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$2,000,000
4 Beds ⋅ 5 Baths ⋅ MDHW2072184 MLS
Listed and Sold Simultaneously. Tucked within the established and sought-after community of Wellington West, this exceptional almost 30-acre property is a rare find in western Howard County — thoughtfully designed for the equestrian lifestyle. Private while having a community feel. Whether you envision a private riding retreat, a working horse farm, or simply wide-open space with room to breathe, this property delivers the infrastructure and acreage to make it possible — all while not sacrificing for a stylish home. The premier equestrian facilities include a customized bright and well-ventilated 110’ X 60’ barn with additional 24’ and 30’ bump outs for added storage and versatility. There are currently six 10’ X 12’ and two 12’ X 16’ matted stalls. This set up allows for an area to exercise under cover or space for additional stalls. The perimeter is fenced with diamond mesh wire with interior fencing that is 3 board. There are four large fields each with a run-in shed and auto waterers. The five smaller paddocks surround the barn area. The arena is grass with a 4’ stone dust track. Approx. 6 acres are wooded and in Forest Conservation. The timeless style of the gracious 5,700+ finished square foot home features a versatile floor plan that transitions effortlessly from everyday comfortable living to gracious entertaining. Four/Five bedrooms ( 1 large bedroom could have a door added to make 2 complete bedrooms) and 4.5 baths give plenty of space in addition to the finished lower level with kitchenette.

15325 Doe Hill Ct, Woodbine
$720,000
3 Beds ⋅ 2 Baths ⋅ MDHW2070296 MLS
Rare Howard County Opportunity! Set on 5.27 private acres, this solid brick rancher offers the perfect blend of country living and endless potential. Bring your horses, hobby farm dreams, or simply enjoy the space to roam. The property is home to mature fig, cherry, and pawpaw trees, along with blueberries, raspberries, and black raspberries—your own backyard harvest awaits! The home is ready for your personal updates, while the expansive lot offers plenty of room to add a pool, gardens, outbuildings, or outdoor entertaining spaces. Enjoy the privacy of rural living with the convenience of nearby commuter routes, shopping, and dining. Properties with this much usable land in Howard County are few and far between—don’t miss your chance to make it your own!

3760 Jennings Chapel Rd, Woodbine
$835,000
3 Beds ⋅ 3 Baths ⋅ MDHW2069682 MLS
DEADLINE for offers to be submitted is 10 AM Wednesday July 22, 2026. Here is the rare combination that you search for and seldom find — a tidy, move-in ready farmette where absolutely nothing has been left to do but move in and enjoy. With nearly 7 level acres, this property is fully fenced and ready for horses or livestock, anchored by a well-maintained rancher and supported by an impressive array of outbuildings and equestrian infrastructure — all with no HOA restrictions standing in your way. At the heart of the property sits a 5-stall center aisle barn, centrally positioned to allow easy access to the multiple fenced paddocks surrounding it. The level terrain is an exceptional asset offering several natural configurations for a future arena. Two run-in sheds provide additional options for easy horsekeeping. The quality constructed ranch style home offers the convenience of true one-level living. An open floorplan gives flexibility to the 3 bedroom and 2.5 bath space. The great room is highlighted by a masonry fireplace and glass doors leading to a sunroom that provides views of the pastures. A full unfinished lower level — complete with a brick fireplace and walk-out access — is an exciting blank canvas to expand the living space. A 2-car attached garage rounds out the home's practical appeal. A substantial 36' x 45' utility building opens up a world of possibilities beyond the barn. Car collectors, hobbyists, mechanics, and anyone with serious equipment or machinery storage needs will appreciate the scale and flexibility this structure provides. Workshop, storage, studio, or all three — the space adapts to your passion. Whether you are downsizing from a larger working farm and need everything dialed in from day one, or finally making the leap to having your horses right outside the back door, this property meets you exactly where you are. Ag recapture tax is due if agricultural use is not continued.

1645 Old Annapolis Rd, Woodbine
$3,900,000
16 Beds ⋅ 12 Baths ⋅ MDHW2044530 MLS
Culturally, historically, and architecturally significant, Oakdale, circa 1838 and 1898, ancestral home of Maryland Governor Edwin Warfield, is a magnificent estate on a tranquil 180-acres only 20 miles from both the Washington and Baltimore beltways. On The National Register of Historic Places, the main house boasts 24 rooms and 5.1 baths, comprising over 9,500 sq. ft. Impressive, original detail and craftsmanship are prominent throughout, including 12-inch-thick brick walls, 12 fireplaces and the grand front porch graced by 18' Roman Doric columns. Additional residences include the Carriage House and Gardener's Cottage. Adjoining the main house via a 120' covered colonnade, Oakdale Hall, circa 2005, is artfully integrated and provides an additional 9 rooms and 5.1 baths comprising 8,870 sq. ft. of space, providing a superb setting for grand entertaining or concerts and a recreation facility along with the adjoining 60x30 pool. Farming and equestrian endeavors are served by a massive 3-level bank-barn stable, plus a silo and an equipment shed. Other outbuildings include a brick smokehouse, pond-side gazebo, and tool shed. The beautiful setting is further enhanced by a stunning 2-acre spring fed pond and several streams. With remarkable visual impact and an evocative setting, Oakdale singularly connects the past and present, offering myriad possibilities on a grand scale for the discerning buyer. Includes the main 175-acre parcel which is in Agricultural Preservation and cannot be subdivided, and a 5.8-acre lot.

16449 Ed Warfield Rd, Woodbine
$3,900,000
16 Beds ⋅ 12 Baths ⋅ MDHW2044536 MLS
Culturally, historically, and architecturally significant, Oakdale, circa 1838 and 1898, ancestral home of Maryland Governor Edwin Warfield, is a magnificent estate on a tranquil 180-acre tract only 20 miles from both the Washington and Baltimore beltways. On The National Register of Historic Places, the main house boasts 24 rooms and 5.1 baths, comprising over 9,500 sq. ft. Impressive, original detail and craftsmanship are prominent throughout, including 12-inch-thick brick walls, 12 fireplaces and the grand front porch graced by 18' Roman Doric columns. Adjoining the main house via a 120' covered colonnade, Oakdale Hall (2005), is artfully integrated and provides an additional 9 rooms and 5.1 baths comprising 8,870 sq. ft. of space. It provides a superb setting for grand entertaining or concerts and as a recreation facility along with the adjoining 60x30 pool. Outbuildings on the estate include the Carriage House and Gardener's Cottage residences, as well as a brick smokehouse, pond-side gazebo, and tool shed. Equestrian endeavors are served by a massive 3-level bank-barn stable, and farming operations are supported by an additional barn along with a silo and an equipment shed. The beautiful setting is further enhanced by a stunning 2-acre spring fed pond and several streams. With remarkable visual impact and an evocative setting, Oakdale singularly connects the past and present, offering myriad possibilities on a grand scale for the discerning buyer. Includes the main 175-acre parcel which is in Agricultural Preservation and cannot be subdivided, and a 5.8-acre lot.

16449 Ed Warfield Rd, Woodbine