108 Pine St Chestertown, MD 21620
Estimated payment $747/month
Highlights
- Rambler Architecture
- Porch
- Heating Available
- No HOA
- Asbestos
About This Home
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.
Listing Agent
(855) 450-0442 dmvbroker@therealbrokerage.com Real Broker, LLC Brokerage Phone: 8554500442 License #609287 Listed on: 04/02/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $1,657
Year Built
- Built in 1957
Lot Details
- 7,500 Sq Ft Lot
- Property is zoned R-2
Home Design
- Rambler Architecture
- Fixer Upper
- Shingle Roof
- Composition Roof
- Shingle Siding
- Asbestos
Interior Spaces
- 910 Sq Ft Home
- Property has 1 Level
Bedrooms and Bathrooms
- 3 Main Level Bedrooms
- 1 Full Bathroom
Parking
- 1 Parking Space
- 1 Driveway Space
Schools
- Kent County High School
Additional Features
- Porch
- Heating Available
Community Details
- No Home Owners Association
- College Heights Subdivision
Listing and Financial Details
- Assessor Parcel Number 1504004418
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $1,657 | $105,700 | $67,500 | $38,200 |
| 2024 | $1,617 | $103,200 | $0 | $0 |
| 2023 | $1,578 | $100,700 | $0 | $0 |
| 2022 | $1,529 | $98,200 | $67,500 | $30,700 |
| 2021 | $1,539 | $98,200 | $67,500 | $30,700 |
| 2020 | $1,539 | $98,200 | $67,500 | $30,700 |
| 2019 | $1,567 | $100,200 | $75,000 | $25,200 |
| 2018 | $1,555 | $100,033 | $0 | $0 |
| 2017 | $1,502 | $99,867 | $0 | $0 |
| 2016 | -- | $99,700 | $0 | $0 |
| 2015 | $1,457 | $99,700 | $0 | $0 |
| 2014 | $1,457 | $99,700 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/08/2026 04/08/26 | Pending | -- | -- | -- |
| 04/02/2026 04/02/26 | For Sale | $115,000 | 0.0% | $126 / Sq Ft |
| 04/01/2026 04/01/26 | Price Changed | $115,000 | -- | $126 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $45,000 | -- |
Source: Bright MLS
MLS Number: MDKE2006322
APN: 04-004418
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Ask me questions while you tour the home.