Round top Rd, Chestertown, MD 21620
OFF MARKET

Round top Rd
Chestertown, MD 21620

  • Studio

$446,100

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $2,636/mo*
Refinance Your Home

$446,100

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $2,636/mo*
Refinance Your Home
Studio
(on 11.36 acres)

Home Value

Trulia Estimate
$446K
Since last month
Increased$8K (+1.7%)
Since last year
Increased$23K (+5.5%)
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 +25% in the last 10 years
MonthEstimated value
2026
August 2026$448K
July 2026$441K
June 2026$430K
May 2026$421K
April 2026$432K
March 2026$431K
February 2026$389K
January 2026$378K
2025
2024
2023

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
Preston Ln, Chestertown, MD
0.89
Single-Family Home
$525,000
08/16/26
3
3
2,824
26889 Morgnec Rd, Chestertown, MD
1.56
Single-Family Home
$700,000
10/22/25
2
2
1,966
113 Pear Tree Point Rd, Chestertown, MD
1.33
Single-Family Home
$175,000
06/05/26
3
1
1,296
492 Pear Tree Point Rd, Chestertown, MD
1.23
Single-Family Home
$850,000
12/19/25
3
2
3,720
143 Char Nor Manor Blvd, Chestertown, MD
1.25
Single-Family Home
$868,000
10/15/25
3
2.5
2,073
127 Char Nor Manor Blvd, Chestertown, MD
1.17
Single-Family Home
$355,000
10/02/25
2
1
832
129 Char Nor Manor Blvd, Chestertown, MD
1.18
Single-Family Home
$412,000
02/20/26
2
1
810
124 Char Nor Manor Blvd, Chestertown, MD
1.20
Single-Family Home
$250,000
11/11/25
2
2
1,024
126 Char Nor Manor Blvd, Chestertown, MD
1.22
Single-Family Home
$349,500
06/05/26
3
2
1,304
111 Cee Jay Rd, Chestertown, MD
1.25
Single-Family Home
$349,000
10/23/25
2
1,400

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
27325 Preston Ln, Chestertown, MD 21620
0.88
$498,300
3
3
2,824
Off Market
Preston Ln, Chestertown, MD 21620
0.89
$525,000
3
3
2,824
Recently Sold
101 Char Nor Manor Blvd, Chestertown, MD 21620
1.04
$387,100
3
1.5
1,156
Off Market
27370 Morgnec Rd, Chestertown, MD 21620
1.05
$334,300
3
1.5
1,008
Off Market
107 Char Nor Manor Blvd, Chestertown, MD 21620
1.06
$416,200
5
3
2,128
Off Market
127 Char Nor Manor Blvd, Chestertown, MD 21620
1.17
$368,000
2
1
832
Off Market
906 Double Creek Point, Chestertown, MD 21620
1.17
$327,200
4
2
1,400
Off Market
118 Char Nor Manor Blvd, Chestertown, MD 21620
1.18
$278,700
3
2
1,114
Off Market
129 Char Nor Manor Blvd, Chestertown, MD 21620
1.18
$412,000
2
1
810
Recently Sold
492 Pear Tree Point Rd, Chestertown, MD 21620
1.23
$850,000
3
2
3,720
Recently Sold
124 Char Nor Manor Blvd, Chestertown, MD 21620
1.20
$250,000
2
2
1,024
Recently Sold
473 Pear Tree Point Rd, Chestertown, MD 21620
1.24
$379,200
3
3
1,512
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Lot Size
11.36 acres

About this House

This single-family home is located at Round top Rd, Chestertown, MD. Round top Rd is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 11.36 acres.
Round top Rd, Chestertown, MD 21620 is a studio single-family home. It is currently off market. The Trulia Estimate is $446,100, with a rent estimate of $2,381/month.

Home Details for Round top Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 11.36 acres

Price and Tax history

YearProperty taxTax assessment
2025Unavailable
$284,000
Home facts updated by county records

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 Round top Rd

  • What is Round top Rd estimated to be worth?
    Trulia's estimated value for Round top Rd in Chestertown, MD is $446,100.
  • 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 Round top Rd?
    The closest schools to Round top Rd in Chestertown, MD are Church Hill Elementary School (Pre-K, rated 5/10), Queen Anne's County High School (rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).
  • How big is the lot at Round top Rd?
    The lot at Round top Rd in Chestertown, MD is about 11.4 acres.

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near Round top Rd

Skip to last item
Skip to first item

Homes for sale near Round top Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item