Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$305,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 2,050 Sq. Ft.
  • 2 Car Garage
  • Updated 4 days ago
See This Home
Save This Home
See This Home
Save This Home
Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday living and entertaining. Conveniently located and ready for its next owner to make it their own.

Full Property Details for 106 Main St

General

  • Price: $305,000
  • Taxes: $2,504 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDCM2007300
  • Updated: 7/1/2026
  • Added to Site: 51 day(s) ago

Interior

  • Interior Features: Combination Kitchen/Dining, Dining Area
  • Fireplace: Yes
  • Number of Fireplaces: 1

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Detached Garage
  • Garage Description: Other

Location

  • County: CAROLINE
  • Driving Directions: Starting Point Easton MD, Head toward E Dover St on S Harrison St. Go for 138 ft. Turn right onto E Dover St (MD-331) Go for 0.3 mi. Continue on Dover Rd (MD-331) Go for 0.5 mi. Continue on Dover Rd (MD-331) Go for 3.8 mi. Continue on Dover Bridge Rd (MD-331) Go for 5.9 mi. Continue on Main St (MD-331). Go for 367 ft. B End at 106 Main St Preston, Maryland 21655-2200. Starting Point Hurlock, MD, Head toward Andrews St on S Main St (MD-331) Go for 0.3 mi. Keep left onto Academy St (MD-331) Go for 0.6 mi. Continue on Elwood Rd (MD-331) Go for 1.9 mi. Turn right onto E New Market Elwood Rd (MD-16/MD-331) toward Easton/Preston Go for 3.3 mi. Turn right toward Preston/Easton Go for 102 ft. Turn left onto Harriet Tubman Underground RR Bywy (MD-16/MD-331) toward Preston/Easton Go for 1.3 mi. Continue on Main St (MD-331) Go for 0.1 mi. Continue on Main St (MD-331) Go for 0.3 mi. End at 106 Main St Preston, Maryland 21655

School Information

  • School District: Caroline County Public Schools

Heating & Cooling

  • Cooling Type: Ductless/Mini-Split
  • Heating Type: Wall Unit
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Septic
  • Water: Public

Structural Information

  • Architectural Style: Cape Cod
  • Structure Type: Detached
  • Construction: Cedar
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Outside Entrance, Unfinished
  • Foundation: Slab
  • Roof: Shingle, Composite
  • Stories Description: Lower 1, Lower 2, Main, Upper 1
  • Square Feet: 2,050
  • Sq. Ft. Source: Estimated
  • Living Area: 1,234 Sq. Ft.
  • Finished Above Grnd: 1,234 Sq. Ft.
  • Year Built: 1925
  • Year Built Source: Estimated

Lot Features

  • Lot Size (Acres): 0.35
  • Lot Size (Sq. Ft.): 15,246
  • Lot Size Source: Estimated
  • Zoning: R1

Financial Considerations

  • Price Per Sq. Ft.: $247.16
  • Tax w/Assessment: $185,200
  • Tax Amount: $2,504
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Keller Williams Realty, Shay M Prattis

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 106 Main St —

  • Shay M Prattis

    Keller Williams Realty

Listing Office Email: steve@srarealty.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 106 Main St

School District:Caroline County Public Schools, Denton, MD
NameGradesDistance
Preston Elementary School
225 Main Street, Preston, MD 21655
PK-50.7 mi
Colonel Richardson Middle School
25390 Richardson Road, Federalsburg, MD 21632
6-85.4 mi
Colonel Richardson High School
25320 Richardson Road, Federalsburg, MD 21632
9-125.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 106 Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/25/2026
Price Reduced
$305,000
-1.61%
MLS
5/16/2026
Listed
$310,000
36.56%
MLS
9/16/2020
Sold
$227,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 106 Main St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$1,824
—
$115,867
7%
2023
$1,824
—
$108,000
3%
2023
$1,824
2%
$105,333
3%
2022
$1,788
—
$102,667
3%
2017
$1,780
1%
$100,000
—
2021
$1,771
-1%
$99,967
—
2020
$1,791
1%
$99,933
—
2019
$1,770
—
$99,900
—
2018
$1,770
-8%
$99,900
-10%
2015
$1,923
7%
$110,400
—
2014
$1,791
—
$110,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 106 Main St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Realty, Shay M Prattis

Similar Properties near 106 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

113 Chamber St, Preston, MD 21655 - Photo 1
$299,000

113 Chamber St  Preston, MD 21655

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,200
    Sq. Ft.
Listed by Keller Williams Realty, Heather Ann Brummell
21611 Everlea Dr, Preston, MD 21655 - Photo 1
$315,000

21611 Everlea Dr  Preston, MD 21655

  • Single Family
  • Active
  • 3
    Beds
  • 2
    Total Baths
  • 1,568
    Sq. Ft.
Listed by Coldwell Banker Waterman Realty, Nicole Marie Giordano
130 Charlotte Ave, Federalsburg, MD 21632 - Photo 1
$295,000

130 Charlotte Ave  Federalsburg, MD 21632

  • Single Family
  • Active
  • 3
    Beds
  • 2
    Total Baths
  • 1,646
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices PenFed Realty, FRANK LITTLE
109 Railroad Ave, East New Market, MD 21631 - Photo 1
$299,900

109 Railroad Ave  East New Market, MD 21631

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 1,567
    Sq. Ft.
Listed by McClain-Williamson Realty, LLC, Tracey Lynn Williamson

Just Listed near 106 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

27311 Patricia Ct, Federalsburg, MD 21632 - Photo 1 Just Listed
$239,000

27311 Patricia Ct  Federalsburg, MD 21632

  • Single Family
  • Active
  • Updated 4 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,872
    Sq. Ft.
Listed by Amy Betts (410) 570-5422
122 Julie Ln, Federalsburg, MD 21632 - Photo 1 Just Listed
$235,000

122 Julie Ln  Federalsburg, MD 21632

  • Townhouse
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,440
    Sq. Ft.
Listed by Remax Vision, Donna D Hollifield
5116 Ocean Gateway, Trappe, MD 21673 - Photo 1 Just Listed
$405,000

5116 Ocean Gateway  Trappe, MD 21673

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,344
    Sq. Ft.
Listed by Keller Williams Flagship, Samantha Boone
28091 Oaklands Cir, Easton, MD 21601 - Photo 1 Just Listed
$1,495,000

28091 Oaklands Cir  Easton, MD 21601

  • Single Family
  • Active
  • Updated 3 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 4,610
    Sq. Ft.
Listed by Benson & Mangold, LLC, Ralph J Latham Jr. and Benson & Mangold, LLC, Shelby D Roney

Price Reduced near 106 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5256 Williamsburg Rd, Federalsburg, MD 21632 - Photo 1 Price Reduced
-$20,000 (-4%)
$480,000

5256 Williamsburg Rd  Federalsburg, MD 21632

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,538
    Sq. Ft.
Listed by Elizabeth Tryon (410) 924-3764
26471 3 Bridges Rd, Federalsburg, MD 21632 - Photo 1 Price Reduced
-$10,000 (-8.33%)
$110,000

26471 3 Bridges Rd  Federalsburg, MD 21632

  • Single Family
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 640
    Sq. Ft.
Listed by Keller Williams Realty, LEE MARLAND
2691 Lorraine Ave, Federalsburg, MD 21632 - Photo 1 Price Reduced
-$5,000 (-1.45%)
$339,500

2691 Lorraine Ave  Federalsburg, MD 21632

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,880
    Sq. Ft.
Listed by XRealty.NET LLC, Norman S Domingo
313 Edmonson Ln, East New Market, MD 21631 - Photo 1 Price Reduced
-$2,490 (-0.67%)
$367,500

313 Edmonson Ln  East New Market, MD 21631

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,659
    Sq. Ft.
Listed by EXP Realty, LLC, Louis Joseph Amabili III

Recent Sales near 106 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

22650 Tanyard Rd, Preston, MD 21655 - Photo 1 Sold
$348,000

22650 Tanyard Rd  Preston, MD 21655

  • Single Family
  • Closed
  • 3
    Beds
  • 1
    Total Bath
  • 1,160
    Sq. Ft.
Listed by The Powell Legacy Group of Coldwell Banker Realty
Sold by Samson Properties, Justin Kennedy
4133 Whiteleyville Rd, Hurlock, MD 21643 - Photo 1 Sold
$335,000

4133 Whiteleyville Rd  Hurlock, MD 21643

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,366
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices PenFed Realty, Pamela Price
Sold by Benson & Mangold, LLC, Judith A Germain
22285 Tanyard Rd, Preston, MD 21655 - Photo 1 Sold
$345,000

22285 Tanyard Rd  Preston, MD 21655

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,503
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, Ralph Wesley Russum and Coldwell Banker Chesapeake Real Estate Company, Kathryn P Moore
Sold by Benson & Mangold, LLC., Michael S Shipley
6539 Cabin Ridge Rd, Hurlock, MD 21643 - Photo 1 Sold
$260,000

6539 Cabin Ridge Rd  Hurlock, MD 21643

  • Mobile Home
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,664
    Sq. Ft.
Listed by Benson & Mangold, LLC, Penny M Introcaso
Sold by Taylor Properties, Justin Ryan Pokrywka

106 Main Street, Preston, MD 21655 (MLS# MDCM2007300) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 106 Main Street is currently listed for $305,000 and was received on May 16, 2026. Want to learn more about 106 Main Street? Do you have questions about finding other Single Family real estate for sale in Preston? You can browse all Preston real estate or contact a Coldwell Banker agent to request more information.

Tour this property