SOLD SEP 11, 2026

Sold on sep 2026

$287,000

•

1,234

sq ft

106 Main St, Preston, MD 21655

Track this home’s value and nearby sales activity

About 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.

Single-familyProperty Type

1925Year Built

0.35 acresLot Size

$233Price/Sq.Ft.

2 car garageParking

Listed by Shay Prattis • Keller Williams Realty

•302-360-0300 (broker)

•steve@srarealty.com (broker)

Bought with Heather Brummell • Keller Williams Realty

•302-360-0300 (broker)

•steve@srarealty.com (broker)

Redfin checked: 3 minutes ago

•Source:BRIGHT MLS #MDCM2007300

Redfin Estimate

$296,131

$9,131 since sold in September 2026$13K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 60.4% higher than the average sale price ($185K) of 6 comparable homes.

SOLD JUL 24, 2026
$80,000
A
3 beds2 baths1,488 sq ft
103 Chambers St, Preston, MD 21655
SOLD SEP 21, 2026
$260,000
B
3 beds2 baths1,677 sq ft
103 Williamson St, Preston, MD 21655
SOLD OCT 29, 2026
$80,000
C
3 beds1 bath1,004 sq ft
22067 Dover Bridge Rd, Preston, MD 21655
SOLD JUL 16, 2026
$133,500
D
3 beds1.5 baths1,300 sq ft
302 Noble St, Hurlock, MD 21643
SOLD JUL 15, 2026
$285,000
E
3 beds2 baths1,922 sq ft
5026 Bethlehem Rd, Preston, MD 21655
SOLD SEP 24, 2026
$269,000
F
3 beds2 baths1,548 sq ft
108 Maryland Ave, Hurlock, MD 21643

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Market trends in 21655, MD

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

97.0%

1.5% MoM

Median sale price

$305K

$47K MoM

Avg. days on market

72d

10 days MoM

Recently sold homes

3 MoM

New listings for sale

$399,000
5 beds3.5 baths2,158 sq ft
315 Hughlett St, Preston, MD 21655
(410) 972-4000
See all

Provided by Redfin

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Rental estimate

Est. $2,155 per month, based on comparable rentals

Sale and tax history for 106 Main St

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #MDCM2007300

Sep 11, 2026

Sold

$287,000

$233/sq ft

Aug 9, 2026

Pending

—

Jul 29, 2026

Price Changed

$287,000

$233/sq ft

Jul 15, 2026

Price Changed

$295,000

$239/sq ft

Jun 25, 2026

Price Changed

$305,000

$247/sq ft

May 16, 2026

Listed

$310,000

$251/sq ft

Public Records

Dec 22, 2020

Sold

$227,000

$184/sq ft

BRIGHT MLS #MDCM124228

Sep 16, 2020

Sold

$227,000

$184/sq ft

Sep 13, 2020

Pending

—

Aug 19, 2020

Contingent

—

Jul 9, 2020

Listed

$239,000

$194/sq ft

+32

Beautifully renovated charming cape cod home in the town of Preston. Beautifully refinished floors and fresh paint brings the charm back to this home. Relax and enjoy on the large front porch or entertain and play in the large fenced back yard. A full unfinished basement for all your storage needs. Plus many updates to include new kitchen appliances, 7 new Ductless HVAC systems, for central air and heat, Tyvek has been wrapped throughout the entire house, new linoleum floors in bathrooms, a new hot water heater, also new insulation, new windows and a sump pump in 2017, a new roof and exterior paint in 2018 and much, much more.

BRIGHT MLS #1000436057

Aug 27, 2015

Sold

$60,000

$49/sq ft

MRIS #CM8536685

Aug 27, 2015

Delisted

—

Aug 27, 2015

Sold

$60,000

$49/sq ft

Aug 5, 2015

Pending

—

Aug 2, 2015

Relisted

—

Jul 30, 2015

Pending

—

Jul 27, 2015

Price Changed

$50/sq ft

Jul 24, 2015

Relisted

—

Jun 10, 2015

Pending

—

May 10, 2015

Price Changed

$57/sq ft

Apr 9, 2015

Price Changed

$62/sq ft

Apr 3, 2015

Relisted

—

Mar 2, 2015

Pending

—

Feb 20, 2015

Price Changed

$65/sq ft

Jan 19, 2015

Listed

$73/sq ft

BRIGHT MLS #1009898800

Oct 2, 2014

Listing Removed

—

Nov 22, 2013

Listed

$159,000

$129/sq ft

Public Records

Dec 7, 2007

Sold

$173,350

$140/sq ft

Public Records

Mar 9, 2004

Sold

$130,500

$106/sq ft

Public Records

Oct 31, 1996

Sold

$78,000

$63/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2026

$2,634 (+5.2%)

$38,300 + $146,900

$185,200

2025

$2,504 (+7.1%)

$38,300 + $146,900

$185,200

2024

$2,338 (+7.7%)

2023

$2,172 (+7.3%)

2022

$2,024 (+7.9%)

$38,300 + $112,300

$150,600

2021

$1,876 (+8.6%)

2020

$1,728 (+2.2%)

2019

$1,691 (+6.1%)

$38,300 + $81,500

$119,800

2017

$1,594

$38,300 + $73,800

$112,100

2016

$1,594 (−3.6%)

$38,300 + $73,800

$112,100

2015

$1,654 (+1.4%)

$57,100 + $60,900

$118,000

2014

$1,631 (+3.8%)

2013

$1,572 (−20.3%)

2012

$1,973 (+3.9%)

2011

$1,899 (+3.2%)

2010

$1,840 (+9.2%)

2009

$1,685

Public record

Beds

—

Baths

1.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

0.35 Acres

Year renovated

—

Sq. Ft.

1,234

Year built

1925

Style

Single Family Residential

County

Caroline County

APN

4 6895

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 2
Garage Features: Other
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Detached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 3

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 1

Interior Information
Interior Features: Combination Kitchen/Dining, Dining Area
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: Yes
Outside Entrance, Unfinished

Exterior

Property Information
Total Below Grade Sq. Ft.: 816
Ownership Interest: Fee Simple
Year Built Source: Estimated

Building Information
Construction Materials: Cedar
Foundation Details: Slab
Other Structures: Above Grade
Roof: Shingle, Composite
Structure Type: Detached

Lot Information
Tidal Water: No

Above Grade Information
Finished Sq.Ft.: 1,234
Finished Sq.Ft. Source: Estimated

Below Grade Information
Unfinished Sq.Ft.: 816
Unfinished Sq.Ft. Source: Estimated

Financial

Tax Information
Tax Assessed Value: $185,200
Tax Year: 2026
Tax Annual Amount: $2,504

Lease Information
Lease Considered: No

Utilities

Utilities Information
Cooling Type: Ductless/Mini-Split
Wall Unit
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Septic
Water Source: Public

Location

School Information
School District Name: CAROLINE COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
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

Public facts

Beds: —
Baths: 1.5
Sq. Ft.: 1,234
Stories: 1.5
Lot Size: 0.35 acres
Style: Single Family Residential
Year Built: 1925
Year Renovated: —
County: Caroline County
APN: 4 6895

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

Preston Elementary School

Public PreK-5 • Assigned • 0.7mi

7/10

Colonel Richardson Middle School

Public 6-8 • Assigned • 5.4mi

6/10

Colonel Richardson High School

Public 9-12 • Assigned • 5.3mi

4/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 104° expected this year, 16 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Preston, MD • 21655

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

85/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.2 hrs

5.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$282,000 – $341,000

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Home values near 106 Main St

Data from public records.

Address	Redfin Estimate
109 Main St, Preston, MD - Beds \| - Baths \| 1080 Sq. Ft.	$154,337
107 Main St, Preston, MD - Beds \| 1 Baths \| 1216 Sq. Ft.	$215,822
117 Main St, Preston, MD - Beds \| 2.5 Baths \| 1472 Sq. Ft.	$276,767
112 Main St, Preston, MD - Beds \| 2 Baths \| 1676 Sq. Ft.	$333,993
100 Main St, Preston, MD - Beds \| 2.5 Baths \| 2332 Sq. Ft.	$416,116
115 Main St, Preston, MD - Beds \| 2.5 Baths \| 2016 Sq. Ft.	$374,172
104 Fooks Ave, Preston, MD - Beds \| 3.5 Baths \| 1880 Sq. Ft.	$351,674

Address	Redfin Estimate
114 Main St, Preston, MD - Beds \| 1 Baths \| 878 Sq. Ft.	$159,455
Main St, Preston, MD - Beds \| - Baths \| - Sq. Ft.	$39,835
98 Main St, Preston, MD 4 Beds \| 3.5 Baths \| 3056 Sq. Ft.	$378,945
108 Main St, Preston, MD - Beds \| 1.5 Baths \| 1858 Sq. Ft.	$267,319
113 Main St, Preston, MD 2 Beds \| 1 Baths \| 648 Sq. Ft.	$224,629
102 Main St, Preston, MD - Beds \| 1 Baths \| 1008 Sq. Ft.	$242,430
102 Division St, Preston, MD 3 Beds \| 2 Baths \| 1344 Sq. Ft.	$319,883

Address	Redfin Estimate
116 Main St, Preston, MD 3 Beds \| 2 Baths \| 1185 Sq. Ft.	$279,482
104 Main St, Preston, MD - Beds \| 2 Baths \| 2035 Sq. Ft.	$321,135
110 Main St, Preston, MD - Beds \| 1 Baths \| 1220 Sq. Ft.	$227,048
119 Main St, Preston, MD 3 Beds \| 2.5 Baths \| 2379 Sq. Ft.	$355,922
118 Main St, Preston, MD 7 Beds \| 5 Baths \| 10000 Sq. Ft.	$786,641
108 Main St, Hurlock, MD - Beds \| - Baths \| - Sq. Ft.	$236,446
100 Fooks Ave, Preston, MD - Beds \| 1 Baths \| 2018 Sq. Ft.	$293,335

Property information provided by BRIGHT MLS when last listed in 2026. This data may not match . Learn more.

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106 Main St, Preston, MD 21655

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About this home

Redfin Estimate

Market trends in 21655, MD

Homeowner tools

Sale and tax history for 106 Main St

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21655

Home values near 106 Main St

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