209 Winterview Dr, Chester, MD 21619
Property image
Property image
OFF MARKET

$551,500

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,100 sqft (on 0.61 acres)

209 Winterview Dr, Chester, MD 21619

Est. Refi. Payment $3,276/mo*
Refinance Your Home
Currently Off Market - Sold Jun 28, 2017 for $372,000

Home Value

Trulia Estimate
$552K
Since last month
Increased$3K (+0.5%)
Since last year
Decreased$5K (-1%)
Since last sale
Increased$180K (+48.3%)
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 +72% in the last 10 years
MonthEstimated value
2026
August 2026$552K
July 2026$549K
June 2026$558K
May 2026$558K
April 2026$556K
March 2026$549K
February 2026$541K
January 2026$546K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
203 Barren Ridge Rd, Chester, MD
0.03
Single-Family Home
$475,000
09/29/25
3
1.5
2,072
2613 Cecil Dr, Chester, MD
0.34
Single-Family Home
$900,000
08/14/26
5
2.5
2,496
1773 Harbor Dr, Chester, MD
0.57
Single-Family Home
$610,000
08/29/25
3
2.5
2,142
104 Woods Rd, Chester, MD
0.51
Single-Family Home
$795,000
12/10/25
5
3.5
3,065
1803 Chester Dr, Chester, MD
0.48
Single-Family Home
$385,000
05/09/26
4
2
1,636
1771 Harbor Dr, Chester, MD
0.56
Single-Family Home
$735,000
09/05/25
5
2.5
2,564
123 Bentons Pleasure Rd, Chester, MD
0.50
Single-Family Home
$740,000
01/09/26
4
2.5
2,791
1905-1907 Keister Dr, Chester, MD
0.26
Single-Family Home
$205,000
12/26/25
3
1
1,600
1903 Churchhill Ln, Chester, MD
0.72
Single-Family Home
$405,000
11/14/25
4
3
1,682
1221 Cox Neck Rd, Chester, MD
0.47
Single-Family Home
$500,000
02/02/26
4
2.5
1,482

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
203 Barren Ridge Rd, Chester, MD 21619
0.03
$494,200
3
1.5
2,072
Off Market
105 Barren Ridge Rd, Chester, MD 21619
0.06
-
4
4.5
3,016
Off Market
300 Skyler Ave, Chester, MD 21619
0.12
$532,700
3
2.5
2,250
Off Market
126 Watermans Cove Ln, Chester, MD 21619
0.12
$559,000
3
3
1,536
For Sale
104 Barren Ridge Rd, Chester, MD 21619
0.10
$459,900
4
2
2,055
Off Market
1905 Roberta Dr, Chester, MD 21619
0.19
$606,700
3
2.5
2,100
Off Market
1106 Cox Neck Rd, Chester, MD 21619
0.23
-
3
3
2,646
Off Market
2513 Cecil Dr, Chester, MD 21619
0.21
$1,290,000
5
2
2,700
For Sale
110 Hopkins Rd, Chester, MD 21619
0.29
$802,800
4
2.5
2,600
Off Market
1905-1907 Keister Dr, Chester, MD 21619
0.26
$205,000
3
1
1,600
Recently Sold
2608 Cecil Dr, Chester, MD 21619
0.26
$694,700
3
2.5
2,336
Off Market
Thompson Creek Rd, Stevensville, MD 21666
0.31
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 209 Winterview Dr.
  • 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
0.61 acres
Living Area
2,100 sqft
Price/Sqft
$263
Parking
Garage

About this House

This single-family home is located at 209 Winterview Dr, Chester, MD. 209 Winterview Dr is in Chester, MD and in ZIP code 21619. This property has 4 bedrooms, 4 bathrooms and approximately 2,100 sqft of floor space. This property has a lot size of 0.61 acres and was built in 1992.
209 Winterview Dr, Chester, MD 21619 is a 4 bedroom, 4 bathroom, 2,100 sqft single-family home built in 1992. It last sold for $372,000 on Jun 28, 2017. More recently, it was listed as a rental in June 2024 with an asking price of $3,500 per month. That rental listing was removed on July 9, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $551,500, with a rent estimate of $3,349/month.

Home Details for 209 Winterview Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Types of Rooms: Dining Room, Family Room, Master Bath
Appliances & Utilities
DishwasherDryerWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: VinylLawn
Parking & Garage
GarageParking: Off Street, Garage

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: 0.61 acres

Price and Tax history

DateEventPrice
Jul 9, 2024
Source: Zillow Rentals
ListingRemoved
Jun 30, 2024
Source: Zillow Rentals
Listed For Rent
$3,500
Jul 24, 2023
Source: Zillow Rentals
ListingRemoved
Jul 11, 2023
Source: Zillow Rentals
Listed For Rent
$3,500
Jun 28, 2017
Source: N/A
Sold
$372,000

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 209 Winterview Dr

  • What is 209 Winterview Dr estimated to be worth?
    Trulia's estimated value for 209 Winterview Dr in Chester, MD is $551,500.
  • What is the price history for 209 Winterview Dr?
    209 Winterview Dr in Chester, MD last sold for $372,000 in June 2017.
  • 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.
  • Does 209 Winterview Dr have laundry facilities?
    Yes, 209 Winterview Dr in Chester, MD has in-unit laundry.
  • How big is the lot at 209 Winterview Dr?
    The lot at 209 Winterview Dr in Chester, MD is about 0.61 acres (26,789 sq ft).

Explore by feature - Pet Friendly

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