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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, a cozy stone fireplace with dramatic stone feature-wall, a handsome slate foyer and front porch, a big sunny great room addition, plus a new roof this year. 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 complete with a brick fireplace, built-in grill, and slate patio. 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 • Landscape will be updated prior to going active on market • 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 • All new kitchen appliances • 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
$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
$750,000
3 Beds ⋅ 1 Baths ⋅ MDCR2035796 MLS
This property consist of 2 separate Parcel with 2 tax records and has 2 dwellings with 2 wells and 2 septic systems , The first dwelling is a very Well maintained single family rancher that features 2 bedrooms and a laundry room on the main floor that use to be the 3rd bedroom. This is a very UNIQUE Property!! , The 2nd dwelling is a separate detached 2 story dwelling that has 2 apartments in it. Apt# 1 is on 1st floor features 2 bedroom with 2 full baths and laundry room . LR Kitchen with island and separate dining area on the main floor. The 2nd floor apartment #2 features 2 bedrooms & 2 full baths and separate laundry room , living room & a spacious Kitchen with separate Dining area. all this is on a beautiful level 1 acre lot. Then there is the 2nd Parcel with a huge detached garage on a level .9840 acre lot. So there are 2 separate tax bills for the 2 properties. Possibility to build a home on that separate Parcel with the huge garage. Apartment #1 is Tenant occupied at $1350.00 monthly rental , Apt. # 2 currently vacant to make it your own use or rent it.

7015 Woodbine Rd, Woodbine
$675,000
3 Beds ⋅ 3 Baths ⋅ MDCR2035266 MLS
New Price Repositioning – Exceptional Value on 3.02 Acres! Welcome to 2319 Braddock Road, a charming Dutch Colonial gracefully situated on a picturesque 3.02-acre homesite, now strategically repositioned at a new price to offer an outstanding opportunity for buyers seeking space, versatility, and exceptional value. With a four-stall stable, tack room, and future growth potential, this property is perfect for bringing your horses, livestock, chickens, and furry friends. Inside, the welcoming foyer is flanked by elegant formal living and dining rooms, each showcasing hardwood flooring and classic moldings. Just beyond the living room, the inviting sunroom serves as a year-round sanctuary with rich Hardie plank walls and ceilings, complemented by its own dedicated heating and cooling system. The spacious eat-in kitchen is beautifully appointed with granite countertops, a center island, pendant lighting, decorative backsplash, and hardwood flooring. Adjacent to the kitchen, the warm and inviting family room is anchored by a cozy fireplace and enhanced by a skylight, built-in cabinetry, and access to both the mudroom and screened porch. A convenient powder room with laundry completes the main level. Upstairs, the primary suite offers luxury vinyl plank flooring and a private en-suite bath. Two additional bedrooms and a full hall bath provide comfortable accommodations for family and guests. The lower level expands the living space with a recreation room and abundant storage options. Outdoor living is truly exceptional. This unique property features a detached studio, perfect for a home office or creative workspace, a screened deck, covered rear deck, expansive driveway, and an ideal setup for those seeking a hobby farm or equestrian lifestyle. Recent improvements provide added peace of mind and include a new hot water heater and microwave (2024), well line replacement, dishwasher, and range (2022), HVAC system (2021), luxury vinyl plank flooring in the primary bedroom and hallway, and a refrigerator (2019). To further enhance the property's long-term value, a brand-new septic drain field has been installed, providing confidence and convenience for the next owner. Now offered at a newly repositioned price, this is an exceptional opportunity to own a beautifully maintained country property with acreage, modern updates, and endless possibilities. Whether you're looking for an equestrian retreat, hobby farm, or simply room to enjoy peaceful country living, 2319 Braddock Road delivers incredible value that is not to be missed.Upstairs, the primary suite offers luxury vinyl plank flooring and a private en-suite bath. Two additional bedrooms and a full hall bath provide comfortable accommodations for family and guests. The lower level expands the living space with a recreation room and abundant storage options. Outdoor living is truly exceptional, this unique property features a detached studio, perfect for a home office, screened deck, covered rear deck, expansive driveway, Recent improvements provide added peace of mind and include a new hot water heater and microwave (2024), well line replacement, dishwasher, and range (2022), HVAC system (2021), and luxury vinyl plank flooring in the primary bedroom and hallway along with a refrigerator (2019). Septic drain to be replaced. Offering a rare combination of acreage, functionality, and rural charm, this remarkable property provides endless possibilities for enjoying country living without sacrificing modern convenience. To add to the great features a new drain field has been placed for the septic system.

2319 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
$599,900
3 Beds ⋅ 3 Baths ⋅ MDCR2032212 MLS
PRICE ADJUSTMENT!!! WELCOME HOME TO THE HIGHLY SOUGHT-AFTER COMMUNITY OF PLEASANT RIDGE. THIS WELL-MAINTAINED, ALL-BRICK, 3-BEDROOM, 2.5-BATH HOME SITS ON 2.18 ACRES AND OFFERS AN OPPORTUNITY TO CREATE YOUR DREAM HOME WHILE ENJOYING THE PRIVACY AND CHARM OF COUNTRY LIVING.FEATURING OVER 3,100 SQUARE FEET, THIS HOME SHOWCASES BEAUTIFULLY MAINTAINED ORIGINAL HARDWOOD FLOORING THROUGHOUT THE MAIN LEVEL. THE SUN-FILLED LIVING ROOM FEATURES VAULTED CEILINGS, CEILING FANS, AND A LARGE BAY WINDOW THAT BRINGS IN AN ABUNDANCE OF NATURAL LIGHT. THE SPACIOUS PRIMARY SUITE OFFERS A PRIVATE BATHROOM. THE LOWER LEVEL INCLUDES A COZY WOOD-BURNING FIREPLACE FOR THOSE WINTER MONTHS, AS WELL AS A HALF BATH FOR GUESTS. WITH ITS BLANK CANVAS, THE LOWER LEVEL ALSO OFFERS THE POTENTIAL FOR AN ADDITIONAL BEDROOM. SLIDING GLASS DOORS OPEN TO A BACKYARD RETREAT, COMPLETE WITH AN IN-GROUND SWIMMING POOL AND POOL HOUSE. THE LEVEL YARD IS IDEAL FOR GARDENING, ENTERTAINING, OR SIMPLY RELAXING OUTDOORS. MAJOR SYSTEMS, INCLUDING THE ROOF, WELL, AND SEPTIC SYSTEM, HAVE BEEN MAINTAINED. ADDITIONALLY, THE HOME FEATURES A 2-CAR GARAGE WITH AMPLE SPACE FOR PARKING AND STORAGE. THIS PROPERTY OFFERS A PEACEFUL SETTING WITH ROLLING LANDSCAPES AND A TRUE SENSE OF TRANQUILITY. WHETHER YOU ARE LOOKING TO RENOVATE, CUSTOMIZE, OR INVEST, THIS IS A UNIQUE OPPORTUNITY TO OWN A HOME ON ACREAGE IN ONE OF CARROLL COUNTY'S MOST SOUGHT-AFTER LOCATIONS AT AN EXCEPTIONAL VALUE. COME TOUR THIS BEAUTIFUL HOME TODAY!

5422 Woodbine Rd, Woodbine