Homes for Sale with a Pool in Woodbine, MD

5 Beds ⋅ 4 Baths ⋅ MDHW2073708 MLS

Welcome to 14788 Carriage Mill Road, a beautifully appointed 5 bedroom, 3.5 bath Colonial situated on 1.38 acres in Carriage Mill Farm community. Offering an exceptional blend of classic charm, modern updates and incredible versatility, this property features a fully accessible,1-level Accessory Dwelling Unit (ADU), an in-ground pool, attached AND detached garages and expansive outdoor spaces! This is truly a property with room for everyone and everything! The main home welcomes you with a 2 story foyer featuring hardwood flooring. The living room and formal dining room are located on either side of the foyer and both feature hardwood floors and abundant natural light. The updated kitchen (2026) features luxury vinyl plank flooring, white quartz countertops, quartz backsplash, stainless steel appliances, a gas range, pantry and center island with seating. A breakfast room conveniently connects the kitchen to the spacious family room, where hardwood floors and generous space create the perfect setting for your gatherings. A powder room and dedicated laundry room complete the main level. Upstairs, you'll find 4 spacious bedrooms and 2 full bathrooms. The primary suite features an ensuite bath with two separate vanities, a shower stall, a soaking tub and two walk-in closets. Bedrooms 2-4 offer generous space and double door closets. Luxury vinyl plank flooring was installed throughout the upper level in 2023. The walkup lower level is partially finished with painted and finished drywall, electrical outlets, temperature controlled, ceiling lights and a gas fireplace. The opportunity to completely finish the lower level is already on its way for a recreation room, fitness room, home office or whatever your needs may be. Rough-in plumbing is in place for added convenience and potential. One of the home's standout features is the separate, one-level ADU, ideal for a family member, au pair, guests, home office or multigenerational living. The ADU offers 2 separate entrances, one being handicap-accessible through the attached garage. The design of the ADU features larger doorways and interior clearances to accommodate a wheelchair. The living room features impressive 14-foot vaulted ceilings and luxury vinyl plank flooring. The ADU kitchen includes quartz countertops, tiled backsplash, stainless steel refrigerator, island with storage and a walk-in pantry. The full bathroom features a tiled shower with bench and a laundry room for convenience. The ADU is independently equipped with its own electric heat pump, water heater and full-length concrete crawl space. Outside, the 1.38-acre setting provides an incredible array of amenities. Enjoy the front porch, back deck, in-ground pool, sauna, hot tub, 2-car detached garage/workshop and organic garden. The in-ground fiberglass pool spans 16'x40' and is equipped with a electric heater and chiller (enjoy the season longer!) and the deep end reaches 8.5 feet. The rear yard is fully fenced with classic white split-rail fencing, creating a wonderful and safe space for your outdoor enjoyment. The main home also offers a 2-car attached garage and a welcoming front porch spanning the front of the home. Howard County Public School System! Recent improvements and updates include: 2026 – Dishwasher, 2026 – Microwave, 2026 – Kitchen Countertops, 2026 – Kitchen Backsplash, 2026 – Roof (All), 2026 – Updated Primary Bathroom, 2025 – HVAC (Main Level), 2025 – Pool (16'x40' Inground Fiberglass W/ Heater & Chiller), 2025 – Electric 6 Person Outdoor Sauna, 2025 – Hot Tub, 2025 – Gas Range, 2023 – Hardwood Floor (Main Level), 2023 – Luxury Vinyl Plank Floors (Upper Level), 2018 – HVAC (Upper Level), 2017 – Septic Tank, 2017 – Water Heater and 2017 – ADU. With its spacious Colonial layout, extensive updates, exceptional ADU and impressive outdoor amenities, 14788 Carriage Mill Road offers a rare opportunity you don't want to miss! Book your showing today!

14788 Carriage Mill Rd, Woodbine

$1,225,000

5 Beds ⋅ 5 Baths ⋅ MDCR2037366 MLS

Welcome to 1650 Village Green Dr., an extraordinary 4.5-acre private estate, with over 5,000 finished sq. ft, in the desirable Woodbine neighborhood of Village Green, offering an exceptional blend of space, luxury, privacy, outdoor living, & modern self-sufficient living. Set at the end of a peaceful dead-end neighborhood, this remarkable property provides a true rural lifestyle while remaining convenient to major commuter routes, shopping, dining and everyday amenities. The private driveway is set back behind a beautiful wooded divide, opening up to the expansive, picturesque view of rolling hills and sweeping green vistas. Stepping inside the front door into the grand two -story foyer, the scale and elegance of this stately brick front Colonial are immediately apparent. Through the entrance foyer you're ushered into a thoughtfully designed main level filled with natural light, all newly refinished hardwood flooring throughout main level, oversized windows, & generous living spaces. The 1st floor features a formal living room, private office/library, elegant dining room with tray ceiling, crown and chair moldings. The expansive gourmet chef’s kitchen features a large center island, granite countertops, five burner gas oven range, an additional oven, making food prep more efficient, glass-front cabinetry, stainless steel appliances, pantry, pendant lighting, glass tile backsplashes & a dedicated coffee bar. The kitchen flows seamlessly into the family room boasting a cozy propane fireplace, at its center, for warming up to cozy nights w/family or guests & brand new carpeting, while the bright sun drenched breakfast room w/a high cathedral ceiling offers direct access to the rear patio and pool access. The attached three-car side loading garage provides convenient access to the kitchen/family room area with an entry landing. Upstairs 4 spacious bedrooms and three full bathrooms are arranged around a dramatic wraparound hallway overlooking the foyer. The luxurious primary suite features a tray ceiling, oversized windows, a versatile sitting room or private office, and a generous walk-in closet. The recently renovated primary bathroom offers custom dual vanities, an oversized tiled walk-in shower with seamless glass doors and windows, a built-in jetted, soaking tub surrounded by floor-to-ceiling tile, LED pendant lights, luxury finishes, and a private water closet. A second large guest bedroom includes a private en-suite bath with a stall shower. The third and fourth bedrooms share a hall full bathroom with a tub/shower and double vanity and dedicated laundry area for everyday convenience. The lower level provides incredible flexibility with three additional finished rooms, including the fifth bedroom with a recently installed, custom full bathroom with tiled walk-in shower and closets, ideal for multigenerational living, au pair or in law suite. Use the other finished rooms for recreation, guests, hobbies, fitness, additional home office, media room, etc., & the abundant unfinished areas await your creative design ideas. A wood burning stove provides heat to the lower level and main level. Outside, the recently installed L-shaped custom saltwater pool creates a private oasis with a sun deck, expansive patio, waterfalls, and fountain features. The 4.5 acres offer extensive yard space, peach, grape, blackberry & Apple trees and beautiful views, remarkable privacy, and room for a more self-sufficient lifestyle. Multiple chicken coops and a livestock pen are already in place with ample room for pigs, or other livestock. Fifty professionally installed, solar photovoltaic panels and a battery storage system provides 100% self-power and meaningful off-grid living capability. Meticulously maintained and thoughtfully designed, this gorgeous property combines peaceful rural living with modern luxury, exceptional indoor and outdoor amenities, privacy, acreage, and energy independence—all in a highly desirable Woodbine location

1650 Village Green Dr, Woodbine

$1,250,000

6 Beds ⋅ 4 Baths ⋅ MDHW2070602 MLS

A private contemporary retreat on over five picturesque acres in the heart of Woodbine! This exceptional property offers the perfect blend of peaceful country living and modern convenience with 6 bedrooms, 4 full bathrooms, an expansive open floor plan, no HOA, and endless opportunities to enjoy both indoor and outdoor living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, exposed wood beams, abundant natural light, and beautiful hardwood floors that create a warm yet dramatic atmosphere. The thoughtfully designed mudroom provides everyday convenience with a main-level laundry area, full bath ideal for pool guests, butler's pantry with granite countertops, and direct access to the attached two-car garage. The beautifully updated kitchen is the heart of the home, featuring black stainless steel appliances, Silestone countertops, Ceramic flooring, with an open concept to the Family Room featuring a cozy wood burning stove, vaulted ceilings with exposed beams, and picturesque views overlooking the resort-style backyard. Whether hosting family gatherings or quiet evenings at home, this space was made to be enjoyed. The spacious living room showcases floor-to-ceiling windows, filling the home with natural light, along with a second wood-burning fireplace and sliding glass doors leading to a large private balcony where you can relax and take in the breathtaking views of the surrounding countryside. The main level also features four generously sized bedrooms, including an impressive primary suite with a large walk-in closet and a luxurious en-suite bath complete with a jetted soaking tub, double vanity, and separate shower. Two beautifully renovated bathrooms (2019) offer today's finishes, including quartz countertops, double vanities, and a custom multi-jet rain shower. The finished walkout lower level expands your living space with two additional bedrooms, a fourth full bath, an oversized family room with recessed lighting, Bose surround sound, access for a 3rd fireplace or wood/Pellet stove, abundant storage, and direct access to the private patio and backyard oasis. Step outside and experience your own private resort. The spectacular lagoon-style heated in-ground pool is surrounded by mature trees and lush landscaping, creating the perfect setting for summer entertaining, weekend relaxation, or simply enjoying the peaceful surroundings. Significant updates include a new roof, and new siding with stone accents (2017), renovated bathrooms (2019), well pump (2024), chimney cap (May 2026), and fresh professional landscaping (June 2026). Offering the privacy of country living while remaining just minutes from major commuter routes, shopping, dining, and top-rated Howard County amenities, this one-of-a-kind property truly offers the best of both worlds. Be sure to explore the virtual tour and experience everything this remarkable home has to offer. An ADDED bonus: The property offers enough space for a future private driveway, should the new owner prefer their own dedicated entrance. Privacy. Space. Stunning views. Resort-style amenities. This is more than a home—it's a lifestyle."

15612 Bushy Park 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

$1,099,000

5 Beds ⋅ 4 Baths ⋅ MDCR2032162 MLS

Welcome to 1687 Village Green Drive in Woodbine, MD! This stunning five-bedroom,three-and-a-half bath home combines traditional elegance with modern comfort. Step inside to find beautiful crown molding throughout the 1st floor and a spacious combination kitchen and dining area, perfect for entertaining. The cozy family room, complete with a gas fireplace, creates a warm and inviting atmosphere. the primery luxurious suite has a full bath with spa-like elements includes separate vanities and a generous walk-in closet. Of the 3 other bedrooms upstairs, one bedroom has built-in shelving with a window bench seating area with storage below. The second bathroom on the second floor has dual vanities. completely beautiful finished basement, you will be amazed at the elegant entertainment room. outside, you'll enjoy a sparkling heated pool, perfect for relaxation, and the outside is an entertainer's delight, with a beautiful fire pit and seating area perfect for relaxing and watching the sunrise or sunset. Don't miss the chance to make this exceptional property your own!

1687 Village Green Dr, 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

Homes for Sale with a Pool in Woodbine, MD

All Homes for Sale with a Pool in Woodbine, MD