345 S Main St · Winterport, ME 04496

$240,000

5 bd · 2.0 ba · 0 sqft · SingleFamily public records · 72 Days on market

Built 1800 0.47 ac lot Est $356k · 33% 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 +15.0/15.0
• Schools +7.9/10.0
• Cash flow +5.3/30.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.1/10.0
• DSCR +0.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Charming Historic Winterport Home -- awaiting NEW owners special offering. .. Step into history with this 1800's gem. Nicely maintained for 230 years old and she is full of original character, come add your own touches - the home features a butler's pantry, formal dining room, two staircases, and a sun-filled kitchen. The main-floor primary / master offers single-level convenience, while the second floor holds four bedrooms plus a small playroom/office area. Sited on . 47 acres with a large 3-bay barn -- ideal for vehicles and generous overhead storage. Large side and back yard for gardening, bbq's and star gazing. 2016 included new roof shingles and a new furnace. 2021 new sump pump. 2024 new propane heater. Heating system serviced fall of 2025. Hardwood floors throughout. Centrally located between Bangor and coastal Belfast, enjoy small-town charm with easy access to city sites and cultural amenities. Penobscot Bay for boating fishing and seasonal fun~ Come see your new HOME~

Key facts

• Large 3 bay barn
• Main floor primary
• Formal dining room

Tags

• BUTLERS PANTRY
• FORMAL DINING ROOM
• TWO STAIRCASES
• SUN FILLED KITCHEN
• MAIN FLOOR PRIMARY
• LARGE 3 BAY BARN

What this means for you Summary

Snapshot

• This is a 5-bed/2.0-bath single-family listed at $240k.

Deal economics

• At list price, monthly cash flow is $-531 ($-6k/yr) — negative.
• To cash-flow at today's rent, offer at most $146k (39.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $123k (48.8% below list).
• Recommended offer: $123k (48.8% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 68/100 on livability (#87 in ME) — a middle-class / working-renter tenant base. Strengths: crime A+, cost of living A+, housing A+; Watch: employment C-, health & safety C-, amenities F.
• RSU 22 (suburban): math 91% / reading 92% proficiency, ranked #16 of 112 in ME (top 14%) — strong family-tenant draw, lease renewals of 3-5y typical.
• Zoned schools: Hampden Academy (math 98% / reading 98%, grade A+, #1 of 108 statewide, top 9%, 811 students, 23% FRL) — zoned schools at 23% FRL track the district average.
• Market conditions: 42 active listings in the ZIP; 143 units permitted in Waldo 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.
• Waldo County population projected to shrink 9% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($226k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 6y ago; this cycle's ask has dropped $45k (16%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $150k; list at $240k implies a 60% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1800 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $122,824 (48.8% 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 72 days. Have you received any prior offers? Is the seller open to a 49% concession, seller financing, or rate buy-down credit?
3. Built in 1800 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 0.51% ✗
• Cap rate: 3.64%
• Cash-on-cash: -9.48%
• DSCR: 0.58
• GRM: 16.3

CMA / ARV

• ARV (median comp): $355,884
• List price: $240,000
• Delta: -32.56%
• Verdict: UNDERPRICED
• Comps: 10 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
52 Mechanic St	0.17mi	5/3.0	2,600	4mo	$404,000	$155	72
20 Water St	0.50mi	4/2.0 (-1)	2,408	10mo	$249,000	$103	51
10 Oak St	0.37mi	4/2.5 (-1)	2,365	18mo	$415,000	$175	49
5 Silver Ln	0.69mi	5/2.0	2,600	17mo	$510,000	$196	41
29 Washington St	0.72mi	4/3.0 (-1)	2,000	15mo	$250,000	$125	33

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: -33.3%
• Equity multiple: -0.08×
• Total profit: $-72,785
• Equity at exit: $35,785

10-year hold

• IRR: -40.9%
• Equity multiple: -0.60×
• Total profit: $-107,241
• Equity at exit: $20,751

Cash invested: $67,200 (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 04496

• Home prices YoY: -8.9%
• Active inventory: 42
• Price-to-rent: 16.3×

Monthly cashflow live

• Estimated rent: $1,228 medium
• Mortgage (P&I): −$1,259
• Tax from tax record: −$143 /mo · $1,712/yr
• Insurance: −$100
• HOA: −$0
• Vacancy / Maint / Mgmt: −$258
• Net cashflow: $-531

Break-even live

Break-even rent $1,900

Max offer price $146,207

Occupancy floor —

Sensitivity live

Price	-10% $-395	-5% $-463	+0% $-531	+5% $-599	+10% $-667
Rent	-10% $-628	-5% $-579	+0% $-531	+5% $-482	+10% $-434
Rate	-1.0pp $-410	-0.5pp $-470	base $-531	+0.5pp $-593	+1.0pp $-656

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: $60,000
• Closing costs: $7,200
• Reserves months: —
• Total cash needed: —

Listing history 29 events

1. 2026-06-21
   days on market $240,000 Active 72 DOM
2. 2026-06-19
   days on market $240,000 Active 70 DOM
3. 2026-06-18
   days on market $240,000 Active 69 DOM
4. 2026-06-17
   days on market $240,000 Active 68 DOM
5. 2026-06-16
   days on market $240,000 Active 67 DOM
6. 2026-06-15
   days on market $240,000 Active 66 DOM
7. 2026-06-14
   days on market $240,000 Active 64 DOM
8. 2026-06-13
   days on market $240,000 Active 63 DOM
9. 2026-06-10
   days on market $240,000 Active 61 DOM
10. 2026-06-09
    days on market $240,000 Active 60 DOM
11. 2026-06-09
    price $240,000 Active 59 DOM
12. 2026-06-08
    days on market $264,978 Active 59 DOM
13. 2026-06-07
    days on market $264,978 Active 58 DOM
14. 2026-06-05
    days on market $264,978 Active 55 DOM
15. 2026-06-03
    days on market $264,978 Active 54 DOM
16. 2026-06-02
    days on market $264,978 Active 53 DOM
17. 2026-06-01
    days on market $264,978 Active 52 DOM
18. 2026-05-31
    days on market $264,978 Active 51 DOM
19. 2026-05-30
    days on market $264,978 Active 50 DOM
20. 2026-05-03
    price $264,978 995-char remark

    Show marketing remark (995 chars)

    Charming Historic Winterport Home -- awaiting NEW owners special offering. .. Step into history with this 1800's gem. Nicely maintained for 230 years old and she is full of original character, come add your own touches - the home features a butler's pantry, formal dining room, two staircases, and a sun-filled kitchen. The main-floor primary / master offers single-level convenience, while the second floor holds four bedrooms plus a small playroom/office area. Sited on . 47 acres with a large 3-bay barn -- ideal for vehicles and generous overhead storage. Large side and back yard for gardening, bbq's and star gazing. 2016 included new roof shingles and a new furnace. 2021 new sump pump. 2024 new propane heater. Heating system serviced fall of 2025. Hardwood floors throughout. Centrally located between Bangor and coastal Belfast, enjoy small-town charm with easy access to city sites and cultural amenities. Penobscot Bay for boating fishing and seasonal fun~ Come see your new HOME~

21. 2026-04-10
    listed $284,978 Active 995-char remark

    Show marketing remark (995 chars)

    Charming Historic Winterport Home -- awaiting NEW owners special offering. .. Step into history with this 1800's gem. Nicely maintained for 230 years old and she is full of original character, come add your own touches - the home features a butler's pantry, formal dining room, two staircases, and a sun-filled kitchen. The main-floor primary / master offers single-level convenience, while the second floor holds four bedrooms plus a small playroom/office area. Sited on . 47 acres with a large 3-bay barn -- ideal for vehicles and generous overhead storage. Large side and back yard for gardening, bbq's and star gazing. 2016 included new roof shingles and a new furnace. 2021 new sump pump. 2024 new propane heater. Heating system serviced fall of 2025. Hardwood floors throughout. Centrally located between Bangor and coastal Belfast, enjoy small-town charm with easy access to city sites and cultural amenities. Penobscot Bay for boating fishing and seasonal fun~ Come see your new HOME~

22. 2021-02-12
    soldstatus $150,000 Closed 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

23. 2020-12-28
    status Pending 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

24. 2020-11-23
    status Active 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

25. 2020-11-02
    status Pending 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

26. 2020-10-29
    status Active 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

27. 2020-10-13
    status Pending 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

28. 2020-10-10
    listed $150,000 Active 738-char remark

    Show marketing remark (738 chars)

    Built in 1800, this beautiful historic home in downtown Winterport holds much of its original character; including a butler's pantry, formal dining room, two staircases and a sunroom off of the kitchen. The master bedroom is located on the first floor and the four bedrooms and a small playroom/ office is located on the second floor. Sitting on . 47 acres is a large 3 bay barn which can be used for vehicles with plenty of room for storage above. In 2016 there were many upgrades to this charming house: new roof shingles and a new furnace was installed. Being centrally located between Bangor and coastal towns, such as Belfast, this home can give you a small town feel with easy access to city and cultural amenities. Priced to sell!

29. 2019-04-01
    price $165,000

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

Tax reassessment forecast ME · Partial reset (capped growth)

• Current annual tax: $1,712 · $143/mo
• Projected year-2 tax: $2,488 · $207/mo
• Expected delta: +$776/yr (+$65/mo · 45.3%)

ⓘ 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 3/10 Moderate 7 d/yr ≥89°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% 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: $14,739
• − Mortgage interest: −$13,444
• − Property taxes: −$1,712
• − Insurance: −$1,200
• − Repairs & maintenance: −$1,179
• − Management: −$1,179
• − Depreciation: −$6,982
• Taxable loss: −$10,957
• Est. tax savings @ 24.0%: +$2,630
• After-tax cash flow: $-3,742/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 22
• NCES district ID: 2314815
• Math proficiency: 91% ▲ 49.00%
• Reading proficiency: 92% ▲ 26.00%
• Median HH income: $65,487
• Composite: 78.68/100
• National rank: #72
• State rank: #16 of 112 in ME

Livability — Winterport

• Score: 68/100
• State rank: #87
• US rank: #9878

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winterport, ME
• Population (ZIP): 3,839

Population outlook (Waldo County) Hauer SSP2

• Today (2025): 39,611 people
• By 2030: 39,475 · -0.3%
• By 2040: 38,245 · -3.4%
• By 2050: 36,078 · -8.9%
• By 2075: 29,774 · -24.8%
• By 2100: 22,172 · -44.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (95%)
• Race & ethnicity: White 95% Two or more races 3% Hispanic / Latino 1%
• Common ancestry: Lithuanian 7% Slovak 3% Romanian 2%

Political lean MEDSL · Waldo

• 2024 margin: Toss-up / Even · D 50.4% · R 47.0% · Other 2.6%
• 2008→2024 swing: -8.3pp toward R · 2008: 11.6pp · 2024: 3.4pp
• All cycles: 2024: D+3.4 2020: D+4.7 2016: D+0.3 2012: D+10.7 2008: D+11.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -24.03%
• Current HPI: 246.1944
• Rent YoY: —
• Metro: —
• State GDP YoY: —
• F500 in state: 0

Price history

+60.6% since first listed

10 events — show timeline

• 2026-05-03 Price Changed $264,978 MREIS
• 2026-04-10 Listed $284,978 MREIS
• 2021-02-12 Sold (MLS) $150,000 MREIS
• 2020-12-28 Pending — MREIS
• 2020-11-23 Relisted — MREIS
• 2020-11-02 Pending — MREIS
• 2020-10-29 Relisted — MREIS
• 2020-10-13 Pending — MREIS
• 2020-10-10 Listed $150,000 MREIS
• 2019-04-01 Price Changed $165,000 MREIS

Property tax history

+1.0%/yr

Latest (2016): $1,712 · +2.5% YoY. Source: county tax records.