26

Pittsville, MD Homes for Sale under $500,000

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  • 34950 Old Ocean City Rd Unit 39563524, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563524, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563524, Pittsville, MD 21850
    /45

    $411,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,217 Sq Ft

    Ruby Plan at Solomon's Place, Pittsville, MD 21850

    As you walk in the first floor is an expansive, open floorplan of the Choice Room, Great Room, Breakfast Nook, and kitchen. The openness of these areas offers plenty of space and ease for informal dining and entertaining. The choice room has the option of substituting it with a private library that can be used as a home office or playroom. The Kitchen has a tremendous amount of space, plenty of

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563524, Pittsville, MD 21850
  • 34780 Main St, Pittsville, MD 21850
    34780 Main St, Pittsville, MD 21850
    34780 Main St, Pittsville, MD 21850
    /51

    $299,990

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft

    34780 Main St, Pittsville, MD 21850

    Welcome to 34780 Main St., ideally located in the heart of Pittsville, offering small-town charm with easy access to Salisbury and the beautiful beaches of Maryland and Delaware. This immaculate one-story rancher features 3 bedrooms, 2 bathrooms, and a spacious, comfortable layout designed for everyday living. Updates in 2026 include fresh interior paint throughout the entire home, new LVP tile

    Julie Woulfe ERA Martin Associates, Shamrock Division

    34780 Main St, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563518, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563518, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563518, Pittsville, MD 21850
    /34

    $441,990

    New Construction
    • 3 - 4 Beds
    • 2 - 3 Baths
    • 1,795+ Sq Ft

    Sussex Plan at Solomon's Place, Pittsville, MD 21850

    Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle.Step into an open-concept floor plan that seamlessly connects the Kitchen, Breakfast area, and Great Room, perfect

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563518, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563519, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563519, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563519, Pittsville, MD 21850
    /5

    $440,990

    New Construction
    • 3 - 4 Beds
    • 2.5 Baths
    • 2,390+ Sq Ft

    Chaucer II Plan at Solomon's Place, Pittsville, MD 21850

    As you walk into the spacious Chaucer II you are greeted by an open concept that includes the Dining area, Kitchen, and Great Room feels as if it is one giant space as you easily move through to the Great Room at the rear of the home. Each room flows effortlessly into the other giving the whole home an open and airy ambiance. The Kitchen has a tremendous amount of space with a plethora of

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563519, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563520, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563520, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563520, Pittsville, MD 21850
    /38

    $397,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,911+ Sq Ft

    Topaz Plan at Solomon's Place, Pittsville, MD 21850

    The Topaz home design is a single-family home, from our signature Gem Series, with 4 bedrooms, 2.5 baths, and a 2-car garage.As you walk in the first floor is an expansive great room with an open floorplan of the kitchen and breakfast nook. The openness of these areas offers plenty of space for informal dining and entertaining. Complement the kitchen by adding an optional Sunroom or add an island

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563520, Pittsville, MD 21850
  • TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    /21

    $441,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,795 Sq Ft

    TBD Old Ocean City Rd, Pittsville, MD 21850

    Welcome to the Sussex, a beautifully designed to-be-built ranch style home by Gemcraft Homes that perfectly blends style, comfort, and functionality with the ease of single-level living. This popular floor plan offers impressive curb appeal and a thoughtfully crafted layout designed to accommodate today's modern lifestyle. Step inside to an inviting open-concept floor plan where the kitchen,

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Old Ocean City Rd, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563527, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563527, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563527, Pittsville, MD 21850
    /4

    $432,990

    New Construction
    • 3 - 4 Beds
    • 2 Baths
    • 1,710+ Sq Ft

    New Castle Plan at Solomon's Place, Pittsville, MD 21850

    The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563527, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563522, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563522, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563522, Pittsville, MD 21850
    /4

    $359,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    Opal Plan at Solomon's Place, Pittsville, MD 21850

    The Opal is a single-family home with 3 bedrooms, 2.5 baths and 2-car garage. The first floor features a great room, laundry, and kitchen. The second floor features 3 bedrooms, and 2 full baths.

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563522, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563525, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563525, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563525, Pittsville, MD 21850
    /41

    $452,990

    New Construction
    • 3 - 4 Beds
    • 2.5 - 3.5 Baths
    • 2,551+ Sq Ft

    Roosevelt Plan at Solomon's Place, Pittsville, MD 21850

    As you walk into the beautiful Roosevelt you are greeted by a large, welcoming foyer with an open formal living room and dining room to either side. The formal living room can be optionally converted to a private study, perfect for use as a home office. The hallway flows to the rear of the home where you are met with an open floorplan of the kitchen, informal breakfast area, and an extensive

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563525, Pittsville, MD 21850
  • TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    /20

    $385,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    TBD Old Ocean City Rd, Pittsville, MD 21850

    Welcome to the Pearl, a beautifully designed new construction home that is to be built in Pittsville, MD, offering 4 bedrooms, 2.5 bathrooms, and a 2-car attached garage. Part of Gemcraft Homes' signature Gem Series, this thoughtfully designed home features an open-concept first floor perfect for both everyday living and entertaining. The spacious great room flows seamlessly into the kitchen and

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Old Ocean City Rd, Pittsville, MD 21850
  • TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    TBD Old Ocean City Rd, Pittsville, MD 21850
    /21

    $411,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,217 Sq Ft

    TBD Old Ocean City Rd, Pittsville, MD 21850

    Welcome to the Ruby, a thoughtfully designed to-be-built home by Gemcraft Homes that offers the perfect blend of space, comfort, and flexibility. The first floor features an expansive open-concept layout where the Great Room, Breakfast area, and Kitchen flow seamlessly together, creating an ideal space for both everyday living and entertaining. The versatile flex can also be configured as a

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Old Ocean City Rd, Pittsville, MD 21850
  • 34910 Main St, Pittsville, MD 21850
    34910 Main St, Pittsville, MD 21850
    /2

    $409,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,462 Sq Ft

    34910 Main St, Pittsville, MD 21850

    The Emerald is the perfect home for single-floor living. Enter through the foyer with two bedrooms and a full bath to the left. Continue down the hallway where the floorplan opens to the large great room and country kitchen with a dining nook. The kitchen offers plenty of cabinet space and a peninsula with an overhang, perfect for entertaining. The expansive owners suite includes a walk in closet

    Gemcraft Homes Builder
    34910 Main St, Pittsville, MD 21850
  • TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    /20

    $451,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,923 Sq Ft

    TBD Main St, Pittsville, MD 21850

    Welcome to the Frankford, a beautifully designed to-be-built home by Gemcraft Homes located in Pittsville, MD. This thoughtfully crafted floor plan offers 3 bedrooms, 2.5 bathrooms, a 2-car attached garage, and the option for a fourth bedroom, providing flexibility to fit your lifestyle. As you enter the home, you are welcomed by a formal dining room, perfect for hosting family gatherings and

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Main St, Pittsville, MD 21850
  • 34762 Main St, Pittsville, MD 21850
    34762 Main St, Pittsville, MD 21850
    34762 Main St, Pittsville, MD 21850
    /37

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    34762 Main St, Pittsville, MD 21850

    Welcome to 34762 Main St, a very nice 3 bedroom/2 bath home priced to sell in Pittsville, MD! Built in 2003, this home has a first floor primary bedroom and full bath, a good sized living area, kitchen with plenty of cabinet space and dining area just off the kitchen. Upstairs, you have 2 bedrooms with lots of closet space and a full bath. The HVAC was replaced in November, 2025 and the water

    BRIAN LINDQUIST 1ST CHOICE PROPERTIES LLC

    34762 Main St, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563517, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563517, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563517, Pittsville, MD 21850
    /31

    $421,990

    New Construction
    • 4 Beds
    • 2.5 - 3.5 Baths
    • 1,916+ Sq Ft

    Hamilton Plan at Solomon's Place, Pittsville, MD 21850

    As you walk into the Hamilton there is a Choice Room that's open to the foyer. Use this space as a formal living room or playroom for the kids. Down the hall is the Great Room. Add an optional fireplace to make an inviting space to gather with the whole family. The Great Room opens up to a classically designed Kitchen. A small Mudroom at the entry to the Garage rounds out this flexible first

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563517, 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
  • 34950 Old Ocean City Rd Unit 39563516, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563516, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563516, Pittsville, MD 21850
    /3

    $418,990

    New Construction
    • 3 - 4 Beds
    • 2 - 3 Baths
    • 1,425+ Sq Ft

    Wilmington Plan at Solomon's Place, Pittsville, MD 21850

    The Wilmington is a modern ranch-style home with 3 bedrooms, 2 baths, and a 2 car garage.The first floor features a dining room as you walk in through the foyer and flows into an open concept floorplan that accommodates the Kitchen and Great Room. The well-equipped kitchen offers plenty of space for informal dining and entertaining. The Great Room, is spacious and is sure to be the center of

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563516, Pittsville, MD 21850
  • TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    /17

    $421,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    TBD Main St, Pittsville, MD 21850

    Introducing the Hamilton, a beautifully designed to-be-built home by Gemcraft Homes in Pittsville, MD, offering the perfect blend of space, comfort, and flexibility. As you enter the home, you're welcomed by a versatile Choice Room off the foyer ideal for a formal living room, home office, playroom, or whatever best fits your lifestyle. Continue down the hall to the spacious Great Room, which

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Main St, Pittsville, MD 21850
  • TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    TBD Main St, Pittsville, MD 21850
    /4

    $418,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    TBD Main St, Pittsville, MD 21850

    Welcome to the Wilmington, a beautifully designed to-be-built ranch home by Gemcraft Homes located in Pittsville, MD. Offering 3 bedrooms, 2 bathrooms, and a 2-car attached garage, this thoughtfully crafted floor plan combines modern design with the convenience of one-level living. As you enter through the foyer, you are greeted by a formal dining room, perfect for hosting family dinners and

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    TBD Main St, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563515, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563515, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563515, Pittsville, MD 21850
    /42

    $385,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,680+ Sq Ft

    Pearl Plan at Solomon's Place, Pittsville, MD 21850

    The Pearl home design is a single-family home, from our signature Gem Series, with 4 bedrooms, 2.5 baths, and a 2-car garage.As you walk in the first floor is an expansive living area with an open floorplan of the great room, kitchen, and breakfast nook. A wide glass sliding door provides an abundance of natural light giving the breakfast nook an airy and fresh atmosphere. As you climb up the

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563515, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563526, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563526, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563526, Pittsville, MD 21850
    /44

    $451,990

    New Construction
    • 3 - 4 Beds
    • 2.5 - 3.5 Baths
    • 1,923+ Sq Ft

    Frankford Plan at Solomon's Place, Pittsville, MD 21850

    The Frankford puts a unique twist on a traditional design that includes 3 bedrooms (optional 4th), 2 baths, 2-car garage, two-story family room, kitchen/breakfast room combination, and separate formal dining room. The first floor laundry and first floor owner's suite with walk-in closet add an enormous amount of convenience to The Frankford.

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563526, Pittsville, MD 21850
  • 34950 Old Ocean City Rd Unit 39563523, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563523, Pittsville, MD 21850
    34950 Old Ocean City Rd Unit 39563523, Pittsville, MD 21850
    /3

    $393,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,462 Sq Ft

    Emerald Plan at Solomon's Place, Pittsville, MD 21850

    The Emerald is the perfect home for single-floor living. Enter through the foyer with two bedrooms and a full bath to the left. Continue down the hallway where the floorplan opens to the large great room and country kitchen with a dining nook. The kitchen offers plenty of cabinet space and a peninsula with an overhang, perfect for entertaining. The expansive owners suite includes a walk in closet

    Gemcraft Homes Builder
    34950 Old Ocean City Rd Unit 39563523, Pittsville, MD 21850
  • 7216 Etonian Ct, Pittsville, MD 21850
    7216 Etonian Ct, Pittsville, MD 21850
    7216 Etonian Ct, Pittsville, MD 21850
    /53

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    7216 Etonian Ct, Pittsville, MD 21850

    Welcome to this cute and charming 3-bedroom, 2-bathroom home nestled on approximately 0.45 acres in the Town of Pittsville! Offering 1,518 square feet of comfortable living space, this home has a warm and inviting feel. The property features a spacious fenced-in backyard, a small rear deck, and a shed for convenient additional storage. Inside, the kitchen has been refreshed with new paint on the

    Macy Bradford RE/MAX Advantage Realty

    7216 Etonian Ct, 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
  • 34339 Pine Meadows Ln, Pittsville, MD 21850
    34339 Pine Meadows Ln, Pittsville, MD 21850
    34339 Pine Meadows Ln, Pittsville, MD 21850
    /62

    $320,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    34339 Pine Meadows Ln, Pittsville, MD 21850

    Small town living starts with breakfast and coffee on the back deck! The remainder of the day can be followed by a full list of possibilities as the location for this one level gem is ideal. Just a short drive to the world-famous Ocean City beaches and Assateague National Seashore where the ponies run free and are often seen frolicking in the ocean. The central location is also close to Salisbury

    Michael Moore Keller Williams Realty Delmarva

    34339 Pine Meadows Ln, Pittsville, MD 21850
Maryland Wicomico County

Real Estate & Homes in Pittsville, MD under $500,000

Home Prices in Pittsville, MD

The median home sale price in Pittsville, MD is $305,000, down 7% year-over-year. Homes in Pittsville sell in 59 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$305,000
Median Single Family Sale Price
$359,990
Median 2 Bedroom Sale Price
$239,999
Average Price Per Sq Ft
$224
Number of Homes for Sale
21
Last 12 months Home Sales
23
Months of Supply
11.00
Median List Price
$359,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-7%
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