Woolford MD Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,463
Status:
NEW LISTING
MLS#:
MDDO2013224
Type:
Single Family-Detached
Subdivision:
WOOLFORD
Lot size:
2.59 Acres
Year built:
2004
Courtesy: Coldwell Banker Realty 410-543-4545
View additional info

ADDITIONAL INFORMATION

Beds:
3
Baths:
2.00
Sq.Ft.:
2,774
Status:
Active
MLS#:
MDDO2012812
Type:
Single Family-Detached
Subdivision:
WOOLFORD
Lot size:
2.7 Acres
Year built:
2001
Courtesy: Coldwell Banker Realty 410-543-4545
View additional info

ADDITIONAL INFORMATION

Coastal living at its finest on Church Creek! Nestled on 2.7 private acres with 262 feet of water frontage, this 3-bedroom, 2-bath home offers an open-concept design with hardwood floors, exposed beams, and a well-appointed kitchen with an island. The primary suite serves as a true sanctuary, featuring a double-sided fireplace enjoyed from both the bedroom and deep soaking tub. Outdoor features include a spacious deck, screened porch, attached oversized 2-car garage, and a private deep-water dock with an 8,000 lb boat lift plus two PWC lifts. Ready for endless water activities, fishing, and sunset views right from your back door. All this just a short trip from Cambridge.

Beds:
7
Baths:
5.00
Sq.Ft.:
4,072
Status:
Active
MLS#:
MDDO2013062
Type:
Single Family-Detached
Subdivision:
MCKEIL POINTE
Lot size:
5.7 Acres
Year built:
2005
Courtesy: Benson & Mangold, LLC 410-228-0800
View additional info

ADDITIONAL INFORMATION

McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

Beds:
4
Baths:
1.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
MDDO2012810
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.92 Acres
Year built:
1900
Courtesy: Keller Williams Realty 302-846-7839
View additional info

ADDITIONAL INFORMATION

*** SELLER WILL PAY 3% TOWARDS BUYERS CLOSING COSTS*** Experience the timeless charm of Maryland's Eastern Shore at 4707 Steamboat Road in the peaceful community of Woolford MD. Just steps from the shores of beautiful Church Creek, this beautifully updated traditional farmhouse offers picturesque water views from the screened front porch and the perfect blend of classic Eastern Shore character and modern comfort. Inside, you'll find a bright, open-concept living and dining area that flows effortlessly into a spacious gourmet kitchen featuring updated cabinetry, a gas range, and upgraded flooring. Original hardwood floors throughout the foyer and first-floor bedrooms preserve the home's timeless appeal, while the generously sized rooms showcase the craftsmanship and charm of a bygone era. Extensive recent improvements make this home truly move-in ready. Recent updates include updated double-pane windows for improved energy efficiency, a new refrigerator (2024), new washer and dryer (2025), a new well pump, an owned water treatment system, energy-efficient mini-split heating and cooling systems, luxury vinyl plank flooring upstairs and downstairs, and a new electrical panel—all completed to provide comfort and peace of mind for the next owner. Step outside and enjoy everything this property has to offer. Sip your morning coffee on the rear deck overlooking the spacious backyard, or unwind on the screened front porch while taking in peaceful views of Church Creek. The large lot offers plenty of room to expand, garden, or build a future garage, while the well-maintained folk barn provides abundant storage and adds authentic character to this charming Eastern Shore setting. Whether you're searching for a full-time residence, a peaceful weekend retreat, or a place to enjoy the slower pace of living, 4707 Steamboat Road offers a rare opportunity to own a beautifully updated farmhouse in one of Dorchester County's most scenic locations. As an added bonus, additional equipment and personal property will convey with an acceptable offer.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDDO2012802
Type:
Single Family-Detached
Subdivision:
TAYLORS ISLAND
Lot size:
2.07 Acres
Year built:
1983
Courtesy: Coldwell Banker Realty 410-543-4545
View additional info

ADDITIONAL INFORMATION

Imagine waking up to sweeping waterfront views, launching your kayak from your private beach, and ending the day with uninterrupted sunset skies right from your own yard! This stunning, completely remodeled coastal retreat combines peace of mind with exceptional investment potential. Featuring a new roof and new HVAC system, every detail of this home has been thoughtfully updated, including fresh LVP flooring throughout with all-new subflooring and beautifully updated bathrooms. The gourmet kitchen boasts sleek granite countertops, perfect for entertaining family and guests. Step outside to enjoy direct waterfront living with a riprapped shoreline and your very own private beach access—ideal for launching kayaks, soaking up sunset views, or enjoying water recreation. Detached garage. Currently operating as an active Airbnb with a proven rental history, this property is ready to generate income from Day 1. Furnishings are negotiable, offering a seamless, plug-and-play opportunity for vacation home buyers or investors alike.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
MDDO2012310
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.56 Acres
Year built:
1953
Courtesy: Long & Foster Real Estate, Inc. 410-546-3211
View additional info

ADDITIONAL INFORMATION

Welcome to your waterfront property! Home boasts nice open living room /dining room area with gorgeous views of the water from the large bay window, and a food bar dividing the rooms. The primary suite allows access to the enclosed sunroom with expansive views of the water. The home features secondary bedroom with water view, a second full bath, a kitchen with a double wall oven, separate cooktop, a bistro area, and a large pantry. Priced with the realization in mind potential buyers may decide to update the kitchen and baths. Property has a second 2 room and bath building. The home is situated on +/- .50 acre. Pier has a 9,000 lb boatlift, swim ladder, water and electric. This home is a Must-See to truly appreciate all it has to offer. Sellers are offering an assumable FHA mortgage at 5.25%. to qualified buyers. Buyer will be responsible to pay sellers the difference between the assumable mortgage amount and the contracted sale price of the home.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,615
Status:
Active
MLS#:
MDDO2012352
Type:
Single Family-Detached
Subdivision:
WOOLFORD
Lot size:
0.72 Acres
Year built:
1990
Courtesy: Benson & Mangold, LLC 410-228-0800
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ADDITIONAL INFORMATION

PRICE ADJUSTMENT! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the rear of the house situated to enjoy the tranquil water views. Roof new in 2026 along with other recent upgrades.

Beds:
1
Baths:
1.00
Sq.Ft.:
1,040
Status:
Active
MLS#:
MDDO2012308
Type:
Single Family-Detached
Subdivision:
DEEP POINT
Lot size:
0.34 Acres
Year built:
1982
Courtesy: Sharon Real Estate P.C. 410-228-2525
View additional info

ADDITIONAL INFORMATION

Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. Property is being sold as-is. Appointment required for all showings.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,633
Status:
Active
MLS#:
MDDO2012022
Type:
Single Family-Detached
Subdivision:
MCKEIL POINTE
Lot size:
6.2 Acres
Year built:
1996
Courtesy: Benson & Mangold, LLC 410-822-6665
View additional info

ADDITIONAL INFORMATION

Fabulous waterfront home with modern flair and a stunning indoor pool, ideally located in McKeil Point, offering effortless one-level living and an open floor plan designed to capture spectacular, unobstructed water views from nearly every room. The thoughtfully designed split-bedroom layout ensures privacy, featuring a serene primary suite with direct access to the indoor pool, a luxurious bath, and a private waterside deck. The spacious kitchen includes a center island with bar seating and flows seamlessly into a separate dining room, perfect for entertaining. A light-filled family room opens to both the indoor pool and expansive waterside deck, creating the ultimate indoor-outdoor lifestyle. Set on over 6 acres along scenic Fishing Creek, the property boasts a rip-rapped shoreline, private pier and boardwalk, abundant wildlife, and a two-car side-loading garage, offering a rare blend of tranquility, space, and waterfront living at its finest with the advantage as a valued vacation rental destination.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,120
Status:
Active
MLS#:
MDDO2011692
Type:
Single Family-Detached
Subdivision:
DEEP POINT
Lot size:
0.89 Acres
Year built:
1950
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

SEIZE THE SUNSET! Enjoy waterfront tranquility right at your back door—and don’t miss this significant price improvement! If you’ve been searching for an immaculate, move-in-ready waterfront home with exceptional first-floor living, this may be the one. Major interior renovations were completed in 2022, and this beautifully updated and meticulously maintained 3-bedroom, 2-bath home offers more than 2,300 square feet of bright, inviting living space designed to showcase the beauty of the Eastern Shore. Panoramic waterfront views greet you from nearly every room, with the living room overlooking the breathtaking vistas of Fishing Creek. Two spacious living areas, each featuring a cozy fireplace, provide plenty of room to relax, entertain, and enjoy the changing seasons.The open gourmet kitchen is the heart of the home, featuring custom finishes, modern updates, and a built-in wine cooler—perfect for preparing meals, gathering with friends, or simply enjoying a quiet evening while taking in the view. Major systems and improvements have already been taken care of, offering peace of mind for the next owner. The roof was replaced in 2018, the HVAC system in 2022, and new thermostats were installed in 2024. An updated sprinkler system, new French gutter drains installed in 2025, and an improved Dry-Zone encapsulated crawl space further enhance the home's efficiency and long-term protection. The crawl space also features a new dehumidifier installed on a raised platform, new insulation, and an indoor monitoring system, all completed in 2026. For additional peace of mind, the home includes transferable USAA flood insurance along with annual Dry-Zone, HVAC, and pest control inspection contracts. Connected to public sewer, this home offers the convenience of simplified ownership from day one.Ideally located just a short distance from historic Cambridge and the Hyatt Regency Chesapeake Bay Golf Resort, with easy access to Easton, Oxford, and St. Michaels. Nature lovers will appreciate the close proximity to Blackwater Wildlife Refuge, where you can explore scenic trails, enjoy kayaking and biking, observe abundant wildlife, and perhaps catch a glimpse of the area's magnificent bald eagles. This is more than a home—it’s an opportunity to embrace the peaceful waterfront lifestyle, spectacular sunsets, and timeless charm of Maryland’s Eastern Shore, with the comfort and confidence of a home where many of the major updates have already been completed.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Woolford Real Estate

Woolford is located in Maryland. Woolford, Maryland has a population of 382. Woolford is less family-centric than the surrounding county with 18.38% of the households containing married families with children. The county average for households married with children is 19.47%.

The median household income in Woolford, Maryland is $59,453. The median household income for the surrounding county is $55,652 compared to the national median of $69,021. The median age of people living in Woolford is 48.5 years.

Woolford Weather

The average high temperature in July is 88.7 degrees, with an average low temperature in January of 28.5 degrees. The average rainfall is approximately 45.9 inches per year, with 10.9 inches of snow per year.

Woolford Map

Woolford Real Estate Market Conditions

  • Median sales price

    N/A
  • # Active listings

    13
    30-day change

Woolford Schools and Demographics

Education near Woolford, MD

City County
High School Graduates 98.27 87.42
College Degree - 2 year 9.9 6.68
College Degree - 4 year 28.22 19.86
Graduate Degree 9.65 6.32
Expenditures per Student 18,266 18,266
Students per Teacher 13.4 13.4

Elementary Schools near Woolford, MD

Grades Students P/T Ratio ZIP
Choptank Elementary School PK - 05 409 12.8 21613
Maple Elementary School PK - 05 475 14 21613
Sandy Hill Elementary School PK - 05 523 13.4 21613
South Dorchester School PK - 08 192 12.4 21622
Warwick Elementary School PK - 05 337 15.3 21664
White Marsh Elementary School PK - 05 380 15.8 21673

Middle Schools near Woolford, MD

Grades Students P/T Ratio ZIP
Mace's Lane Middle School 06 - 08 533 14.6 21613

High Schools near Woolford, MD

Grades Students P/T Ratio ZIP
Cambridge-South Dorchester High School 09 - 12 782 14.5 21613

Ungraded Schools near Woolford, MD

Grades Students P/T Ratio ZIP
Dorchester County Career and Technology Center UG - UG 0 0 21613
Judith P. Hoyer Early Childhood Center UG - UG 0 21613

Demographics near Woolford, MD

City County
Neighborhood Type Small town
Population 382 32,486
Population Density 41 60
Median Age 48.5 44.1
People per Household 2.8 2.4
Median Household Income 59,453 55,652
Average Income per Capita 31,887 31,983

Real estate near Woolford