1514 Deep Point Road

House from pier
Home from pier
Driveway leading to 3-car carport
Dining Room
Living Room Gas Fireplace
Living Room
Sunroom
Sunroom
Kitchen View 1
Kitchen View 2
Kitchen View 3
Gallery Image 12
Main Bedroom Bath
Bedroom 2
Guest Bath
Guest Bath
Guest Cottage View 2
Guest cottage full-bath
Great place to relax
Landscaping
Side view
Sidewalk to carport
Your personal pier and boat lift
The views never end
Swim Ladder
Boat lift
Pier
View from the pier
A Beautiful sunset view
Active
$669,900
2 beds1,352 sqft$495/sqft
1514 Deep Point Rd, Woolford, MD 21677
Est: $3,793/moGet pre-approved
Single FamilyProperty Type
0.56 acresLot Size
1953Year Built
$495/sq ftPrice per sq ft
9 carsParking Spaces

Description

Welcome to your private piece of paradise! Not only do you get gorgeous waterfront and sunset views, but you also get a beautiful home and guest cottage. Freshly painted main bath, new thermopane windows, newer roof, meticulous landscaping, 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 over half an acre, giving you...Welcome to your private piece of paradise! Not only do you get gorgeous waterfront and sunset views, but you also get a beautiful home and guest cottage. Freshly painted main bath, new thermopane windows, newer roof, meticulous landscaping, 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 over 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, wonderful 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 double wall ovens and a 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, full- bath guest cottage for your overnight guests, or use it as an Airbnb. Just imagine yourself out there, entertaining on your huge, over half-acre waterfront lot. Barbecues 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 up 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. Fish and crab from your private pier. 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; 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. Taylors Island is about 10 minutes away by car; Cambridge is about 20 minutes away for shopping, dining, and more. Low tide mean is 3'.
34 days on Market
  • Listed by: Theresalaina Kaye Barnett 410.330.1247 theresalaina.barnett@longandfoster.com • Long & Foster Real Estate, Inc.
Last updated: 08/14/2026 03:06 PM • Source: BRIGHT, MLS#: MDDO2012310

Location

Listing Courtesy of Long & Foster Real Estate, Inc.
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$3,793 per month

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Property Taxes

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Property Information for 1514 Deep Point Road

Property Details
  • Taxes: $4,660 / year
  • MLS Type: Residential / Fee Simple
  • County: Dorchester County
  • Tax ID Number: 1016003131
  • Ownership: Fee Simple
  • Condo Coop Association: No
  • HOA: No
  • Structure Type: Detached
  • Style: Ranch/Rambler
  • Levels/Stories: 1
  • Waterfront: Yes
  • Views: River
  • Garage: No
  • Expected On Market Date: 07-01-2026
  • Subdivision: NONE AVAILABLE
  • Subdivision: NONE AVAILABLE (DORCHESTER MD)
  • Total Parking Spaces: 9
  • Central Air: No
  • Basement: No
  • Room Count: 7
  • Above Grade Finished SQFT: 1,352.00
  • Above Grade Fin SQFT Source: Assessor
  • Below Grade Finished SQFT: .00
  • Below Grade Fin SQFT Source: Assessor
  • Below Grade Unfinished SQFT: .00
  • Below Grade Unfin SQFT Source: Assessor
  • Total Below Grade SQFT: .00
  • Total Below Grade SQFT Source: Assessor
  • New Construction: No
  • Property Condition: Very Good
Building Information
  • Stories: 1
  • Year Built: 1953
  • Lot Size: 0.56 AC / 24,393 SF
Location
Location
  • In City Limits: No
  • School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
  • School District County ID: 121139665361
  • SchoolDistrictSource: 3rd Party
  • High School: CAMBRIDGE-SOUTH DORCHESTER (DORCHESTER MD)
  • HighSchoolSource: Listing Agent
  • County: DORCHESTER
Waterfront / Water Access
Waterfront / Water Access
  • Water View: Yes
  • Water Access: Yes
  • Water Access Features: Boat - Powered, Personal Watercraft (PWC)
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: Yes
  • Water Body Type: River
  • Water Frontage In Feet: 100.0
  • Mean Low Water Feet: 3.00
Association / Community Info
Association / Community Info
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $429,400
  • Year Assessed: 2026
  • County Tax: $4,660
  • Improvement Assessed Value: $215,700
  • Land Assessed Value: $213,700
  • Clean Green Assessed: No
  • Land Use Code: R
  • Loss Mitigation Fee: No
  • Agricultural Tax Due: No
  • Historic: No
  • Zoning: RR
  • Tax Lot: 20P21
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Lease Information
Lease Information
  • Pets Allowed: No
Rooms
Main
  • # Bedrooms Count Main Level: 2
  • # Bathrooms Count Main Level: 2
  • # Bathrooms Full Main Level: 2
Rooms
  • Room List: Living Room, Dining Room, Kitchen, Sun/Florida Room, Laundry
  • Stories: Main
Rooms Information
Room 1
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
Room 2
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
Room 3
  • Room Type: Living Room
  • Room Level: Main
  • Room Exists: Yes
Room 4
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
Room 5
  • Room Type: Sun/Florida Room
  • Room Level: Main
  • Room Exists: Yes
Building Info
Building Info
  • Total Finished SQFT: 1,352.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Road Surface Type: Black Top
  • Parcel ID: 5324223
Parking
Parking
  • Type Of Parking: Detached Carport, Driveway
  • Driveway - # of Spaces: 6
  • Detached Carport - # of Spaces: 3.0
  • Parking Features: Gravel Driveway
Interior Features
Interior Features
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Gas/Propane, Screen
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Microwave, Oven - Double, Refrigerator, Washer, Water Heater
  • Accessibility Features: 32"+ wide Doors, Accessible Switches/Outlets
  • Security Features: Security System
  • Window Features: Energy Efficient
Exterior Features
Exterior Features
  • Pool: No Pool
  • Horse: No
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Private
  • Sewer Septic: Public Septic
  • Electric Service: 200+ Amp Service
Confidential Data
Listing Office
  • List Agent AOR: Coastal Association of REALTORS (MD)

Property History for 1514 Deep Point Road

DateEvent & SourcePriceAppreciation
Aug 12, 2026

Price Change

BRIGHT #MDDO2012310

$669,900—
Aug 3, 2026

Price Change

BRIGHT #MDDO2012310

$719,900—
Aug 3, 2026

Listed (Active)

BRIGHT #MDDO2012310

—
DateEvent & SourcePrice
08/12/2026

Price Change

BRIGHT #MDDO2012310

$669,900
08/03/2026

Price Change

BRIGHT #MDDO2012310

$719,900
08/03/2026

Listed (Active)

BRIGHT #MDDO2012310

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 1514 Deep Point Road

Taxable ValueLand$213,700Additions$215,700Total$429,400
Tax Record2025$4,720 ($393 / month)
Home Facts
Beds0Baths2Total Finished SqFt1,352 SqFtAbove Grade Finished SqFt1,352 SqFtStories1Lot Size24,393 SqFtStyleSingle Family ResidenceYear Built1953Year Renovated1953ZoningRRCountyDORCHESTERAPN16-003131

Schools near 1514 Deep Point Road

This home is within Dorchester County Public Schools.
Rating
School
Type
Grades
Distance
South Dorchester School
Public - PK to 8
Cambridge-South Dorchester High School
Public - 9 to 12
Dorchester County Career And Technology Center
Public - 9 to 12
Judith P. Hoyer Early Childhood Center
Public - PK to 5
Rating
School
Distance
South Dorchester School
PublicPK to 8

Cambridge-South Dorchester High School
Public9 to 12

Dorchester County Career And Technology Center
Public9 to 12

Judith P. Hoyer Early Childhood Center
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1514 Deep Point Road, Woolford, MD 21677

1514 Deep Point Road is a single family home for sale in Woolford, MD 21677. This property was listed for sale on July 1, 2026 by Long & Foster Real Estate, Inc., it's currently listed at $669,900. It has been on the market for a total of 34 days and was last sold on April 14, 2022. This listing's school district is Dorchester County Public Schools. Nearby schools include South Dorchester School, Cambridge-South Dorchester High School and Dorchester County Career And Technology Center. 1514 Deep Point Road is a 2-bed, 2-bath, 1,352 sqft single family home built in 1953.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Long & Foster Real Estate, Inc.

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 08/14/2026 03:06 PM