OFF MARKET

Off Market Jun 2023 for $350K

$380,334

Est. refi paymentEst. refi $2,265/mo

•

1,688

sq ft

414 Pine Tree Rd, Chestertown, MD 21620

About this home

Reduced for a quick sale! Don’t miss out! Country living at its best! Just under 1 acre, this 4 bedroom home boasts an open floorplan, separate level laundry/mudroom with skylight, and a spacious basement for storage or drywall finish for extra living space. The main level includes all bedrooms, eat-in kitchen with bright white cabinets, separate dining room, living room, and a additional family room or office. Within the last 2 years a 500 square foot addition has been added, the roof replaced, new siding, new gutters, new windows, and a brand new septic system installed. There is also the possibility to expand for even more home square footage! Head outdoors to enjoy the sizeable fenced yard with plenty of room for chickens, growing vegetables, landscaping, entertaining on the deck, or simply relaxing by the firepit. Eastern Shore living is calling! This property is located in Queen Anne's County, just minutes to Rt. 301. BONUE: Seller is including a 1 year Home Warranty with the house sale!!

Single-familyProperty Type

1968Year Built

0.98 acresLot Size

$225Est. Price/Sq.Ft.

Listed by Kim Raeder • Keller Williams Select Realtors of Annapolis

•410-972-4000 (broker)

•bburris@kw.com (broker)

Bought with Kate Meckley • Foraker Realty Co.

•484-406-3004 (broker)

Redfin checked: 4 minutes ago

•Source:BRIGHT MLS #MDQA2006134

Redfin Estimate

$380,334

$30K since sold in June 2023$3,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.4% higher than the average sale price ($358K) of 6 comparable homes.

SOLD APR 10, 2026
$299,900
A
4 beds2 baths1,782 sq ft
213 Groff Rd, Millington, MD 21651
SOLD MAY 4, 2026
$480,000
B
4 beds2 baths1,848 sq ft
101 Pine Tree Rd, Chestertown, MD 21620
SOLD JUN 29, 2026
$460,000
C
3 beds2 baths1,664 sq ft
118 Grant Ct, Chestertown, MD 21620
SOLD AUG 7, 2026
$180,000
D
3 beds1 bath1,440 sq ft
1826 Sudlersville Rd, Sudlersville, MD 21668
SOLD JUN 5, 2026
$349,500
E
3 beds2 baths1,304 sq ft
126 Char Nor Manor Blvd, Chestertown, MD 21620
SOLD MAY 19, 2026
$376,000
F
3 beds2 baths1,432 sq ft
136 Hilltop Dr, Chestertown, MD 21620

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,733/mo

Redfin rental estimate

List your home for rent

Market trends in 21620, MD

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.0%

1.0% MoM

Median sale price

$362K

$17K MoM

Avg. days on market

46d

14 days MoM

Recently sold homes

9 MoM

New listings for sale

NEW 19 HRS AGO
$38,200,000
4 beds2 baths2,330 sq ft
8184 Rock Hall Rd, Chestertown, MD 21620
(410) 778-3779
NEW 25 HRS AGO
$1,195,000
2 beds1 bath806 sq ft
302 S Mill St, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$345,000
3 beds1.5 baths1,398 sq ft
217 Edmore Rd, Chestertown, MD 21620
(410) 810-0010
$369,000
2 beds1.5 baths1,036 sq ft
101 S College Ave, Chestertown, MD 21620
(410) 810-0010
$649,000
4 beds3 baths2,864 sq ft
22400 Great Oak Landing Rd, Chestertown, MD 21620
(410) 778-0330
FOR SALE BY OWNER
$435,000
3 beds2 baths1,956 sq ft
233 Duke of Kent St, Chestertown, MD 21620
$524,900
3 beds2.5 baths2,076 sq ft
1003 Twin Ct, Chestertown, MD 21620
(410) 778-3779
$295,000
1 bed1 bath— sq ft
117 N Water St Unit 3B, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$304,000
3 beds2 baths1,232 sq ft
7464 Shortall St, Chestertown, MD 21620
(410) 476-2201
$299,900
3 beds1 bath1,056 sq ft
124 Wilton Rd, Chestertown, MD 21620
(410) 810-0010
See all

Provided by Redfin

Sale history for 414 Pine Tree Rd

Date

Event

Price

BRIGHT MLS #MDQA2006134

Jun 27, 2023

Sold

$350,000

$207/sq ft

May 25, 2023

Pending

—

May 24, 2023

Price Changed

$349,900

$207/sq ft

Apr 16, 2023

Price Changed

$360,500

$214/sq ft

Apr 7, 2023

Listed

$375,000

$222/sq ft

Apr 7, 2023

Coming Soon

$375,000

$222/sq ft

BRIGHT MLS #MDQA146966

Jun 30, 2021

Sold

$260,000

$154/sq ft

May 21, 2021

Contingent

—

May 7, 2021

Relisted

—

Apr 9, 2021

Contingent

—

Mar 25, 2021

Price Changed

$259,900

$154/sq ft

Mar 16, 2021

Listed

$262,500

$156/sq ft

+23

One of a kind raised ranch home with open floorplan and rear split level mudroom entrance. This unique home has been carefully updated and has plenty of spaces for everyone to enjoy. A bright and cheerful kitchen perfect for the cook, a cozy living room with a bay window and hardwood floors, a partial dry basement for hobbies and storage, a Trex deck for entertaining, and a huge backyard for games and play! NEW roof, NEW siding, NEW gutters, NEW windows, Updated Kitchen and appliances, and fresh landscaping. Best of all, the seller just installed a BRAND NEW SEPTIC SYSTEM! This property is located in Northern Queen Anne's County and just minutes to Rt. 301, perfect for commuting north or south. Neighboring a fantastic new community of homes in the $300,000-400,000 range! NO HOA on this lot! Come check this out and you will fall in love, this is a GREAT PLACE TO CALL HOME!

MRIS #QA7824883

Nov 29, 2012

Sold

$34,058

$20/sq ft

Oct 29, 2012

Pending

—

Oct 23, 2012

Price Changed

$33/sq ft

Oct 23, 2012

Relisted

—

Aug 15, 2012

Pending

—

Aug 9, 2012

Price Changed

$35/sq ft

Aug 2, 2012

Price Changed

$46/sq ft

Jul 2, 2012

Price Changed

$52/sq ft

Jun 1, 2012

Price Changed

$59/sq ft

Apr 23, 2012

Listed

$67/sq ft

BRIGHT MLS #1003954678

Nov 29, 2012

Sold

$34,058

$20/sq ft

Oct 29, 2012

Listing Removed

—

Apr 23, 2012

Listed

$55,250

$33/sq ft

MRIS #QA6815209

Jan 1, 2009

Delisted

—

Dec 2, 2008

Price Changed

Nov 10, 2008

Price Changed

Nov 6, 2008

Price Changed

Nov 2, 2008

Price Changed

Oct 9, 2008

Price Changed

Oct 1, 2008

Price Changed

Sep 25, 2008

Price Changed

Aug 24, 2008

Price Changed

Jul 11, 2008

Listed

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$2,378 (+15.1%)

2024

$2,066 (+17.8%)

$60,600 + $185,500

$246,100

2023

$1,753 (+21.7%)

2022

$1,441 (+8.5%)

2021

$1,328 (+5.0%)

$63,700 + $82,900

$146,600

2020

$1,265 (+5.0%)

2019

$1,204

2018

$1,204

$49,900 + $69,400

$119,300

2017

$1,204 (−4.5%)

$49,900 + $69,400

$119,300

2016

$1,261 (+0.7%)

2015

$1,252 (+0.8%)

2014

$1,243

$64,900 + $58,400

$123,300

2013

$1,243 (+2.5%)

2012

$1,213 (−14.9%)

2011

$1,426 (+37.9%)

2010

$1,034 (+8.9%)

2009

$950

Tax history for 414 Pine Tree Rd

Year

Property tax

Land + Additions

Assessment*

2025

$2,378 (+15.1%)

2024

$2,066 (+17.8%)

$60,600 + $185,500

$246,100

2023

$1,753 (+21.7%)

2022

$1,441 (+8.5%)

2021

$1,328 (+5.0%)

$63,700 + $82,900

$146,600

2020

$1,265 (+5.0%)

2019

$1,204

2018

$1,204

$49,900 + $69,400

$119,300

2017

$1,204 (−4.5%)

$49,900 + $69,400

$119,300

2016

$1,261 (+0.7%)

2015

$1,252 (+0.8%)

2014

$1,243

$64,900 + $58,400

$123,300

2013

$1,243 (+2.5%)

2012

$1,213 (−14.9%)

2011

$1,426 (+37.9%)

2010

$1,034 (+8.9%)

2009

$950

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.98 Acres

Year renovated

—

Sq. Ft.

1,688

Year built

1968

Style

Single Family Residential

County

Queen Anne's County

APN

07 014325

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

Jul 1, 2024 • Final

Residential solar panels

Install roof-mounted solar panels on an existing single-family home.

Electrical

Solar

Jul 7, 2022 • Final

Addition to residence

Construct additions to a residence, including a family and recreation room on the side of the house and a master bedroom suite on the rear. Convert an existing front bedroom into an office.

Addition

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Parking

Parking Information
Driveway

Interior

Bedroom Information
# of Bedrooms On Main Level: 4

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Flooring Type: Hardwood
Not Furnished
Interior Features: Breakfast Area, Combination Dining/Living, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Country, Kitchen - Table Space
Living Area Sq.Ft. Source: Assessor

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Bedroom 1, Laundry, Bathroom 1, Master Bathroom
Laundry Type: Lower Floor

Basement Information
Basement: Yes
Connecting Stairway, Poured Concrete

Exterior

Property Information
Total Below Grade Sq. Ft.: 644
Improvement Assessed Value: $185,500
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor

Building Information
Construction Materials: Frame
Foundation Details: Slab
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Patio(s), Porch(es)
Roof: Architectural Shingle
Structure Type: Detached
Other Structures: Shed
Building Not Winterized

Exterior Information
Play Area
Fencing: Privacy, Partially, Panel, Wood

Lot Information
Lot Features: Rear Yard, Rural, Trees/Wooded
Tidal Water: No

Land Information
Land Assessed Value: $60,600

Above Grade Information
Finished Sq.Ft.: 1,688
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 644
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $1,381
Tax Assessed Value: $179,767
Tax Year: 2023
Tax Annual Amount: $1,381

Assessments Information
Year Assessed: 2023

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Electric Previous 12 Months: $1,500
Electric Average / Month: $125
Central, Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well
Municipal Trash: No

Location

School Information
High School: QUEEN ANNE'S COUNTY
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Cross Street: Pondtown
Directions: MD-313 N Turn left onto Merrick Corner Rd Turn right onto Big Woods Rd Turn left onto MD-302 W Turn right onto Benton Corners Rd Continue onto MD-290 N Turn left onto Pondtown Rd Turn right onto Pine Tree Rd

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,688
Stories: 1.0
Lot Size: 0.98 acres
Style: Single Family Residential
Year Built: 1968
Year Renovated: —
County: Queen Anne's County
APN: 07 014325

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Sudlersville Elementary School

Public PreK-4 • Assigned • 4.3mi

7/10

Sudlersville Middle School

Public 5-8 • Assigned • 4.6mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 13.9mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Chestertown, MD • 21620

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$362,000 – $438,000

Sell confidently with a local market expert in Chestertown. 3 minutes to get started.

Nearby similar homes

$25,000

— beds— baths672 sq ft

316 Middle St, Millington, MD 21651

(410) 488-3124

$162,000

Land— sq ft

441 Eagle Manor Dr, Church Hill, MD 21623

(410) 643-4663

OPEN SEP 6, 12PM TO 2PM

$399,000

4 beds2 baths2,156 sq ft

11944 Augustine Herman Hwy, Kennedyville, MD 21645

(410) 778-0330

$379,900

2 beds1 bath832 sq ft

31673 W Edge Rd, Millington, MD 21651

(410) 810-0010

$515,000

7 beds5 baths3,836 sq ft

11960 Flour Mill St, Kennedyville, MD 21645

(410) 778-0330

FOR SALE BY OWNER

$435,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

New listings for sale in 21620

NEW 19 HRS AGOVIDEO TOUR

$38,200,000

4 beds2 baths2,330 sq ft

8184 Rock Hall Rd, Chestertown, MD 21620

(410) 778-3779

NEW 25 HRS AGO

$1,195,000

2 beds1 bath806 sq ft

302 S Mill St, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$345,000

3 beds1.5 baths1,398 sq ft

217 Edmore Rd, Chestertown, MD 21620

(410) 810-0010

$369,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

$649,000

4 beds3 baths2,864 sq ft

22400 Great Oak Landing Rd, Chestertown, MD 21620

(410) 778-0330

FOR SALE BY OWNER

$435,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

$524,900

3 beds2.5 baths2,076 sq ft

1003 Twin Ct, Chestertown, MD 21620

(410) 778-3779

$295,000

1 bed1 bath— sq ft

117 N Water St Unit 3B, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$304,000

3 beds2 baths1,232 sq ft

7464 Shortall St, Chestertown, MD 21620

(410) 476-2201

Home values near 414 Pine Tree Rd

Data from public records.

Address	Redfin Estimate
336 Pine Tree Road, Chestertown, MD - Beds \| 2 Baths \| 924 Sq. Ft.	$147,420
330 Pine Tree Road, Chestertown, MD - Beds \| 2 Baths \| 1568 Sq. Ft.	$378,755

Address	Redfin Estimate
426 Pine Tree Road, Chestertown, MD - Beds \| 3 Baths \| 1680 Sq. Ft.	$372,831
326 Pine Tree Road, Chestertown, MD - Beds \| 1 Baths \| 916 Sq. Ft.	$220,007

Address	Redfin Estimate
340 Pine Tree Road, Chestertown, MD - Beds \| - Baths \| 1080 Sq. Ft.	$188,810
422 Pine Tree Road, Chestertown, MD - Beds \| 2.5 Baths \| 2016 Sq. Ft.	$216,210

Property information provided by BRIGHT MLS when last listed in 2023. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Chestertown	Agents near me	Rockville, MD homes for sale	Chestertown Housing Market
Houses for sale near me	Baltimore, MD homes for sale	Frederick, MD homes for sale
Land for sale near me	Bethesda, MD homes for sale	Columbia, MD homes for sale
Open Houses near me	Silver Spring, MD homes for sale	Chestertown Property Records
Condos for sale near me	Bowie, MD homes for sale	MD New Listings

Aberdeen homes for sale
Stevensville homes for sale
Middle River homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 414 Pine Tree Rd

Tax history for 414 Pine Tree Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 414 Pine Tree Rd

More real estate resources