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

1925 Anchorage Dr
Chester, MD 21619

4 Beds
2 Baths
1,800 sqft (on 0.31 acres)

$451,700

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $2,658/mo*

Refinance Your Home

$451,700

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $2,658/mo*

Refinance Your Home

4 Beds

2 Baths

1,800 sqft

(on 0.31 acres)

Local Information

-- mins to

Commute Destination

Description

TOTAL TRANSFORMATION THROUGH-OUT. HOME OFFERS 4 B.R. & 2 FULL BATHS. HARDWOOD FLOORS THROUGH-OUT MAIN , CUSTOM MOLDING, TILE BATHS ,FRESHLY PAINTED & NEW CARPET IN B.R..KITCHEN HAS GRANITE COUNTERS, 42 IN CABINETS & S/S APPLIANCES , ALL CONVEY. ENJOY THE OUTSIDE ON HUGE SCREENED IN REAR DECK & PRIVATE SIDE DECK. UPPER LEVEL MASTER B.R. HAS PRIVATE BALCONY .SUPER BATH W/ SEP. SOAKING TUB & SHOWER.

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 1925 Anchorage Dr

Interior Features
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: Central, OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2
Interior Details Types of Rooms: Dining Room, Sun Room
Appliances & Utilities DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Vinyl

Property Information
Year Built Year Built: 1991
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.31 acres

Price History for 1925 Anchorage Dr

Date	Price	Event	Source
11/20/2013	$292,000	Sold	N/A
Recording Date 11/20/2013 Contract Date 10/25/2013 County Transfer Tax $1,460 Total Transfer Tax $2,190
10/05/2013	$299,890	Pending	Agent Provided

09/20/2013	$299,890	PriceChange	Agent Provided
Price Change $10 (-0%)
09/05/2013	$299,900	Listed For Sale	Agent Provided

05/23/2013	$175,000	Sold	N/A
Recording Date 05/23/2013 Contract Date 05/06/2013 County Transfer Tax $875 Total Transfer Tax $1,750
02/23/2013	$229,500	PriceChange	Agent Provided
Price Change $25,500 (-10%)
01/08/2013	$255,000	Listed For Sale	Agent Provided

12/05/2012	$366,000	Sold	N/A
Recording Date 12/05/2012 Contract Date 09/25/2012 County Transfer Tax $1,830 Total Transfer Tax $3,660
12/20/2005	$298,000	Sold	N/A
Recording Date 12/20/2005 County Transfer Tax N/A Total Transfer Tax N/A
09/25/2001	$148,000	Sold	N/A
Recording Date 09/25/2001 County Transfer Tax N/A Total Transfer Tax N/A
07/15/1997	$121,000	Sold	N/A
Recording Date 07/15/1997 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$3,338
Assessment	$354,367

Home facts updated by county records

Comparable Sales for 1925 Anchorage Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1906 Harbor Dr, Chester, MD	0.17	Single-Family Home	$295,000	09/26/25	4	2	1,750
2747 Cecil Dr, Chester, MD	0.05	Single-Family Home	$350,000	06/13/25	3	2	1,560
1903 Churchhill Ln, Chester, MD	0.22	Single-Family Home	$405,000	11/14/25	4	3	1,682
1839 Harbor Dr, Chester, MD	0.40	Single-Family Home	$350,000	02/06/26	4	2	2,035
2723 Cox Neck Rd, Chester, MD	0.18	Single-Family Home	$447,500	10/17/25	4	2.5	1,600
2653 Cox Neck Rd, Chester, MD	0.31	Single-Family Home	$374,000	01/02/26	3	2	1,560
1921 Harbor Dr, Chester, MD	0.10	Single-Family Home	$519,900	05/21/26	3	2.5	2,000
2707 Cox Neck Rd, Chester, MD	0.23	Single-Family Home	$435,000	08/04/25	3	2.5	1,568
1803 Chester Dr, Chester, MD	0.55	Single-Family Home	$385,000	05/09/26	4	2	1,636
2614 Ellicott Dr, Chester, MD	0.36	Single-Family Home	$495,000	07/31/25	3	2	1,400

Nearby homes

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

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OFF MARKET
Est. $434,000
4 bd
2 ba
1,560 sqft
1926 Sherman Dr,
Chester, MD 21619
Rosendale Realty
OFF MARKET
Est. $361,700
3 bd
2 ba
1,560 sqft
2747 Cecil Dr,
Chester, MD 21619
Anne Arundel Properties, Inc.
SOLD
MAY 21, 2026
$519,900
3 bd
2.5 ba
2,000 sqft
1921 Harbor Dr,
Chester, MD 21619
Coldwell Banker Waterman Realty
FOR SALE
0.28 ACRES
$464,900
4 bd
2 ba
1,750 sqft
1906 Harbor Dr,
Chester, MD 21619
Five Star Real Estate
OFF MARKET
16 & 17 Cecil Dr,
Chester, MD 21619
Berkshire Hathaway Homeservice Homesale Realty
SOLD
OCT 17, 2025
$447,500
4 bd
2.5 ba
1,600 sqft
2723 Cox Neck Rd,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Cox Neck Rd,
Chester, MD 21619
Berkshire Hathaway Homeservice Homesale Realty
OFF MARKET
Est. $434,400
3 bd
2.5 ba
1,297 sqft
2719 Cox Neck Rd,
Chester, MD 21619
Compass
OFF MARKET
Est. $435,800
3 bd
2 ba
1,160 sqft
1907 Churchhill Ln,
Chester, MD 21619
Keller Williams Flagship
SOLD
NOV 14, 2025
$405,000
4 bd
3 ba
1,682 sqft
1903 Churchhill Ln,
Chester, MD 21619
Alberti Realty, LLC
OFF MARKET
Est. $447,200
4 bd
2.5 ba
2,286 sqft
2709 Cox Neck Rd,
Chester, MD 21619
Keller Williams Realty Centre
SOLD
MAR 23, 2026
$310,000
2 bd
1 ba
832 sqft
1870 Harbor Dr,
Chester, MD 21619
RE/MAX Executive

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Additional Cost

Assigned Schools

These are the assigned schools for 1925 Anchorage 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
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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 1925 Anchorage 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
$480,000
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
$665,000
4 bd
2.5 ba
2,564 sqft
303 Creeks End Ln,
Stevensville, MD 21666
Paul Wesley Real Estate
$650,000
4 bd
2.5 ba
2,570 sqft
479 Creeks End Ln,
Stevensville, MD 21666
EXP Realty, LLC
FORECLOSURE
$240,000
3 bd
2 ba
1,160 sqft
108 Price Rd,
Chester, MD 21619
Thurston Wyatt Real Estate, LLC
0.43 ACRES
$725,000
5 bd
3.5 ba
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
$579,000
3 bd
3 ba
1,536 sqft
126 Watermans Cove Ln,
Chester, MD 21619
Coldwell Banker Realty
0.36 ACRES
$519,500
4 bd
2.5 ba
1,704 sqft
606 Kimberly Way,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
See more homes for sale in
Chester
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Off Market Homes Near 1925 Anchorage 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
$559,900
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2223,
Chester, MD 21619
KOVO 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
SOLD
MAY 18, 2026
$514,990
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2222,
Chester, MD 21619
KOVO Realty
SOLD
MAY 15, 2026
$452,000
4 bd
2.5 ba
1,900 sqft
128 John Patrick Dr,
Stevensville, MD 21666
Samson Properties
See more homes for sale in
Chester
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Homes for rent near 1925 Anchorage 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
$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
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
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1925 Anchorage Dr, Chester, MD 21619 is a 4 bedroom, 2 bathroom, 1,800 sqft single-family home built in 1991. This property is not currently available for sale. 1925 Anchorage Dr was last sold on Nov 20, 2013 for $292,000. The current Trulia Estimate for 1925 Anchorage Dr is $451,700.

1925 Anchorage Dr
Chester, MD 21619

$451,700

$451,700

Local Information