411 Pine Tree Rd, Chestertown, MD 21620
OFF MARKET

$655,900

Trulia Estimate
  • 3 Beds
  • 3 Baths

411 Pine Tree Rd, Chestertown, MD 21620

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Home Value

Trulia Estimate
$656K
Since last month
Increased$2K (+0.2%)
Since last year
Increased$71K (+12.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +282% in the last 10 years
MonthEstimated value
2026
August 2026$656K
August 2026$650K
July 2026$654K
June 2026$678K
May 2026$694K
April 2026$744K
March 2026$678K
February 2026$686K
January 2026$681K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
105 Pearl Creek Ln, Chestertown, MD
0.19
Single-Family Home
$459,000
03/27/26
3
2.5
1,961
2032 Pondtown Rd, Chestertown, MD
0.38
Single-Family Home
$365,000
05/29/26
3
2
1,120
1517 Dudley Corners Rd, Millington, MD
0.65
Single-Family Home
$220,000
05/18/26
6
3
2,948
1904 Pondtown Rd, Chestertown, MD
0.27
Single-Family Home
$247,500
08/10/26
3
1
1,967
108 Springbrook Ln, Millington, MD
0.63
Single-Family Home
$475,900
04/17/26
3
2
1,677
101 Pine Tree Rd, Chestertown, MD
0.96
Single-Family Home
$480,000
05/04/26
4
2
1,848
1614 Dudley Corners Rd, Millington, MD
1.01
Single-Family Home
$760,000
07/06/26
2
3,400
201 Dogwood Lodge Ln, Millington, MD
2.28
Single-Family Home
$785,000
10/03/25
3
2
1,841
2010 McGinnes Rd, Chestertown, MD
1.60
Single-Family Home
$354,900
11/10/25
3
1
1,253
321 Front St, Crumpton, MD
1.89
Single-Family Home
$385,000
06/12/26
3
2.5
1,484

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1814 Pondtown Rd, Chestertown, MD 21620
0.15
$91,000
3
1
973
Off Market
105 Pearl Creek Ln, Chestertown, MD 21620
0.19
$459,000
3
2.5
1,961
Recently Sold
1906 Pondtown Rd, Chestertown, MD 21620
0.26
$110,000
-
-
-
For Sale
1904 Pondtown Rd, Chestertown, MD 21620
0.27
$247,500
3
1
1,967
Recently Sold
2032 Pondtown Rd, Chestertown, MD 21620
0.38
$365,000
3
2
1,120
Recently Sold
136 Pearl Creek Ln, Chestertown, MD 21620
0.35
-
3
2.5
1,460
Off Market
305 Pine Tree Rd, Chestertown, MD 21620
0.45
$271,900
2
1
826
Off Market
200 Ashley Ln, Chestertown, MD 21620
0.47
$476,900
3
1.5
1,656
Off Market
206 Springbrook Ln, Millington, MD 21651
0.57
$451,700
3
2
1,680
Off Market
224 Spring Rd, Millington, MD 21651
0.63
-
-
-
-
Off Market
404 Spring Rd, Chestertown, MD 21620
0.64
$19,500
-
-
-
For Sale
1517 Dudley Corners Rd, Millington, MD 21651
0.66
$220,000
6
3
2,948
Recently Sold

Local Information

  • Map ViewExplore the area around 411 Pine Tree Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2011
23.74 acre lot

About this House

Great opportunity to own 24 acres. House is only one year new, with many upgrades. Cook's kitchen with stainless appliances , granite counters and a center island. Beautiful hardwood flooring throughout main level. Upstairs has two bedrooms with separate entries to the main bath.Tons of storage.For the hunters there are turkey and deer in abundance. There is also a add' perc.To many details to....
411 Pine Tree Rd, Chestertown, MD 21620 is a 3 bedroom, 3 bathroom single-family home built in 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $655,900, with a rent estimate of $2,678/month.

Home Details for 411 Pine Tree Rd

Interior Features

Heating & Cooling
Heating: Heat Pump, StoveHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticTypes of Rooms: Dining Room, Mud Room

Exterior Features

Exterior Home Features
Roof: OtherExterior: Vinyl

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 23.74 acres

Price and Tax history

DateEventPrice
Aug 9, 2023
Source: Bright MLS #MDQA2006410
ListingRemoved
$999,998
Jun 28, 2023
Source: Bright MLS #MDQA2006410
PriceChange
$999,998
Price decreased by 0%
Jun 12, 2023
Source: Bright MLS #MDQA2006410
PriceChange
$999,999
Price decreased by 9%
May 25, 2023
Source: Bright MLS #MDQA2006410
Listed For Sale
$1,099,999
May 22, 2013
Source: Agent Provided
ListingRemoved
$349,900

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
5MoM

Around this home

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 411 Pine Tree Rd

  • What is 411 Pine Tree Rd estimated to be worth?
    Trulia's estimated value for 411 Pine Tree Rd in Chestertown, MD is $655,900.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • What are the closest schools to 411 Pine Tree Rd?
    The closest schools to 411 Pine Tree Rd in Chestertown, MD are Queen Anne's County High School (rated 7/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).
  • How big is the lot at 411 Pine Tree Rd?
    The lot at 411 Pine Tree Rd in Chestertown, MD is about 23.7 acres.

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