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

1908 Harbor Dr
Chester, MD 21619

3 Beds
1.5 Baths
1,066 sqft (on 0.28 acres)

$370,800

Trulia Estimate

as of May 18, 2026

Est. Refi. Payment $2,050/mo*

Refinance Your Home

$370,800

Trulia Estimate

as of May 18, 2026

Est. Refi. Payment $2,050/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,066 sqft

(on 0.28 acres)

Local Information

-- mins to

Commute Destination

Description

AVAILABLE AGAIN! Contract fell through. Welcome home to this adorable single family home in Harborview Community of Kent Island! Beautiful low maintenance engineered wood floors throughout. Open floor plan with sliding glass doors leading to large Trex deck and a fully fenced yard. Talk about wow factor...this large yard is perfect for entertaining or letting your pups run! Many upgrades inside and out...new 30 year 3 tab architectual shingle roof, new AC unit (2016), upgraded updated kitchen with brand new built in microwave, new well pump, new siding (2018)
3rd bedroom has been opened up as a spacious dressing suite--ideal as it is or quick and easy conversion back to a 3rd bedroom! Open living room with ceiling mounted projector is perfect for cozy movie nights! New privacy fence being installed this week!! Harborview is just two miles east of the Chesapeake bay Bridge- an easy commute to Annapolis or DC. Located just minutes away from the Cross Island Trail and all the Island has to offer! One acre field with pavilion and playground -Community events including Easter egg hunt and community picnic make this sought after community ideal!

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 1908 Harbor Dr

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Vinyl
Parking & Garage Parking Spaces: 4

Property Information
Year Built Year Built: 1955
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.28 acres

Price History for 1908 Harbor Dr

Date	Price	Event	Source
09/21/2022	$327,000	Sold	Bright MLS #MDQA2004276
Recording Date 09/21/2022 County Transfer Tax N/A Total Transfer Tax N/A
08/25/2022	$317,000	Contingent	Bright MLS #MDQA2004276

08/17/2022	$317,000	Listed For Sale	Bright MLS #MDQA2004276

08/08/2022		ListingRemoved	Bright MLS #MDQA2004276

08/02/2022	$317,000	Contingent	Bright MLS #MDQA2004276

07/28/2022	$317,000	PriceChange	Bright MLS #MDQA2004276
Price Change $7,000 (-2%)
07/20/2022	$324,000	Listed For Sale	Bright MLS #MDQA2004276

07/18/2022		ListingRemoved	Long & Foster Broker Feed

06/23/2022	$329,000	Pending	Bright MLS #MDQA2003492

06/07/2022	$329,000	PendingToActive	Bright MLS #MDQA2003492

05/30/2022	$329,000	Contingent	Bright MLS #MDQA2003492

05/25/2022	$329,000	PriceChange	Bright MLS #MDQA2003492
Price Change $10,000 (-3%)
05/17/2022	$339,000	Listed For Sale	Bright MLS #MDQA2003492

05/04/2022		ListingRemoved	N/A

03/17/2022	$340,000	Listed For Sale	N/A

02/26/2021	$315,000	ListingRemoved	Long & Foster Broker Feed #MDQA146226

12/20/2020	$315,000	Listed For Sale	Agent Provided

04/22/2019	$275,000	Sold	N/A
Recording Date 04/22/2019 Contract Date 04/17/2019 County Transfer Tax $7 Total Transfer Tax $14
07/16/2009	$215,000	Sold	N/A
Recording Date 07/16/2009 Contract Date 07/14/2009 County Transfer Tax N/A Total Transfer Tax N/A
12/07/2006	$290,000	Sold	N/A
Recording Date 12/07/2006 County Transfer Tax N/A Total Transfer Tax N/A
05/09/2006	$225,000	Sold	N/A
Recording Date 05/09/2006 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$2,745
Assessment	$291,433

Home facts updated by county records

Comparable Sales for 1908 Harbor Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1906 Harbor Dr, Chester, MD	0.01	Single-Family Home	$295,000	09/26/25	4	2	1,750
1870 Harbor Dr, Chester, MD	0.09	Single-Family Home	$310,000	03/23/26	2	1	832
2747 Cecil Dr, Chester, MD	0.22	Single-Family Home	$350,000	06/13/25	3	2	1,560
2644 Cecil Dr, Chester, MD	0.28	Single-Family Home	$382,000	03/20/26	3	2	1,108
2653 Cox Neck Rd, Chester, MD	0.22	Single-Family Home	$374,000	01/02/26	3	2	1,560
2614 Ellicott Dr, Chester, MD	0.19	Single-Family Home	$495,000	07/31/25	3	2	1,400
1903 Churchhill Ln, Chester, MD	0.05	Single-Family Home	$405,000	11/14/25	4	3	1,682
1921 Harbor Dr, Chester, MD	0.09	Single-Family Home	$512,175	04/16/26	3	2.5	2,000
2707 Cox Neck Rd, Chester, MD	0.19	Single-Family Home	$435,000	08/04/25	3	2.5	1,568
1839 Harbor Dr, Chester, MD	0.29	Single-Family Home	$350,000	02/06/26	4	2	2,035

Assigned Schools

These are the assigned schools for 1908 Harbor 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

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
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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
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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
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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
APPLY INSTANTLY
PET FRIENDLY
$2,700/mo
3 bd
2.5 ba
29 Queen Mary Ct #29D,
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
$3,750/mo
3 bd
2.5 ba
312 Topside Dr #223,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,200/mo
2 bd
1 ba
480 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$1,850/mo
1 bd
1 ba
460 Main St #1000-A,
Stevensville, MD 21666
APPLY INSTANTLY
$2,200/mo
3 bd
2 ba
1508 Marion Quimby Dr #8,
Stevensville, MD 21666
APPLY INSTANTLY
FURNISHED
$3,800/mo
4 bd
3.5 ba
103 Swan Cove Ln #103,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
1 ba
440 Main St #1000-B,
Stevensville, MD 21666
See more homes for rent in
Chester
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Homes for sale near 1908 Harbor Dr

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0.28 ACRES
$464,900
4 bd
2 ba
1,750 sqft
1906 Harbor Dr,
Chester, MD 21619
Five Star Real Estate
0.27 ACRES
$495,000
3 bd
2 ba
1,804 sqft
1848 Harbor Dr,
Chester, MD 21619
EXP Realty, LLC
0.35 ACRES
$464,000
3 bd
2 ba
2,016 sqft
1906 Stevens Dr,
Chester, MD 21619
RE/MAX Executive
0.35 ACRES
$475,000
3 bd
2.5 ba
1,728 sqft
1916 Stevens Dr,
Chester, MD 21619
Coldwell Banker Realty
0.35 ACRES
$1,495,000
3 bd
4 ba
4,208 sqft
1719 Harbor Dr,
Chester, MD 21619
Chesapeake Real Estate Associates, LLC
NEW - 5 HRS AGO
FORECLOSURE
$240,000
3 bd
2 ba
1,160 sqft
108 Price Rd,
Chester, MD 21619
Thurston Wyatt Real Estate, LLC
$579,000
3 bd
3 ba
1,536 sqft
126 Watermans Cove Ln,
Chester, MD 21619
Coldwell Banker Realty
$665,000
4 bd
2.5 ba
2,564 sqft
303 Creeks End Ln,
Stevensville, MD 21666
Paul Wesley Real Estate
0.28 ACRES
$445,000
3 bd
2.5 ba
1,296 sqft
200 Newtown Rd,
Chester, MD 21619
Samson Properties
0.61 ACRES
$315,000
3 bd
1 ba
1,119 sqft
126 State St,
Stevensville, MD 21666
Benson & Mangold, LLC
See more homes for sale in
Chester
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Additional Cost

Homes for rent near 1908 Harbor Dr

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APPLY INSTANTLY
$1,650/mo
1 bd
1 ba
700 sqft
1910 Churchhill Ln,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,700/mo
3 bd
2.5 ba
1,680 sqft
29 Queen Mary Ct #29D,
Chester, MD 21619
APPLY INSTANTLY
$2,800/mo
3 bd
3 ba
1,450 sqft
932 Kimberly Way,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,950/mo
4 bd
2.5 ba
1,852 sqft
2605 Harrington Rd,
Chester, MD 21619
$2,600/mo
3 bd
2.5 ba
1,747 sqft
400 Schooner Way #37,
Chester, MD 21619
See more homes for rent in
Chester
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Off Market Homes Near 1908 Harbor Dr

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SOLD
MAY 15, 2026
$452,000
4 bd
2.5 ba
1,900 sqft
128 John Patrick Dr,
Stevensville, MD 21666
Samson Properties
SOLD
MAY 15, 2026
$499,990
2 bd
2.5 ba
2,003 sqft
630 Warbler Way #2212,
Chester, MD 21619
KOVO Realty
SOLD
MAY 14, 2026
$524,900
2 bd
2.5 ba
2,003 sqft
630 Warbler Way #2211,
Chester, MD 21619
KOVO Realty
SOLD
MAY 14, 2026
$445,000
2 bd
2 ba
1,104 sqft
23 Queen Victoria Way,
Chester, MD 21619
RE/MAX Executive
SOLD
MAY 12, 2026
$390,000
3 bd
1 ba
1,056 sqft
320 McKay Rd,
Stevensville, MD 21666
Samson Properties
SOLD
MAY 9, 2026
$385,000
4 bd
2 ba
1,636 sqft
1803 Chester Dr,
Chester, MD 21619
Keller Williams Legacy
SOLD
MAY 8, 2026
$501,200
3 bd
2 ba
1,400 sqft
1363 Calvert Rd,
Chester, MD 21619
Revol Real Estate, LLC
SOLD
MAY 6, 2026
$405,000
2 bd
2 ba
1,380 sqft
27F Queen Mary Ct,
Chester, MD 21619
SOLD
MAY 5, 2026
$300,000
2 bd
2 ba
1,120 sqft
102 Bobbitt Ct,
Stevensville, MD 21666
Keller Williams Legacy
SOLD
MAY 5, 2026
$335,000
2 bd
2.5 ba
1,747 sqft
206 Ringneck Ct,
Chester, MD 21619
See more homes for sale in
Chester
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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
PET FRIENDLY
$2,700/mo
3 bd
2.5 ba
1,680 sqft
29 Queen Mary Ct #29D,
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
$2,600/mo
3 bd
2.5 ba
1,747 sqft
400 Schooner Way #37,
Chester, MD 21619
PET FRIENDLY
$1,950/mo
2 bd
1.5 ba
1,200 sqft
2201 Main St #105,
Chester, MD 21619
8 rentals with air conditioning in Chester, MD

1908 Harbor Dr, Chester, MD 21619 is a 3 bedroom, 2 bathroom, 1,066 sqft single-family home built in 1955. This property is not currently available for sale. 1908 Harbor Dr was last sold on Sep 21, 2022 for $327,000. The current Trulia Estimate for 1908 Harbor Dr is $370,800.

1908 Harbor Dr
Chester, MD 21619

$370,800

$370,800

Local Information