139 Prospect St · Chestertown, MD 21620

$225,000

3 bd · 1.0 ba · 1,200 sqft · SingleFamily public records · 87 Days on market

Built 1991 6,350 sqft lot $188/sqft · 14% below area Est $260k · 14% under

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Why this score? — see what drove the D- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• ARV discount +13.6/15.0
• Cash flow +8.9/30.0
• Livability +3.3/5.0
• DSCR +2.5/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +2.2/10.0
• Schools +1.7/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Charming and inviting! Welcome to 139 Prospect St. , a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

Key facts

• 6,350 sq ft lot
• Built 1991
• Listed 86 days

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $225k.

Deal economics

• At list price, monthly cash flow is $-180 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $193k (14.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $161k (28.4% below list).
• Recommended offer: $161k (28.4% below list) — sets the bar for 1% rule.
• Cap rate 5.3% vs local median 2.7% in Chestertown — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 66/100 on livability (#238 in MD) — a middle-class / working-renter tenant base. Strengths: health & safety A-; Watch: employment D+, amenities F, commute F.
• Kent County Public Schools (rural): math 10% / reading 28% proficiency, ranked #20 of 24 in MD (top 83%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Zoned schools: H. H. Garnett Elementary (math 8% / reading 17%, grade F, #538 of 860 statewide, top 64%, 347 students, 100% FRL); Kent County Middle School (math 7% / reading 29%, grade F, #165 of 225 statewide, top 75%, 399 students, 64% FRL); Kent County High (math 27% / reading 57%, grade F, #126 of 222 statewide, top 57%, 531 students, 54% FRL) — zoned schools average 73% FRL vs 47% district-wide (26 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 126 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals leasing fast (median 0d on market — plan ~1-2 weeks tenant-placement turnaround); solid renter incomes; 50 units permitted in Kent County in 2024 (0 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Kent County population projected at -20% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 87 days — a 6% lower offer ($212k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $60k; list at $225k implies a 275% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 60% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $161,134 (28.4% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 87 days. Have you received any prior offers? Is the seller open to a 28% concession, seller financing, or rate buy-down credit?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
6. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
7. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
8. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
9. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.72% ✗
• Cap rate: 5.33%
• Cash-on-cash: -3.42%
• DSCR: 0.85
• GRM: 11.6

CMA / ARV

• ARV (median comp): $260,358
• List price: $225,000
• Delta: -13.58%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 9 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
141 Prospect St	0.01mi	4/1.5 (+1)	1,156 (-4%)	4mo	$120,000	$104	83
631 High St	0.14mi	3/1.5	1,234 (+3%)	21mo	$250,000	$203	69
112 Elm St	0.56mi	3/1.0	1,356 (+13%)	0mo	$249,000	$184	52
202 Glen St	0.64mi	3/1.0	1,252 (+4%)	14mo	$290,000	$232	52
5 Rolling Rd	0.74mi	3/1.0	1,202 (+0%)	19mo	$239,000	$199	50
420 Cannon St	0.34mi	2/2.0 (-1)	1,080 (-10%)	11mo	$350,000	$324	49
111 Elm St	0.58mi	3/1.0	1,275 (+6%)	18mo	$212,000	$166	48
304 Hadaway Dr	0.65mi	3/2.0	1,325 (+10%)	11mo	$250,000	$189	40
106 Pine St	0.53mi	3/1.0	1,376 (+15%)	24mo	$269,975	$196	31

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -22.1%
• Equity multiple: 0.24×
• Total profit: $-47,948
• Equity at exit: $33,548

10-year hold

• IRR: -16.1%
• Equity multiple: 0.10×
• Total profit: $-56,651
• Equity at exit: $19,454

Cash invested: $63,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Maryland: 27 Tenant-Leaning · D+14
• County: — inherits STATE
• City: — inherits STATE

Failure-to-pay is dismissed if cured before judgment; Baltimore has just-cause; strict deposit rules.

Methodology + full state rankings →

ZIP-level market 21620

• Home prices YoY: -5.3%
• Active inventory: 126
• Price-to-rent: 11.6×

Monthly cashflow live

• Estimated rent: $1,611 medium
• Mortgage (P&I): −$1,180
• Tax from tax record: −$179 /mo · $2,149/yr
• Insurance: −$94
• HOA: −$0
• Vacancy / Maint / Mgmt: −$338
• Net cashflow: $-180

Break-even live

Break-even rent $1,839

Max offer price $193,243

Occupancy floor —

Sensitivity live

Price	-10% $-52	-5% $-116	+0% $-180	+5% $-243	+10% $-307
Rent	-10% $-307	-5% $-243	+0% $-180	+5% $-116	+10% $-52
Rate	-1.0pp $-66	-0.5pp $-123	base $-180	+0.5pp $-238	+1.0pp $-297

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $56,250
• Closing costs: $6,750
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
103 S Lynchburg St Chestertown, MD	2.0	1.5	1040	$1,400	$1.35	0d	1	0.17mi
104 Maple Ave Unit 3 Chestertown, MD	2.0	1.0	800	$1,520	$1.90	19d	1	0.65mi
104 Maple Ave Unit 6 Chestertown, MD	2.0	2.0	900	$2,050	$2.28	0d	1	0.65mi
7501 Church Hill Rd Unit 5 Chestertown, MD	2.0	1.0	1000	$1,800	$1.80	0d	1	1.02mi

Listing history 18 events

1. 2026-06-21
   days on market $225,000 Active 87 DOM
2. 2026-06-18
   days on market $225,000 Active 84 DOM
3. 2026-06-17
   days on market $225,000 Active 83 DOM
4. 2026-06-16
   days on market $225,000 Active 82 DOM
5. 2026-06-15
   days on market $225,000 Active 81 DOM
6. 2026-06-13
   days on market $225,000 Active 79 DOM
7. 2026-06-13
   days on market $225,000 Active 78 DOM
8. 2026-06-09
   days on market $225,000 Active 75 DOM
9. 2026-06-08
   days on market $225,000 Active 74 DOM
10. 2026-06-07
    days on market $225,000 Active 73 DOM
11. 2026-06-04
    days on market $225,000 Active 70 DOM
12. 2026-06-03
    days on market $225,000 Active 69 DOM
13. 2026-06-02
    days on market $225,000 Active 68 DOM
14. 2026-06-01
    days on market $225,000 Active 67 DOM
15. 2026-05-31
    days on market $225,000 Active 66 DOM
16. 2026-03-27
    listed $225,000 Active 1040-char remark

    Show marketing remark (1040 chars)

    Charming and inviting! Welcome to 139 Prospect St. , a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

17. 2026-03-26
    historical $225,000 1040-char remark

    Show marketing remark (1040 chars)

    Charming and inviting! Welcome to 139 Prospect St. , a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

18. 1991-09-06
    soldstatus $60,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast MD · Partial reset (capped growth)

• Current annual tax: $2,149 · $179/mo
• Projected year-2 tax: $2,301 · $192/mo
• Expected delta: +$152/yr (+$13/mo · 7.1%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 8/10 Severe 7 d/yr ≥104°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 60% chance of damaging wind over 30 yrs
• 🫁 Air quality 6/10 Major 9 unhealthy d/yr today · 13 by 30 yrs out

Taxation est. · year 1

• Rental income: $19,336
• − Mortgage interest: −$12,603
• − Property taxes: −$2,149
• − Insurance: −$1,125
• − Repairs & maintenance: −$1,547
• − Management: −$1,547
• − Depreciation: −$6,545
• Taxable loss: −$6,180
• Est. tax savings @ 24.0%: +$1,483
• After-tax cash flow: $-674/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Kent County Public Schools
• NCES district ID: 2400450
• Math proficiency: 10% ▼ -13.00%
• Reading proficiency: 28% ▼ -9.00%
• Median HH income: $53,748
• Composite: 17.37/100
• National rank: #9072
• State rank: #20 of 24 in MD

Livability — Chestertown

• Score: 66/100
• State rank: #238
• US rank: #11931

Category grades

Amenities F Commute F Cost of living C+ Crime B- Employment D+ Housing C Health & safety A- User ratings C+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Chestertown, MD
• County: Kent County · 13,810 people
• City population: 13,810
• Metro: Baltimore-Columbia-Towson, MD
• Population (ZIP): 13,810
• Household income: $80,530
• Rent vs Own: 28.0% rent · 72.0% own
• Severe rent burden: 444.0

Population outlook (Kent County) Hauer SSP2

• Today (2025): 18,915 people
• By 2030: 18,192 · -3.8%
• By 2040: 16,601 · -12.2%
• By 2050: 15,089 · -20.2%
• By 2075: 12,441 · -34.2%
• By 2100: 10,191 · -46.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (77%)
• Race & ethnicity: White 77% Black 14% Hispanic / Latino 4% Two or more races 3% Asian 1%
• Common ancestry: Romanian 4% Slovak 2% Lithuanian 1%
• Foreign-born: 4% · Canada
• Languages at home: 96% English-only · Spanish 2% Other Indo-European 1%

Political lean MEDSL · Kent

• 2024 margin: Toss-up / Even · D 47.4% · R 50.2% · Other 2.3%
• 2008→2024 swing: -3.3pp toward R · 2008: 0.5pp · 2024: -2.8pp
• All cycles: 2024: R+2.8 2020: D+1.2 2016: R+4.6 2012: R+0.9 2008: D+0.5

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -15.95%
• Current HPI: 286.6638
• Rent YoY: —
• Metro: Baltimore-Columbia-Towson, MD
• State GDP YoY: ▲ 2.97%
• F500 in state: 12

Industry mix (Fortune 500 HQ in MD)

Industry	F500 HQs	Revenue
▸Aerospace / Defense	1	$71B
▸Utilities	1	$25B
▸Hotels	1	$24B
▸Consumer Goods	1	$7B
▸Real Estate	1	$6B
▸Chemicals	1	$2B

Price history

+275.0% since first listed

3 events — show timeline

• 2026-03-27 Listed $225,000 BRIGHT MLS
• 2026-03-26 Coming Soon $225,000 BRIGHT MLS
• 1991-09-06 Sold (Public Records) $60,000 Public Records

Property tax history

+2.7%/yr

Latest (2025): $2,149 · +10743050.0% YoY. Source: county tax records.