30

Chaptico, MD Homes for Sale

Section Image Section Image
  • 0 Greens Crossing Way, Great Mills, MD 20634
    0 Greens Crossing Way, Great Mills, MD 20634
    /2

    $250,000

    • Land
    • 72.84 Acres
    • $3,432 per Acre

    0 Greens Crossing Way, Great Mills, MD 20634

    73.30 total acres consisting of 2 lots. All wooded. Great for hunting or exploring nature as it gets very close to the St. Mary's River. This is an Open Space parcel so no building permitted. Great price for a LOT of land.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (240) 262-0566

    0 Greens Crossing Way, Great Mills, MD 20634
  • 46369 Hattons Rest Ln, Lexington Park, MD 20653
    46369 Hattons Rest Ln, Lexington Park, MD 20653
    46369 Hattons Rest Ln, Lexington Park, MD 20653
    /50

    $1,850,000

    • 5 Beds
    • 6 Baths
    • 7,376 Sq Ft

    46369 Hattons Rest Ln, Lexington Park, MD 20653

    Welcome to The Retreat at Hattons Rest! A truly exceptional private waterfront estate set on a secluded 5.26-acre peninsula with an impressive 1,100 feet of pristine shoreline along the historic St. Mary's River. This magnificent 7,376-square-foot custom all-brick colonial home offers stunning water views from the kitchen and family room, where expansive windows perfectly capture the river's

    Agent Photo

    Gil Poudrier

    TTR Sotheby's International Realty

    (240) 655-8402

    46369 Hattons Rest Ln, Lexington Park, MD 20653
  • 20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    /65

    $1,450,000 Open Fri 3PM - 6PM

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft

    20045 Tower Hill Rd, Leonardtown, MD 20650

    Set quietly within 12 picturesque acres overlooking a peaceful creek, Tower Hill Retreat offers an extraordinary opportunity to experience refined country living in a natural setting. This impressive estate features 5 bedrooms (with potential for a sixth) and 5 full and 2 half bathrooms in a thoughtfully designed and exceptionally versatile floor plan. Rich hardwood and tile flooring extend

    Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
  • 0 Third St, Piney Point, MD 20690
    0 Third St, Piney Point, MD 20690
    0 Third St, Piney Point, MD 20690
    /20

    $32,900

    • Land
    • 0.27 Acre
    • $121,852 per Acre

    0 Third St, Piney Point, MD 20690

    Looking for the perfect spot to build your dream home? This is a 0.27-acre (12,000 sq ft) lot in Tall Timbers, MD. Property is a buy-and-hold opportunity until sewer might become available with the Lighthouse development down the road. Enjoy the coastal charm, nestled in a quiet, near-the-water community, only minutes away from Piney Point Lighthouse & Beach and St. George Island Beach. The much

    Krista Depenthal Lands2Love

    0 Third St, Piney Point, MD 20690
  • 18832 Piney Point Rd, Valley Lee, MD 20692
    18832 Piney Point Rd, Valley Lee, MD 20692
    /2

    $79,900 Coming Soon

    • Land
    • 3.57 Acres
    • $22,381 per Acre

    18832 Piney Point Rd, Valley Lee, MD 20692

    Welcome to 18832 Piney Point Road! This property spans 3.57 acres and includes two lots within one parcel. It offers a great opportunity to build or add to your investment portfolio.

    Jonathan Benya EXP Realty, LLC

    18832 Piney Point Rd, Valley Lee, MD 20692
  • 17863 2nd St, Tall Timbers, MD 20690
    17863 2nd St, Tall Timbers, MD 20690
    /2

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    17863 2nd St, Tall Timbers, MD 20690

    Freshly painted and ready for it's next chapter! This delightful 3-bedroom home in Tall Timbers offers comfortable living with plenty of potential to make it your own. Featuring a light and bright interior with new paint throughout, it’s the perfect canvas for your personal style. Enjoy the peaceful surroundings of this sought-after community while still being just minutes from local

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /10

    $1,999,999

    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • 20225 Point Lookout Rd, Great Mills, MD 20634
    20225 Point Lookout Rd, Great Mills, MD 20634
    20225 Point Lookout Rd, Great Mills, MD 20634
    /6

    $290,000

    • Land
    • 0.57 Acre
    • $508,772 per Acre

    20225 Point Lookout Rd, Great Mills, MD 20634

    Bring your vision to life with this unique opportunity in Great Mills! This offering includes four separate parcels, all zoned commercial—ideal for a wide range of business ventures. Access to public water and sewer. With access on both Route 5 and Flat Iron Road, the property offers exceptional visibility and access in a high-traffic area. Don’t miss the chance to invest in a prime location with

    Billy Rabbitt The Southside Group Real Estate

    20225 Point Lookout Rd, Great Mills, MD 20634
  • 46080 Usher Ln, Valley Lee, MD 20692
    46080 Usher Ln, Valley Lee, MD 20692
    46080 Usher Ln, Valley Lee, MD 20692
    /3

    $125,000

    • Land
    • 2.58 Acres
    • $48,450 per Acre

    46080 Usher Ln, Valley Lee, MD 20692

    If you’re looking for a manageable homesite that still gives you breathing room, this 2.58-acre wooded lot in Valley Lee is a standout. Tucked into a quiet, natural setting, it offers the kind of privacy and space that’s getting harder to find—without feeling overwhelming. The parcel is partially cleared, making it easier to visualize your future home placement, driveway approach, and outdoor

    Robert Gauger EXP Realty, LLC

    46080 Usher Ln, Valley Lee, MD 20692
  • 46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    /32

    $679,900 New Construction

    • 2,643 Sq Ft

    46234 Stasha Ct, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE CANTERBURY II Model *** GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this CANTERBURY II

    Lisa Riggleman RE/MAX One

    46234 Stasha Ct, Drayden, MD 20630
  • 45903 Burns Dr, Valley Lee, MD 20692
    45903 Burns Dr, Valley Lee, MD 20692
    45903 Burns Dr, Valley Lee, MD 20692
    /40

    $444,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft

    45903 Burns Dr, Valley Lee, MD 20692

    Welcome home! Nestled on a this 2+ private lot framed by mature trees, this spacious rambler offers the perfect blend of comfort and style. Generous family room with a stunning bay window that flows into the dining area and a bright, well-lit kitchen featuring maple cabinets with cherry finish, Corian counters, and a center island. Designed with a thoughtful split-bedroom floor plan, the generous

    Tracey Summers CENTURY 21 New Millennium

    45903 Burns Dr, Valley Lee, MD 20692
  • 19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor Ct, Drayden, MD 20630
    /45

    $635,900 New Construction

    • 2,240 Sq Ft

    19103 Windsor Ct, Drayden, MD 20630

    ** ONE ACRE Plus Wooded Level LOT *** The Stella Model or Select from one of our other Plans ** To Be Built ** Still time to Customize Selections and upgrades *** FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge Pantry *** STAINLESS Appliances *** First Floor Primary Bedroom complete with walk in Closet *** Master Bath with Soak Tub and Walk in Shower *** Tow Additional Main Floor

    Lisa Riggleman RE/MAX One

    19103 Windsor Ct, Drayden, MD 20630
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    /13

    $170,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    *Back on the market. A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • 46175 N Greens Rest Dr, Great Mills, MD 20634
    46175 N Greens Rest Dr, Great Mills, MD 20634
    46175 N Greens Rest Dr, Great Mills, MD 20634
    /8

    $269,700

    • Land
    • 1.63 Acres
    • $165,460 per Acre

    46175 N Greens Rest Dr, Great Mills, MD 20634

    One of the few remaining pristine lots left in Riverside Farms! 1.63 acre lot with permits, approved site plan, grading, and foundation in for 4BR, 3-4 BA 3500+ sq. ft. custom rambler with basement. Handicap accessible! This desirable neighborhood offers a community park, ball fields, walking trails, picnic areas, and community pier.Conveniently, located close to Leonardtown and Pax River

    Joe and Judi Limerick CENTURY 21 New Millennium

    46175 N Greens Rest Dr, Great Mills, MD 20634
  • 19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    /30

    $776,220 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,253 Sq Ft

    19166 N Porto Bello Dr, Drayden, MD 20630

    The PARKER Model, Elevation One ** Please excuse our mess while construction is underway ** Wonderful Front Porch ** One Acre Plus WOODED Level Lot **FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge PANTRY *** Upgraded STAINLESS Appliances *** First Floor Primary Bedroom complete with Custom Box Ceiling *** Master Bath with CUSTOM Walk in SHOWER w/Custom Seat ** Two Additional Main

    Lisa Riggleman RE/MAX One

    19166 N Porto Bello Dr, Drayden, MD 20630
  • 45656 Edge Mill Ct, Great Mills, MD 20634
    45656 Edge Mill Ct, Great Mills, MD 20634
    45656 Edge Mill Ct, Great Mills, MD 20634
    /101

    $625,000

    • 5 Beds
    • 3.5 Baths
    • 5,270 Sq Ft

    45656 Edge Mill Ct, Great Mills, MD 20634

    If space, comfort, and entertaining are on your wish list, this 5-bedroom Colonial with over 5,600 finished square feet and a fully finished basement checks every box.Welcome to 45656 Edge Mill Court, an elegant Colonial tucked away on a quiet cul-de-sac in the sought-after Woodland Park community of Great Mills, Maryland. Offering more than 5,600 square feet of beautifully finished living

    Randell Dofat EXP Realty, LLC

    45656 Edge Mill Ct, Great Mills, MD 20634
  • 17377 Piney Point Rd, Piney Point, MD 20674
    17377 Piney Point Rd, Piney Point, MD 20674
    /2

    $99,000

    • Land
    • 0.52 Acre
    • $190,385 per Acre

    17377 Piney Point Rd, Piney Point, MD 20674

    Discover the opportunity to create your ideal home on this 22,782 square foot parcel (just over half an acre) located on Piney Point in scenic St. Mary's County. Identified as Adjusted Parcel 174, this property offers a peaceful setting with convenient access to the waterfront lifestyle that makes Piney Point such a desirable destination. With no existing improvements, the lot provides a blank

    Matthew Burgan Infinitas Realty Group

    17377 Piney Point Rd, Piney Point, MD 20674
  • 17262 Larimer St, Piney Point, MD 20674
    17262 Larimer St, Piney Point, MD 20674
    17262 Larimer St, Piney Point, MD 20674
    /44

    $324,900

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    17262 Larimer St, Piney Point, MD 20674

    Welcome home to your beautiful move in ready home with WATER ACCESS! This home features 3 bedrooms and 2 full bathrooms. As you enter, you will love the open concept feel of the kitchen, dining, and living room. The kitchen features concrete countertops and a new stove (2025). The living room features a built in electric fireplace. The large primary bedroom features a walk in closet and a

    Kristen Willets RE/MAX One

    17262 Larimer St, Piney Point, MD 20674
  • 0 Holly St, Piney Point, MD 20674
    0 Holly St, Piney Point, MD 20674
    /2

    $60,000

    • Land
    • 0.28 Acre
    • $214,286 per Acre

    0 Holly St, Piney Point, MD 20674

    Build a new home on this 12000 Sg ft lot located in Piney Point. Maryland. Public sewer available for hookup.

    Mike Jordan CENTURY 21 New Millennium

    0 Holly St, Piney Point, MD 20674
  • 17615 Driftwood Dr, Tall Timbers, MD 20690
    17615 Driftwood Dr, Tall Timbers, MD 20690
    17615 Driftwood Dr, Tall Timbers, MD 20690
    /59

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,945 Sq Ft

    17615 Driftwood Dr, Tall Timbers, MD 20690

    If you've been waiting for a great house to hit the market, here's your chance. Located in The Landings at Piney Point, this sought-after location offers a desirable waterfront location and unparalleled community amenities. Enjoy the private, deep water marina with your own deeded boat slip (#58) that has a 10,000 lbs boat lift and direct access to the Potomac River. Soak up the sun at the

    Matthew Burgan Infinitas Realty Group

    17615 Driftwood Dr, Tall Timbers, MD 20690
  • 45252 Happyland Rd, Valley Lee, MD 20692
    45252 Happyland Rd, Valley Lee, MD 20692
    45252 Happyland Rd, Valley Lee, MD 20692
    /5

    $150,000

    • Land
    • 1.75 Acres
    • $85,714 per Acre

    45252 Happyland Rd, Valley Lee, MD 20692

    1.75 cleared acres zoned commercial. The address of 45252 Happyland Rd was assigned afterCommercial Outparcel C had an approved Perc. St. Mary’s County zoning is Rural Commercial Limited(RCL). Find information on uses of an RCL lot online at St. Mary's County comprehensive zoning ordinance. Excerpt from ordinance (RCL Jul 24, 2007... By the enactment of County Commissioners Ordinance No.

    Lawrence Lessin Save 6, Incorporated

    45252 Happyland Rd, Valley Lee, MD 20692
  • 0 Piney Point Rd, Callaway, MD 20620
    0 Piney Point Rd, Callaway, MD 20620
    /2

    $85,000

    • Land
    • 1.5 Acres
    • $56,667 per Acre

    0 Piney Point Rd, Callaway, MD 20620

    Discover the perfect canvas for your dream home on this 1.5-acre parcel of land, nestled in a vibrant community that offers both tranquility and convenience. Imagine waking up each day surrounded by nature, with ample space to create your own private oasis while still being just moments away from local amenities. This prime piece of land is situated in an area known for its friendly atmosphere

    Jessica Raley CENTURY 21 New Millennium

    0 Piney Point Rd, Callaway, MD 20620
  • Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    /2

    $160,000

    • Land
    • 2.37 Acres
    • $67,511 per Acre

    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 6 of Mount Pleasant Farms Minor Subdivision off Drayden Road on Hebb Road. Build your dream home on this beautiful, lot and enjoy the peaceful tranquility of nature and the beauty of Southern Maryland sunsets at their finest. Ap5proved perc for septic, utilities to be installed underground, call with any questions.

    Charlotte Long EXP Realty, LLC

    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    /2

    $175,000

    • Land
    • 2.45 Acres
    • $71,429 per Acre

    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 2 of Mount Pleasant Farms Minor Subdivision off Drayden Road on Hebb Road. Build your dream home on this beautiful, private, partially wooded lot and enjoy the peaceful tranquility of nature and the beauty of Southern Maryland sunsets at their finest. This lot has mostly woods and slopes down in the back, perfect for a home with a walk out basement. Approved perc for septic, utilities to be

    Charlotte Long EXP Realty, LLC

    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $205,000

    • Land
    • 5 Acres
    • $41,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 45546 Bethson St, California, MD 20619
    45546 Bethson St, California, MD 20619
    45546 Bethson St, California, MD 20619
    /28

    $495,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,021 Sq Ft

    45546 Bethson St, California, MD 20619

    Awesome 4 br. 2.5 bath with lots of upgrades and unique features. Upgraded hardwood floors, granite countertops, stainless steel appliances, cabinets, alarm system, sprinkler system and fenced in backyard. Enjoy this single owner home in a popular neighborhood minutes from NAS PAX RIVER. Home has been immaculately kept and ready for a buyer.

    Ross Simone RE/MAX Realty Group

    45546 Bethson St, California, MD 20619
  • 19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    /31

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    19163 N Porto Bello Ln, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE ARUNDEL Model, Elevation II*** 2 CAR GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this

    Lisa Riggleman RE/MAX One

    19163 N Porto Bello Ln, Drayden, MD 20630
  • 19285 Vanderhoof Ln, Valley Lee, MD 20692
    19285 Vanderhoof Ln, Valley Lee, MD 20692
    19285 Vanderhoof Ln, Valley Lee, MD 20692
    /3

    $135,000

    • Land
    • 4.24 Acres
    • $31,840 per Acre

    19285 Vanderhoof Ln, Valley Lee, MD 20692

    Rare 4.239-acre wooded sanctuary with approved perc in Valley Lee, the perfect canvas for your dream retirement home or development opportunity. This pristine parcel combines natural serenity with practical build-ready advantages. Mature trees provide exceptional privacy and natural cooling, ideal for a one-level custom home designed for comfortable retirement living. The approved percolation

    Robert Gauger EXP Realty, LLC

    19285 Vanderhoof Ln, Valley Lee, MD 20692
  • 17860 3rd St, Tall Timbers, MD 20690
    17860 3rd St, Tall Timbers, MD 20690
    /2

    $49,000

    • Land
    • 0.18 Acre
    • $272,222 per Acre

    17860 3rd St, Tall Timbers, MD 20690

    Discover the opportunity to build your dream home on this .184-acre wooded lot in Tall Timbers, Maryland! Tucked away in a peaceful setting, this property offers the perfect blend of privacy and natural beauty while still being conveniently located near local amenities, marinas, and waterfront recreation. The lot features public sewer availability, helping simplify the building process, while a

    Brittany Russell CENTURY 21 New Millennium

    17860 3rd St, Tall Timbers, MD 20690
Maryland St Marys County Chaptico

Real Estate & Homes for Sale in Chaptico, MD

Frequently Asked Questions

What are the most popular zip codes in Chaptico, MD?
The most popular zip codes in Chaptico, MD include 20650, 20692, 20634, 20690 and 20630.
What are the most popular neighborhoods near Chaptico, MD?
The most popular neighborhoods near Chaptico, MD are Piney Point, Saint George Island, Mechanicsville and Newburg.
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group