115 Brookside Dr Unit 2-12 · Winchendon, MA 03447

$155,000

2 bd · 1.0 ba · 780 sqft · SingleFamily · 345 Days on market

Built 1987 Good condition 10,018 sqft lot $199/sqft · 8% below area Est $168k · 8% under $154/mo HOA · 8% of rent ↓ 13% since listing

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Why this score? — see what drove the B 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 +24.2/30.0
• ARV discount +11.0/15.0
• Appreciation +10.0/10.0
• DSCR +7.8/10.0
• 1% rule +7.5/10.0
• Condition / age +3.8/5.0
• Livability +3.6/5.0
• Schools +2.7/10.0
• Rent growth +2.5/5.0

Listing remarks MLS

One of the nicest homes in a very quiet location in the Woodbrook Camp and Tennis Club. Woodbrook is a seasonal gated community offering tennis, a swimming pool, beach access on Sip Pond, boat launch, playground and numerous social and recreational activities. The yearly fee includes water & sewer, electric and trash, recreation and association dues. This home has been meticulously renovated and cared for, and is being sold furnished. Spacious living room with a vaulted ceiling, 2 well sized bedrooms and a large eat-in kitchen make this home unique. Enjoy the large, flat yard for gardening. Relax on the backyard deck or join in any of the many activities available in the community. The home is available for a quick closing!

Key facts

• Boat launch
• Large flat yard
• Beach access

Tags

• SEASONAL GATED COMMUNITY
• BEACH ACCESS
• BOAT LAUNCH
• METICULOUSLY RENOVATED
• LARGE FLAT YARD
• BACKYARD DECK

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $155k. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $184 ($2k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $155k).
• Recommended offer: $136k (12.0% below list) — sets the bar for market timing.
• Cap rate 8.7% vs local median 4.2% in Winchendon — 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 71/100 on livability (#125 in MA) — a middle-class / working-renter tenant base. Strengths: housing A+, health & safety A+, crime A-; Watch: schools F, amenities F.
• Monadnock Regional School District (rural): math 25% / reading 36% proficiency, ranked #82 of 98 in NH (top 84%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 166 units permitted in Cheshire County in 2024 (0 in 5+ unit buildings).

Forward outlook

• In year one you build about $17k of equity ($1k loan paydown + $16k appreciation (10.0% local appreciation)).
• Cheshire County population projected at -18% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $43k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$42k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 345 days — a 12% lower offer ($136k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: flood insurance adds $125/mo.
• Climate carrying-cost: in FEMA flood zone A (mandatory federal flood insurance) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $136,400 (12.0% below list)

Questions for the listing agent

1. It's been on market 345 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
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. Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
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: 1.25% ✓
• Cap rate: 8.69%
• Cash-on-cash: 8.56%
• DSCR: 1.38
• GRM: 6.6

CMA / ARV

• ARV (median comp): $167,988
• List price: $155,000
• Delta: -7.73%
• Verdict: FAIR
• Comps: 14 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
240 Pine Tree Ln	0.13mi	2/1.0	803 (+3%)	9mo	$320,000	$399	81
25 S Pond Rd	0.27mi	2/1.0	682 (-13%)	7mo	$118,450	$174	60

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

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 28.0%
• Equity multiple: 3.22×
• Total profit: $96,356
• Equity at exit: $139,636

10-year hold

• IRR: 24.5%
• Equity multiple: 7.33×
• Total profit: $274,922
• Equity at exit: $301,131

Cash invested: $43,400 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 20 Strongly Tenant-Friendly
• State Massachusetts: 20 Strongly Tenant-Friendly · D+15
• County: — inherits STATE
• City: — inherits STATE

Cambridge / Boston historically rent-controlled (preempted 1994 but consideration ongoing); strong tenant protections; court backlogs.

Methodology + full state rankings →

ZIP-level market 03447

• Home prices YoY: 24.0%
• Price-to-rent: 6.6×

Monthly cashflow live

• Estimated rent: $1,943 medium
• Mortgage (P&I): −$813
• Tax est. 1.5%: −$194 /mo · $2,325/yr
• Insurance: −$65
• Flood insurance flood zone: −$125 /mo · $1,502/yr
• HOA: −$154
• Vacancy / Maint / Mgmt: −$408
• Net cashflow: $184

Break-even live

Break-even rent $1,709

Max offer price $155,000

Occupancy floor 86%

Sensitivity live

Price	-10% $291	-5% $238	+0% $184	+5% $131	+10% $77
Rent	-10% $31	-5% $108	+0% $184	+5% $261	+10% $338
Rate	-1.0pp $262	-0.5pp $224	base $184	+0.5pp $144	+1.0pp $103

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: $38,750
• Closing costs: $4,650
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $154 · $1,848/yr
• Likely covers: watersewertrashelectricpoolsecurity

Listing history 19 events

1. 2026-06-19
   days on market $155,000 Active 345 DOM
2. 2026-06-18
   days on market $155,000 Active 344 DOM
3. 2026-06-17
   days on market $155,000 Active 343 DOM
4. 2026-06-16
   days on market $155,000 Active 342 DOM
5. 2026-06-15
   days on market $155,000 Active 341 DOM
6. 2026-06-14
   days on market $155,000 Active 339 DOM
7. 2026-06-12
   days on market $155,000 Active 338 DOM
8. 2026-06-09
   days on market $155,000 Active 335 DOM
9. 2026-06-08
   days on market $155,000 Active 334 DOM
10. 2026-06-07
    days on market $155,000 Active 333 DOM
11. 2026-06-07
    days on market $155,000 Active 332 DOM
12. 2026-06-03
    days on market $155,000 Active 329 DOM
13. 2026-06-02
    days on market $155,000 Active 328 DOM
14. 2026-06-01
    days on market $155,000 Active 327 DOM
15. 2026-05-31
    days on market $155,000 Active 326 DOM
16. 2026-05-30
    days on market $155,000 Active 325 DOM
17. 2026-04-08
    price $155,000 739-char remark

    Show marketing remark (739 chars)

    One of the nicest homes in a very quiet location in the Woodbrook Camp and Tennis Club. Woodbrook is a seasonal gated community offering tennis, a swimming pool, beach access on Sip Pond, boat launch, playground and numerous social and recreational activities. The yearly fee includes water & sewer, electric and trash, recreation and association dues. This home has been meticulously renovated and cared for, and is being sold furnished. Spacious living room with a vaulted ceiling, 2 well sized bedrooms and a large eat-in kitchen make this home unique. Enjoy the large, flat yard for gardening. Relax on the backyard deck or join in any of the many activities available in the community. The home is available for a quick closing!

18. 2025-09-26
    price $164,000 739-char remark

    Show marketing remark (739 chars)

    One of the nicest homes in a very quiet location in the Woodbrook Camp and Tennis Club. Woodbrook is a seasonal gated community offering tennis, a swimming pool, beach access on Sip Pond, boat launch, playground and numerous social and recreational activities. The yearly fee includes water & sewer, electric and trash, recreation and association dues. This home has been meticulously renovated and cared for, and is being sold furnished. Spacious living room with a vaulted ceiling, 2 well sized bedrooms and a large eat-in kitchen make this home unique. Enjoy the large, flat yard for gardening. Relax on the backyard deck or join in any of the many activities available in the community. The home is available for a quick closing!

19. 2025-07-09
    listed $179,000 Active 739-char remark

    Show marketing remark (739 chars)

    One of the nicest homes in a very quiet location in the Woodbrook Camp and Tennis Club. Woodbrook is a seasonal gated community offering tennis, a swimming pool, beach access on Sip Pond, boat launch, playground and numerous social and recreational activities. The yearly fee includes water & sewer, electric and trash, recreation and association dues. This home has been meticulously renovated and cared for, and is being sold furnished. Spacious living room with a vaulted ceiling, 2 well sized bedrooms and a large eat-in kitchen make this home unique. Enjoy the large, flat yard for gardening. Relax on the backyard deck or join in any of the many activities available in the community. The home is available for a quick closing!

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

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone A · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 2/10 Low 7 d/yr ≥91°F today · 17 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 14% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $23,312
• − Mortgage interest: −$8,682
• − Property taxes: −$2,325
• − Insurance: −$2,278
• − Repairs & maintenance: −$1,865
• − Management: −$1,865
• − HOA: −$1,848
• − Depreciation: −$4,509
• Taxable loss: −$60
• Est. tax savings @ 24.0%: +$14
• After-tax cash flow: $2,226/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.

Condition & rehab AI · 6 photos

Good 75/100 Cosmetic rehab

This home is in good condition with a good condition score of 75. It has been meticulously renovated and is move-in ready. The home has a good layout and is located in a quiet community with many amenities. The home's value can be further increased with some cosmetic updates and improvements.

Value-add opportunities

• Both Paint the exterior — Fresh paint can enhance curb appeal and property value.
• Both Replace the ceiling fan — A modern ceiling fan can improve both aesthetics and energy efficiency.
• Both Install new flooring in the kitchen — New flooring can significantly improve the kitchen's appearance and functionality.
• Both Paint the interior walls — Fresh paint can make the interior look more inviting and modern.
• Both Replace the kitchen appliances — Modern appliances can increase the home's appeal and value.
• Both Landscaping improvements — Enhanced landscaping can improve curb appeal and property value.
• Both Install new windows — New windows can improve energy efficiency and increase the home's value.
• Both Replace the HVAC system — A new HVAC system can improve comfort and energy efficiency, increasing the home's value.
• Both Install a new roof — A new roof can improve the home's value and longevity.

Renovation cost estimate screening

Value-add ROI direction

• Both Paint the exterior — Fresh paint can enhance curb appeal and property value. ↑
• Both Replace the ceiling fan — A modern ceiling fan can improve both aesthetics and energy efficiency. ↑
• Both Install new flooring in the kitchen — New flooring can significantly improve the kitchen's appearance and functionality. ↑
• Both Paint the interior walls — Fresh paint can make the interior look more inviting and modern. ↑
• Both Replace the kitchen appliances — Modern appliances can increase the home's appeal and value. ↑
• Both Landscaping improvements — Enhanced landscaping can improve curb appeal and property value. ↑
• Both Install new windows — New windows can improve energy efficiency and increase the home's value. ↑
• Both Replace the HVAC system — A new HVAC system can improve comfort and energy efficiency, increasing the home's value. ↑
• Both Install a new roof — A new roof can improve the home's value and longevity. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Monadnock Regional School District
• NCES district ID: 3304890
• Math proficiency: 25% ▼ -16.00%
• Reading proficiency: 36% ▼ -6.00%
• Median HH income: $56,314
• Composite: 27.18/100
• National rank: #7024
• State rank: #82 of 98 in NH

Livability — Winchendon

• Score: 71/100
• State rank: #125
• US rank: #6726

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 2,317

Population outlook (Cheshire County) Hauer SSP2

• Today (2025): 74,613 people
• By 2030: 72,495 · -2.8%
• By 2040: 66,778 · -10.5%
• By 2050: 60,963 · -18.3%
• By 2075: 49,511 · -33.6%
• By 2100: 39,687 · -46.8%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (91%)
• Race & ethnicity: White 91% Two or more races 8% Hispanic / Latino 7%
• Hispanic origin (detail): Puerto Rican 6%
• Common ancestry: Lithuanian 11% Romanian 7% Slovene 4%
• Foreign-born: 2% · Canada
• Languages at home: 94% English-only · Spanish 5% French/Haitian/Cajun 1%

Political lean MEDSL · Cheshire

• 2024 margin: Lean D (+9.8) · D 54.4% · R 44.6% · Other 1.1%
• 2008→2024 swing: -17.8pp toward R · 2008: 27.6pp · 2024: 9.8pp
• All cycles: 2024: D+9.8 2020: D+17.2 2016: D+12.6 2012: D+24.8 2008: D+27.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 76.42%
• Current HPI: 394.7824
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.28%
• F500 in state: 38

Industry mix (Fortune 500 HQ in MA)

Industry	F500 HQs	Revenue
▸Technology	3	$17B
▸Insurance	2	$84B
▸Retail	2	$76B
▸Life Sciences	1	$43B
▸Energy Technology	1	$31B
▸Aerospace / Defense	1	$18B

Price history

-13.4% since first listed

3 events — show timeline

• 2026-04-08 Price Changed $155,000 PrimeMLS
• 2025-09-26 Price Changed $164,000 PrimeMLS
• 2025-07-09 Listed $179,000 PrimeMLS