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$495,000
3 Beds ⋅ 2 Baths ⋅ MDCR2036684 MLS
Welcome to 5829 Woodbine Rd! Situated on nearly a full acre with no HOA, this meticulously updated 3-bedroom, 2-bathroom home offers exceptional capital improvements and outstanding outdoor living. Inside, the main living room features rich hardwood flooring that flows into the custom kitchen equipped with ceramic tile floors and 5-year-young KitchenAid appliances. Both full bathrooms, one on the upper level and one on the lower level, were completely renovated 5 years ago. Extensive mechanical and structural upgrades completed 5 years ago include a 30-year architectural shingle roof, new windows, replaced HVAC systems throughout, an upgraded 200-amp electrical panel, plus a new washing machine. The exterior boasts professional landscaping on fully fenced grounds, a storage shed, a fire pit, and a upper deck with a patio below. Parking is effortless with two extra-wide driveways, a circular driveway, and a dedicated 50-amp outdoor receptacle for RV power. This turnkey property combines complete functional peace of mind with expansive outdoor freedom in Woodbine.

5829 Woodbine Rd, Woodbine
$795,000
3 Beds ⋅ 2 Baths ⋅ MDHW2071606 MLS
Rare opportunity for a private country homestead on one of western Howard County’s prettiest and most prestigious rural road: Jennings Chapel! Surrounded by agriculture, just beyond the farms on the south side of the road is the 6,000+ acre Patuxent River State Park with hiking trails, bridle paths, hunting and fishing – giving you that unique sense of being a world away while still remaining convenient to top schools, shopping, restaurants, and major commuter routes. This solid 1968 3-bedroom, 2 bath 2 BA ranch-style home with 2-car garage, offering one-level living, retains much of its original Mid-Century Modern lines, including corner-wrap windows. Judiciously updated over the years, the interior highlights include original hardwood floors, an inviting stone fireplace with dramatic stone feature-wall, a handsome slate foyer and front porch, a big sunny great room addition, plus a new roof installed January 2026. Enjoy the convenience of main-level laundry or easily relocate it to the semi-finished basement which already features roughed-in plumbing for a future bathroom expansion. The back deck overlooks a gracious, beautifully landscaped backyard. A brick path winds down to a spectacular outdoor entertaining pavilion, slate patio floor with a very MCM-style brick fireplace & built-in grill. The beautifully proportioned 3-acre level lot offers ultimate freedom with NO HOA. It provides the perfect layout for a hobby farm, 4H animals, a pony, large organic gardens, a private soccer field, or a future pool. This property is turn-key and move-in ready, allowing you to phase-in your personal style as time and funds allow. With a current one-level footprint of 1,642 square feet on 3 private acres, there is plenty of expansion potential to build up, out, or add-on whenever you are ready. UPDATES 2026: • new roof on house (January) and pavilion (July), both with CertainTeed Landmark 50 yr. shingle * new skylights with remote controlled built-in blinds in great room • New landscaping • Septic Tank Certified, with all items on the report rectified (see disclosures for report) • Water Quality Test (see disclosures for report) • Fresh Paint throughout 2025: Septic pumped 2022: • New 80 Gallon Hot Water Heater • Installed water neutralizer • New refrigerator and range • New washer/dryer • Kitchen and sunroom/greatroom flooring replaced with floating laminate • Hardwood floors refinished • Property is lead-free paint certified • Blew insulation into the floor of the attic space • Replaced all fixtures and vanities in both bathrooms (exception hall bathtub) • Chimney rebuilt from the roof up and relined the flu w a stainless steel insulated flu liner, parged the smoke chamber and installed a new 13”x13” top closing damper. 2019: A/C added 1990: Great Room/Sunroom Addition 1989: Electrical Updated with 150 amp service

3301 Jennings Chapel Rd, 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
$575,000
3 Beds ⋅ 2 Baths ⋅ MDCR2036036 MLS
Welcome to this timeless all brick Rancher nestled on a picturesque 1.01 acre lot in the highly desirable Winfield area of Woodbine! Lovingly maintained by its owners, this exceptional 3 bedroom, 2 bath home offers classic craftsmanship, spacious living areas, and breathtaking views from both the front and rear of the property. A welcoming covered front porch leads you inside to a spacious living room where a beautiful brick wood burning fireplace and expansive picture window frame the picturesque front yard, filling the home with natural light while showcasing the peaceful setting. Rich wood trimmed windows throughout the home add warmth and timeless character. The heart of the home is the impressive oversized family room, featuring beautiful knotty pine accents and centered around a fireplace with a Fisher wood burning stove insert, creating a warm and inviting gathering space perfect for relaxing or entertaining. Just beyond, step down into the generously sized formal dining room, highlighted by a striking exposed brick chimney and expansive windows overlooking the beautiful backyard and scenic countryside beyond, creating the perfect backdrop for everyday meals or holiday gatherings. The spacious kitchen offers abundant space and flows seamlessly into the main living areas. Three amply sized bedrooms provide comfortable living, including one bedroom showcasing charming knotty pine walls and a cedar lined closet. Two full bathrooms, a convenient mudroom with main level laundry, an attic with pull down stairs, and an abundance of closets and storage throughout the home add to the home's thoughtful functionality. The unfinished walkout basement presents endless possibilities for future living space while already offering exceptional utility with a workshop area and shelving. Outside, enjoy over an acre of beautifully maintained grounds with sweeping views from every direction, mature landscaping, and plenty of space to garden, entertain, or simply enjoy the peaceful surroundings. Completing the property is an oversized attached two car garage and an expansive driveway providing ample parking for family and guests. This well cared for home offers the perfect combination of timeless charm, generous living spaces, exceptional storage, and incredible potential. Whether you're enjoying your morning coffee from the front porch or taking in the peaceful countryside from the rear of the home, the beautiful views in every direction make this property truly special.

5049 Braddock Rd, Woodbine
$649,000
3 Beds ⋅ 2 Baths ⋅ MDHW2068672 MLS
Welcome to 1420 Daisy Road, known locally as Walnut Hill, a living piece of American history nestled in the horse country of western Howard County, circa 1776. Walnut Hill is more than a home with history; its story is rooted in the red Maryland clay, its original log cabin bones, and locally quarried stone. Every brushstroke, molding, and wood panel was thoughtfully selected to honor the home’s Revolutionary-era origins. Perched gently above the surrounding countryside, Walnut Hill overlooks a patchwork of farm fields and the heirloom walnut trees that inspired the estate’s name. Upon entering the home, you are greeted by an enchanting living room showcasing original log cabin construction, remarkable beamed ceilings, and stacked and notched log walls. The grand dining room features custom crown molding, rich wood wainscoting, a brass chandelier with a ceiling medallion, and an impressive fireplace accented by brass sconces. The main level is complete with a kitchen, a full bathroom, and a cedar closet. Upstairs, three bright bedrooms are served by a remodeled full bathroom finished with porcelain tile and contemporary fixtures. A large upper-level den centered around a beautifully framed period fireplace offers flexible living space ideal for a library, study, or sitting room. Situated on a 43,342 square foot lot with heirloom walnut trees and sweeping countryside vistas, this one-of-a-kind property is a peaceful retreat steeped in history. Located in the scenic countryside of western Howard County, Woodbine is known for its rolling farmland, equestrian estates, and serene rural setting with convenient access to Baltimore, Washington, D.C., Frederick, and Columbia. Nearby are local restaurants, farm markets, parks, and outdoor recreation, including Western Regional Park and Piney Run Park. The property is served by highly regarded Howard County schools, including Lisbon Elementary, Glenwood Middle, and Glenelg High School.

1420 Daisy Rd, Woodbine