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$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
$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
$700,000
5 Beds ⋅ 4 Baths ⋅ MDCR2032950 MLS
Come see your new home today! Nestled in the heart of Woodbine, this beautifully maintained 5-bedroom, 3.5-bath home sits on a peaceful 1-acre lot offering the perfect blend of comfort, flexibility, and country charm. Featuring a renovated kitchen, brand-new roof, and new LVP flooring and fresh paint in the basement, this move-in ready home also includes a private in-law suite with a convenient kitchenette — ideal for multigenerational living, guests, or added rental potential. Enjoy tranquil country living with plenty of space to relax, entertain, and unwind.

6441 Woodbine Rd, Woodbine
$749,000
5 Beds ⋅ 3 Baths ⋅ MDHW2068370 MLS
WELCOME HOME to this BEAUTIFULLY RENOVATED rancher that sits on 1+ scenic acres, backing to open farmland with breathtaking views from the new deck and screened-in porch. A welcoming CIRCULAR driveway offers plenty of parking and adds to the home's CHARMING curb appeal. Inside, the heart of the home is a BRIGHT, EAT-IN KITCHEN with QUARTZ countertops that are perfectly paired with an eye-catching electric FIREPLACE in the dining area—featuring a sleek, floor-to-ceiling black-and-white granite façade. The living room captures the peaceful beauty of the backyard, with SLIDING GLASS DOORS that walk out to the NEW DECK, while built-in Bluetooth speakers let you enjoy your favorite music in the kitchen, living room, deck, and PATIO. CUSTOM BUILT-IN cabinetry offers the perfect place for your entertainment center. HUGE SCREENED IN PORCH off of kitchen is perfect for entertaining. Three generous bedrooms on the main level include a PRIMARY SUITE with large, custom closets and ensuite bathroom. The hall bathroom offers a stylish design, complete with a tub/shower combo. Downstairs, the WALK-OUT LOWER LEVEL has two additional bedrooms—one of which is especially spacious and includes a cozy sitting area with a wood-burning fireplace. You'll also find a kitchenette and laundry area plus an OFFICE AND BONUS ROOM. A FULL BATHROOM makes this perfect for an in-law suite or rental Outside, you'll find a large shed and a DETACHED, HEATED oversized 2-car garage with remote entry. From top to bottom, this home is move-in ready, thoughtfully designed, and filled with MODERN COMFORTS surrounded by peaceful countryside charm. GLENELG HIGH SCHOOL DISTRICT!

16480 Ed Warfield Rd, Woodbine
$765,000
4 Beds ⋅ 5 Baths ⋅ MDCR2034212 MLS
Beautiful custom home on a 1.5 acre private woodland lot . Features 4BR/3BA with 2 half BA, including a rare MAIN LEVEL IN-LAW SUITE with a private entrance. Enjoy a designer kitchen, hardwood floors, and a spa-like master bath, along with an upgraded heating furnace (2024). The finished walk-out basement leads to an outdoor oasis with professional hardscaping, a two-tier deck, and multiple patios. Situated in a premier school district minutes from everything. The perfect combination of privacy, style, and convenience!

5519 Woodbine Rd, Woodbine