140 Dudley St · Brookline, MA 02445

$2,698,000

5 bd · 3.5 ba · 3,648 sqft · SingleFamily public records · 84 Days on market

Built 1925 0.33 ac lot $740/sqft · 18% below area Est $3360k · 20% under

---

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
• Appreciation +10.0/10.0
• Schools +6.4/10.0
• Livability +4.2/5.0
• Rent growth +2.9/5.0
• Condition / age +2.5/5.0
• Cash flow +1.1/30.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back living room with a gas fireplace, a gracious dining room with its own fireplace, and an eat-in kitchen that opens to a covered deck and patio—perfect for entertaining. The main level also includes a private home office, a powder room, and a sun-filled, oversized family room with direct access to a second patio. Upstairs on the 2nd and 3rd levels are five bedrooms and an additional home office, including a spacious primary suite with an ensuite bath, walk-in closet, and private deck. The lower level offers a dedicated exercise area, laundry room, abundant storage, and an attached two-car garage. Ideally located near The Street, Wegmans, Longwood Medical Area, public transportation, and Boston.

Key facts

• 0.33 acre lot
• 2 garage spots
• Built 1925

What this means for you Summary

Snapshot

• This is a 5-bed/3.5-bath single-family listed at $2.70M.

Deal economics

• At list price, monthly cash flow is $-11k ($-132k/yr) — negative.
• To cash-flow at today's rent, offer at most $748k (72.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $799k (70.4% below list).
• Recommended offer: $748k (72.3% below list) — sets the bar for cash-flow.

Location & tenants

• Location reads 84/100 on livability (#16 in MA, #704 nationally) — a professional / high-income tenant draw. Strengths: schools A+, crime A+, commute A+; Watch: amenities D+, cost of living F.
• Brookline (suburban): math 66% / reading 73% proficiency, ranked #29 of 302 in MA (top 10%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 10% free/reduced lunch — higher-income household profile.
• Market conditions: Rents rising (+1.5%/yr); 83 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 958 units permitted in Norfolk County in 2024 (305 in 5+ unit buildings).
• At $7,995/mo this rent would consume 69% of the median local household income ($140k/yr) (locally 1138% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $288k of equity ($19k loan paydown + $270k appreciation (10.0% local appreciation)).
• Norfolk County population projected at +10% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• By year 2, paydown + projected appreciation supports a ~$464k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 84 days — a 6% lower offer ($2.54M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 19y ago; this cycle's ask has dropped $242k (8%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $1.56M; list at $2.70M implies a 73% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo; built in 1925 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe flood risk; major wind risk, 61% chance of damaging wind over 30y; extreme-heat days projected 7→14/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $748,446 (72.3% 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 84 days. Have you received any prior offers? Is the seller open to a 72% concession, seller financing, or rate buy-down credit?
3. Built in 1925 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
8. 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?
9. 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.
10. 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.
11. 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: 0.30% ✗
• Cap rate: 1.41%
• Cash-on-cash: -17.44%
• DSCR: 0.22
• GRM: 28.1

CMA / ARV

• ARV (median comp): $3,359,625
• List price: $2,698,000
• Delta: -19.69%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
43 Druce St	0.69mi	5/4.5	3,658 (+0%)	1mo	$3,285,000	$898	62
34 Hyslop Rd	0.56mi	5/4.5	4,001 (+10%)	1mo	$4,125,000	$1,031	53
185 Tappan St	0.62mi	5/5.5	3,593 (-2%)	9mo	$4,350,000	$1,211	53
24 Blake Rd	0.59mi	4/2.5 (-1)	3,377 (-7%)	2mo	$2,850,000	$844	49
323 Clark Rd	0.74mi	5/4.5	3,370 (-8%)	4mo	$2,995,000	$889	46
47 Cotswold Rd	0.66mi	5/3.5	3,342 (-8%)	14mo	$3,218,000	$963	44
55 Clark Rd	0.58mi	6/3.5 (+1)	3,433 (-6%)	20mo	$2,040,000	$594	42
115 Clark Rd	0.50mi	4/4.5 (-1)	4,182 (+15%)	4mo	$3,400,000	$813	40
16 Blake Rd	0.58mi	4/2.5 (-1)	3,842 (+5%)	19mo	$1,990,000	$518	39
311 Clark Rd	0.72mi	6/2.5 (+1)	3,356 (-8%)	11mo	$2,375,000	$708	35
170 Reservoir Rd	0.73mi	5/3.0	3,146 (-14%)	12mo	$2,850,000	$906	31
92 Dean Rd	0.73mi	6/3.5 (+1)	3,161 (-13%)	11mo	$2,336,000	$739	29

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 · 1.47% rent growth · sell at horizon

5-year hold

• IRR: 12.0%
• Equity multiple: 2.00×
• Total profit: $753,717
• Equity at exit: $2,430,572

10-year hold

• IRR: 12.5%
• Equity multiple: 4.64×
• Total profit: $2,747,882
• Equity at exit: $5,241,621

Cash invested: $755,440 (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 02445

• Home prices YoY: 5.5%
• Rents YoY: 1.5%
• Active inventory: 83
• Price-to-rent: 28.1×

Monthly cashflow live

• Estimated rent: $7,995 medium
• Mortgage (P&I): −$14,149
• Tax from tax record: −$2,024 /mo · $24,283/yr
• Insurance: −$1,124
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,679
• Net cashflow: $-11,036

Break-even live

Break-even rent $21,964

Max offer price $748,446

Occupancy floor —

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: $674,500
• Closing costs: $80,940
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
158 Cypress St Brookline, MA	6.0	3.0	3000	$7,500	$2.50	43d	1	0.64mi
161 Clinton Rd Brookline, MA	5.0	3.5	3494	$9,250	$2.65	43d	1	0.65mi
58 Brook St Unit NA Brookline, MA	4.0	4.5	3150	$10,000	$3.17	24d	1	1.32mi
206 Winchester St Unit 206 Brookline, MA	4.0	3.0	2500	$6,200	$2.48	4d	1	1.40mi

Listing history 21 events

1. 2026-06-18
   days on market $2,698,000 Active 84 DOM
2. 2026-06-17
   days on market $2,698,000 Active 83 DOM
3. 2026-06-16
   days on market $2,698,000 Active 82 DOM
4. 2026-06-15
   days on market $2,698,000 Active 81 DOM
5. 2026-06-13
   statusdays on market $2,698,000 Active 79 DOM
6. 2026-06-10
   status $2,698,000 Extended 75 DOM
7. 2026-06-09
   days on market $2,698,000 Active 75 DOM
8. 2026-06-08
   days on market $2,698,000 Active 74 DOM
9. 2026-06-07
   days on market $2,698,000 Active 73 DOM
10. 2026-06-04
    days on market $2,698,000 Active 70 DOM
11. 2026-06-03
    days on market $2,698,000 Active 69 DOM
12. 2026-06-02
    days on market $2,698,000 Active 68 DOM
13. 2026-06-01
    days on market $2,698,000 Active 67 DOM
14. 2026-05-31
    days on market $2,698,000 Active 66 DOM
15. 2026-05-02
    price $2,698,000 960-char remark

    Show marketing remark (960 chars)

    This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back living room with a gas fireplace, a gracious dining room with its own fireplace, and an eat-in kitchen that opens to a covered deck and patio—perfect for entertaining. The main level also includes a private home office, a powder room, and a sun-filled, oversized family room with direct access to a second patio. Upstairs on the 2nd and 3rd levels are five bedrooms and an additional home office, including a spacious primary suite with an ensuite bath, walk-in closet, and private deck. The lower level offers a dedicated exercise area, laundry room, abundant storage, and an attached two-car garage. Ideally located near The Street, Wegmans, Longwood Medical Area, public transportation, and Boston.

16. 2026-03-26
    listed $2,940,000 New 960-char remark

    Show marketing remark (960 chars)

    This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back living room with a gas fireplace, a gracious dining room with its own fireplace, and an eat-in kitchen that opens to a covered deck and patio—perfect for entertaining. The main level also includes a private home office, a powder room, and a sun-filled, oversized family room with direct access to a second patio. Upstairs on the 2nd and 3rd levels are five bedrooms and an additional home office, including a spacious primary suite with an ensuite bath, walk-in closet, and private deck. The lower level offers a dedicated exercise area, laundry room, abundant storage, and an attached two-car garage. Ideally located near The Street, Wegmans, Longwood Medical Area, public transportation, and Boston.

17. 2007-06-19
    historical 363-char remark

    Show marketing remark (363 chars)

    Chestnut Hill - Waterviews of The Reservoir and glorious outdoor recreational opportunities serve as the backdrop to this 10 room, 1925 brick Colonial with slate roof, 3 fireplaces, 3.5 baths, multiple decks and gazebo. A house of distinct merit. This home is minutes from Boston, The Heath School, Brookline High School, and a multitude of shopping alternatives.

18. 2007-06-18
    soldstatus $1,560,000 Sold 363-char remark

    Show marketing remark (363 chars)

    Chestnut Hill - Waterviews of The Reservoir and glorious outdoor recreational opportunities serve as the backdrop to this 10 room, 1925 brick Colonial with slate roof, 3 fireplaces, 3.5 baths, multiple decks and gazebo. A house of distinct merit. This home is minutes from Boston, The Heath School, Brookline High School, and a multitude of shopping alternatives.

19. 2007-06-18
    soldstatus $1,560,000

    Show marketing remark (363 chars)

    Chestnut Hill - Waterviews of The Reservoir and glorious outdoor recreational opportunities serve as the backdrop to this 10 room, 1925 brick Colonial with slate roof, 3 fireplaces, 3.5 baths, multiple decks and gazebo. A house of distinct merit. This home is minutes from Boston, The Heath School, Brookline High School, and a multitude of shopping alternatives.

20. 2007-04-02
    listed $1,575,000 363-char remark

    Show marketing remark (363 chars)

    Chestnut Hill - Waterviews of The Reservoir and glorious outdoor recreational opportunities serve as the backdrop to this 10 room, 1925 brick Colonial with slate roof, 3 fireplaces, 3.5 baths, multiple decks and gazebo. A house of distinct merit. This home is minutes from Boston, The Heath School, Brookline High School, and a multitude of shopping alternatives.

21. 1977-08-01
    soldstatus $107,500

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

Tax reassessment forecast MA · Partial reset (capped growth)

• Current annual tax: $24,283 · $2,024/mo
• Projected year-2 tax: $28,734 · $2,395/mo
• Expected delta: +$4,451/yr (+$371/mo · 18.3%)

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

Climate risk First Street

• 🌊 Flood 8/10 Severe FEMA zone X (unshaded) · 78% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥96°F today · 14 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 61% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $95,938
• − Mortgage interest: −$151,130
• − Property taxes: −$24,283
• − Insurance: −$14,157
• − Repairs & maintenance: −$7,675
• − Management: −$7,675
• − Depreciation: −$78,487
• Taxable loss: −$187,469
• Est. tax savings @ 24.0%: +$44,993
• After-tax cash flow: $-87,439/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: Brookline
• NCES district ID: 2503150
• Math proficiency: 66% ▼ -8.00%
• Reading proficiency: 73% ▼ -4.00%
• Median HH income: $97,931
• Composite: 63.51/100
• National rank: #610
• State rank: #29 of 302 in MA

Livability — Brookline

• Score: 84/100
• State rank: #16
• US rank: #704

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Brookline, MA
• County: Norfolk County · 644,082 people
• City population: 76,871
• Metro: Boston-Cambridge-Newton, MA-NH
• Population (ZIP): 22,560
• Household income: $139,747
• Rent vs Own: 47.9% rent · 52.1% own
• Severe rent burden: 1138.0

Population outlook (Norfolk County) Hauer SSP2

• Today (2025): 737,259 people
• By 2030: 755,213 · +2.4%
• By 2040: 786,961 · +6.7%
• By 2050: 813,019 · +10.3%
• By 2075: 861,214 · +16.8%
• By 2100: 845,063 · +14.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (67%)
• Race & ethnicity: White 67% Asian 14% Two or more races 10% Hispanic / Latino 7% Black 4%
• Hispanic origin (detail): Puerto Rican 1% Cuban 1%
• Common ancestry: Scotch-Irish 6% Italian 4% Romanian 2%
• Foreign-born: 23% · Canada, China, South Korea
• Languages at home: 71% English-only · Chinese 6% Spanish 5% Other Indo-European 5%

Political lean MEDSL · Norfolk

• 2024 margin: Strong D (+28.8) · D 63.3% · R 34.6% · Other 2.1%
• 2008→2024 swing: +10.2pp toward D · 2008: 18.5pp · 2024: 28.8pp
• All cycles: 2024: D+28.8 2020: D+36.3 2016: D+27.9 2012: D+16.1 2008: D+18.5

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 15.27%
• Current HPI: 291.0769
• Rent YoY: ▲ 1.47%
• Metro: Boston-Cambridge-Newton, MA-NH
• 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

+2409.8% since first listed

7 events — show timeline

• 2026-05-02 Price Changed $2,698,000 MLS PIN
• 2026-03-26 Listed $2,940,000 MLS PIN
• 2007-06-19 Listing Removed — MLS PIN
• 2007-06-18 Sold (Public Records) $1,560,000 Public Records
• 2007-06-18 Sold (MLS) $1,560,000 MLS PIN
• 2007-04-02 Listed $1,575,000 MLS PIN
• 1977-08-01 Sold (Public Records) $107,500 Public Records

Property tax history

+2.9%/yr

Latest (2023): $24,283 · +2.7% YoY. Source: county tax records.