Middletown VA Homes For Sale

A true once in a lifetime opportunity awaits. If you are looking for something unique with the character and charm of yesteryear but all the modern conveniences we have grown reliant upon this gorgeous small farm is the one you have been waiting for. Meticulously brought back to the former grandeur it once beheld you will be awestruck by it's timeless beauty. From the soaring ten foot ceilings restored original wood staircase and gleaming countertops it is a true gem. It will suit every stage of life with a full primary suite on each of the two levels it leaves you open to unlimited possibilities. Two large guest bedrooms on the second level with jaw dropping views through the valley make it hard to pick which bedroom to choose! On the second story there is a full bathroom with tub shower in addition to the ensuite bath off the second level primary. Huge walk in closets adorn each of the primary bedrooms and one of the guest bedrooms. The second level also boasts a full laundry room with views over the barn! Back down stairs the kitchen with leathered granite counters and a traditional farm sink shine in such a way you may forget to look up to see the glass doored cabinets that stretch to the ceiling behind you! a full pantry tucked away on the far wall gives you even more space to store! All appliances HVAC Plumbing and Electric have been replaced throughout the home. The timeless touches of the original exposed beams interior doors, built ins and fireplace have be restored and kept. The fireplace had been converted prior to current owners stewardship, however to what is unknown and it has never been used by current seller and therefor conveys as is. All of the appliances are brand new and all warranties transfer as well as a two year WDI warranty. Septic also was updated and a brand new survey is on file of the property lines. Outside you will find several fantastic outbuildings and 5 fabulous acres! The large classic red barn can suit a variety of needs from horses to cattle, it suits any type of livestock you can imagine and with a little imagination would be a great place to host social gatherings. Already set up with a concrete floor and double loft to store equipment, hay, straw or other crops in addition to having some livestock pens you really can choose the direction to take your adventure. The 5 acres will amaze you, there isn't a single unusable piece of ground on this property! The fields have been routinely farmed for hay and are clean, rolling and fertile making it one of the most useful little farms I have come across. It would easily make a lovely little horse farm or what ever your heart desires! Open houses October 24 and October 25th check back for the zillow tour and floor plans drone videos and pictures to be uploaded soon.

1449 Reliance Rd, Middletown

Listing courtesy of Samson Properties. Contact:

$600,000

Beautiful 8.79-acre property on N. Buckton Road in Middletown offering mountain views and plenty of room to spread out! Zoned RA, this acreage offers a variety of potential uses, subject to applicable zoning requirements and approvals. Enjoy a country setting with convenient access to I-81 and I-66 for commuting. Bring your plans and explore the possibilities!

Lot 96 Buckton, Middletown

Listing courtesy of RE/MAX Real Estate Connections. Contact:

$850,000

A distinctive land offering in historic Middletown Virginia! Encompassing approximately 12.36 +- acres , this property presents a rare opportunity in the Northern Shenandoah Valley. Situated along Veterans Road, and nearby the Historic Cedar Creek Battlefield, this parcel presents a compelling combination of location, acreage, and opportunity. Currently zoned RA, this parcel is being offered independently as well as available for sale as part of a larger two-parcel offering.

Lot 20 Veterans, Middletown

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

$67,500

Level Lot in the Town of Middletown ready for your dream home. Located just off of Main Street, lot shares a driveway with 7709 Main Street to access property. Owner can continue driveway to house once built. Lot sits behind two houses. Public water/sewer available. Easy access to I-81 for commuters, minutes from Winchester, shopping, restaurant's and more! *Listing agent is related to owner.

Main St, Middletown

Listing courtesy of Realty ONE Group Old Towne. Contact:

$9,000,000

4 Beds ⋅ 2 Baths

Discover an exceptional investment opportunity with this expansive 361.24-acre farm (consisting of 9 parcels of land). This property is a canvas for your vision, offering a multitude of possibilities. The lot features a unique blend of partly wooded areas and open spaces, providing a perfect backdrop for various agricultural ventures or recreational developments. With its agricultural use along with the presence of historical resources, the land is a great candidate for conservation tax credits. The potential is limitless, and the natural beauty of the land enhances its appeal. With road frontage along I-66 and Reliance Road (State Route 627), and its close proximity to the Virginia Inland Port, accessibility is a key advantage, ensuring that your investment is not only visible but also easily reachable. This feature is crucial for any future development or agricultural operations, allowing for seamless transportation of goods. There are two farmhouses located on the property, but both will require substantial renovations for livability. Seven out of the nine parcels included in the sale receive a reduced tax assessment due to being located within an agricultural land use designation. Two of the parcels were too small to receive the designation. Property is being sold "As-Is, Where-Is."

1258 Reliance Rd, Middletown

Listing courtesy of Farms & Acreage, Inc.. Contact:

$379,999

3 Beds ⋅ 3 Baths

NEW ROOF INSTALLED AUGUST 2026! Set along Historic Route 11 between Middletown and Stephens City, this single-level 4-bedroom, 3-bathroom home sits on a 0.43-acre lot and has received steady updates over the past four years. Inside, two bedrooms plus the living and dining rooms feature updated flooring, and one bathroom has been fully remodeled. New carpet was recently added in the mudroom and the primary suite's step-in closet, bringing recent updates to three of the four bedrooms and two of the three full bathrooms. Major system upgrades add long-term value: a new roof installed by Cenvar, a newer refrigerator and dishwasher in the kitchen, and a newer washing machine in the laundry area, all completed within the last two to four years. The detached garage includes a 240V outlet, a practical feature for RV, fifth-wheel, or EV charging needs. The backyard offers a semi-secluded layout suited for gardening, relaxing, or entertaining. Location adds everyday convenience along Route 11, with easy access for commuting between Middletown and Stephens City. The area is also known for the annual Route 11 Yard Crawl each August, a regional shopping tradition that draws visitors along this corridor. Ongoing growth nearby, including new retail development a few minutes away, continues to add convenience to the area.

6666 Valley Pike, Middletown

Listing courtesy of Homecoin.com. Contact:

$469,900

4 Beds ⋅ 3 Baths

"Beautiful On Birmingham" This 4-bedroom, 2 1/2 bath colonial style home is ready for you to move right in! As you enter, you'll be welcomed by the open floor plan! With a large island and plenty of cabinet space the kitchen was built for everyday life and entertainment. Spacious family room, eating area and first floor flex room perfect for a home office! Upstairs you'll find a large primary bedroom with a walk-in-closet and private bathroom. 3 additional bedrooms on the upper level as well as a full hallway bathroom and upstairs laundry room. Unfinished walk-out basement with a full rough-in for the possibility of adding an additional bathroom. Two car garage that was painted and has wooden ceiling shelves that were added. Step out back to a massive deck that was just added in 2026 and a wooden fence that was added in 2023. Additional upgrades include hardware added to the kitchen cabinets, basement staircase painted, board and batten design added to laundry room as well as laundry room cabinets added. Close to I-81 and Rt. 66 making commuting a dream!

122 Birmingham Dr, Middletown

Listing courtesy of Samson Properties. Contact:

$324,900

4 Beds ⋅ 1 Baths

This charming ranch-style home, beautifully renovated in 2018, offers a perfect blend of comfort and modern living. Nestled on a serene half-acre lot, the property features a welcoming interior with four spacious bedrooms and a thoughtfully designed layout. Updated flooring throughout, complemented by upgraded countertops in the eat-in kitchen, which seamlessly connects to the dining area-ideal for gatherings. The main level includes a convenient entry-level bedrooms and a luxurious walk-in shower in the bathroom. Step outside to discover a private oasis with an above-ground pool, surrounded by lush landscaping and mature trees, providing a tranquil view of the pasture and woods. The exterior is enhanced by thoughtful features such as exterior lighting and flood lights, ensuring safety and ambiance. Located in a peaceful rural setting, this home is part of a friendly community that values connection and outdoor living. Nearby parks offer recreational opportunities, while local schools are known for their commitment to education. With easy access to public services and a gravel driveway accommodating up to four vehicles, convenience is at your fingertips. This property is not just a house; it's a place to create lasting memories. Experience the joy of living in a home that combines modern amenities with the charm of nature.

1810 Chapel Rd, Middletown

Listing courtesy of Colony Realty. Contact:

$995,000

Rare opportunity to own 63.48± acres in northern Warren County featuring a scenic mix of open fields, mature woodlands, and West Run Creek winding through the property. Whether you're seeking a private estate, recreational retreat, hunting property, or long-term land investment, this property offers exceptional privacy and natural beauty with potential for future low-density residential development and subdivision opportunities subject to county approvals. Existing well, septic, electric service, and a 1,430 SF manufactured home convey as-is. Enjoy a secluded rural setting while remaining conveniently located near Front Royal, Middletown, Strasburg, and Winchester, with excellent access to Route 522, I-66, I-81, shopping, restaurants, and regional employment centers.

105 Ridgemont Rd, Middletown

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$815,000

6 Beds ⋅ 4 Baths

Discover a rare opportunity to own an exceptional custom residence where timeless craftsmanship, refined comfort, and peaceful natural surroundings come together. Nestled on five picturesque wooded acres within an exclusive lake community in Middletown, this remarkable estate offers over 4,700 square feet of beautifully designed living space, creating the perfect balance of luxury, privacy, and everyday functionality. Thoughtfully designed, the home features six bedrooms and three-and-a-half bathrooms, providing exceptional flexibility. A dedicated office on the main level creates an elegant work-from-home space, while an expansive loft offers endless possibilities as a library, media lounge, or additional gathering area. The spacious primary suite is conveniently located on the first floor, featuring access to the deck, a stone fireplace and private ensuite bathroom. At the heart of the home, the chef-inspired kitchen is equipped with newer appliances—all less than five years old—and seamlessly flows into generous living and dining spaces designed for effortless entertaining. The walk-out lower level is partially finished and already plumbed for a future full bath, offering exceptional potential to create a luxury guest suite, fitness studio, wine cellar, home theater, or recreation space tailored to your vision. Step outside to experience the home's true sanctuary. A custom multi-level deck overlooks the wooded landscape, providing multiple outdoor living spaces for entertaining or quiet relaxation. A reinforced section has already been engineered to accommodate a hot tub, creating the perfect setting for enjoying peaceful evenings beneath the stars. Exceptional features continue with an oversized two-car garage and the added confidence of a whole-home gas generator, ensuring comfort and peace of mind in every season. Residents enjoy access to the community's private lake, offering opportunities for fishing, kayaking, and embracing the beauty of the surrounding countryside. Despite its serene setting, the property remains conveniently located near commuter routes, historic Middletown, wineries, outdoor recreation, and all that the Shenandoah Valley has to offer. Offering an extraordinary combination of luxury, privacy, and room to grow, this distinguished estate is more than a home—it's a lifestyle.

816 Great Lake Dr, Middletown

Listing courtesy of Realty ONE Group Old Towne. Contact: