Middlebrook Homes for Sale

Middlebrook Homes for Sale

Welcome to Middlebrook, Virginia—a hidden gem nestled in the heart of Augusta County! This charming community offers a perfect blend of rural tranquility and modern convenience, making it an ideal place for families, retirees, and anyone looking to embrace a slower pace of life. With scenic views of the Blue Ridge Mountains and a rich history that dates back to the early 19th century, Middlebrook is not just a place to live; it’s a place to call home.

The town is surrounded by lush farmland and natural beauty, providing residents with ample opportunities for outdoor activities, from hiking and biking to fishing and horseback riding. The community is known for its friendly atmosphere, where neighbors become friends and local events bring everyone together. Enjoy the beauty of changing seasons as you watch the landscape transform, creating picture-perfect scenes year-round.

For those considering a move, Middlebrook boasts a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re looking for a cozy cottage, a spacious family home, or a charming farmhouse, the real estate options here are as inviting as the community itself. Many properties feature expansive yards, stunning views, and easy access to local amenities, ensuring that you can enjoy the best of both country living and modern conveniences.

Explore the possibilities that Middlebrook has to offer, and discover why so many are choosing to make this picturesque town their home. With a vibrant community spirit and a wealth of natural beauty at your doorstep, Middlebrook is waiting for you to start your next chapter!

Newest Middlebrook Homes for Sale

4 Beds ⋅ 1 Baths ⋅ 679689 MLS

Classic Traditional Two Story Farm House in Middlebrook Village - Blending original character with modern upgrades. Beautifully refinished hardwood and heart pine floors. Living room with relaxing views, formal dining with built-in, modern kitchen has new stainless appliances and a eat-in nook. Main floor laundry, updated full bathroom and pantry. Four large bedrooms (Easy main floor bedroom for one level living) and storage. Improvements include new roof, new siding, new 200 amp electric, new mini split system in all rooms for heat and air conditioning. High Speed Internet! Almost level yard and deck, circular drive with plenty of parking. A rare opportunity to own a historic property in the quaint small community of Middlebrook which has its own amenities including a doctor's office, general store (which serves lunch daily), post office, and library.

3615 Middlebrook Village Rd, Middlebrook

Listing courtesy of REAL ESTATE PLUS. Contact:

3 Beds ⋅ 4 Baths ⋅ 678432 MLS

"Windemere Croft"~ Old European English Tudor in Summerdean, Constructed by the Personal Stonemason to a well-known California Actor. One owner home on 6.7 manicured acres with Creek and Springs. 5500 Square feet offering 3 Bedrooms, 3.5 Baths, Family Room with Stone Fireplace, Living Room with Fireplace, Formal Dining, Designer Kitchen with Granite and Woodstove, 2 Almost New Bosch Heat Pumps, All rooms are Oversized Perfect for Entertaining, Stone Patios, Too many Amenities to list, Ask for a Detailed description, Perfect for a Vineyard and B&B. Concrete block construction. Bottom floor is faced in 8” thick natural stone from the property. Inner walls are 2 X 4 insulated sheet rock, making downstairs walls 22” thick. ,Plat and Description under paperclip. Manifold control panel plumbing system w/ hot water on demand.

229 Summerdean Rd, Middlebrook

Listing courtesy of REAL ESTATE PLUS. Contact:

3 Beds ⋅ 2 Baths ⋅ 677452 MLS

Welcome to the peaceful village of Middlebrook! Quiet, country living with a beautiful backdrop! This two story home has a huge back yard with gorgeous views, and a garden ready for planting. Two beautiful stone gas-powered fireplaces and a backup generator to give year round peace of mind that you can weather any storm or power outage. Original cabin beams are exposed in many of the rooms, giving the home a classic look highly sought-after in today's modern world. Beautiful wood floors throughout the upstairs! Features a front porch and a back deck for entertaining and enjoying the scenery. Two sheds in great condition convey. Reach out to tour today! Sold as-is.

3648 Middlebrook Village Rd, Middlebrook

Listing courtesy of Weichert Realtors Nancy Beahm Real Estate. Contact: 540-433-6666

3 Beds ⋅ 1 Baths ⋅ VAAG2002824 MLS

Experience turnkey living at 38 Cherry Grove Road in the charming Village of Middlebrook! This completely renovated 3-bedroom, 1-bath home has been beautifully updated from top to bottom and is ready for its next owner. Enjoy brand-new appliances, modern finishes, updated fixtures, fresh interiors, and a bright, inviting layout designed for comfortable everyday living. Nestled in a peaceful and tranquil setting, this home offers the perfect balance of modern convenience and small-town charm. Whether you are relaxing after a long day or entertaining family and friends, you will appreciate the warmth, comfort, and low-maintenance lifestyle this property provides. Rarely does a move-in-ready opportunity like this become available in Middlebrook. Buyers looking for value, style, and serenity will not want to miss this one. Schedule your private showing today. Two Large Historic School Houses Included in Price.

38 Cherry Grove Road, Middlebrook

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

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Ashley Dudley | Broker Owner

Ashley Dudley is a Shenandoah Valley based real estate broker known for her heart-forward approach, deep local knowledge, and steady guidance through every step of the buying and selling journey. As the Broker Owner of HomeGrown Real Estate, Ashley has built a client-centered brand that blends expertise, community connection, and the belief that real estate should feel personal… not overwhelming. Rooted in New Market and serving Shenandoah County, Rockingham County, Page County, Augusta County and the surrounding Valley, Ashley has helped countless clients navigate moves of every kind. First-time buyers searching for their foothold. Growing families moving into their next chapter. Long-time locals preparing to let go of a home filled with memories. Out-of-state buyers relocating to the mountains. Investors looking to build something lasting. Ashley guides each one with clarity, patience, and an eye for strategy. Her background as a business owner and her commitment to honest communication make her a trusted partner in a fast-moving market. She’s hands-on, detail-driven, and known for making complex processes feel manageable. Whether it's pricing a home with precision, negotiating with confidence, or helping sellers prepare their home for the market, Ashley brings both expertise and empathy to the table. At the heart of her work is a simple mission… helping people plant roots to grow their future here in the Valley. It’s a mission reflected in her community involvement, her HomeGrown events, and the relationships she builds long after closing day. When she’s not working with clients, Ashley is exploring local with her husband, Rustin, snuggling her pups, Molly and Minnie, planning community events, or dreaming up new ways to support her agents and elevate the real estate experience in the Shenandoah Valley. If you’re looking for a Realtor who knows the Valley, cares deeply about her clients, and brings both heart and strategy to every move, Ashley is ready to help you take your next step home.

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Amber Fleck | Realtor

Amber Fleck is a dedicated Realtor with HomeGrown Real Estate serving the Shenandoah Valley and surrounding communities. Amber helps buyers and sellers navigate the real estate market with confidence, clear communication, and genuine care. She believes every client deserves a smooth and enjoyable experience from the first conversation to the closing table. After graduating from James Madison University in 2019, Amber made the Shenandoah Valley her home and quickly fell in love with its mountain views, hiking trails, rivers, and local restaurants. She uses her deep local knowledge to help clients find the right home, whether they are first time home buyers, relocating to Virginia, upsizing, downsizing, or searching for land with mountain views. Amber focuses on honest guidance, strong negotiation, and marketing strategies that help sellers earn top dollar. Her philosophy is simple. You should live where you love. She is committed to helping clients plant roots and build their future in a community she adores.

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Courtney May | Realtor

Courtney May is a proud Augusta County native and Fort Defiance graduate whose resilience during the COVID-19 era shaped her dedication to helping others. Eager to serve her community, she became a licensed real estate professional and is grateful to assist neighbors with their real estate needs—whether buying or selling, and no matter the stage of life they’re in.Courtney is especially passionate about first-time homebuyers, believing homeownership is a life-changing milestone and not just a transaction. Her personalized approach and local expertise allow her to guide new buyers through the process with confidence and care.Outside of real estate, Courtney enjoys spending time with family, friends, and her dog while exploring the beauty of Augusta County. Her goal remains simple—serve her community with integrity, enthusiasm, and heart.

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Jessica Harrison | Associate Broker

Jessica is a trusted Associate Broker with HomeGrown Real Estate, proudly serving the Shenandoah Valley and surrounding communities. She works closely with buyers and sellers to provide clear communication, thoughtful guidance, and a smooth experience from the first conversation through the closing table. Jessica believes real estate is deeply personal, and every client deserves to feel informed, supported, and confident at every step. With a background in both real estate and insurance, Jessica brings a unique and well-rounded perspective to every transaction. She helps clients look beyond the surface by considering market value, long-term risk, and overall investment strategy. Her clients value her attention to detail, responsiveness, and calm, steady approach during what can often feel like a big life decision. Jessica enjoys helping clients navigate a wide range of goals, whether purchasing a primary residence, exploring investment opportunities, or planning for what comes next. With a strategic mindset and genuine care for the people she serves, she is committed to helping clients make smart, confident decisions and build a future they feel good about calling home.

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Abby Neese | Realtor

Born and raised in Shenandoah County, Abby brings a deep-rooted understanding of the local community and its unique charm to her real estate career. With over 10 years of experience in property management, she’s developed a strong foundation in client service, attention to detail, and navigating the complexities of the housing market. Now, she’s excited to transition that expertise into helping buyers and sellers achieve their real estate goals. Abby’s background has equipped her with a keen eye for property value, market trends, and the importance of clear communication—skills she uses to guide clients through every step of the buying or selling process with confidence and ease. Outside of real estate, she enjoys spending time on the golf course, cheering on her kids at their sporting events, exploring antique shops, and making lasting memories with family. Abby is passionate about building relationships and helping others find not just a house, but a place they can truly call home.

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