Welcome to your private piece of paradise! Freshly painted, new thermopane windows, newer roof, and priced to sell quickly! Once you step through the front door, the captivating view through the living room bay window will leave you breathless. Not only is this 2-bedroom, 2-full-bath home well-maintained, but it also sits on half an acre, giving you plenty of room for entertaining. As much as the intoxicating waterfront views beckon you to your private pier, the house calls you home. Once you walk in, you don't want to leave. This home features a main bedroom with a full bath, a secondary bedroom, a large living room, a beautiful kitchen, and a formal dining room with a breakfast bar that is great for holiday entertaining. Spread your party snacks on the bar or use it for extra seating. It has a gorgeous view of the water. The kitchen has plenty of room and is a cook's dream with the double wall ovens and separate stovetop. There is a large pantry for storing your non-perishables. A large guest bathroom, laundry room, and sunroom featuring large windows and sliding glass doors to the patio. This is a remarkable, well-cared-for home that includes a 2-room and full- bath guest cottage for your overnight guests, or use it as an Airbnb. Just imagine yourself out there, entertaining on your huge half-acre waterfront lot. Barbeques with family, friends, and neighbors, or fishing and crabbing off your personal pier. Or... picture being out on your boat, pulling off from your private dock, cruising on the water, breeze in your hair, sun shining down. Perhaps you decide on waterfront dining at one of the nearby restaurants, or just a day of fishing, and when the day is done, you either tie back off at your private dock, or hoist your boat up using your personal 9,000 lb boat lift. The pier has electricity, water, and a swim ladder. The possibilities of waterfront living are endless. You may decide you want to use this property for year-round living, summer vacationing, or as an Airbnb. You could live in the main house and rent out the guest cottage as an Airbnb; the possibilities are endless. There is so much more here; you need to take a look, and perhaps you may see your waterfront homeownership dreams come true. This could be your dream come true Low tide mean is 3'. Seller is offering $25,000 toward closing to a qualified buyer with a full price during open house on Sunday, August 9th only.
- MLS# MDDO2012310
- Date Listed05/18/2026
- Days on Realty 85 Days
- Bedrooms 2
- Bathrooms 2 Full baths
- Lot Size 0.56 acres (24,393 sq. ft)
- Subdivision NONE AVAILABLE
- County Dorchester
- Year Built 1953
- Square Feet 1,352 sq. ft
- Price Per Sq. Ft $532.47
Interior Features
- Cooling Heat Pump(s)
- Heating Heat Pump(s)
Exterior / Lot Features
- Roof -
- Lot Size Acres 0.56
- Lot Size SQFT 24,393.00
- Lot Features -
Financial Considerations
- Tax Amount $4,660
- Terms Cash, Conventional, FHA, VA Loan
Schools near 21677
Explore the local neighborhood highlights and top-rated schools near 21677 in Woolford, MD.
Nearby Schools
Source: School Digger
Sales & Tax History
Source: Public Records
Local Neighborhood Highlights for 21677
Discover key demographics, population statistics, and environmental insights for the Woolford, MD area.
Population & Environment
Source: Sperling's Best Places
0/100
Car-Dependent
Walk Score ®
0/100
Minimal Transit
Transit Score ®
25/100
Bikable
Bike Score ®
Overview
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 1/100, Transit Score: 0/100, Bike Score: 25/100.
Property Change History
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Points of Interest near 1514 Deep Point Rd, Woolford, MD 21677
Frequently Asked Questions for 1514 Deep Point Rd
Source: Realty.com
1514 Deep Point Rd, Woolford, MD 21677 in NONE AVAILABLE, Woolford, MD 21677 is a single family listed at $719,900. Highlights include 2 bedrooms, 2 bathrooms, 1,352 sq. ft., built in 1953, 0.56 acre lot, $532 per sq. ft.. Realty.com has 37 photos, sales history, school insights, and mortgage tools for this listing.
Realty.com has 37 photos of 1514 Deep Point Rd.
Our records indicate that 1514 Deep Point Rd was built in 1953.
The full address for this home is 1514 Deep Point Rd, Woolford, MD 21677.
1514 Deep Point Rd has been listed on Realty.com since Mon May 18, 2026
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 1/100, Transit Score: 0/100, Bike Score: 25/100.
There are 3 schools assigned to this home. Check out the schools near 1514 Deep Point Rd. Maple Elementary School (Grades: PK - 5), Mace's Lane Middle School (Grades: 6 - 8), Cambridge-south Dorchester High School (Grades: 9 - 12)
Listing provided courtesy of:
Long & Foster Real Estate, Inc.
(tel: 410-546-3211)
Listing agent:
Theresalaina Barnett
(tel: 410-330-1247)
(#3364540)
This content last refreshed on 2026-08-11 09:29:43. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.