75 Lee St · Brookline, MA 02445

$3,950,000

4 bd · 4.5 ba · 3,484 sqft · SingleFamily public records · 57 Days on market

Built 1950 0.58 ac lot $1134/sqft · 50% above area Est $4913k · 20% 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
• 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 +0.0/30.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Direct and unbeatable water views of the 32-acre Brookline Reservoir Park. This one-of-a-kind sun-drenched contemporary home features spectacular scenic water and park views, decent upscale neighborhood and yet super convenience to city life. It is with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms. The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Special features also include a security system & a hydro-air Buderus boiler. Upon entering this house, you feel transported to a Zen peaceful sanctuary. Fabulous location, easy access to all that Brookline and Boston has to offer.

Key facts

• Water views
• Renovated bathrooms
• Maple flooring

Tags

• WATER VIEWS
• BROOKLINE RESERVOIR PARK
• SLATE ROOF
• MAPLE FLOORING
• RENOVATED BATHROOMS
• CUSTOM POGGENPOHL KITCHEN

What this means for you Summary

Snapshot

• This is a 4-bed/4.5-bath single-family listed at $3.95M.

Deal economics

• At list price, monthly cash flow is $-18k ($-221k/yr) — negative.
• To cash-flow at today's rent, offer at most $693k (82.5% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $770k (80.5% below list).
• Recommended offer: $693k (82.5% below list) — sets the bar for cash-flow.
• Cap rate 0.7% vs local median 1.2% in Brookline — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

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; 14 comparable units currently listed for rent nearby; rentals at typical pace (median 15d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 958 units permitted in Norfolk County in 2024 (305 in 5+ unit buildings).
• At $7,696/mo this rent would consume 66% 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 $422k of equity ($27k loan paydown + $395k 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 ~$679k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 57 days — a 3% lower offer ($3.83M) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 27y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $2.58M; list at $3.95M implies a 53% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate 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 $692,700 (82.5% 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 57 days. Have you received any prior offers? Is the seller open to a 82% concession, seller financing, or rate buy-down credit?
3. Built in 1950 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
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: 0.19% ✗
• Cap rate: 0.69%
• Cash-on-cash: -20.01%
• DSCR: 0.11
• GRM: 42.8

CMA / ARV

• ARV (median comp): $4,913,147
• List price: $3,950,000
• Delta: -19.60%
• 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	0.65mi	5/4.5 (+1)	3,658 (+5%)	1mo	$3,285,000	$898	55
24 Blake Rd	0.66mi	4/2.5	3,377 (-3%)	2mo	$2,850,000	$844	54
323 Clark Rd	0.73mi	5/4.5 (+1)	3,370 (-3%)	4mo	$2,995,000	$889	53
167 Willard Rd	0.67mi	4/3.5	3,298 (-5%)	9mo	$3,400,000	$1,031	48
185 Tappan St	0.66mi	5/5.5 (+1)	3,593 (+3%)	9mo	$4,350,000	$1,211	47
34 Hyslop Rd	0.52mi	5/4.5 (+1)	4,001 (+15%)	1mo	$4,125,000	$1,031	45
47 Cotswold Rd	0.65mi	5/3.5 (+1)	3,342 (-4%)	14mo	$3,218,000	$963	42
385 Lee St	0.64mi	4/3.5	3,094 (-11%)	10mo	$1,900,000	$614	39
164 Willard Rd	0.67mi	5/4.0 (+1)	3,214 (-8%)	13mo	$3,752,500	$1,168	38
342 Clark Rd	0.73mi	4/4.5	3,116 (-11%)	13mo	$2,700,000	$866	37
170 Reservoir Rd	0.61mi	5/3.0 (+1)	3,146 (-10%)	12mo	$2,850,000	$906	34
333 Clark Rd	0.74mi	5/3.5 (+1)	3,100 (-11%)	6mo	$2,487,000	$802	33

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: 10.4%
• Equity multiple: 1.87×
• Total profit: $963,633
• Equity at exit: $3,558,473

10-year hold

• IRR: 11.5%
• Equity multiple: 4.38×
• Total profit: $3,735,868
• Equity at exit: $7,673,981

Cash invested: $1,106,000 (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: 42.8×

Monthly cashflow live

• Estimated rent: $7,696 high
• Mortgage (P&I): −$20,714
• Tax from tax record: −$2,159 /mo · $25,904/yr
• Insurance: −$1,646
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,616
• Net cashflow: $-18,439

Break-even live

Break-even rent $31,036

Max offer price $692,700

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: $987,500
• Closing costs: $118,500
• Reserves months: —
• Total cash needed: —

Rent comps 14 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
161 Clinton Rd Brookline, MA	5.0	3.5	3494	$9,250	$2.65	43d	1	0.64mi
315 Goddard Ave #315 Brookline, MA	3.0	3.5	3500	$6,900	$1.97	24d	1	0.81mi
1728 Beacon St Brookline, MA	3.0	2.0	2350	$7,500	$3.19	5d	1	0.94mi
1716 Beacon St Brookline, MA	3.0	2.0	2500	$6,750	$2.70	5d	1	0.94mi
1714 Beacon St Brookline, MA	3.0	2.0	2350	$6,750	$2.87	12d	1	0.94mi
1714 Beacon St Unit 2 Brookline, MA	3.0	2.0	2350	$6,750	$2.87	5d	1	0.94mi
636 Washington St Unit 1281997P Brookline, MA	1.0–3.0	1.0–2.0	6216	$7,601	$1.22	10d	2	0.98mi
119 Westbourne Ter Brookline, MA	5.0	3.0	2400	$10,500	$4.38	43d	1	1.23mi
119 Westbourne Ter Brookline, MA	5.0	3.0	2375	$10,500	$4.42	23d	1	1.23mi
119 Westbourne Ter Unit 2 Brookline, MA	5.0	3.5	2400	$10,500	$4.38	5d	1	1.23mi
40 Atherton Rd Brookline, MA	5.0	2.0	2400	$7,500	$3.12	14d	1	1.32mi
58 Brook St Unit NA Brookline, MA	4.0	4.5	3150	$10,000	$3.17	24d	1	1.40mi
206 Winchester St Unit 206 Brookline, MA	4.0	3.0	2500	$6,200	$2.48	5d	1	1.42mi
115 Grove St Chestnut Hill, MA	3.0	3.0	2546	$5,400	$2.12	24d	1	1.48mi

Listing history 25 events

1. 2026-06-18
   days on market $3,950,000 Active 57 DOM
2. 2026-06-17
   days on market $3,950,000 Active 56 DOM
3. 2026-06-16
   days on market $3,950,000 Active 55 DOM
4. 2026-06-15
   days on market $3,950,000 Active 54 DOM
5. 2026-06-13
   days on market $3,950,000 Active 52 DOM
6. 2026-06-09
   days on market $3,950,000 Active 48 DOM
7. 2026-06-08
   days on market $3,950,000 Active 47 DOM
8. 2026-06-07
   days on market $3,950,000 Active 46 DOM
9. 2026-06-04
   days on market $3,950,000 Active 43 DOM
10. 2026-06-03
    days on market $3,950,000 Active 42 DOM
11. 2026-06-02
    days on market $3,950,000 Active 41 DOM
12. 2026-06-01
    days on market $3,950,000 Active 40 DOM
13. 2026-05-31
    days on market $3,950,000 Active 39 DOM
14. 2026-04-22
    listed $3,950,000 New 1006-char remark

    Show marketing remark (1006 chars)

    Direct and unbeatable water views of the 32-acre Brookline Reservoir Park. This one-of-a-kind sun-drenched contemporary home features spectacular scenic water and park views, decent upscale neighborhood and yet super convenience to city life. It is with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms. The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Special features also include a security system & a hydro-air Buderus boiler. Upon entering this house, you feel transported to a Zen peaceful sanctuary. Fabulous location, easy access to all that Brookline and Boston has to offer.

15. 2019-07-31
    soldstatus $2,579,000 Sold 995-char remark

    Show marketing remark (995 chars)

    Spectacular water views of Reservoir Park.This one of a kind sun drenched contemporary home with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms.The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Lower level entertainment room. The garage is unique and can be opened up to hold up to 5 cars or be used as a finished mudroom space and storage. Special features also include a security system & a hydro air Buderus boiler. Upon entering this home you feel transported to a zen peaceful sanctuary. Fabulous location, easy access to all that Boston has to offer. Heath School

16. 2019-04-25
    status Under Agreement 995-char remark

    Show marketing remark (995 chars)

    Spectacular water views of Reservoir Park.This one of a kind sun drenched contemporary home with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms.The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Lower level entertainment room. The garage is unique and can be opened up to hold up to 5 cars or be used as a finished mudroom space and storage. Special features also include a security system & a hydro air Buderus boiler. Upon entering this home you feel transported to a zen peaceful sanctuary. Fabulous location, easy access to all that Boston has to offer. Heath School

17. 2018-11-16
    listed $2,980,000 New 995-char remark

    Show marketing remark (995 chars)

    Spectacular water views of Reservoir Park.This one of a kind sun drenched contemporary home with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms.The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Lower level entertainment room. The garage is unique and can be opened up to hold up to 5 cars or be used as a finished mudroom space and storage. Special features also include a security system & a hydro air Buderus boiler. Upon entering this home you feel transported to a zen peaceful sanctuary. Fabulous location, easy access to all that Boston has to offer. Heath School

18. 2003-03-31
    soldstatus $1,100,000
19. 2003-03-28
    soldstatus $1,100,000
20. 2003-02-03
    historical
21. 2002-08-07
    listed $1,550,000
22. 1999-06-29
    soldstatus $815,000
23. 1999-06-28
    soldstatus $815,000
24. 1999-05-11
    historical
25. 1999-04-02
    listed $819,000

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

Tax reassessment forecast MA · Partial reset (capped growth)

• Current annual tax: $25,904 · $2,159/mo
• Projected year-2 tax: $37,244 · $3,104/mo
• Expected delta: +$11,340/yr (+$945/mo · 43.8%)

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

Climate risk First Street

• 🌊 Flood 5/10 Major FEMA zone X (unshaded) · 24% 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: $92,353
• − Mortgage interest: −$221,261
• − Property taxes: −$25,904
• − Insurance: −$19,750
• − Repairs & maintenance: −$7,388
• − Management: −$7,388
• − Depreciation: −$114,909
• Taxable loss: −$304,248
• Est. tax savings @ 24.0%: +$73,020
• After-tax cash flow: $-148,247/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

+382.3% since first listed

12 events — show timeline

• 2026-04-22 Listed $3,950,000 MLS PIN
• 2019-07-31 Sold (MLS) $2,579,000 MLS PIN
• 2019-04-25 Pending — MLS PIN
• 2018-11-16 Listed $2,980,000 MLS PIN
• 2003-03-31 Sold (MLS) $1,100,000 MLS PIN
• 2003-03-28 Sold (Public Records) $1,100,000 Public Records
• 2003-02-03 Listing Removed — MLS PIN
• 2002-08-07 Listed $1,550,000 MLS PIN
• 1999-06-29 Sold (Public Records) $815,000 Public Records
• 1999-06-28 Sold (MLS) $815,000 MLS PIN
• 1999-05-11 Listing Removed — MLS PIN
• 1999-04-02 Listed $819,000 MLS PIN

Property tax history

+3.1%/yr

Latest (2023): $25,904 · +2.7% YoY. Source: county tax records.