20 Chestnut St · Rockland, ME 04841

$445,000

3 bd · 1.5 ba · 2,728 sqft · MultiFamily public records · 118 Days on market

Built 1880 10,018 sqft lot $163/sqft · at area comps Est $430k · at est.

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Why this score? — see what drove the C+ 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).

• Cash flow +26.8/30.0
• DSCR +9.2/10.0
• 1% rule +7.1/10.0
• Schools +6.8/10.0
• ARV discount +5.9/15.0
• Livability +3.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks MLS

20 Chestnut stands out as a handsome New England-style residence designed for both grand and compact living: ideal for owners seeking extra income, or those wanting additional space for family and friends. Its flexible configuration also appeals to investors, thanks to a blend of large and small living areas and generous parking accommodations. The primary side of the property includes three bedrooms and two full bathrooms. Inside, you will find gracious, wide trim around interior windows and doorways, lending a classic New England charm. Recent renovations have modernized the space, with a new propane furnace installed, an updated kitchen featuring brand-new appliances, and a completely renovated full bathroom on the first floor and laundry closet. Upstairs, the second story houses three spacious bedrooms and another full bathroom, offering comfortable and functional living quarters. The property also includes a charming one-bedroom apartment. This unit features a full bathroom, private entry, a sitting deck, and its own driveway, making it perfect for guests or as a rental opportunity. All will enjoy the property's proximity to Rockland's vibrant harbor, golf course, museums, theater, shops, coffee spots, and restaurants. Everyday conveniences are within reach, including nearby medical facilities, fitness centers, hiking trails, and recreational lakes.

Key facts

• New propane furnace
• Nearby harbor
• Updated kitchen

Tags

• NEW PROPANE FURNACE
• UPDATED KITCHEN
• NEW FULL DOWNSTAIRS BATHROOM
• PRIVATE ENTRY
• SEPARATE DRIVEWAY
• NEARBY HARBOR

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath multifamily listed at $445k.

Deal economics

• At list price, monthly cash flow is $1k ($15k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $445k).
• Recommended offer: $405k (9.0% below list) — sets the bar for market timing.
• Cap rate 9.6% vs local median 3.3% in Rockland — 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 62/100 on livability (#116 in ME) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+, crime A-; Watch: schools D, amenities F, commute F.
• RSU 13 (town): math 77% / reading 85% proficiency, ranked #84 of 112 in ME (top 75%) — strong family-tenant draw, lease renewals of 3-5y typical.
• Market conditions: 71 active listings in the ZIP; 160 units permitted in Knox County in 2024 (58 in 5+ unit buildings).
• At $5,376/mo this rent would consume 114% of the median local household income ($57k/yr) (locally 279% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $13k of value loss. Plan a longer hold.
• Knox County population projected at -14% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $125k cash investment doubles in ~10 years — after that, you're playing with house money.

Negotiation context

• It's been on market 118 days — a 9% lower offer ($405k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $44k (9%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1880 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 73% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $404,950 (9.0% below list)

Questions for the listing agent

1. It's been on market 118 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Built in 1880 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
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. 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.
7. 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.
8. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 1.21% ✓
• Cap rate: 9.58%
• Cash-on-cash: 11.74%
• DSCR: 1.52
• GRM: 6.9

CMA / ARV

• ARV (median comp): $429,767
• List price: $445,000
• Delta: 3.54%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
25 James St	0.15mi	4/2.0 (+1)	2,886 (+6%)	11mo	$350,000	$121	67

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: 1.2%
• Equity multiple: 1.04×
• Total profit: $5,581
• Equity at exit: $66,351

10-year hold

• IRR: 10.8%
• Equity multiple: 1.84×
• Total profit: $105,044
• Equity at exit: $38,475

Cash invested: $124,600 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 41 Moderately Tenant-Leaning
• State Maine: 41 Moderately Tenant-Leaning · D+2
• County: — inherits STATE
• City: — inherits STATE

Portland has rent control referendum (2020); strong habitability; security deposit caps.

Methodology + full state rankings →

ZIP-level market 04841

• Home prices YoY: -17.8%
• Active inventory: 71
• Price-to-rent: 18.2×

Monthly cashflow live

• Estimated rent: $5,376 high
• Mortgage (P&I): −$2,334
• Tax from tax record: −$509 /mo · $6,108/yr
• Insurance: −$185
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,129
• Net cashflow: $1,219

Break-even live

Break-even rent $3,833

Max offer price $445,000

Occupancy floor 72%

3-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
1× unit	3	1	$2,042
▸ 2× units	1	1	$3,334
Total (3 units)			$5,376

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: $111,250
• Closing costs: $13,350
• Reserves months: —
• Total cash needed: —

Listing history 16 events

1. 2026-06-18
   days on market $445,000 Active 118 DOM
2. 2026-06-17
   days on market $445,000 Active 117 DOM
3. 2026-06-16
   days on market $445,000 Active 116 DOM
4. 2026-06-15
   days on market $445,000 Active 115 DOM
5. 2026-06-14
   days on market $445,000 Active 113 DOM
6. 2026-06-10
   days on market $445,000 Active 110 DOM
7. 2026-06-09
   days on market $445,000 Active 109 DOM
8. 2026-06-08
   days on market $445,000 Active 108 DOM
9. 2026-06-07
   days on market $445,000 Active 107 DOM
10. 2026-06-03
    days on market $445,000 Active 103 DOM
11. 2026-06-02
    days on market $445,000 Active 102 DOM
12. 2026-06-01
    days on market $445,000 Active 101 DOM
13. 2026-05-31
    days on market $445,000 Active 100 DOM
14. 2026-05-31
    days on market $445,000 Active 99 DOM
15. 2026-03-25
    listed $489,000 Active 1376-char remark

    Show marketing remark (1376 chars)

    20 Chestnut stands out as a handsome New England-style residence designed for both grand and compact living: ideal for owners seeking extra income, or those wanting additional space for family and friends. Its flexible configuration also appeals to investors, thanks to a blend of large and small living areas and generous parking accommodations. The primary side of the property includes three bedrooms and two full bathrooms. Inside, you will find gracious, wide trim around interior windows and doorways, lending a classic New England charm. Recent renovations have modernized the space, with a new propane furnace installed, an updated kitchen featuring brand-new appliances, and a completely renovated full bathroom on the first floor and laundry closet. Upstairs, the second story houses three spacious bedrooms and another full bathroom, offering comfortable and functional living quarters. The property also includes a charming one-bedroom apartment. This unit features a full bathroom, private entry, a sitting deck, and its own driveway, making it perfect for guests or as a rental opportunity. All will enjoy the property's proximity to Rockland's vibrant harbor, golf course, museums, theater, shops, coffee spots, and restaurants. Everyday conveniences are within reach, including nearby medical facilities, fitness centers, hiking trails, and recreational lakes.

16. 2026-02-21
    listed $489,000 Active 1081-char remark

    Show marketing remark (1081 chars)

    Handsomely situated on a quiet tree lined street surprisingly close to Rockland's downtown, 20 Chestnut is a resilient New Englander offering both grand and compact living spaces. If you are seeking a multigenerational home or keen to collect additional income by renting the other side of the house - book a showing to truly see yourself here. Gracious wide trim adorns interior windows and doorways. Recent updates to the main house include a new propane furnace, updated kitchen with all new appliances and new full downstairs bathroom. The second story offers three large bedrooms and a full bathroom. The attached one bedroom with one full bathroom in-law apartment has a private entry, sitting deck and separate driveway. Find yourself thriving in this neighborhood and taking advantage of Rockland's nearby harbor, golf course, museums, theatre, shops, coffee destinations, and restaurants. With nearby medical facilities, fitness centers, hiking trails, and recreational lakes you will certainly enrich your life as resident on Chestnut Street, Rockland and Midcoast Maine.

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

Tax reassessment forecast ME · Partial reset (capped growth)

• Current annual tax: $6,108 · $509/mo
• Projected year-2 tax: $6,108 · $509/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 4/10 Moderate 7 d/yr ≥85°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 73% chance of damaging wind over 30 yrs
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $64,512
• − Mortgage interest: −$24,927
• − Property taxes: −$6,108
• − Insurance: −$2,225
• − Repairs & maintenance: −$5,161
• − Management: −$5,161
• − Depreciation: −$12,945
• Taxable income: $7,985
• Est. tax owed @ 24.0%: −$1,916
• After-tax cash flow: $12,712/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: RSU 13
• NCES district ID: 2314787
• Math proficiency: 77% ▲ 51.00%
• Reading proficiency: 85% ▲ 36.00%
• Median HH income: $43,177
• Composite: 67.81/100
• National rank: #363
• State rank: #84 of 112 in ME

Livability — Rockland

• Score: 62/100
• State rank: #116
• US rank: #16831

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Rockland, ME
• County: Knox County · 7,035 people
• City population: 7,035
• Metro: nan
• Population (ZIP): 7,035
• Household income: $56,533
• Rent vs Own: 38.0% rent · 62.0% own
• Severe rent burden: 279.0

Population outlook (Knox County) Hauer SSP2

• Today (2025): 39,304 people
• By 2030: 38,497 · -2.1%
• By 2040: 36,090 · -8.2%
• By 2050: 33,681 · -14.3%
• By 2075: 29,934 · -23.8%
• By 2100: 24,633 · -37.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (97%)
• Race & ethnicity: White 97% Two or more races 3%
• Common ancestry: Slovak 12% Serbian 8% Lithuanian 5%
• Foreign-born: 1% · Canada
• Languages at home: 97% English-only · French/Haitian/Cajun 2%

Political lean MEDSL · Knox

• 2024 margin: D (+18.6) · D 58.2% · R 39.6% · Other 2.1%
• 2008→2024 swing: -2.8pp toward R · 2008: 21.4pp · 2024: 18.6pp
• All cycles: 2024: D+18.6 2020: D+19.9 2016: D+14.3 2012: D+22.6 2008: D+21.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -73.90%
• Current HPI: 341.7862
• Rent YoY: —
• Metro: nan
• State GDP YoY: —
• F500 in state: 0

Price history

+0.0% since first listed

2 events — show timeline

• 2026-03-25 Listed $489,000 MREIS
• 2026-02-21 Listed $489,000 MREIS

Property tax history

+3.0%/yr

Latest (2025): $6,108 · +17.0% YoY. Source: county tax records.