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Homes for Sale in 20621

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  • 36685 Owens Dr, Maddox, MD 20621
    36685 Owens Dr, Maddox, MD 20621
    36685 Owens Dr, Maddox, MD 20621
    /17

    $45,000

    • Land
    • 10,018 Sq Ft
    • $195,652 per Acre

    36685 Owens Dr, Maddox, MD 20621

    Build your home or a second home here in this quiet community. Neatly tucked away. This lot is cleared with a buffer for privacy. Minutes walk to the private pier, boating and fishing. Beautiful views of the Wicomico River. Come see the possibilities.

    Agent Photo

    Myra Wallace

    Samson Properties

    (227) 230-0359

    36685 Owens Dr, Maddox, MD 20621
  • 0 Dannys Ln, Chaptico, MD 20621
    0 Dannys Ln, Chaptico, MD 20621
    /2

    $75,000

    • Land
    • 1.47 Acres
    • $51,020 per Acre

    0 Dannys Ln, Chaptico, MD 20621

    Perked lot for sale in the heart of Chaptico. A private, flat and cleared lot ready for you to bring your vision to life.

    Darrin Carter RE/MAX One

    0 Dannys Ln, Chaptico, MD 20621
  • 0 Lagoon Dr, Maddox, MD 20621
    0 Lagoon Dr, Maddox, MD 20621
    /2

    $5,000

    • Land
    • 10,018 Sq Ft
    • $21,739 per Acre

    0 Lagoon Dr, Maddox, MD 20621

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 6/19/2026 @ 10:00 AM. Bidding ends 6/23/2026 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $5,000 This lot of land is located in Chaptico, MD within St. Mary’s County. The property is in close proximity to Wicomico Shores Golf Course, Christ Episcopal Church, Bachelor's Hope,

    Adam Shpritz Ashland Auction Group LLC

    0 Lagoon Dr, Maddox, MD 20621
  • 0 Mill Point Rd, 4, Chaptico, MD 20621
    0 Mill Point Rd, 4, Chaptico, MD 20621
    0 Mill Point Rd, 4, Chaptico, MD 20621
    /7

    $10,000

    • Land
    • 10,890 Sq Ft
    • $40,000 per Acre

    0 Mill Point Rd, 4, Chaptico, MD 20621

    Build your dream home on this lot in Chaptico.

    Billy Rabbitt The Southside Group Real Estate

    0 Mill Point Rd, 4, Chaptico, MD 20621
  • 23690 Maddox Rd, Chaptico, MD 20621
    23690 Maddox Rd, Chaptico, MD 20621
    23690 Maddox Rd, Chaptico, MD 20621
    /4

    $599,900

    New Construction Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,022 Sq Ft

    23690 Maddox Rd, Chaptico, MD 20621

    New Construction in Chaptico! Adorable Cape Cod situation on over one acre, surrounded by mature trees, creek, gorgeous pastoral views and beautiful Chaptico Sunsets! This Cape Cod welcomes you home from your hectic day to a serene surrounding with a convenient location to all amenities. You are only minutes away from Leonardtown shopping /entertainment and Pax River /Dalgren. The main level

    Michele Hughes RE/MAX Realty Group

    23690 Maddox Rd, Chaptico, MD 20621
  • 36724 Fielding Dr, Chaptico, MD 20621
    36724 Fielding Dr, Chaptico, MD 20621
    36724 Fielding Dr, Chaptico, MD 20621
    /21

    $45,000

    • Land
    • 10,018 Sq Ft
    • $195,652 per Acre

    36724 Fielding Dr, Chaptico, MD 20621

    Three adjoining lots (15, 16, and 17) are being offered together as a package sale, providing added space and flexibility for future plans. A unique opportunity to own multiple adjacent parcels in Longview Beach! Property owners current on HOA dues enjoy access to community amenities including the beach, boat ramp, fishing pier, basketball and tennis courts, playground, picnic areas, and

    CHRISSY HAYWARD RE/MAX One

    36724 Fielding Dr, Chaptico, MD 20621
  • 36031 Bay Dr, Chaptico, MD 20621
    36031 Bay Dr, Chaptico, MD 20621
    36031 Bay Dr, Chaptico, MD 20621
    /21

    $200,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    36031 Bay Dr, Chaptico, MD 20621

    Opportunity meets lifestyle in this charming water-view rambler overlooking the Wicomico River, located in the desirable Mill Point Shores community. Positioned just across the street from waterfront homes, this property offers the feel of waterfront living without the premium price—an ideal opportunity for buyers looking to invest, create a weekend retreat, or customize a home to their vision.

    Frank McKnew RE/MAX Realty Group

    36031 Bay Dr, Chaptico, MD 20621
  • 36031 Bay Dr, Chaptico, MD 20621
    36031 Bay Dr, Chaptico, MD 20621
    36031 Bay Dr, Chaptico, MD 20621
    /21

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    36031 Bay Dr, Chaptico, MD 20621

    Opportunity meets lifestyle in this charming water-view rambler overlooking the Wicomico River, located in the desirable Mill Point Shores community. Positioned just across the street from waterfront homes, this property offers the feel of waterfront living without the premium price—an ideal opportunity for buyers looking to invest, create a weekend retreat, or customize a home to their vision.

    Frank McKnew RE/MAX Realty Group

    36031 Bay Dr, Chaptico, MD 20621
  • 36061 Roosevelt Blvd, Chaptico, MD 20621
    36061 Roosevelt Blvd, Chaptico, MD 20621
    36061 Roosevelt Blvd, Chaptico, MD 20621
    /14

    $189,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    36061 Roosevelt Blvd, Chaptico, MD 20621

    Welcome to 36061 Roosevelt Boulevard, a solid brick raised rambler nestled in the established Mill Point Shores community of Chaptico, Maryland. This three-bedroom, two-full-bath home offers 1,780 square feet of above-grade living space and sits on a quarter-acre lot, providing a peaceful setting with room to personalize and add value. Built in 1945, the home features classic brick construction,

    Mr. Nathaniel Arnold Epique Realty

    36061 Roosevelt Blvd, Chaptico, MD 20621
  • 36070 Carver Rd, Chaptico, MD 20621
    36070 Carver Rd, Chaptico, MD 20621
    /2

    $9,950

    • Land
    • 11,325 Sq Ft
    • $38,269 per Acre

    36070 Carver Rd, Chaptico, MD 20621

    Enjoy the natural beauty and privacy of Southern Maryland while benefiting from the community's water access and nearby outdoor recreational opportunities. No perc test information is currently available, and buyers are encouraged to perform their own due diligence regarding building suitability and utility availability. Conveniently located within commuting distance of Lexington Park, Waldorf,

    Darrin Carter RE/MAX One

    36070 Carver Rd, Chaptico, MD 20621
  • 0 Sunset Dr, Chaptico, MD 20621
    0 Sunset Dr, Chaptico, MD 20621
    /2

    $12,000

    $13K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $48,000 per Acre

    0 Sunset Dr, Chaptico, MD 20621

    Motivated Seller!!! Looking for a lot in a water access community? Take a look at this flat, mostly cleared lot in desirable Southern Maryland. The community has beach access, club house, boat ramp, and much more. Buyer to perform all due diligence.

    Stephanie Rivers The Southside Group Real Estate

    0 Sunset Dr, Chaptico, MD 20621
  • 0 Bay Dr Unit MDSM2028630, Chaptico, MD 20621
    0 Bay Dr Unit MDSM2028630, Chaptico, MD 20621
    0 Bay Dr Unit MDSM2028630, Chaptico, MD 20621
    /9

    $18,000

    • Land
    • 11,325 Sq Ft
    • $69,231 per Acre

    0 Bay Dr Unit MDSM2028630, Chaptico, MD 20621

    Mills Point is Gorgeous! Looking for a lot in a water access community? Take a look at this lot. Buyer to perform all due diligence.

    Kesha Catlin KC Realty Group

    0 Bay Dr Unit MDSM2028630, Chaptico, MD 20621
Maryland St Marys County Chaptico 20621

Real Estate & Homes for Sale in 20621

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