SHELDRAKE Dr, Chestertown, MD 21620
OFF MARKET

SHELDRAKE Dr
Chestertown, MD 21620

    (on 0.34 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
    26236 E Old Gate, Millsboro, DE
    0.00
    Single-Family Home
    $374,990
    08/29/25
    3
    2
    1,576
    26218 E Old Gate, Millsboro, DE
    0.00
    Single-Family Home
    $349,990
    08/27/25
    3
    2
    1,390
    22735 Pelican Point, Millsboro, DE
    0.00
    Single-Family Home
    $364,990
    10/27/25
    3
    2
    1,390
    29845 Plantation Dr, Millsboro, DE
    0.41
    Single-Family Home
    $369,000
    05/15/26
    3
    2.5
    2,226
    28524 Dupont Blvd, Millsboro, DE
    0.52
    Single-Family Home
    $600,000
    01/28/26
    -
    1,749
    29843 Plantation Dr, Millsboro, DE
    0.43
    Single-Family Home
    $394,000
    12/19/25
    3
    3.5
    2,073
    32407 Flamingo Dr, Millsboro, DE
    0.00
    Single-Family Home
    $388,000
    04/01/26
    3
    2
    1,860
    29745 Highbridge Way, Millsboro, DE
    0.00
    Single-Family Home
    $421,950
    06/11/26
    3
    2
    1,857
    402 Old Landing Rd, Millsboro, DE
    0.58
    Single-Family Home
    $315,000
    10/10/25
    3
    2
    1,800
    27004 Greenleaf Dr, Millsboro, DE
    0.42
    Single-Family Home
    $390,000
    10/10/25
    4
    2.5
    1,903

    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
    26408 E Old Gate, Millsboro, DE 19966
    0.00
    $412,600
    4
    2.5
    1,998
    Off Market
    26426 E Old Gate, Millsboro, DE 19966
    0.00
    $470,800
    5
    3
    2,238
    Off Market
    37091 Havelock Ct, Millsboro, DE 19966
    0.00
    -
    3
    2.5
    2,182
    Off Market
    26198 E Old Gate, Millsboro, DE 19966
    0.00
    $394,400
    3
    2
    1,390
    Off Market
    33 Beacon, Millsboro, DE 19966
    0.00
    $512,700
    3
    3
    2,266
    Off Market
    33499 Marina Bay, Millsboro, DE 19966
    0.00
    $396,900
    4
    3.5
    2,400
    Off Market
    27302 18th 324 Millsboro #324, Millsboro, DE 19966
    0.00
    $436,900
    4
    3.5
    2,195
    Off Market
    33503 Marina Bay, Millsboro, DE 19966
    0.00
    $406,400
    4
    3.5
    2,400
    Off Market
    33501 Marina Bay, Millsboro, DE 19966
    0.00
    $415,300
    4
    3.5
    2,400
    Off Market
    31422 N Fayetteville, Millsboro, DE 19966
    0.00
    $350,400
    3
    2.5
    2,413
    Off Market
    37209 N Fayetteville, Millsboro, DE 19966
    0.00
    $380,000
    3
    3.5
    2,413
    Off Market
    26260 Milby, Millsboro, DE 19966
    0.00
    $364,300
    3
    2.5
    2,195
    Off Market

    Local Information

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

    Home Highlights

    Lot Size
    0.34 acres

    About this House

    SHELDRAKE Dr is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 0.34 acres.
    SHELDRAKE Dr, Chestertown, MD 21620 is a unknown. It last sold for $4,000 on Aug 27, 1999. It is currently off market. The Trulia Estimate rent is $2,145/month.

    Home Details for SHELDRAKE Dr

    Property Information

    Property Type / Style
    Property Type: Unknown

    Interior Features

    Fireplace & Spa
    Fireplace

    Lot Information

    Lot Area: 0.34 acres

    Price and Tax history

    DateEventPrice
    Aug 27, 1999
    Source: N/A
    		Sold
    $4,000

    Market trends in Millsboro

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    $413K
    $13.33K    MoM
    Sale-to-List Price
    98.0%
    0.1%    MoM
    Price per sq ft
    $205
    $9    MoM
    Available listings
    317
    13    MoM

    Around this home

    What Locals Say about Millsboro

    At least 112 Trulia users voted on each feature.

    • 95 % Say car is needed

    • 86 % Say parking is easy

    • 82 % Say it's dog friendly

    • 80 % Say there's holiday spirit

    • 77 % Say yards are well-kept

    • 70 % Say it's quiet

    • 60 % Say kids play outside

    • 60 % Say people would walk alone at night

    • 55 % Say neighbors are friendly

    • 54 % Say there's wildlife

    • 48 % Say they plan to stay for at least 5 years

    • 41 % Say it's walkable to restaurants

    • 39 % Say there are sidewalks

    • 37 % Say streets are well-lit

    • 37 % Say there are community events

    • 30 % Say it's walkable to grocery stores

    Sourced by Trulia users. Learn more about our methodology.
    • Jillc
      "It’s a dog friendly area with a dedicated dog park & a great park by water to walk your dog. my dog give it two paws 🐾 up."
      1
      Flag
    • Kmcoj
      "My neighborhood has very limited access to public transportation. You really need a car to get anywhere "
      0
      Flag
    • Jdacb
      "Easy, since I drive to western Sussex. Traffic tends to be heavier closer to the beach. New bypass in Millsboro will be a plus. "
      0
      Flag
    • Tracy Wright
      "A quiet area for young families and retired folks to enjoy a time of Tranquility and peace in this beautiful community filled with tall trees!"
      2
      Flag
    • Holly Rubick
      "It’s a friendly, dog-walking community. Quiet golf-cart neighborhood with community gatherings that give opportunities to meet others. "
      0
      Flag
    • Elaine.burg
      "It’s a growing area and is close to several state parks and beaches. There is shopping nearby and many families with young children live in the area. "
      2
      Flag
    • Trulia User
      "I’ve lived here 3 years I can’t wait to get home from work…..shopping banking personal business is convenient to my home…..everything is at least 5 minutes from the house…..also you have beaches.boating.crabbing fishing what else could you need"
      0
      Flag
    • Trulia User
      "I just got married to a hooper on the lakeside it's a wonderful place to be were moving soon but I will miss it alot thank u for watching out for our kids and everyone the guards keep people very safe and I really appreciate it all."
      0
      Flag
    • Trulia User
      "It’s the perfect place for people who want to spend time on the water. Our HOA and marina are inexpensive annual fees. Great community. Annual Owners picnic at the pavilion "
      0
      Flag
    • Trulia User
      "It is a neighborhood that has been lost in time. It is a place where your neighbors know each other and doors are left open, and people get together for happy hour. It’s a private secret how great this little area is"
      0
      Flag
    • Adam P.
      "I live in a golf course neighborhood located in millsboro. Not all of millsboro is created equal. Some parts you don’t want to be in after dark and others you would. "
      56
      Flag
    • Maria T. F.
      "It’s a very friendly neighborhood. Everywhere you go people are nice for the most part. The streets are very safe."
      0
      Flag
    • Ljones6118
      "I just moved here and I love the neighborhood.. pretty quiet and neighbors seem really nice.. everything is well maintained and they even have a park to take my son and swing on it and play on the playground and lots of posts with dog bags to pick up dog poop! Very clean and very nice neighborhood and it’s close to local places to eat and grocery stores and other neighborhoods "
      31
      Flag
    • Jimmy
      "A lot of community/church/city sponsored events. Parades, fairs, seasonal events are constantly provided."
      8
      Flag
    • Laraoneil60
      "Marina community on beautiful Indian River, extremely low HOA & boat slip fees. This is the place to live if you are an active family "
      0
      Flag
    • Bethtommy
      "I have the woods behind my house and the bay down the street I like my neighbors they are very friendly"
      0
      Flag
    • v Mc
      "Very friendly people around here. Love the birds and wildlife. Great food great atmosphere for kids. "
      0
      Flag
    • Lois T.
      "No public transportation not easy to commute. Must have vehicle to get around. Have to walk at least 1/2 mile just to get up public transportation stop."
      0
      Flag
    • Kyndmama
      "Millsboro is a nice place to live, in town it’s easy to walk from end to end. Lots of good shopping on the highway. The only downside is the schools and roads aren’t accommodating to the amount of residents that live here. It can talk several minutes to travel short distances during commuting time and beach traffic in summer. Still trying to pass a referendum to get larger schools, kids are packed in like sardines. Town has lots of potential, just got to get family friendly people to come out and support the community. "
      41
      Flag
    • Piconnect
      "My neighborhood sucks. People are unfriendly. Traffic is terrible. Roads are too narrow. There are no sidewalks. "
      0
      Flag
    • Kyndmama
      "It’s a nice area, plenary of families, we need more infrastructure for walking around, but besides that, it’s a great town to live in. I’m renting, and looking to buy a home here."
      20
      Flag
    • Mariaedavis
      "Nice quiet neighborhood. Close to everything but far enough away not to get caught up in traffic. The bay view is absolutely gorgeous"
      0
      Flag
    • Tammy R.
      "Lives in millsboro for 3 years..close knit family/community..loved it..want to move back if I am able to"
      8
      Flag
    • Wergonnam8kamark
      "Drive attentively. Be on the look out for stray dogs. Traffic is heavy here, always be watching you kids."
      0
      Flag
    • Bautij94
      "I am trying to move here and it seems impossible to find a place to rent. It seems like a great place to live but just impossible."
      12
      Flag
    • Roguegirl80
      "I've lived in my neighborhood for 9 years. The neighbors are friendly but everyone pretty much stays to themselves. The kids get together to play. Overall, it's a great area."
      13
      Flag

    LGBTQ Local Legal Protections

    Frequently asked questions about SHELDRAKE Dr

    • What is the price history for SHELDRAKE Dr?
      SHELDRAKE Dr in Chestertown, MD last sold for $4,000 in August 1999.
    • Is Chestertown a buyer's or seller's market?
      Chestertown is currently a balanced market, based on recent for-sale activity.
    • What's the median sale price in Chestertown?
      The median sale price in Chestertown is $413K. That is up $13.33K from the prior month.
    • What do residents say about Chestertown?
      Residents describe Chestertown, MD as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.

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