214 Pine Tree Rd, Chestertown, MD 21620
OFF MARKET

214 Pine Tree Rd
Chestertown, MD 21620

  • Studio
  • 2 Baths
  • 1,232 sqft (on 3.43 acres)

$294,800

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $1,744/mo*
Refinance Your Home

$294,800

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $1,744/mo*
Refinance Your Home
Studio
2 Baths
1,232 sqft
(on 3.43 acres)

Local Information

  • Map ViewExplore the area around 214 Pine Tree Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1992
Lot Size
3.43 acres
Living Area
1,232 sqft
Price/Sqft
$239

About this House

This single-family home is located at 214 Pine Tree Rd, Chestertown, MD. 214 Pine Tree Rd is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 1,232 sqft of floor space. This property has a lot size of 3.43 acres and was built in 1992.
214 Pine Tree Rd, Chestertown, MD 21620 is a studio, 2 bathroom, 1,232 sqft single-family home built in 1992. It last sold for $5,000 on Apr 15, 1981. It is currently off market. The Trulia Estimate is $294,800, with a rent estimate of $2,478/month.

Home Details for 214 Pine Tree Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 3.43 acres

Price History for 214 Pine Tree Rd

DatePriceEventSource
04/15/1981$5,000Sold
N/A

Market trends in Chestertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM
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Property Tax and Assessment

Year2025
Tax$2,117
Assessment$218,400
Home facts updated by county records

Comparable Sales for 214 Pine Tree Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Springbrook Ln, Millington, MD
0.19
Single-Family Home
$475,900
04/17/26
3
2
1,677
101 Pine Tree Rd, Chestertown, MD
0.37
Single-Family Home
$480,000
05/04/26
4
2
1,848
105 Pearl Creek Ln, Chestertown, MD
0.55
Single-Family Home
$459,000
03/27/26
3
2.5
1,961
2032 Pondtown Rd, Chestertown, MD
0.88
Single-Family Home
$365,000
05/29/26
3
2
1,120
2405 McGinnes Rd, Chestertown, MD
0.77
Single-Family Home
$3,319,000
02/06/26
2
1,428
1520 Dudley Corners Rd, Millington, MD
0.98
Single-Family Home
$297,500
08/20/25
3
2.5
1,912
1517 Dudley Corners Rd, Millington, MD
0.91
Single-Family Home
$220,000
05/18/26
6
3
2,948
2010 McGinnes Rd, Chestertown, MD
1.33
Single-Family Home
$354,900
11/10/25
3
1
1,253
1614 Dudley Corners Rd, Millington, MD
1.04
Single-Family Home
$760,000
07/06/26
2
3,400
2101 Dudley Corners Rd, Crumpton, MD
1.18
Single-Family Home
$250,000
10/30/25
2
1
1,200

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Assigned Schools

These are the assigned schools for 214 Pine Tree Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Homes for sale near 214 Pine Tree Rd

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Off Market Homes Near 214 Pine Tree Rd

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