Pyles Dr, Chestertown, MD 21620
OFF MARKET

Pyles Dr
Chestertown, MD 21620

    (on 2.46 acres)

    Home Value

    Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

    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
    22481 Goose Hollow Dr, Chestertown, MD
    0.24
    Single-Family Home
    $335,320
    08/18/26
    3
    2
    1,296
    10087 John Carvill Rd, Chestertown, MD
    0.76
    Single-Family Home
    $695,000
    05/18/26
    3
    2
    1,566
    10050 Forrest Ln, Chestertown, MD
    0.78
    Single-Family Home
    $905,000
    11/14/25
    4
    2
    1,820
    10165 John Carvill Rd, Chestertown, MD
    0.90
    Single-Family Home
    $525,000
    10/17/25
    3
    2.5
    2,774
    10230 John Carvill Rd, Chestertown, MD
    1.07
    Single-Family Home
    $740,000
    01/15/26
    4
    3
    2,350
    10175 John Carvill Rd, Chestertown, MD
    0.96
    Single-Family Home
    $609,000
    08/27/25
    5
    3.5
    3,155
    22570 Bay Shore Rd, Chestertown, MD
    1.20
    Single-Family Home
    $435,000
    09/30/25
    3
    2
    1,788
    22950 Fairgale Farm Ln, Chestertown, MD
    1.11
    Single-Family Home
    $1,000,000
    04/14/26
    3
    1,836
    8833 Georgetown Rd, Chestertown, MD
    1.64
    Single-Family Home
    $359,000
    02/03/26
    4
    2
    1,625
    9126 Fairlee Rd, Chestertown, MD
    1.73
    Single-Family Home
    $125,000
    04/03/26
    3
    1.5
    1,216

    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
    22481 Goose Hollow Dr, Chestertown, MD 21620
    0.24
    $335,320
    3
    2
    1,296
    Recently Sold
    9762 Vogeler Dr, Chestertown, MD 21620
    0.22
    $908,200
    2
    1.5
    1,521
    Off Market
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    0.57
    $1,450,000
    4
    5
    4,257
    For Sale
    10044 John Carvill Rd, Chestertown, MD 21620
    0.69
    $1,526,600
    5
    4
    3,477
    Off Market
    Fairgale Farm Ln, Chestertown, MD 21620
    0.70
    -
    -
    -
    -
    Off Market
    10087 John Carvill Rd, Chestertown, MD 21620
    0.76
    $695,000
    3
    2
    1,566
    Recently Sold
    10050 Forrest Ln, Chestertown, MD 21620
    0.78
    $905,000
    4
    2
    1,820
    Recently Sold
    22956 Fairgale Farm Ln, Chestertown, MD 21620
    0.83
    $1,354,000
    5
    4.5
    6,459
    Off Market
    10165 John Carvill Rd, Chestertown, MD 21620
    0.90
    $532,100
    3
    2.5
    2,774
    Off Market
    10175 John Carvill Rd, Chestertown, MD 21620
    0.96
    $618,000
    5
    3.5
    3,155
    Off Market
    10230 John Carvill Rd, Chestertown, MD 21620
    1.07
    $740,000
    4
    3
    2,350
    Recently Sold
    10262 John Carvill Rd, Chestertown, MD 21620
    1.15
    $1,513,200
    5
    2
    3,788
    Off Market

    Local Information

    • Map ViewExplore the area around Pyles Dr.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    Home Highlights

    Lot Size
    2.46 acres

    About this House

    Pyles Dr is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 2.46 acres.
    Pyles Dr, Chestertown, MD 21620 is a unknown. It last sold for $20,500 on Nov 4, 2015. It is currently off market. The Trulia Estimate rent is $1,319/month.

    Home Details for Pyles Dr

    Property Information

    Property Type / Style
    Property Type: Unknown

    Interior Features

    Fireplace & Spa
    Fireplace

    Lot Information

    Lot Area: 2.46 acres

    Price and Tax history

    DateEventPrice
    Nov 4, 2015
    Source: N/A
    		Sold
    $20,500
    Mar 23, 2007
    Source: N/A
    		Sold
    $170,000

    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
    5    MoM

    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 Pyles Dr

    • What is the price history for Pyles Dr?
      Pyles Dr in Chestertown, MD last sold for $20,500 in November 2015.
    • 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 Pyles Dr?
      The closest schools to Pyles Dr in Chestertown, MD are Kent County High School (rated 5/10), Kent County Middle School (rated 3/10), Rock Hall Elementary School (Pre-K, rated 8/10).

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