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Homes for Sale with a Pool in Woodbine, MD

Welcome to your dedicated resource for homes for sale with a pool in Woodbine, MD. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Woodbine, MD agent, Ryan Breeden specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Woodbine, MD

$1,500,000
5 Beds 5 Baths MDHW2070694 MLS
Nestled on over a picturesque acre in the desirable Belle Haven Estates community, this stunning Colonial showcases a timeless stone façade accented by rich burgundy shutters, lush professional landscaping, and a long private driveway. Offering 6,459 finished square feet, the home features a thoughtfully designed traditional floor plan, hardwood floors, recent interior updates including newly installed carpet, and an entertainer's dream backyard. // A grand two-story foyer creates a memorable first impression and is flanked by an elegant formal living room and a formal dining room enhanced with classic wainscoting, chair rail molding, and a timeless chandelier. At the heart of the home, the spacious eat-in kitchen is beautifully appointed with stainless steel appliances, including a refrigerator replaced in 2024, granite countertops, a center island with seating, pendant lighting, a subway tile backsplash, a built-in writing station, and a breakfast bar overlooking the sun-filled breakfast room with access to the rear deck. Just beyond, the bright breakfast room offers another inviting space to relax with direct deck access, while a conveniently located laundry room completes this wing of the main level. // Open to the kitchen, the breathtaking two-story family room impresses with soaring coffered ceilings, expansive lower windows topped by dramatic arched upper windows, and a striking floor-to-ceiling stone gas fireplace that serves as the focal point of the space. Just off the family room, a private study offers the perfect work-from-home space and is complemented by a dual-entry full bathroom, accessible from both the study and hallway, featuring recently updated lighting and mirror. // Ascend to the upper level, where a lofted hallway overlooking the family room leads to the luxurious Owner's Suite. This private retreat features hardwood flooring, an elegant tray ceiling, a spacious dressing area, a large walk-in closet, and a separate sitting room framed by decorative columns and complete with a granite-topped wet bar. The spa-inspired ensuite bathroom offers dual vanities, a corner soaking tub, and a frameless glass-enclosed shower. Three additional bedrooms complete the upper level. Two share a convenient dual-entry full bathroom, while the fourth bedroom features its own private ensuite bathroom and a walk-in closet. // The fully finished lower level expands the home's exceptional living space with luxury vinyl tile flooring throughout an expansive recreation room, providing endless possibilities for a media room, game room, or additional lounge area. A versatile bonus room is ideal for a home gym, hobby room, or flex space, while a spacious fifth bedroom with exterior access to the pool patio and a full bathroom make this level ideal for guests or multigenerational living. Two generous storage and utility rooms, along with a water heater replaced in 2023, complete the lower level. // Designed for both entertaining and everyday enjoyment, the backyard is a true private retreat. The expansive deck overlooks a heated, fenced, and filtered saltwater in-ground pool surrounded by a spacious patio, with a shaded lounge area beneath the deck for relaxing on warm afternoons. Beyond the pool, the large fenced backyard backs to a picturesque farm, providing peaceful pastoral views and an exceptional sense of privacy.

2826 Bridalwreath Ct, 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

$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

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