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50645 Holly Point RoadDameron, MD 20628Price: $7,500,000

  • Price: $7,500,000
  • Est. Mortgage of $/month
  • 39 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Aug 20, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $7,500,000List Price
  • 4Bedrooms
  • 3Bathrooms
  • 3,268Square Feet
Nestled within the prestigious St. Jeromes subdivision, this exquisite Bayfront residence offers an unparalleled lifestyle defined by luxury and tranquility. Spanning over 175 acres just with the main house, this coastal architectural masterpiece seamlessly blends sophisticated design with nature's beauty, providing a serene retreat for discerning homeowners. Step inside to discover a harmonious open floor plan adorned with rich hardwood. The expansive family room, complete with a cozy wood-burning fireplace and elegant mantel, invites relaxation and gatherings. The kitchen is a culinary enthusiast's dream, featuring an island, ample pantry space, and an inviting eat-in area. The primary suite is a sanctuary of comfort, boasting a Bayfront view, and a luxurious primary bath equipped with a walk-in shower. Additional highlights include built-ins, recessed lighting, and a dedicated entry-level bedroom, ensuring convenience and style throughout. The exterior of this residence is equally impressive, showcasing extensive hardscaping that enhances the property's aesthetic appeal. Enjoy the ultimate outdoor lifestyle with a private beach, perfect for sunbathing or leisurely strolls along the sandy shore. The roof deck offers panoramic views of the Chesapeake Bay, while the tennis court (should you choose to restore it) provides an active lifestyle option right at your doorstep. Multiple patios and decks create inviting spaces for al fresco dining and entertaining, all set against a backdrop of lush greenery and serene Chesapeake Bay views. This premium lot is a true gem, bordered by trees and offering a secluded atmosphere that feels worlds away from the hustle and bustle. With direct access to the Bay, indulge in fishing, boating, or simply soaking in the natural beauty that surrounds you. Ample parking with an attached garage and expansive driveway. Breathtaking views of the Bay, pond, and wooded areas create a picturesque setting that changes with the seasons. Located just steps from the water's edge, this home offers a unique opportunity to embrace a lifestyle centered around nature and luxury. With over 6,136 feet of water-frontage, this property provides direct access to the Chesapeake Bay, where swimming, kayaking, and water skiing await. This exceptional residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and the beauty of nature. Experience the ultimate in coastal living, where every day feels like a vacation. Sale includes 91 lots in St. Jeromes shores and 71 lots in Bay Harbor totaling approximately 280 acres. There is nothing else like this in Southern Maryland. Your legacy awaits.
Listed by Jessica D Raley of CENTURY 21 New Millennium

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • Date Listed07/16/2026
  • ZoningRPD
  • UsmAreaDameron

Parking

  • Parking FeaturesAsphalt Driveway
  • Parking TypesAttached Garage, Driveway, Off Street
  • Total Garage And Parking Spaces10

Location

  • Address50645 Holly Point Road
  • Area Total3,268
  • SubdivisionSt Jeromes
  • TownDameron
  • StateMD
  • Zip20628
  • CountySaint Marys

Interior

  • FlooringHardwood, Carpet, Luxury Vinyl Plank, Ceramic Tile
  • Appliances IncludedBuilt-In Microwave, Dishwasher, Exhaust Fan, Refrigerator, Oven/Range - Electric
  • Heating YNYes
  • CoolingCeiling Fan(s), Central A/C

Utilities

  • Water SourcePrivate
  • SewerPrivate Septic Tank
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterElectric
  • Heating FuelElectric
  • Heat SystemHeat Pump(s)

Water Body

  • Water View YNYes
  • Waterfront FeaturesSandy Beach, Navigable Water
  • WaterfrontYes
  • Water Body TypeBay
  • Water Body NameChesapeake Bay
  • Water FeaturesBoat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, Waterski/Wakeboard
  • Water AccessYes
  • Dock Type And FeaturesPrivate, Pier (Perpendicular)
  • Dock1

Basic Information

  • MLS NumberMDSM2027830
  • Ownership InterestFee Simple
  • List Price$7,500,000
  • Square Feet3,268
  • Acreage280
  • Year Built1978
  • MLS Property TypeResidential
  • StatusACT

Building

  • ViewBay, Pond, Trees/Woods, Water, Panoramic
  • Water Oriented YNYes
  • Rooms
    • Bathroom 2
    • Bathroom 3
    • Bedroom 2
    • Bedroom 3
    • Bedroom 4
    • Dining Room
    • Family Room
    • Foyer
    • Kitchen
    • Other
    • Primary Bathroom
    • Primary Bedroom
    • Storage Room
    • Study
    • Sun/Florida Room
  • Door FeaturesSliding Glass
  • Interior FeaturesBathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Built-Ins, Carpet, Cedar Closet(s), Ceiling Fan(s), Dining Area, Elevator, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Pantry, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Walk-in Closet(s), Wood Floors
  • High School DistrictSt. Mary's County Public Schools
  • LocationTypeBayfront
  • Broker NameCENTURY 21 New Millennium
  • Building Number50645
  • Directions*GPS WILL NOT GET YOU THERE* You must schedule an appointment to get accurate directions. No drive-by's please, you won't be able to see or enter the property without the gate code.
  • Distance To Body Of Water UnitsFeet
  • Num Attached Garage Spaces2
  • Main Level Total Baths1
  • Main Level Bedrooms1
  • Main Level Full Baths1
  • Upper Levels Total Full Baths2
  • Upper Levels Total Bedrooms3
  • Upper Levels Total Baths2
  • Upper Level1 Bedrooms3
  • Upper Level1 Full Baths2
  • Upper Level1 Total Baths2
  • Story ListMain, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsConcrete, Glass, Stick Built
  • Property StyleCoastal
  • Bedrooms4
  • Full Bath3
  • Bathroom3
  • Levels2
  • Fireplace FeaturesWood, Mantel(s)
  • Fireplace YNYes
  • Fireplace1
  • Elevators1
  • Garage TypeAdditional Storage Area, Garage - Front Entry
  • Garage Spaces2
  • GarageYes
  • Patio And Porch FeaturesDeck(s), Patio(s), Porch(es)

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Assessment Amount1454567
  • Tax Year2025
  • Taxes$13,716
  • Assessment Year2025

Basic Information

Property

  • Road Surface TypePaved
  • Property ConditionExcellent
  • New Construction YNN
  • Lot Description
    • Additional Lot(s)
    • Backs to Trees
    • Fishing Available
    • Front Yard
    • Hunting Available
    • Landscaping
    • Level
    • No Thru Street
    • Partly Wooded
    • Pond
    • Premium
    • Private
    • Rear Yard
    • Secluded
    • SideYard(s)
    • Trees/Wooded

Exterior

  • RoofArchitectural Shingle
  • FoundationSlab
  • Exterior FeaturesPrivate Beach, Roof Deck, Tennis Court(s)

Property Information

  • Lot Size Square Feet12,196,800
  • Above Grade Finished Area3268

Amenities

  • PoolNo Pool
  • Accessibility AmenitiesOther, Elevator
  • PricePerSqFt2295
  • Other Amenities
    • Beachfront
    • Dock
    • Fireplace
    • Tennis
    • Water View
    • Waterfront

Other

  • Additional Parcels Descriptionapproximately 164 lot's included at this price located in St. Jeromes and Bay Harbor including the lot beside the main house
  • Additional Parcels YNY
  • View Count5

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated August 23, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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