Harbor Dr, Chester, MD 21619
OFF MARKET

$513,800

Trulia Estimate
  • Studio

Harbor Dr, Chester, MD 21619

Est. Refi. Payment $3,030/mo*
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Home Value

Trulia Estimate
$514K
Since last month
Decreased$1K (-0.2%)
Since last year
Increased$19K (+3.8%)
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 +4% in the last 10 years
MonthEstimated value
2026
August 2026$514K
August 2026$513K
July 2026$515K
June 2026$516K
May 2026$516K
April 2026$517K
March 2026$513K
February 2026$514K
January 2026$498K
2025

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
1921 Harbor Dr, Chester, MD
0.02
Single-Family Home
$519,900
05/21/26
3
2.5
2,000
1914 Anchorage Dr, Chester, MD
0.08
Single-Family Home
$299,900
06/08/26
3
2
1,800
2723 Cox Neck Rd, Chester, MD
0.11
Single-Family Home
$447,500
10/28/25
-
1,560
2723 Cox Neck Rd, Chester, MD
0.11
Single-Family Home
$447,500
10/17/25
4
2.5
1,600
1906 Harbor Dr, Chester, MD
0.11
Single-Family Home
$430,000
08/10/26
4
2
1,750
1903 Churchhill Ln, Chester, MD
0.15
Single-Family Home
$405,000
11/14/25
4
3
1,682
1910 Sherman Dr, Chester, MD
0.16
Single-Family Home
$337,200
06/30/26
1
1,596
1872 Harbor Dr, Chester, MD
0.17
Single-Family Home
$445,000
07/31/26
3
2
1,486
1870 Harbor Dr, Chester, MD
0.19
Single-Family Home
$310,000
03/23/26
2
1
832
2653 Cox Neck Rd, Chester, MD
0.22
Single-Family Home
$374,000
01/02/26
3
2
1,560

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
1921 Harbor Dr, Chester, MD 21619
0.02
$519,900
3
2.5
2,000
Recently Sold
1914 Anchorage Dr, Chester, MD 21619
0.08
$299,900
3
2
1,800
Recently Sold
16 & 17 Cecil Dr, Chester, MD 21619
0.07
-
-
-
-
Off Market
1906 Harbor Dr, Chester, MD 21619
0.11
$430,000
4
2
1,750
Recently Sold
1907 Churchhill Ln, Chester, MD 21619
0.12
$444,100
3
2
1,160
Off Market
1926 Sherman Dr, Chester, MD 21619
0.14
$439,200
4
2
1,560
Off Market
2723 Cox Neck Rd, Chester, MD 21619
0.11
$468,100
4
2.5
1,600
Off Market
2719 Cox Neck Rd, Chester, MD 21619
0.11
$428,400
3
2.5
1,297
Off Market
2747 Cecil Dr, Chester, MD 21619
0.13
$370,300
3
2
1,560
Off Market
1903 Churchhill Ln, Chester, MD 21619
0.15
$405,000
4
3
1,682
Recently Sold
Cox Neck Rd, Chester, MD 21619
0.11
-
-
-
-
Off Market
2709 Cox Neck Rd, Chester, MD 21619
0.13
$457,700
4
2.5
2,286
Off Market

Local Information

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

About this House

Harbor Dr is in Chester, MD and in ZIP code 21619.
Harbor Dr, Chester, MD 21619 is a studio property. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $513,800, with a rent estimate of $2,665/month.

Price and Tax history

DateEventPrice
Apr 21, 2026
Source: Bright MLS #MDQA2015496
ListingRemoved
$519,900
Feb 11, 2026
Source: Bright MLS #MDQA2015496
PriceChange
$519,900
Price increased by 4%
Oct 30, 2025
Source: Bright MLS #MDQA2015496
Listed For Sale
$499,900

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
5MoM

Around this home

What Locals Say about Chester

At least 36 Trulia users voted on each feature.

  • 88 % Say parking is easy

  • 88 % Say car is needed

  • 86 % Say people would walk alone at night

  • 83 % Say it's dog friendly

  • 83 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 65 % Say neighbors are friendly

  • 64 % Say kids play outside

  • 64 % Say there's wildlife

  • 57 % Say yards are well-kept

  • 53 % Say there are sidewalks

  • 49 % Say they plan to stay for at least 5 years

  • 48 % Say there are community events

  • 44 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 17 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Dlmaheux
    "I’ve been here 20 years and don’t even lock my doors the majority of the time. Super safe. Wonderful sense of community all around "
    0
    Flag
  • Colinjgallagher525
    "Tucked away million dollar homes with great down-to-earth people living in them. It’s a warm community and bay living at its finest. "
    0
    Flag
  • Peggy Young
    "Board meetings, water aerobics, pickle ball, tennis, a gym, kayaking, paddle boarding. Mah jongg, bingo, games day, social committee,walking club "
    0
    Flag
  • Trulia User
    "Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
    0
    Flag
  • Peggy.young
    "Lots of spaces to walk dogs, lots of people who love dogs. Great way to meet neighbors. Just about everyone on the shore has a dog. Also a number of good kennels for when you travel. "
    3
    Flag
  • Taylor T.
    "Lots of dogs everyone walks them all hours of the night and their is little stops with bags to pick up Feeses "
    0
    Flag
  • kara
    "I've lived here for three years and the neighbors are very friendly mostly. They look out for each other..."
    0
    Flag
  • Robert M Heyn
    "Its always so pleasant here in Chester. Its like Everyone says HI and knows one another. The school systems are great and Chester is central located to all surrounding areas of shopping, dining, water, Annapolis and Easton. Some of tue most beautiful views in the MD pertaining to water and nature."
    1
    Flag
  • J0J0s4X4
    "They are required to clean up after them. The HOA used to pay a pooper scooper company which provided pooper containers, scoops, and bags after used to be deposited in the container. The Board decided that the dog owners should pick up the cost of picking up after their dogs and quit paying the $26,000 per year for the company."
    0
    Flag
  • Wilson
    "Not very many families, but within a great school district. Good community for people who don’t really have children. "
    0
    Flag
  • J0J0s4X4
    "it is a child friendly development and very safe. also, most homeowners have video security systems."
    0
    Flag
  • Peggy y.
    "Chester is a real community, where you know just about everyone. I live in a condo, so life is as easy as it gets. There are lots of walking trails, and you are always a stone’s throw from the Chesapeake Bay or the Chester River."
    3
    Flag
  • Eric D.
    "I live in this area. Great place to raise a family. Access to beaches, parks, cross island trail."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about Harbor Dr

  • What is Harbor Dr estimated to be worth?
    Trulia's estimated value for Harbor Dr in Chester, MD is $513,800.
  • Is Chester a buyer's or seller's market?
    Chester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Chester?
    Residents describe Chester, MD as easy to park in, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Chester, MD.
  • What are the closest schools to Harbor Dr?
    The closest schools to Harbor Dr in Chester, MD are Bayside Elementary School (rated 8/10), Kent Island Elementary School (Pre-K), Kent Island High School (rated 6/10).

Explore by feature - Air Conditioning

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