Is parking easy in Chester, MD?

As of early 2026, 88% of users say parking is easy

Is a car needed in Chester, MD?

As of early 2026, 88% of users say car is needed

Would people walk alone at night in Chester, MD?

As of early 2026, 86% of users say people would walk alone at night

Is Chester, MD dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Is Chester, MD quiet?

As of early 2026, 83% of users say it's quiet

Does Chester, MD show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

Are neighbors friendly in Chester, MD?

As of early 2026, 64% of users say neighbors are friendly

Is there wildlife in Chester, MD?

As of early 2026, 64% of users say there's wildlife

Do kids play outside in Chester, MD?

As of early 2026, 64% of users say kids play outside

Are yards well-kept in Chester, MD?

As of early 2026, 57% of users say yards are well-kept

Does Chester, MD have sidewalks?

As of early 2026, 53% of users say there are sidewalks

Do residents of Chester, MD plan to stay at least 5 years?

As of early 2026, 48% of users say they plan to stay for at least 5 years

Are there community events in Chester, MD?

As of early 2026, 48% of users say there are community events

Are the streets well-lit in Chester, MD?

As of early 2026, 44% of users say streets are well-lit

Is Chester, MD walkable to restaurants?

As of early 2026, 41% of users say it's walkable to restaurants

Is Chester, MD walkable to grocery stores?

As of early 2026, 17% of users say it's walkable to grocery stores

OFF MARKET

216 Winterview Dr
Chester, MD 21619

3 Beds
2.5 Baths
1,844 sqft (on 0.60 acres)

$489,100

Trulia Estimate

as of May 31, 2026

Est. Refi. Payment $2,893/mo*

Refinance Your Home

$489,100

Trulia Estimate

as of May 31, 2026

Est. Refi. Payment $2,893/mo*

Refinance Your Home

3 Beds

2.5 Baths

1,844 sqft

(on 0.60 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 216 Winterview Dr, Chester, MD. 216 Winterview Dr is in Chester, MD and in ZIP code 21619. This property has 3 bedrooms, 3 bathrooms and approximately 1,844 sqft of floor space. This property has a lot size of 0.60 acres and was built in 1992.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 216 Winterview Dr

Interior Features
Heating & Cooling Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet
Interior Details Types of Rooms: Family Room
Appliances & Utilities DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Vinyl

Property Information
Year Built Year Built: 1992
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Building
Levels, Entrance, & Accessibility Disabled Access

Community
Units in Building: 1

Lot Information
Lot Area: 0.60 acres

Price History for 216 Winterview Dr

Date	Price	Event	Source
12/19/2019	$315,000	Sold	N/A
Recording Date 12/19/2019 Contract Date 12/12/2019 County Transfer Tax $16 Total Transfer Tax $32
11/07/2019	$319,900	Pending	Agent Provided

09/01/2019	$319,900	PriceChange	Agent Provided
Price Change $9,100 (-3%)
07/10/2019	$329,000	PriceChange	Agent Provided
Price Change $6,000 (-2%)
06/12/2019	$335,000	Listed For Sale	Agent Provided

06/23/2016	$339,900	ListingRemoved	Agent Provided

02/23/2016	$339,900	PriceChange	Agent Provided
Price Change $20,100 (-6%)
08/04/2015	$360,000	Listed For Sale	Agent Provided

11/02/1999	$175,926	Sold	N/A
Recording Date 11/02/1999 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$3,324
Assessment	$352,867

Home facts updated by county records

Comparable Sales for 216 Winterview Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
300 Skyler Ave, Chester, MD	0.14	Single-Family Home	$507,500	06/26/25	3	2.5	2,250
203 Barren Ridge Rd, Chester, MD	0.04	Single-Family Home	$475,000	09/29/25	3	1.5	2,072
1905-1907 Keister Dr, Chester, MD	0.23	Single-Family Home	$205,000	12/26/25	3	1	1,600
110 Hopkins Rd, Chester, MD	0.31	Single-Family Home	$764,419	06/20/25	4	2.5	2,600
1809 Stevens Dr, Chester, MD	0.58	Single-Family Home	$445,000	08/14/25	4	2.5	1,896
1773 Harbor Dr, Chester, MD	0.57	Single-Family Home	$610,000	08/29/25	3	2.5	2,142
1803 Chester Dr, Chester, MD	0.47	Single-Family Home	$385,000	05/09/26	4	2	1,636
2644 Cecil Dr, Chester, MD	0.50	Single-Family Home	$382,000	03/20/26	3	2	1,108
2653 Cox Neck Rd, Chester, MD	0.65	Single-Family Home	$374,000	01/02/26	3	2	1,560
102 Barren Ridge Rd, Chester, MD	0.08	Single-Family Home	$325,000	04/01/26		2	1,654

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $680,400
4 bd
4.5 ba
3,016 sqft
105 Barren Ridge Rd,
Chester, MD 21619
Coldwell Banker Waterman Realty
SOLD
SEP 29, 2025
$475,000
3 bd
1.5 ba
2,072 sqft
203 Barren Ridge Rd,
Chester, MD 21619
Keller Williams Gateway LLC
OFF MARKET
Est. $468,000
4 bd
2 ba
2,055 sqft
104 Barren Ridge Rd,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $523,800
3 bd
2.5 ba
2,250 sqft
300 Skyler Ave,
Chester, MD 21619
RE/MAX Realty Services
FOR SALE
$579,000
3 bd
3 ba
1,536 sqft
126 Watermans Cove Ln,
Chester, MD 21619
Coldwell Banker Realty
FOR SALE
0.43 ACRES
$725,000
5 bd
3.5 ba
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
OFF MARKET
Est. $613,200
3 bd
2.5 ba
2,100 sqft
1905 Roberta Dr,
Chester, MD 21619
Clark & Co Realty, LLC
OFF MARKET
Est. $526,700
4 bd
3 ba
2,560 sqft
1903 Roberta Dr,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $573,500
3 bd
3 ba
2,646 sqft
1106 Cox Neck Rd,
Chester, MD 21619
Rosendale Realty
SOLD
DEC 26, 2025
$205,000
3 bd
1 ba
1,600 sqft
1905-1907 Keister Dr,
Chester, MD 21619
VYBE Realty
OFF MARKET
Est. $702,000
3 bd
2.5 ba
2,336 sqft
2608 Cecil Dr,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $493,700
4 bd
2 ba
2,000 sqft
1911 Keister Dr,
Chester, MD 21619
Coldwell Banker Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 216 Winterview Dr.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
64 % Say neighbors are friendly
64 % Say there's wildlife
64 % Say kids play outside
57 % Say yards are well-kept
53 % Say there are sidewalks
48 % 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
Resident
2y ago
"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
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Colinjgallagher525
Resident
2y ago
"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
Resident
2y ago
"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
Resident
2y ago
"Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
0
Flag
Peggy.young
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"Not very many families, but within a great school district. Good community for people who don’t really have children. "
0
Flag
J0J0s4X4
Resident
7y ago
"it is a child friendly development and very safe. also, most homeowners have video security systems."
0
Flag
Peggy y.
Resident
8y ago
"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.
11y ago
"I live in this area. Great place to raise a family. Access to beaches, parks, cross island trail."
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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APPLY INSTANTLY
PET FRIENDLY
$1,850 - $2,995/mo
Total price
Studio-2 bd
1-2 ba
Bay Manor Shops and Apartments | 214 Pier 1 Rd #225,
Stevensville, MD 21666
PET FRIENDLY
INCOME RESTRICTED
$1,083/mo
1 bd
1 ba
101 Ellicott Dr #1B-1Ba-552Sqft,
Chester, MD 21619
PET FRIENDLY
INCOME RESTRICTED
$1,091/mo
2 bd
1 ba
39 Sherman Way #a656b564b,
Chester, MD 21619
PET FRIENDLY
$3,450/mo
3 bd
3 ba
906 Moorings Cir #9,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,700/mo
3 bd
1 ba
440 Main St #1000-C,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$1,700/mo
1 bd
1 ba
440 Main St #1000-A,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,200/mo
2 bd
1 ba
480 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
FURNISHED
$3,800/mo
4 bd
3.5 ba
103 Swan Cove Ln #103,
Chester, MD 21619
NEW - 1 DAY AGO
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
1 ba
460 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
$2,200/mo
3 bd
2 ba
1508 Marion Quimby Dr #8,
Stevensville, MD 21666
See more homes for rent in
Chester
Take a look

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Explore by feature

PET FRIENDLY
INCOME RESTRICTED
$1,083/mo
1 bd
1 ba
101 Ellicott Dr #1B-1Ba-552Sqft,
Chester, MD 21619
PET FRIENDLY
INCOME RESTRICTED
$1,091/mo
2 bd
1 ba
39 Sherman Way #a656b564b,
Chester, MD 21619
APPLY INSTANTLY
$1,650/mo
1 bd
1 ba
700 sqft
1910 Churchhill Ln,
Chester, MD 21619
APPLY INSTANTLY
FURNISHED
$3,800/mo
4 bd
3.5 ba
3,000 sqft
103 Swan Cove Ln #103,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,950/mo
4 bd
2.5 ba
1,852 sqft
2605 Harrington Rd,
Chester, MD 21619
PET FRIENDLY
$1,950/mo
2 bd
1.5 ba
1,200 sqft
2201 Main St #105,
Chester, MD 21619
6 rentals with air conditioning in Chester, MD

Homes for sale near 216 Winterview Dr

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$579,000
3 bd
3 ba
1,536 sqft
126 Watermans Cove Ln,
Chester, MD 21619
Coldwell Banker Realty
0.43 ACRES
$725,000
5 bd
3.5 ba
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
0.35 ACRES
$464,000
3 bd
2 ba
2,016 sqft
1906 Stevens Dr,
Chester, MD 21619
RE/MAX Executive
0.27 ACRES
$480,000
3 bd
2 ba
1,804 sqft
1848 Harbor Dr,
Chester, MD 21619
EXP Realty, LLC
0.28 ACRES
$464,900
4 bd
2 ba
1,750 sqft
1906 Harbor Dr,
Chester, MD 21619
Five Star Real Estate
0.28 ACRES
$430,000
3 bd
2.5 ba
1,296 sqft
200 Newtown Rd,
Chester, MD 21619
Samson Properties
$650,000
4 bd
2.5 ba
2,570 sqft
479 Creeks End Ln,
Stevensville, MD 21666
EXP Realty, LLC
$665,000
4 bd
2.5 ba
2,564 sqft
303 Creeks End Ln,
Stevensville, MD 21666
Paul Wesley Real Estate
FORECLOSURE
$240,000
3 bd
2 ba
1,160 sqft
108 Price Rd,
Chester, MD 21619
Thurston Wyatt Real Estate, LLC
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 216 Winterview Dr

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SOLD
MAY 29, 2026
$599,900
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2233,
Chester, MD 21619
KOVO Realty
SOLD
MAY 28, 2026
$612,500
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2232,
Chester, MD 21619
KOVO Realty
SOLD
MAY 27, 2026
$714,280
5 bd
2.5 ba
3,864 sqft
1000 Chesapeake Dr,
Stevensville, MD 21666
Coldwell Banker Realty
SOLD
MAY 27, 2026
$559,900
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2223,
Chester, MD 21619
KOVO Realty
SOLD
MAY 26, 2026
$550,000
3 bd
2.5 ba
1,804 sqft
64 Long Creek Dr,
Stevensville, MD 21666
Coldwell Banker Realty
SOLD
MAY 22, 2026
$417,500
3 bd
2 ba
1,312 sqft
635 Davol Rd,
Stevensville, MD 21666
Blackwell Real Estate, LLC
SOLD
MAY 21, 2026
$470,000
4 bd
3 ba
2,640 sqft
620 Old Love Point Rd,
Stevensville, MD 21666
Berkshire Hathaway HomeServices PenFed Realty
SOLD
MAY 21, 2026
$519,900
3 bd
2.5 ba
2,000 sqft
1921 Harbor Dr,
Chester, MD 21619
Coldwell Banker Waterman Realty
SOLD
MAY 21, 2026
$255,000
2 bd
1.5 ba
968 sqft
7 Mariners Way #2,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
SOLD
MAY 20, 2026
$557,620
4 bd
2 ba
1,907 sqft
716 Cloverfields Dr,
Stevensville, MD 21666
Rosendale Realty
See more homes for sale in
Chester
Take a look

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Homes for rent near 216 Winterview Dr

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APPLY INSTANTLY
$1,650/mo
1 bd
1 ba
700 sqft
1910 Churchhill Ln,
Chester, MD 21619
APPLY INSTANTLY
FURNISHED
$2,950/mo
3 bd
2 ba
2,073 sqft
410 Main St,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,950/mo
4 bd
2.5 ba
1,852 sqft
2605 Harrington Rd,
Chester, MD 21619
APPLY INSTANTLY
$2,250/mo
3 bd
2 ba
1,440 sqft
1101 Romancoke Rd,
Stevensville, MD 21666
$6,000/mo
3 bd
4 ba
3,062 sqft
1006 Bayside Dr,
Stevensville, MD 21666
PET FRIENDLY
$2,550/mo
2 bd
2.5 ba
1,232 sqft
341 Creekside Commons Ct,
Stevensville, MD 21666
See more homes for rent in
Chester
Take a look

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216 Winterview Dr, Chester, MD 21619 is a 3 bedroom, 3 bathroom, 1,844 sqft single-family home built in 1992. This property is not currently available for sale. 216 Winterview Dr was last sold on Dec 19, 2019 for $315,000. The current Trulia Estimate for 216 Winterview Dr is $489,100.

216 Winterview Dr
Chester, MD 21619

$489,100

$489,100

Local Information