53 School House Road

Classic country elegance with comfortable living space is what you will find in this meticulously maintained four bedroom brick home on 2.33 acres. Convenient to Route 211, schools, services and even a winery, it is an excellent jumping-off point for the commuter or weekender alike. Both Comcast cable and Sprint cell service are available, which… Read more »

Old Jenkins Farm

Old Jenkins Farm is a treasured family farm in the picturesque F.T. Valley near Sperryville. With grand rolling meadows, several streams, large old oaks, a good pond site and old stone walls the property transports you to an earlier simpler time. The original farmhouse, circa 1925,  has been updated with a simple but sophisticated flair,… Read more »

Sampy Lane Cabin

Sampy Lane Cabin is a picturesque retreat located in Huntly, Virginia, only a short distance from Flint Hill, Front Royal, and Marshall. Interstate 66 is easily accessible from Front Royal, making this an easy and short commute for anyone traveling to and from Northern Virginia or Washington DC. The property consists of 25 +/- mostly… Read more »

The Farm on Grindstone Road

Hidden away in a quiet corner of Rappahannock County, The Farm on Grindstone Road has streams, mature forest, a series of rolling meadows and great views – in other words, this is the ideal small farm. Put it to work with livestock, hay and grapes or simply enjoy the quiet beauty of an awesome tract… Read more »

Rattlesnake Hollow

No matter how you like to spend your free time, this is the home for you. The 4 bedroom oversized rambler sits in the middle of 41.5 acres and offers perfect privacy to its residents. With two ponds and plenty of small streams, the wild game is quite abundant. If you enjoy working with your… Read more »

Rattlesnake Hollow

No matter how you like to spend your free time, this is the home for you. The 4 bedroom over-sized rambler sits in the middle of 91.5 acres and offers perfect privacy to its residents. With two ponds and plenty of small streams, the wild game is quite abundant. If you enjoy working with your… Read more »

60 Headwaters Road

Headwaters Retreat is located high above Rappahannock County overlooking rolling farmland with the Blue Ridge mountains as a scenic backdrop. The property consists of 13 +/- acres that are mostly open and rolling. Easily accessible year round, the property can be used as a full time residence or part time retreat. The home features 3… Read more »

Turkey Ridge on the Hazel River

The land on Turkey Ridge is a nature lover’s paradise. The property consists of 75 +/- acres; 60 in Rappahannock County and 15 in neighboring Culpeper County. A strong stream meanders through the property along peaceful meadows and rock outcroppings down to the Hazel River. The property has several hundred feet of river frontage. The… Read more »

Country Cottage

Patricia Obregon, our Rental Agent Specialist, will be happy to assist you in your country rental property search. Please email her at patricia@cheriwoodard.com or send a text message to 540-522-7827 to schedule a viewing appointment. Please allow 24 hour notice for all showings. No phone calls please. Country Cottage features four bedrooms, two full bathrooms, a… Read more »

160 Gay Street

Gay Street Inn is one of the best known Bed and Breakfasts in Rappahannock County, Virginia.  The inn  has an excellent location, cozy facilities, and a sustainable business model, with plenty of room for growth.  The home and property are in excellent condition so you can move right in — the owners imagine that the transition to… Read more »

10 Farm Lane

Lovely three bedroom house on 1+ acres on hillside overlooking town of Sperryville. The well constructed, fully insulated, one story home features central HVAC, and offers comfortable, easy-living. House currently has three bedrooms with closets, full bath, a center hall connecting to living, dining rooms and a full kitchen. Architectural drawings available for future expansion. Mostly… Read more »

Blue Sky

Blue Sky is 14.28 acres of rolling fields and forest on a quiet country road. Protected by a hardwood forest on the perimeter and a dense stand of pines along the road, the property is tucked away in a gentle valley that feels very private. About half of the land is cleared and ideal for… Read more »

Rolling Creek

A serene hideaway in the woods, Rolling Creek offers a combination of solitude, comfort, and convenience. The 21.6 acre +/- property shares two boundaries with Shenandoah National Park and is just down the road from two park trail heads. The unique two bedroom house has all the charm of a mountain getaway together with modern conveniences,… Read more »

Thorn Woods Hideout

This is the best deal on land we’ve seen in Rappahannock County in many years! Thorn Woods is 62.8 acres for $225,000 or just under $3,600 per acre. This is by far the lowest per acre price for land in Rappahannock county. There are two lots included in the 62.8 acres, which adds even more… Read more »

Yeawood Retreat

Hidden away in the quiet Yeawood neighborhood off of Slate Mills Road, this 25 acre (+/-) property is a diamond in the rough. Surrounded by wooded lots on all sides and backing to a 580-acre parcel to the east, peace and privacy are assured. Several streams, tributaries to the Hazel River, criss-cross the property while the interesting rolling… Read more »

Liberty Springs Farm

Rolling hills laced with springs and streams along with breathtaking Blue Ridge mountain views all come together to create an unparalleled country retreat.  Your dreams of building a small cabin, cultivating a large vegetable garden and planting a vineyard are all possible  on this 26 +/- acre parcel. The property is centrally located in the… Read more »

The Cabin on Jackson Lane

Designed as a cozy weekend retreat in the woods, the Cabin on Jackson Lane is surrounded by lovely gardens, mountain laurel and grand old oaks. It is completely private, easy living and a welcome oasis from hectic city living. The new “old” Hearthstone log cabin built in 1990 marries modern conveniences and energy efficiencies with… Read more »

Yeawood Drive Lot 11

Parcel 11 in the quiet Yeawood neighborhood off of Slate Mills Road is 12.37 acres of tranquility. Surrounded by wooded parcels on all sides and backing to a 580 acre parcel to the east, peace and privacy are assured. Three streams, tributaries to the Hazel River, criss-cross the property while the interesting rolling topography gives many options for building sites.… Read more »

Yeawood Drive Lot 10

Hidden away in the quiet Yeawood neighborhood off of Slate Mills Road, this 12.57 acre parcel is a diamond in the rough. Surrounded by wooded lots on all sides and backing to a 580 acre parcel to the east, peace and privacy are assured. Three streams, tributaries to the Hazel River, criss-cross the property while the interesting rolling… Read more »

1001 Quaker Run Road

River Rock Camp beckons with possibilities. This 8.6 acre property was once a a favorite family retreat and jumping-off point for outdoor adventures. Now the kids are grown and it is time for someone new to make memories here. River Rock Camp was built circa 1940 using native stone, blending with that found in Quaker Run flowing right… Read more »

17 Kilby Farm Lane

Breathtaking mountain views and extensive mature gardens make Kilby Farm House a true Rappahannock retreat. This renovated farm house includes 3 bedrooms and 3 full bathrooms one of which is located in the large finished basement. A spacious office/library room is located directly off the dining area and entrance hall. There is a large eat… Read more »

Pearl Lane

In the hills above Sperryville lie these mostly wooded lots, totaling 6 acres, waiting to be made a home. The property is ideal for a family homestead. There is ample room for a large garden and children playing the days away. These 2 adjoining 3-acre lots are surrounded by mature forest, a lovely mountain stream… Read more »

2409 Champe Plain Road

Located on a small knoll with a great view that sweeps down the front yard and out to the farmland below, this tidy little 3 bedroom brick rambler offers the best of country living.  Only minutes from the Old Rag trail head and close to the Hughes River, the outdoor activities are plentiful.  Scenic Champe… Read more »

Sunset View Farm

Sunset View Farm is the perfect combination of open view and privacy, rolling pasture and woods, natural area and usable farmland. The home features a first-floor master suite, gourmet kitchen, and a charming front porch. Thoughtfully sited on its 25.5 acres, the home backs to a wooded area while affording a wide open view of the… Read more »

106 Piedmont Avenue

On a picturesque side street, bordering the Inn at Little Washington’s expansive gardens, this carefully restored Victorian farmhouse offers gracious entertaining spaces, lovely mountain and pastoral views, and the convenience and charm of 21st-century village living. Set on a beautifully landscaped half acre, this large home features an elegant 2-story side porch and a spacious… Read more »

96 Mt Marshall Road

Mount Marshall Meadow is 25 acres of mountain woodland, grassy meadow, meandering creeks, and beautiful mountain views. Splendidly located only 3.5 miles from the Town of “Little” Washington, Virginia, and just steps from the Mount Marshall Trail Head, it would make a perfect base for your Rappahannock County adventures. The property adjoins the Shenandoah National… Read more »

Whorton Hollow Road

With fine mountain views, gently rolling pastures, deep rich soils and plenty of water, this 60-acre property is the best mid-sized tract of land on the market in Rappahannock County. Hayfields at Castleton has approximately 45 acres of open land that is buffered by forests on the north and south so it is fairly private. Mill… Read more »

Sharp Rock Road

This well designed home is minutes from Old Rag Mountain, Shenandoah National Park, Sharp Rock Vineyard and numerous rivers and streams. The home was built in 1962 and had major renovations completed in 2006. It features 3 bedrooms, 3 full baths, guest room, spacious kitchen, dining room, laundry room, gas fireplace and central air and… Read more »

Kilby Farm Lane

96 Kilby Farm Lane is the perfect country retreat, homestead or hunt box. Located on the outskirts of Sperryville, this 3 bedroom, 4 bath home has excellent mountain and pastoral views. The private 12.6 acre property is an ideal mix of open fields and woods and it includes a large pond that provides visual interest… Read more »

Emmett Road Cabin

The perfect weekend escape or full time country residence for any nature enthusiast. The property is located at the base of the Shenandoah National Park in Etlan. As you approach the property you are greeted by the majestic views of Old Rag and the Blue Ridge Mountains. The home is tucked on a hillside and… Read more »

Hilltop Haven

Perched gently on a hilltop, above the nearby Piney River, sits this lovely home with new deep blue stain on its cedar siding and white painted trim, waiting to become the perfect full time home or weekend retreat for its new owners. Split rail fencing embraces the entrance to this property. As you drive up… Read more »

Rattlesnake Hollow

This 50 acre property encompasses much of the southern and eastern face of Carson Mountain offering impressive views of the Blue Ridge foothills to the East. The property forms a gentle bowl with several small streams that run down Carson Mountain and eventually run into the Rappahannock River. The land is heavily forested with second… Read more »

Banco Overlook

True to its name, Banco Overlook offers commanding views of the FT Valley. The 47 acre +/- property rises from the valley floor up the side of Deal Mountain. Along the way to the top, there are several knolls that would make excellent home sites offering complete privacy and outstanding views. From the ridgeline, the… Read more »

The Ridge

Inspired by artists and designed by Jay Tucker, a well known local architect, The Ridge is at peace with its surroundings. Sitting on 22.1 acres +/-, this magnificent two bedroom, two bath home is the perfect retreat from the hustle and bustle of city life. A 2 room artist’s studio (which could easily be converted… Read more »

Zachary Taylor Highway

Patricia Obregon, our Rental Agent Specialist,  will be happy to assist you in your country rental property search. Please email her at patricia@cheriwoodard.com or send a text message to 540-522-7827 to schedule a viewing appointment. Please allow 24 hour notice for all showings. No phone calls please.  Maison Latouraudois is a historical gem located in scenic Flint Hill, Virginia. The… Read more »

Sundown Lane

Sundown is a quaint country bungalow located on a private road just minutes from the town of Sperryville. A private, and also accessible, country retreat it is an ideal home for anyone looking to escape city life. The home features hardwood floors, three spacious bedrooms, two full baths, laundry room and a mudroom off the… Read more »

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Ashton Farm

Ashton Farm is an idyllic country farm located in a small dell at the base of Walden Mountain. The heart of the property is a historic 3 bedroom farmhouse that has been lovingly updated to make it comfortable and convenient for everyday use. The 16 acre property is fenced, cross-fenced and perfectly suited for small… Read more »

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White Oak Cabin

Steeped in history and filled with charm, this 3 bedroom, 2 bathroom home on five acres is sure to be the perfect respite from the hustle and bustle of city life. The heart of the home is a log cabin that once served as the postmaster’s home (and office) serving all of Weakley Hollow in… Read more »

388 Fodderstack Road

Only minutes from the famed Inn at Little Washington and in the heart of Virginia’s wine country lies an idyllic country retreat known as Fidler’s Green. The property is located on the scenic Fodderstack Road that runs from the Town of Little Washington to the Village of Flint Hill. This 3 bedroom, 2 1/2 bath… Read more »

The Oaks

The Oaks is a Rappahannock County Treasure. This gem of a house is an exceptional example of a quirky rambling country home chock full of personality. It is sited on a gentle knoll under a stand of impressive aged oaks that stand guard like gnarly old sentinels. Surrounding the home are fieldstone lined ornamental gardens,… Read more »

The Hudson House

This spacious and comfortable  home near Old Rag Mountain is ideal for those who love the outdoors. Only 0.7 miles from the Old Rag Mountain parking lot and across the road from the Hughes River  this is a nature lover’s perfect retreat.  The Hudson House by the Side of the Road was  built in two stages,… Read more »

The Hideaway on the Hill

The Hideaway on the Hill is the perfect launching point for your weekend adventures. Perched above the village of Sperryville, this sturdy brick three-bedroom two-bath home combines low maintenance with a great location on a 0.76 acre parcel. Walk two-tenths of a mile to the village of Sperryville for galleries, restaurants, shops and the post… Read more »

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Boxwood Cottage

If you want a cottage with lots of charm in a secluded setting, look no further. Boxwood Cottage is an old homestead overlooking a perfect pond at the base of Old Rag Mountain. The grounds around the cottage are lushly landscaped with mature shade trees, old stone walls, stone planting beds and numerous impressive old… Read more »

Cottage Green

In the quaint country village of Flint Hill, tucked under a canopy of trees, you will find Cottage Green. The deceivingly spacious cottage features three bedrooms, one full bath, and two bonus rooms. The property is convenient to Warrenton, Front Royal and Interstate 66 via a drive on scenic Crest Hill Road. The house sits… Read more »

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Elmer’s Antiques

If your dream has been to run your own antiques business in a vibrant country community, this 2.50 acres with five separate buildings is the place for you! Located near the small and bustling village of Sperryville, Virginia in the foothills of the Blue Ridge Mountains, this business was known for decades as “Elmer’s Antiques”… Read more »

Poplar Hollow Retreat

Tucked in a small clearing on a wooded 33 acre +/- lot, this thoughtfully designed home is the perfect country retreat. Large windows throughout the home provide lots of natural light so even though you are tucked into the forest, your home has plenty of light. The majority of the property is heavily wooded with… Read more »

Horn Hollow Lane

Horn Hollow Lane is 50 acres of hidden treasure located in one of the most scenic hollows in Madison County. From a perfectly private location near the end of Horn Hollow Lane, the property has an idyllic setting with achingly beautiful views of fields, forested foothills and the majestic Blue Ridge Mountains. The property has… Read more »

The Home in Harris Hollow

The Home in Harris Hollow is the ideal country cottage – rustic yet refined, easy keeping and not at all fussy. It has an ideal location in a picturesque valley just outside of Little Washington that’s near the headwaters of the Rush River. The 7.5 acre property is at about 1,200 feet in elevation on… Read more »

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Fishhawk Pass

Fishhawk Pass is understated luxury at its best. This extremely well-constructed, well-thought-out home combines classic elegance with modern technology and contemporary style. Located off of the scenic Ben Venue Road on a private lane just south of the village of Flint Hill, the 30-acre property has open pasture near the road frontage and is wooded… Read more »

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FT Valley Road

This 36.549 +/- acre property is mostly open and flat with gentle knolls. There are impressive views in every direction. It also has the ideal and rare combination of easy accessibility and long views making it an enviable home site. The property is excellent agricultural land that is currently being used for soybean and corn… Read more »