next chapter. Offered completely turnkey! Walnut Hill currently operates as a highly successful luxury Airbnb with an exceptional income stream and glowing guest reviews. No start-up capital, proven, earning and ramping!

13722 Hiddenhollow Ln, Leesburg

Listing courtesy of Compass. Contact:

$115,000

INVESTOR ALERT! This home would be a great flip or great for a small family just starting out that wants to make it their own. Ready to be renovated. Lot is a decent size. All appliances included. Shed staying in its AS IS condition. Seller says come take a look and make your offer. No info on septic. At this price, this home wont last. AS IS SALE

5 Ward Ave, Leesburg

Listing courtesy of Collini Real Estate LLC. Contact:

$175,000

Former fellowship hall with a spacious, open recreation area that can accommodate a variety of gathering layouts. The adjoining kitchen offers a long run of cabinets and counter space, a central worktable, and a multi-basin sink. Additional rooms provide space for an office or storage. The building has a prominent street-facing entrance and a generous grassy area. A versatile property with potential for community, meeting, or other uses, subject to zoning and required approvals. Sold as is; buyer is responsible for inspections, certifications, and any needed repairs. Zoned VC-Village Center

108 New St, Leesburg

Listing courtesy of Keller Williams Prime Realty. Contact:

$250,000

A unique opportunity to own a traditional church property filled with character and historic charm. Upon entering, visitors are welcomed into a spacious foyer and gathering room featuring beautiful stained-glass windows, rich wood trim, and ample space for greeting guests, fellowship, meetings, or small gatherings before entering the main sanctuary. The sanctuary features rows of original-style wooden pews, additional stained-glass windows, a raised altar area, rich wood accents, and an ornate pressed-tin ceiling. The building also includes an additional flexible-use room, restroom, storage space, and an exterior accessibility ramp. An interior entrance provides access to the basement utility area containing the heating system and other mechanical equipment. The cemetery located on the right side of the church is included with the property. The church and cemetery parcel is identified as Block 00289, Lot 00016. Also included is Block 00284, Lot 00004.01, a separate corner lot located at New Street and Station Road, catty corner from the church. The church at 8 Station Road does not currently have a designated parking area. Subject to all required municipal, zoning, and other approvals, the additional lot may offer the potential to create parking for the church. The property is located within the VC–Village Center District. Potential uses within this zoning district may include certain small-scale businesses and shops, a winery, daycare center, private educational center, clubs or lodges, nursery, nonprofit assembly hall, studio, workshop, and other permitted uses. All proposed uses and improvements are subject to municipal review and approval. Buyers are responsible for confirming zoning, permitted uses, parking requirements, and intended plans directly with the township. The property and included lot are being sold completely AS IS. Buyer is responsible for all inspections, certifications, repairs, approvals, and due diligence.

8 Station Rd, Leesburg

Listing courtesy of Keller Williams Prime Realty. Contact:

$245,000

This charming Cape Cod home, built in 1945, offers a delightful blend of classic character and modern comfort. Step inside to discover a warm and inviting interior featuring beautiful hardwood floors and an open floor plan that seamlessly connects the dining and living areas. With three cozy bedrooms, including an entry-level option, this home is designed for convenience and ease. The full basement provides ample storage and potential for customization, while the main floor laundry hookups add to the practicality of daily living. Enjoy the fresh air on the spacious deck, perfect for entertaining or simply unwinding after a long day. Set on a generous 0.42-acre corner lot, the outdoor space offers endless possibilities for gardening, play, or relaxation. The detached garage provides additional storage and parking convenience. Located in a vibrant community, this home is just a short distance from local parks, schools, and essential public services, making it an ideal spot for those who value accessibility and community engagement. With a new septic, water treatment sytem, roof and central air system installed in 2024, as well as fresh paint and a remodeled bathroom all in 2024, this home is move in ready. Experience the charm and comfort of this lovely residence, where every detail invites you to create lasting memories.

647 Main St, Leesburg

Listing courtesy of The Property Co of NJ, LLC. Contact:

$999,000

4 Beds ⋅ 2 Baths

INCREDIBLE opportunity to own a beautifully renovated historic Colonial in downtown Leesburg’s Historic District, offering 1.106 acres, four bedrooms, distinctive historic outbuildings, and walkable access to downtown shops, restaurants, and community amenities! Combining timeless architectural character with modern updates, this exceptional property features an original restored carriage barn and historic kitchen house, creating a unique estate-like setting rarely found in an in-town location. Inside, original pine hardwood floors throughout reflect the home’s historic charm. The inviting living room features a wood-burning stove, while the dining area offers an ideal setting for entertaining. The updated galley kitchen blends everyday functionality with the home’s classic character. The main-level primary suite provides a private retreat, with potential for a screened porch overlooking the grounds. The beautifully renovated bath combines historic elegance and modern comfort with a classic clawfoot tub, oversized walk-in shower, and heated tile flooring. Three additional bedrooms upstairs offer flexible space for family, guests, or home offices. An enclosed, window-lined sleeping porch has been converted into an updated laundry area with built-in storage. Major improvements include NEW HVAC (2026), updated electrical and plumbing (2015), conversion from oil to natural gas heating (2015), central air conditioning and spray-foam attic insulation (2017), custom storm windows, and a new asphalt driveway (September 2026). The professionally waterproofed basement offers valuable storage and potential for a wine cellar, hobby space, or future finishing. Additional improvements include professional underpinning at the rear of the property, a professionally releveled detached shed, and low-voltage pipe warmers for added protection during freezing temperatures.The expansive grounds feature mature landscaping, gardens, a stone terrace, and mature sour cherry, apple, and nut trees, providing space for outdoor entertaining, gardening, recreation, and relaxation. The beautifully restored original carriage barn preserves an important piece of the property’s history, while its finished, weatherproofed upper loft provides versatile attic-style storage. The historic kitchen house, once the property's separate cooking space, remains a remarkable architectural feature and is currently used as a playhouse. With more than an acre in the heart of Leesburg, the property may offer potential for an accessory dwelling unit (ADU), subject to Loudoun County zoning, permitting, and other applicable approvals. Explore possibilities for multigenerational living, a private home office, or additional living space, subject to feasibility and approval. This is truly an exceptional home in an exceptional location!

431 S King St, Leesburg

Listing courtesy of Momentum Realty LLC. Contact:

$582,000

2 Beds ⋅ 2 Baths

Welcome Home to this 1920 Classic Colonial in the heart of Downtown Leesburg! A rare opportunity to own a piece of history. Location, Location, Location! NO HOA! This charming home has 2 bedrooms, 2 full baths and original Hardwood Pine Floors in the living room and freshly painted!! The back yard is fully fenced with a deck and spacious patio providing outdoor space for al-fresco dining and entertaining as you unwind & relax well into the evening! The deep lot allows room for expansion! The unbeatable location is just steps away from Leesburg’s vibrant historic downtown, you’re moments from award-winning restaurants, local shops, coffee spots, entertainment, W&OD trail, libraries and more! Outdoor enthusiasts will appreciate being just minutes from Ida Lee Park, offering miles of walking trails, athletic fields, tennis courts, a recreation center, pools, and year-round community activities. Shopping is just around the corner at the Leesburg Premium Outlets, while commuters will enjoy quick access to Route 7 and the Dulles Greenway, making travel throughout Northern Virginia a breeze. You're also only a short drive from One Loudoun, featuring premier shopping, dining, entertainment, and nightlife. And if you love Virginia wine country, you're in the heart of it all. Some of Loudoun County's most celebrated wineries, breweries, cideries, and farm breweries are just minutes away! It’s not just a home, it’s a lifestyle! Opportunities like this don’t come often. Own a piece of Historic Leesburg and make it your own!

221 South St Se, Leesburg

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$845,000

New Roof 2026 I Single Level Living This is your rare opportunity to own a beautifully renovated ranch-style home just a short walk from Historic Downtown Leesburg! Welcome to 131 Woodberry Road, where small-town charm meets modern comfort in an unbeatable location. Enjoy easy access to downtown Leesburg’s restaurants, shops, cafés and local events, with the W&OD Trail and Ida Lee Park, all within walking distance of your new home. This thoughtfully renovated 3BR, 1.5 bath home offers the ease of single-level living with beautiful hardwood floors, abundant natural light, and a warm inviting living room, centered around a wood burning fireplace. The light and bright kitchen features lots of storage, quartz countertops, stainless steel appliances, and beautiful porcelain tile flooring. The flexible floor plan provides options for guests, a home office, or additional living space. Step out back onto a spacious 550 sq.ft. deck overlooking the 0.29-acre lot, surrounded by mature trees. Your deck provides plenty of room for entertaining, relaxing or gardening. You will truly enjoy sipping your morning coffee on your 170 sq.ft covered front porch as you watch the morning sunrise With major renovations and a new roof, this home combines character with valuable upgrades. Beautifully maintained, conveniently located and full of charm, this home offers a unique opportunity to enjoy the best of Leesburg living with Historic Downtown right at your fingertips.

131 Woodberry Rd Ne, Leesburg

Listing courtesy of Real Broker, LLC. Contact:

$1,290,000

4 Beds ⋅ 3 Baths

Turn of the century renovated farmhouse on 33 acres with 1/2 mile of Catoctin Creek frontage. This is an exceptional parcel partially wooded and open with a possible extraordinary building site overlooking the Catoctin Creek and countryside. The Farmhouse has been completely renovated top to bottom with finished attic and stone basement. There are 4 BR and 2.5 baths., hardwood floors throughout. The kitchen and baths are beautiful. A renowned designer/stager with their skillful art has made this home a showplace. The Farmhouse is frame built clad with aluminum siding and is a three story home, side gabled with a centered steep pitch front gable and a fantastic rubble stone basement. The exterior has important embellishments with period detailing including scale shingles within the gables, turned porch spindles and flat jig saw cut trim. The covered full width front porch has round porch posts and the decorative balustrades and brackets. There are two additional covered side porches. There is a symmetrical facade and a standing metal seamed roof. This home has four finished levels including the basement and the walk-up attic. The updated interior is complete top to bottom job with current baths and kitchen. The full home renovation kept important architectural details including the original banister with turned balustrades, wood doors and window trim. This home has a large bright and airy rooms, porches to relax on, and separate cozy and inviting living spaces. This property is unique and the possibilities are endless. Possible two parcel subdivision, brewery, winery, other agriculture opportunities are available.

13049 Loyalty Rd, Leesburg

Listing courtesy of RE/MAX Executives. Contact:

$699,000

NEW PRICE - $699,000! A fresh new look and a new opportunity to own this charming 1923 farmhouse on 3.25 acres just minutes from downtown Hamilton and Leesburg. Recent updates include fresh paint, new front porch flooring, and a brand-new septic system. Full of classic farmhouse character, the home features charming details including a wood stove and built-ins, with plenty of outdoor space for entertaining, gardening, animals, or simply enjoying the acreage. The property offers a private, secluded feel while keeping shopping, dining, and major commuter routes just minutes away. Country living without feeling far from everything - now offered under $700K!

39014 Hughesville Rd, Leesburg

Listing courtesy of Samson Properties. Contact:

$975,000

2 Beds ⋅ 3 Baths

Built in 1795 and just a few blocks from the heart of downtown Leesburg, 222 West Market gives you something that is genuinely hard to find: a historic home with real character, a completely rebuilt interior, private outdoor space, and a two-story garage, all in a location where you can walk out the door and enjoy downtown. The interior was gutted and rebuilt in 1998 by Randy and Deloris DeHart, with the work later recognized with a 2000 Architectural Excellence Award. Their daughter, a landscape architect, designed the grounds, and that attention to how the house and outdoor spaces work together is still obvious today. The BRICK COURTYARD is one of the places that makes this house memorable. It is tucked behind the home, with planting beds, an arbor, and a water feature filled with fish, lily pads, and water plants. There is even a resident frog who has apparently decided he lives here too. Sit outside with coffee, dinner, or a glass of wine and the sound of the water makes it easy to forget you are right in the middle of town. Inside, you get the character of a historic home without giving up comfortable room sizes. The FAMILY ROOM is nearly 23 feet long with a fireplace and radiant heat underfoot. The large front STUDY has another fireplace and enough room to work from home, read, or create a separate sitting space. The KITCHEN sits between the two with rich wood cabinetry, double wall ovens, a pantry, and direct access to the courtyard, so indoor and outdoor living connect naturally. Upstairs, the floor plan gives you TWO GENEROUS BEDROOMS instead of a collection of smaller rooms. The PRIMARY SUITE is more than 20 feet deep with its own fireplace, multiple closets, and a private bath with a skylight that brings in natural light. The second bedroom is also spacious, with another full bath nearby. LAUNDRY ON THE BEDROOM LEVEL makes everyday life easier. A long driveway runs to the back of the property, where the oversized TWO-STORY STUCCO GARAGE sits tucked away from the street. You get real off-street garage parking in downtown Leesburg, plus unfinished space above for storage or future possibilities. And then there is the LOCATION. King Street, downtown restaurants, shops, coffee, events, and the W&OD Trail are all close by. Dinner does not have to involve getting in the car. Neither does a morning walk, a bike ride, or an afternoon downtown. 222 West Market is considered one of the buildings that helps give the Leesburg Old & Historic District its historic character and charm. With its history, architecture, private courtyard, garage, and walkable downtown location, it offers a way of living that is very hard to recreate anywhere else. This one is very special.

222 W Market St W, Leesburg

Listing courtesy of Samson Properties. Contact:

$450,000

**NEW, NEW, NEW!** If you’re looking for a home where the big-ticket updates have already been taken care of, this is the one! **PLUS $5,000 OFF YOUR CLOSING COSTS!!!**. This beautifully updated three-level Leesburg home has been extensively improved inside and out, including a **NEW HVAC system with whole-house dehumidifier and 10-year warranty (2026), NEW attic insulation (2026), NEW deck structural supports and joists (2026), NEW plumbing from the house to the street (2025), NEW washer (2023), NEW electrical panel (2021), NEW roof (2021), and NEW windows and sliding glass doors (2020)!** And the updates don’t stop there. The kitchen was remodeled in 2020 with **quartz countertops, stainless steel appliances, an eat-in area with table space, and a breakfast bar**, while LVP flooring runs throughout the main level. New ceiling fans in every room add even more comfort. The kitchen opens directly to the deck, creating an ideal flow for everyday living and entertaining. The spacious upper-level primary suite features a walk-in closet and updated full bathroom. On the lower level, a versatile bonus room provides the flexibility for a **fourth bedroom, guest room, home office, gym, or flex space**, while the recreation room offers comfortable additional living space and walks out to the patio and fenced backyard. Outside, enjoy the newly reinforced deck with **new structural supports and joists in 2026** and newer deck boards installed in 2023. The fenced backyard backs to open space and includes a storage shed, offering privacy and a peaceful place to relax or entertain. Additional improvements include a **water heater replaced in 2015 and updated exterior lighting (2015)**. With so many major systems, structural components, and finishes already updated, this home offers the rare opportunity to simply move in and enjoy—with far less to worry about down the road. All of this in a fantastic Leesburg location with convenient access to **Dulles International Airport, Metro, vineyards, Leesburg Premium Outlets, restaurants, shopping, entertainment, and Washington, DC.** **Extensively updated. Exceptionally maintained. Truly move-in ready. Come see everything that’s NEW!**

309 Shenandoah St Se, Leesburg

Listing courtesy of Samson Properties. Contact:

$150,000

4 Beds ⋅ 1 Baths

This spacious 2 story home with a full front covered porch is located in the historic area of Leesburg. The living room has an open staircase and large picture window, the formal dining room also has a large picture window and brick fireplace, the kitchen features white cabinets, a lot of cabinet space and double bowl sink. Off the kitchen is the laundry room with utilities. Also on the main floor is an office, family room and bedroom. Upstairs has 3 bedrooms and a full bathroom. There is a back staircase too. Located close to the Delaware River, shore points and Rt 55 for traveling.

628 Main, Leesburg

Listing courtesy of S. Kelly Real Estate LLC. Contact:

$1,495,000

4 Beds ⋅ 4 Baths

Historic Sleepy Hollow Farm: A Timeless Loudoun County Quaker Stone House. Listed on the National Register of Historic Places, this 11.45-acre farm offers total privacy and a breathtaking sense of arrival. As you come around the bend at the bottom of the long driveway, the gorgeous 1769 stone house suddenly comes into view against a backdrop of mature woods and rolling land. Welcoming you to the home is a classic covered front porch that spans the original section of the house, looking out over the historic stone spring house that still stands proudly in front of the residence. The main home totals approximately 3,600 square feet of finished space. It is anchored by the original 2-over-2 Quaker stone core featuring its visible 250-year timeline cornerstone, wavy glass windows, original plaster walls and ceilings, and intact wood floors that are likely original heart of pine. An 1867 expansion introduced a formal dining room and a lower chamber, which features a cozy, finished 400-square-foot walk-out den showcasing exposed stone walls and an authentic brick floor. A thoughtful two-story frame addition, added in1985 on the back of the house, expands the home for practical country living, adding a large country kitchen, which could be used as a comfortable dining or sitting area, a powder room, and a spacious laundry room. The second level features a primary suite with walk-in closets, a full bath, plus an additional bedroom, another full bath, and a powder room in the hallway of the original core house. Underneath this addition, a generous unfinished lower-level space provides excellent room for utility and storage. Remarkably, the residence relied directly on water from the historic spring house for centuries, right up until 2010 when a new well was added to fully modernize the home's water system. The house and pool area are nestled in front of the trees, beautifully framed by boxwood plantings. Outside, the rolling acreage is fully set up for a functional hobby farm or equestrian life, complete with a natural pond, two 4-stall barns, two run-in sheds, and an in-ground pool with several possibilities. This is a rare opportunity to own a beautifully preserved, classic piece of history on highly desired Thomas Mill Road. Fios is here. Seller's specific instructions: Listing agent must be present at showings. 24 hour notice to show. Buyers must be accompanied by their buyer agent and have a current lender pre-approval.

39902 Thomas Mill Rd, Leesburg

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$950,000

4 Beds ⋅ 3 Baths

CHARMING FARMHOUSE ON 20 PRIVATE ACRES WITH BARNS, POND & VIEWS! Nestled at the end of a long private gravel driveway lined with towering pines, this charming two-level Colonial farmhouse is tucked away on a breathtaking 20-acre rural property in the sought-after Chestnut Hill farming community. Offering privacy, tranquility, and endless possibilities for farming, horses, hobbies, or simply enjoying country living, this exceptional property combines comfortable living with ultimate privacy. Recently refreshed with neutral paint throughout and new luxury vinyl plank flooring on the main level, the home features over 2,300 square feet of living space. A welcoming full front porch provides the perfect place to relax and take in the pastoral surroundings, including views of the neighboring historic Chestnut Hill Mansion! Inside, a two-story foyer welcomes you into the home. The main level offers a convenient bedroom and/or office and full bath, a spacious living room, and a large country kitchen that opens seamlessly to both the screened porch and expansive rear deck. The front porch connects to a side porch, creating multiple outdoor spaces to enjoy the peaceful setting and sweeping pasture views in every direction. The upper level features a spacious primary suite with vaulted ceilings, a walk-in closet, and a private bath with separate shower and soaking tub. Two additional bedrooms, a secondary full bath, and an upper-level laundry room provide added convenience. The property is truly a rare rural retreat! A private pond sits beyond the home, while several outbuildings provide incredible flexibility for agricultural, equestrian, storage, workshop, or recreational uses. Highlights include a picturesque bank barn offering 2,280 square feet with unforgettable panoramic farm views, a 2,000-square-foot common stable, and a 1,680-square-foot three-wall storage shed, and two additional storage sheds. With no HOA and abundant open space, the opportunities are endless. Farm, fish, raise animals, cultivate gardens, pursue your hobbies, or simply enjoy the serenity and beauty of Loudoun County's countryside. House and property sold strictly as-is. Ideally located just off James Monroe Highway, the property offers convenient access to major commuter routes while remaining worlds away from the hustle and bustle. Enjoy nearby farmers markets, roadside farm stands, and the charm of Lucketts Village. Historic downtown Leesburg, with its vibrant dining, shopping, and entertainment scene, is just minutes away. Easy access to Maryland makes this an exceptional location for commuters seeking the best of rural living without sacrificing convenience. A rare opportunity to own a private farmstead in one of Loudoun County's most picturesque settings. Property sold in As-Is condition, Seller prefers Entitle First Title in Leesburg.

42277 Chestnut Hill Ln, Leesburg

Listing courtesy of Real Broker, LLC. Contact:

$399,900

Price improvement - the best value in Leesburg! Welcome to this charming townhome in the established Virginia Knolls community, just moments from the heart of historic downtown Leesburg. Thoughtfully maintained and updated over the years, this home offers a blend of character and everyday convenience.<br> </br> The kitchen was refreshed in 2018 with new countertops, sink, backsplash, flooring, stove, and microwave, creating a bright and functional space for daily living. More recent improvements include the garbage disposal (2024), and dishwasher (2026). Heating system was replaced in 2020. Solar panels were installed in 2022, a great way to subsidize your energy bill!<br> </br> The sunroom off the kitchen provides flexible living space, perfect for a home office, playroom, or cozy sitting area overlooking the backyard. Upstairs, you'll find three comfortable bedrooms and a full bath. Primary bedroom includes a HUGE walk-in-closet! Outside, enjoy a private outdoor space, low HOA, and an unbeatable location. Easy parking with lots in the rear, across the street, and ample street parking. Close to parks, shopping, dining, the W&OD Trail, and all the boutiques, restaurants, and year-round events that make downtown Leesburg such a special place to call home.

326 Shenandoah St Se, Leesburg

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$949,999

5 Beds ⋅ 3 Baths

Discover the perfect blend of modern updates and peaceful surroundings in this beautifully renovated rancher, nestled on a private lot surrounded by mature trees and lush landscaping. Gorgeous hardwood floors flow throughout the main level, where a spacious living room welcomes you with soaring vaulted ceilings, a striking fireplace with built-ins, and a stunning wall of windows that frames picturesque outdoor views. The beautifully updated gourmet kitchen features stainless steel appliances, modern finishes, abundant cabinetry, and generous counter space, creating the perfect space for everyday living and entertaining. Three comfortable bedrooms complete the main level. The fully finished lower level offers exceptional flexibility with a spacious primary suite featuring an updated en suite bath and walk-in closet. A convenient kitchenette and beautiful LVP flooring make this level ideal for guests, multi-generational living, or potential rental opportunities. Outside, enjoy the tranquility of nature from the deck or patio overlooking the private backyard with plenty of room for gardening, outdoor entertaining, and recreation. A large storage shed provides additional space for tools and equipment. The oversized two-car garage offers ample storage, while the extended driveway provides abundant additional parking. The home is serviced by Verizon FiOS internet, providing reliable high-speed connectivity. Move-in ready and thoughtfully updated throughout, this exceptional home also enjoys convenient access to local wineries, offering the perfect balance of privacy and nearby amenities.

39030 Mount Gilead Rd, Leesburg

Listing courtesy of Redfin Corporation. Contact:

$549,990

5 Beds ⋅ 4 Baths

Welcome to 109 Mayfair Drive NE, a beautifully maintained 5-bedroom, 3.5-bath home in one of Leesburg's most established neighborhoods. Thoughtfully updated and filled with inviting living spaces, this home offers the perfect balance of comfort, style, and functionality. The updated kitchen serves as the heart of the home, featuring modern finishes and ample space for both everyday living and entertaining. Bright, spacious living areas provide a warm and welcoming atmosphere, while the flexible floor plan offers room to grow, work from home, or host guests with ease. Step outside to enjoy the private backyard—an ideal setting for relaxing, gardening, or gathering with family and friends throughout the year. Located just minutes from historic downtown Leesburg, you'll enjoy convenient access to local shops, restaurants, parks, wineries, and major commuter routes, all while being part of a charming, established community. Offering five spacious bedrooms, three and a half baths, an updated kitchen, no HOA, and an exceptional location, 109 Mayfair Drive NE is a wonderful place to call home. Come join us for our open house this Saturday September 19th from 12pm-2pm!

109 Mayfair Dr Ne, Leesburg

Listing courtesy of EXP Realty, LLC. Contact:

$635,000

Don't miss this rare and affordable opportunity to buy in a highly desired location! Our price has been REDUCED $60K and a $5000. credit is offered towards buyer's closing costs to buy down your INTEREST RATE! Plus, a FREE 1 year homebuyer warranty! This home, with no HOA, is at an entry-level price point to live within a short walk to historic downtown Leesburg, the Rust Library and Ida Lee Recreation Park. A solid, all brick home, on a quarter acre corner lot with a welcoming, covered front porch invites you into this freshly painted and move-in ready home. Step into the spacious living room with a huge picture window and custom built-in shelves surrounding the gas fireplace. The dining room, also with a huge picture window, is decorated with chair molding and built-in cabinets. The kitchen, updated with new LVP flooring, includes double sinks, side by side fridge with ice/water dispenser, built in microwave, compact dishwasher and a gas stove. On the same level, the home boasts 3 generously sized bedrooms, all with cedar lined closets, with an en-suite bathroom for the primary bedroom and a full bathroom in the hall. The walk out lower level has a huge family room with a cozy wood burning fireplace and brand new carpeting, plus a bonus room, and the utility room with washer/dryer hook ups, an abundance of storage and a half bath. Central HVAC system was updated in 2022 and ceiling fans are installed in all 3 bedrooms, dining room and the family room. Outside you'll find a tastefully landscaped yard and plenty of parking for your family and friends, with the driveway descending behind the home with a lower level parking area and garage. The detached outdoor shed has an exterior electric charging station for your car or RV. Don’t miss this opportunity, bring your best offer!

204 Ayr St Nw, Leesburg

Listing courtesy of Tunell Realty, LLC. Contact:

$349,900

HURRY, HURRY, HURRY Big cash flow potential! Great value add Large 5 unit apartment building with 4 one bedroom units and 1 two bedroom unit in Historical Mansion with lots of charm and character. Needs work and currently vacant ready for rehab. Some improvements already made (roof, separate electric, concrete work, stone driveway, some flooring, etc). Owners are highly motivated to sell and looking for offers. Make your best deal for a really great buy! Estimated cost to complete renovations $125-150K 1 Bedroom units in the area rent from $1000-1400/month 2 Bedroom units in the area rent from $1300-1800/month.

4 Ward Ave, Leesburg

Listing courtesy of M Riccardi Agency Inc. Contact:

$3,649,500

6 Beds ⋅ 5 Baths

At the end of a gently winding country road, where Loudoun County’s storied landscape unfolds in quiet beauty, there lies a place where history lingers and new memories are waiting to be written—37961 Forest Mills Road. This remarkable estate tells a story nearly two centuries in the making. Dating to approximately 1830, the main residence stands as a living piece of Virginia’s heritage—gracefully preserved and thoughtfully partially renovated in 2026 to honor its historic character while enhancing comfort for modern living. With six bedrooms, three full baths, and two half baths, the home offers both scale and intimacy. Set within a natural hollow and embraced by rolling hills and mature trees, the residence enjoys a rare sense of shelter and serenity—protected from the outside world, yet open to the beauty of the surrounding landscape. Here, sunlight filters softly through the canopy, and every season unfolds like a painting beyond your windows. Wide-plank floors, period details, and timeworn textures echo its past, while carefully updated spaces provide ease for today’s lifestyle. Each room feels deeply connected to the land, offering peaceful, private views in every direction. The story extends well beyond the main home. Across the property, a beautifully reimagined carriage house, fully renovated in 2026, offers two bedrooms and one bath—perfect for guests, extended stays, or income potential. A second residence, a charming colonial-style home with three bedrooms and two baths, adds further flexibility for multi-generational living or rental opportunities. The land itself invites possibility. Two barns—one large and one medium-sized—stand ready for equestrian use, storage, or creative adaptation. A picturesque pond reflects the surrounding greenery, while a swimming pool provides a tranquil setting for relaxation and entertaining during warmer months. And everywhere you look, there is history. During the Civil War, the property served as a vital local supply post—its grounds quietly witnessing a defining chapter in the nation’s past. In later years, a noted National Geographic cartographer called this land home, drawn by its perspective and natural beauty. Even earlier, a natural water spring on the property served as an important watering site for the nearby village of Lincoln, making this land a place of gathering and sustenance for the community. Even the trees here tell a story. Identified by a local arborist, the property is home to several rare and noteworthy tree specimens, adding both distinction and natural significance to the landscape. Today, 37961 Forest Mills Road offers a rare blend of heritage and opportunity. The estate supports a range of uses, including private residential living, income-producing rentals with two additional homes, or hospitality ventures such as a bed and breakfast, vacation rental, or wedding and event venue. All of this is protected within a conservation easement, preserving the land’s beauty and ensuring its legacy endures. Here, life unfolds differently. Mornings begin with mist rising through the hollow, afternoons stretch across open fields and shaded paths, and evenings settle gently beneath a canopy of stars. It is a place of quiet refuge, rich history, and endless potential. More than an address, this is a legacy— a story rooted in the land, waiting for its next chapter to be written.

37961 Forest Mills Rd, Leesburg

Listing courtesy of Realty World Homes & Castles. Contact:

$3,649,500

6 Beds ⋅ 5 Baths

At the end of a gently winding country road, where Loudoun County’s storied landscape unfolds in quiet beauty, there lies a place where history lingers and new memories are waiting to be written—37961 Forest Mills Road. This remarkable estate tells a story nearly two centuries in the making. Dating to approximately 1830, the main residence stands as a living piece of Virginia’s heritage—gracefully preserved and thoughtfully partially renovated in 2026 to honor its historic character while enhancing comfort for modern living. With six bedrooms, three full baths, and two half baths, the home offers both scale and intimacy. Set within a natural hollow and embraced by rolling hills and mature trees, the residence enjoys a rare sense of shelter and serenity—protected from the outside world, yet open to the beauty of the surrounding landscape. Here, sunlight filters softly through the canopy, and every season unfolds like a painting beyond your windows. Wide-plank floors, period details, and timeworn textures echo its past, while carefully updated spaces provide ease for today’s lifestyle. Each room feels deeply connected to the land, offering peaceful, private views in every direction. The story extends well beyond the main home. Across the property, a beautifully reimagined carriage house, fully renovated in 2026, offers two bedrooms and one bath—perfect for guests, extended stays, or income potential. A second residence, a charming colonial-style home with three bedrooms and two baths, adds further flexibility for multi-generational living or rental opportunities. The land itself invites possibility. Two barns—one large and one medium-sized—stand ready for equestrian use, storage, or creative adaptation. A picturesque pond reflects the surrounding greenery, while a swimming pool provides a tranquil setting for relaxation and entertaining during warmer months. And everywhere you look, there is history. During the Civil War, the property served as a vital local supply post—its grounds quietly witnessing a defining chapter in the nation’s past. In later years, a noted National Geographic cartographer called this land home, drawn by its perspective and natural beauty. Even earlier, a natural water spring on the property served as an important watering site for the nearby village of Lincoln, making this land a place of gathering and sustenance for the community. Even the trees here tell a story. Identified by a local arborist, the property is home to several rare and noteworthy tree specimens, adding both distinction and natural significance to the landscape. Today, 37961 Forest Mills Road offers a rare blend of heritage and opportunity. The estate supports a range of uses, including private residential living, income-producing rentals with two additional homes, or hospitality ventures such as a bed and breakfast, vacation rental, or wedding and event venue. All of this is protected within a conservation easement, preserving the land’s beauty and ensuring its legacy endures. Here, life unfolds differently. Mornings begin with mist rising through the hollow, afternoons stretch across open fields and shaded paths, and evenings settle gently beneath a canopy of stars. It is a place of quiet refuge, rich history, and endless potential. More than an address, this is a legacy— a story rooted in the land, waiting for its next chapter to be written.

37961 Forest Mills Rd, Leesburg

Listing courtesy of Realty World Homes & Castles. Contact:

$695,000

A Century of Character in Downtown Leesburg Leesburg Historic District, Leesburg, VA 3 BD | 1 BA | 1/3 Acre Lot | Built 1910 | Detached 2-Car Garage | Sold As-Is Steeped in history and full of original charm, this 1910 craftsman-era home sits proudly in the heart of Leesburg's beloved Historic District — lovingly cared for by the same family for over 50 years. Offered for sale as-is, this is a rare chance to own a piece of Leesburg history and make it your own. Step up onto the welcoming covered front porch — the perfect spot for a morning coffee — and into a home that has been cherished across generations. Inside, warm and cozy bedrooms invite rest, while the bathroom retains its original claw-foot tub, a true hallmark of the era. Original hardwood floors are believed to lie beneath the current flooring, waiting to be uncovered and restored to their former glory. The property sits on an exceptional 1/3-acre lot — a genuinely rare find in downtown Leesburg — offering space, privacy, and possibilities that simply don't come along often in this location. A detached two-car garage adds even more practical value. Whether you're a preservation enthusiast, an investor, or a buyer dreaming of restoring a classic home to its original splendor, this property delivers unmatched potential in one of Northern Virginia's most sought-after historic neighborhoods. Properties like this — with this much soul — rarely come to market. HISTORIC DISTRICT NOTICE: This property lies within the Town of Leesburg Historic District. Future exterior renovations and alterations are subject to review and approval by the Leesburg Board of Architectural Review (BAR). Prospective buyers are encouraged to familiarize themselves with applicable guidelines prior to making an offer. ADDITIONAL NOTICE: The home is currently occupied and furnished. AI-assisted editing was used to remove furnishings from interior listing photos. Property is being sold strictly as-is.

245 W Market St, Leesburg

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$2,500,000

Just north of the Town of Leesburg, this renovated Craftsman sits on more than 40 acres across two parcels, surrounded by open pasture, seasonal mountain views, and easy access to Loudoun County’s well-known wineries, breweries, and gathering spots. Thoughtfully expanded for true one-level living, the main floor is filled with character-rich details, including salvaged architectural doors, paneling, and trim. The gourmet kitchen features warm wood floors, a six-burner gas stove, and a custom island crafted from wood taken from the property’s original log cabin. A substantial addition created a private main-level primary suite with a beautifully finished bath, walk-in closet, and its own laundry. Two additional bedrooms—one with an en-suite bath—offer comfortable accommodations, and a dedicated office with a large closet could easily serve as a fourth bedroom. The family room and adjoining dining area both feature heated stone floors, walls of windows, and French doors that open directly to outdoor living spaces. The property also includes a historic log house that was original to the land. Relocated to its current site, it now offers two bedrooms, a full bath, and its own kitchen—ideal for guests, extended family, or possible rental use—while still showcasing vaulted ceilings, a stone fireplace, and beautiful floors. Equestrian amenities include an 11-stall barn with an extra-wide center aisle, a spacious tack room with a powder room, a dog wash station, and a heated and cooled gathering room. Approximately 15 acres are fenced and complemented by run-in sheds and a pond. Zoned AR-1 with no easements, this is a rare opportunity to own a versatile country property that blends history, comfort, and wide-open space just minutes from Leesburg.

43470 Evans Pond Rd, Leesburg

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$348,990