9

Pittsville, MD Homes for Sale with Acreage

Section Image
  • 8225 Whitesville Rd, Pittsville, MD 21850
    8225 Whitesville Rd, Pittsville, MD 21850
    8225 Whitesville Rd, Pittsville, MD 21850
    /45

    $590,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    8225 Whitesville Rd, Pittsville, MD 21850

    Luxury country living! Built in 2020 with 3 bedrooms, 2 bathrooms, on 2 acres of land with multiple outbuildings - let alone the list of finishes (available upon request)! Inside, the home feels fresh and updated with new carpet in the living room and primary bedroom, luxury vinyl flooring in the secondary bedrooms, and fresh paint throughout. The flow of the home connects naturally to the

    Summer Forbes Coastal Life Realty Group LLC

    8225 Whitesville Rd, Pittsville, MD 21850
  • 0 Casher Wells Rd, Pittsville, MD 21850
    0 Casher Wells Rd, Pittsville, MD 21850
    0 Casher Wells Rd, Pittsville, MD 21850
    /27

    $179,000

    • Land
    • 6.39 Acres
    • $28,013 per Acre

    0 Casher Wells Rd, Pittsville, MD 21850

    Looking for some acreage to build your house, pole building, horse pasture, yard birds, garden, homestead or just plain space to spread out, then this is an ideal tract that is situated just far enough removed but still close enough to run up to the store or such in a couple minutes time. The property has a total of 6.39 acres that is mostly cleared except for a wooded buffer in the rear. Good

    Jay Phillips Holiday Real Estate

    0 Casher Wells Rd, Pittsville, MD 21850
  • 7676 Maple St, Pittsville, MD 21850
    7676 Maple St, Pittsville, MD 21850
    7676 Maple St, Pittsville, MD 21850
    /38

    $225,000

    • 2 Beds
    • 1 Bath
    • 828 Sq Ft

    7676 Maple St, Pittsville, MD 21850

    Welcome home! This Home, in the Branchwood Neighborhood, which is conveniently located just north of US 50, in Pittsville, MD. Near the Heart of Pittsville, Main Town Center, and a short distance to Ocean City, MD Beaches, and Salisbury, MD. This Home sits on a larger open 1 acre lot. Features a first-floor primary bedroom, and second bedroom and a bonus room on the second floor! Spacious

    Karen Oass Long & Foster Real Estate, Inc.

    7676 Maple St, Pittsville, MD 21850
  • 0 Casher Wells Rd, Pittsville, MD 21850
    0 Casher Wells Rd, Pittsville, MD 21850
    0 Casher Wells Rd, Pittsville, MD 21850
    /13

    $550,000

    • Land
    • 44.58 Acres
    • $12,337 per Acre

    0 Casher Wells Rd, Pittsville, MD 21850

    Two parcels spanning a total of 44.58 acres within Pittsville town limits available for sale! The gently rolling tract offers clear build site potential with ample frontage for a custom development entrance while preserving privacy. The existing timber on the property offers a buyer additional value with a recent timber cruise completed this year. The property’s topography affords multiple

    Kelly Jeter SVN |Miller Commercial Real Estate

    0 Casher Wells Rd, Pittsville, MD 21850
  • 35326 Mount Hermon Rd, Pittsville, MD 21850
    35326 Mount Hermon Rd, Pittsville, MD 21850
    35326 Mount Hermon Rd, Pittsville, MD 21850
    /66

    $215,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft

    35326 Mount Hermon Rd, Pittsville, MD 21850

    Country Living with Endless Potential!Welcome to this great opportunity in Parsonsburg, Maryland! Situated on approximately 4.5 acres, this property offers the space, privacy, and peaceful setting of country living while still being conveniently located approximately 15 minutes from Salisbury and 15 minutes from the Ocean City beaches.This one-level home features a comfortable

    Jennifer Kukel Keller Williams Realty Delmarva

    35326 Mount Hermon Rd, Pittsville, MD 21850
  • 6445 60 Foot Rd, Pittsville, MD 21850
    6445 60 Foot Rd, Pittsville, MD 21850
    6445 60 Foot Rd, Pittsville, MD 21850
    /43

    $899,000

    • 4 Beds
    • 4.5 Baths
    • 4,311 Sq Ft

    6445 60 Foot Rd, Pittsville, MD 21850

    This private retreat, ideally positioned between Salisbury and Ocean City, offers a rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on just over 9 beautiful acres, the property includes a stately brick Georgian style residence, a gunite saltwater pool, an attached 3 car garage and a versatile 5 car detached garage, all surrounded by State

    Brandon Shostak Meredith Fine Properties

    6445 60 Foot Rd, Pittsville, MD 21850
  • 0 Lot 4a Main St Unit MDWC2021284, Pittsville, MD 21850
    0 Lot 4a Main St Unit MDWC2021284, Pittsville, MD 21850
    0 Lot 4a Main St Unit MDWC2021284, Pittsville, MD 21850
    /8

    $212,000

    • Land
    • 3.03 Acres
    • $69,967 per Acre

    0 Lot 4a Main St Unit MDWC2021284, Pittsville, MD 21850

    Highly sought after over 3 acre lot located in the Town of Pittsville. Conveniently located right across from the school. Approximately 1/2 acre cleared with remaining balance wooded. Public Water and Sewer possible with approval from Town of Pittsville. Please call Town of Pittsville with any questions in regards to obtaining an EDU to build on the property (410-835-8872).

    Andrew Rayne Whitehead Real Estate Exec.

    0 Lot 4a Main St Unit MDWC2021284, Pittsville, MD 21850
  • 7745 Gumboro Rd, Pittsville, MD 21850
    7745 Gumboro Rd, Pittsville, MD 21850
    7745 Gumboro Rd, Pittsville, MD 21850
    /22

    $460,000

    • Land
    • 7.77 Acres
    • $59,202 per Acre

    7745 Gumboro Rd, Pittsville, MD 21850

    A unique Opportunity awaits for this property, which is ideally located for many possible commercial ventures, within the Town of Pittsville on a major north south State Highway that leads to Millsboro DE from US Rt 50. Located just 25-30 minutes from The Coastal Beaches of Ocean City, Assateague Island, Fenwick Island Bethany etc! Also 10-15 minutes to Arthur Perdue Stadium, Shopping and

    Rusty Molnar Keller Williams Realty Delmarva

    7745 Gumboro Rd, Pittsville, MD 21850
  • 8255 Whitesville Rd, Pittsville, MD 21850
    8255 Whitesville Rd, Pittsville, MD 21850
    8255 Whitesville Rd, Pittsville, MD 21850
    /32

    $200,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 825 Sq Ft

    8255 Whitesville Rd, Pittsville, MD 21850

    Situated on spacious 2 acres in Pittsville, this well-maintained, private drive, single-story home offers the perfect blend of space, convenience, and Eastern Shore charm. Whether you're looking for an investment opportunity, a place to downsize, or simply a quieter lifestyle, this property has plenty to offer. Multiple storage sheds, a garage, a carport, and a pool provide ample space for

    Victor J King Real Broker, LLC

    8255 Whitesville Rd, Pittsville, MD 21850
Maryland Wicomico County

Homes for Sale with Acreage in Pittsville, MD

Home Prices in Pittsville, MD

The median home sale price in Pittsville, MD is $305,000, down 8% year-over-year. Homes in Pittsville sell in 55 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$305,000
Median Single Family Sale Price
$367,495
Median 2 Bedroom Sale Price
$261,250
Average Price Per Sq Ft
$217
Number of Homes for Sale
22
Last 12 months Home Sales
21
Months of Supply
12.60
Median List Price
$367,495
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-8%
How to Buy a Home How to Finance a Home How to Sell a Home

In Pittsville, there are currently 9 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 Pittsville, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Pittsville and discover the potential and freedom that comes with owning your own piece of property.

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