108 Pine St, Chestertown, MD 21620
SOLD
JUN 30, 2026

108 Pine St
Chestertown, MD 21620

  • 3 Beds
  • 1 Bath
  • 910 sqft

$85,000

Last Sold: Jun 30, 2026
26% below list $115K
$93/sqft
Est. Refi. Payment $554/mo*
Refinance Your Home

$85,000

Last Sold: Jun 30, 2026
26% below list $115K
$93/sqft
Est. Refi. Payment $554/mo*
Refinance Your Home
3 Beds
1 Bath
910 sqft

Local Information

  • Map ViewExplore the area around 108 Pine St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+, comparable renovated properties in this location are selling for $275K-$300K, creating potential equity of $80K-$125K for buyers with vision and capability. Close proximity to Washington College creates built-in rental demand from students, faculty, and staff. Plus easy access to Downtown Chestertown shops, restaurants, and waterfront parks are minutes away on foot. Starbucks and grocery stores are easily accessible. This is a prime location renovation opportunity where comparable updated homes command premium pricing. The renovation reality. This property requires full renovation and is priced accordingly. Systems, finishes, and layout will need comprehensive updating. Estimated investment ranges from $60,000 to $80,000+ depending on finish level and scope decisions. This is a project for experienced investors, renovation contractors, or buyers with construction capability who understand forced appreciation through strategic improvements. The opportunity math works. Purchase at $115,000. Invest $60K-$80K in renovations. All-in cost: $175K-$195K. Recent comparable sales for fully renovated 3-bedroom homes in walkable Chestertown locations are selling in the $275K-$300K range. Your potential equity position: $80,000 to $125,000 upon completion. Multiple exit strategies. Flip after renovation for immediate profit. Hold as rental property serving Washington College market with strong rental history in the area. Owner-occupy and build instant equity while creating your ideal home. The location flexibility supports whatever investment strategy fits your goals. Property sold AS-IS. Serious buyers should conduct thorough inspections and due diligence. This is a renovation project, not a cosmetic update - price reflects condition and opportunity. Act quickly on clear value plays. Properties offering this equity spread in prime walkable locations move fast when priced correctly.
108 Pine St, Chestertown, MD 21620 is a 3 bedroom, 1 bathroom, 910 sqft single-family home built in 1957. It last sold for $85,000 on Jun 30, 2026 (26% below the $115,000 asking price). It is currently off market. The Trulia Estimate rent is $1,755/month.

Home Highlights

Parking
1 Open Spaces
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
$93/sqft
Listed
97 days ago

Home Details for 108 Pine St

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 910 Square Feet
Appliances & Utilities
Appliances: Water Heater
Heating & Cooling
Heating: OtherHas CoolingAir Conditioning: OtherHas HeatingHeating Fuel: Other
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Roof: Shingle CompositionPatio / Porch: PorchOther Structures: Above Grade, Below GradeNo Private Pool
Parking & Garage
Open Parking Spaces: 1No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 910 Square Feet

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: OtherArchitecture: Ranch/Rambler
Building
Construction Materials: Shingle Siding, AsbestosNot a New Construction
Property Information
Condition: FixerParcel Number: 1504004418

Price & Status

Price
List Price: $115,000Price Per Sqft: $93/sqft
Status Change & Dates
Off Market Date: Tue Jun 30 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERTOWNCommunity: College Heights
School Information
Elementary School District: Kent County Public SchoolsJr High / Middle School District: Kent County Public SchoolsHigh School: Kent CountyHigh School District: Kent County Public Schools

Building

Building Area
Building Area: 910 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 7500 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: OtherListing Agreement Type: Exclusive Right To SellListing Terms: Cash, FHA 203(k)

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDKE2006322Municipality: ChestertownAbove Grade Unfinished Area: 910

Additional Information

Source Internet Entire Listing Display: Y
Last check for updates: about 2 hours ago
Listed by Mr. David J Moore, (410) 777-5848
Real Broker, LLC
Listing Team: David J. Moore & Associates
Bought with: Michelle Abplanalp, (443) 496-4255, Rosendale Realty
Source: Bright MLS, MLS#MDKE2006322

Price History for 108 Pine St

DatePriceEventSource
06/30/2026$85,000Sold
Bright MLS #MDKE2006322
06/10/2026$115,000ContingentBright MLS #MDKE2006322
05/05/2026$115,000PendingToActiveBright MLS #MDKE2006322
04/08/2026$115,000PendingBright MLS #MDKE2006322
04/02/2026$115,000Listed For SaleBright MLS #MDKE2006322
08/23/1996$45,000Sold
N/A

Market trends in Chestertown

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
1MoM
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Property Tax and Assessment

Year2025
Tax$3,313
Assessment$105,700
Home facts updated by county records

Comparable Sales for 108 Pine St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
112 Elm St, Chestertown, MD
0.08
Single-Family Home
$249,000
06/12/26
3
1
1,356
141 Prospect St, Chestertown, MD
0.52
Single-Family Home
$120,000
02/27/26
4
1.5
1,156
304 Hadaway Dr, Chestertown, MD
0.14
Single-Family Home
$250,000
07/31/25
4
2
1,325
202 Valley Rd, Chestertown, MD
0.24
Single-Family Home
$325,000
06/17/26
3
1
1,427
132 Prospect St, Chestertown, MD
0.50
Single-Family Home
$155,000
05/13/26
2
1
910
205 Pine St, Chestertown, MD
0.16
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
110 Philosophers Ter, Chestertown, MD
0.66
Single-Family Home
$175,000
07/25/25
2
1
896
126 Metcalf Rd, Chestertown, MD
0.36
Single-Family Home
$230,000
11/20/25
3
2
1,140

Nearby homes

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Assigned Schools

These are the assigned schools for 108 Pine St.
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 Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

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Apartments for Rent

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7 rentals with air conditioning in Chestertown, MD

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Homes for sale near 108 Pine St

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Off Market Homes Near 108 Pine St

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information