17

Chestertown, MD Homes for Sale with Acreage

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  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /5

    $60,000

    • Land
    • 3 Acres
    • $20,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    $5K PRICE DROP
    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Unsuccessful land evaluation

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /2

    $135,000

    $15K PRICE DROP
    • Land
    • 1.8 Acres
    • $75,000 per Acre

    109 2nd St, Chestertown, MD 21620

    Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton,

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • 1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    /4

    $110,000

    • Land
    • 1.93 Acres
    • $56,995 per Acre

    1906 Pondtown Rd, Chestertown, MD 21620

    Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes.

    Lonnie Gilmore Keller Williams Flagship

    1906 Pondtown Rd, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • 22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    /50

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 240 Round Top Rd, Chestertown, MD 21620
    240 Round Top Rd, Chestertown, MD 21620
    /2

    $295,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,132 Sq Ft

    240 Round Top Rd, Chestertown, MD 21620

    COMING SOON!! Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced

    Karen Clark Clark & Co Realty, LLC

    240 Round Top Rd, Chestertown, MD 21620
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $385,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 8312 Broad Neck Rd, Chestertown, MD 21620
    8312 Broad Neck Rd, Chestertown, MD 21620
    8312 Broad Neck Rd, Chestertown, MD 21620
    /47

    $380,000

    • 3 Beds
    • 1.5 Baths
    • 3,292 Sq Ft

    8312 Broad Neck Rd, Chestertown, MD 21620

    Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment.A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business,

    Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, Chestertown, MD 21620
  • 8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    /74

    $824,900

    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,495,000

    $155K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 23741 L Rd, Chestertown, MD 21620
    23741 L Rd, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $344,000

    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
Maryland Kent County

Homes for Sale with Acreage in Chestertown, MD

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $361,950, down 5% year-over-year. Homes in Chestertown sell in 42 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$361,950
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$262,400
Median 2 Bedroom Sale Price
$323,250
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
31
Last 12 months Home Sales
96
Months of Supply
3.90
Median List Price
$355,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 17 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Chestertown, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Chestertown and discover the potential and freedom that comes with owning your own piece of property.

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