37 Prospect St · Greenwich, CT 06830

$1,699,000

7 bd · 3.5 ba · 2,592 sqft · MultiFamily public records · 26 Days on market

Built 1908 6,098 sqft lot

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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).

• Appreciation +8.4/10.0
• ARV discount +7.5/15.0
• Cash flow +7.2/30.0
• Schools +6.6/10.0
• Livability +4.0/5.0
• Rent growth +3.3/5.0
• Condition / age +2.5/5.0
• DSCR +1.4/10.0
• 1% rule +0.9/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 2 units. confirmed

Listing remarks MLS

Modern duplex renovated in 2002. Carport parking and lots of storage underneath. Water views from rear deck. Rear unit has a loft with high ceilings and Alcove or Study , possible home office use. R-6 Zone. Ten minute walk to Greenwich Train. There are many activities within walking distance. Live in one unit and rent other for extra income or rent both. For further details call L.B.

Key facts

• Private deck
• Fully renovated
• Separate laundry

Tags

• FULLY RENOVATED
• MODERN KITCHEN
• PRIVATE DECK
• OFF-STREET PARKING
• OPEN-CONCEPT EAT-IN KITCHEN
• SEPARATE LAUNDRY

Property features AI

Finance

• Financial info: Two rental units with current monthly rents reported: Unit 1 $3,500; Unit 2 $5,500

Exterior

• Parking: Off-street parking with space for 4 vehicles
• Utilities: Public water
• Home design: Built in 1908, effectively updated in 2023; Vinyl siding; Asphalt roof
• Construction: Vinyl siding construction; Asphalt roof; Year built 1908 (effective year 2023)
• Exterior features: Public water; Zoned R-6

Interior

• Kitchen: Unit 1: one kitchen on first floor; Unit 2: one kitchen on second floor
• Bedrooms: Unit 1: one bedroom on the main level and two bedrooms on the second floor; Unit 2: three bedrooms on the third floor
• Bathrooms: Three total bathrooms; Unit 1: one full bath on second floor and one powder room on first floor; Unit 2: one full bath on second floor and one full bath on third floor
• Heating & cooling: Natural gas heating with hot water system; Window air conditioning units
• Interior features: Two-unit building (duplex/multi-family)
• Laundry & utility: Unit 1: laundry room on second floor; Unit 2: laundry room on third floor

What this means for you Summary

Snapshot

• This is a 2 × 3-bed/1.5-bath units multifamily listed at $1.70M.

Deal economics

• At list price, monthly cash flow is $-2k ($-28k/yr) — negative. Per door: $-1k/mo.
• To cash-flow at today's rent, offer at most $1.28M (24.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.00M (41.0% below list).
• Recommended offer: $1.00M (41.0% below list) — sets the bar for 1% rule.
• Cap rate 4.7% vs local median 1.1% in Greenwich — 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 80/100 on livability (#23 in CT, #1,655 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, health & safety A+; Watch: amenities D, cost of living F.
• Greenwich School District (suburban): math 64% / reading 73% proficiency, ranked #12 of 153 in CT (top 8%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 11% free/reduced lunch — higher-income household profile.
• Zoned schools: Hamilton Avenue School (math 32% / reading 47%, grade F, #298 of 553 statewide, top 56%, 294 students, 56% FRL); Western Middle School (math 50% / reading 59%, grade B-, #67 of 175 statewide, top 39%, 617 students, 38% FRL) — zoned schools average 47% FRL vs 11% district-wide (36 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Zoned-school proficiency averages 47% at this address vs 68% district-wide (-22 pts) — the specific schools serving this property underperform the Greenwich School District average; the district grade overstates school quality for this exact location.
• Market conditions: Rents rising (+3.4%/yr); 128 active listings in the ZIP; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).

Forward outlook

• In year one you build about $129k of equity ($12k loan paydown + $117k appreciation (6.9% local appreciation)).
• By year 2, paydown + projected appreciation supports a ~$206k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 26 days — a 2% lower offer ($1.67M) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 30y 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 $695k; list at $1.70M implies a 144% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo; built in 1908 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe flood risk; major wind risk, 60% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,001,800 (41.0% 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. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1908 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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 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: 0.59% ✗
• Cap rate: 4.66%
• Cash-on-cash: -5.84%
• DSCR: 0.74
• GRM: 14.1

CMA / ARV

No comps found within radius.

Projected returns pro-forma

6.89% appreciation · 3.36% rent growth · sell at horizon

5-year hold

• IRR: 12.9%
• Equity multiple: 1.91×
• Total profit: $433,858
• Equity at exit: $1,165,371

10-year hold

• IRR: 13.4%
• Equity multiple: 3.90×
• Total profit: $1,381,429
• Equity at exit: $2,202,902

Cash invested: $475,720 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Connecticut: 27 Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

Methodology + full state rankings →

ZIP-level market 06830

• Home prices YoY: 4.1%
• Rents YoY: 3.4%
• Active inventory: 128
• Price-to-rent: 28.3×

Monthly cashflow live

• Estimated rent: $10,018 high
• Mortgage (P&I): −$8,910
• Tax from tax record: −$613 /mo · $7,352/yr
• Insurance: −$708
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,104
• Net cashflow: $-2,372

Break-even live

Break-even rent $13,020

Max offer price $1,280,039

Occupancy floor —

Sensitivity live

Price	-10% $-1,410	-5% $-1,891	+0% $-2,372	+5% $-2,853	+10% $-3,333
Rent	-10% $-3,163	-5% $-2,767	+0% $-2,372	+5% $-1,976	+10% $-1,580
Rate	-1.0pp $-1,516	-0.5pp $-1,940	base $-2,372	+0.5pp $-2,812	+1.0pp $-3,260

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

Units	Beds	Baths	Est. rent
▸ 2× units	3	1.5	$10,018
Total (2 units)			$10,018

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: $424,750
• Closing costs: $50,970
• Reserves months: —
• Total cash needed: —

Listing history 31 events

1. 2026-06-21
   days on market $1,699,000 Active 26 DOM
2. 2026-06-18
   days on market $1,699,000 Active 23 DOM
3. 2026-06-17
   days on market $1,699,000 Active 22 DOM
4. 2026-06-16
   days on market $1,699,000 Active 21 DOM
5. 2026-06-15
   days on market $1,699,000 Active 20 DOM
6. 2026-06-13
   days on market $1,699,000 Active 18 DOM
7. 2026-06-10
   days on market $1,699,000 Active 15 DOM
8. 2026-06-09
   days on market $1,699,000 Active 14 DOM
9. 2026-06-08
   days on market $1,699,000 Active 13 DOM
10. 2026-06-07
    days on market $1,699,000 Active 12 DOM
11. 2026-06-03
    days on market $1,699,000 Active 8 DOM
12. 2026-06-03
    days on market $1,699,000 Active 7 DOM
13. 2026-06-01
    days on market $1,699,000 Active 6 DOM
14. 2026-05-31
    days on market $1,699,000 Active 5 DOM
15. 2026-05-21
    listed $1,699,000 Active
16. 2020-05-26
    historical Temp Off Market
17. 2020-03-13
    listed $1,150,000 Active
18. 2015-04-10
    soldstatus $695,000 388-char remark

    Show marketing remark (388 chars)

    Modern duplex renovated in 2002. Carport parking and lots of storage underneath. Water views from rear deck. Rear unit has a loft with high ceilings and Alcove or Study , possible home office use. R-6 Zone. Ten minute walk to Greenwich Train. There are many activities within walking distance. Live in one unit and rent other for extra income or rent both. For further details call L.B.

19. 2015-04-10
    soldstatus $695,000

    Show marketing remark (388 chars)

    Modern duplex renovated in 2002. Carport parking and lots of storage underneath. Water views from rear deck. Rear unit has a loft with high ceilings and Alcove or Study , possible home office use. R-6 Zone. Ten minute walk to Greenwich Train. There are many activities within walking distance. Live in one unit and rent other for extra income or rent both. For further details call L.B.

20. 2015-03-27
    historical 388-char remark

    Show marketing remark (388 chars)

    Modern duplex renovated in 2002. Carport parking and lots of storage underneath. Water views from rear deck. Rear unit has a loft with high ceilings and Alcove or Study , possible home office use. R-6 Zone. Ten minute walk to Greenwich Train. There are many activities within walking distance. Live in one unit and rent other for extra income or rent both. For further details call L.B.

21. 2015-03-25
    historical
22. 2015-01-20
    listed $699,000
23. 2015-01-09
    listed $699,000 388-char remark

    Show marketing remark (388 chars)

    Modern duplex renovated in 2002. Carport parking and lots of storage underneath. Water views from rear deck. Rear unit has a loft with high ceilings and Alcove or Study , possible home office use. R-6 Zone. Ten minute walk to Greenwich Train. There are many activities within walking distance. Live in one unit and rent other for extra income or rent both. For further details call L.B.

24. 2014-09-17
    historical
25. 2014-09-17
    historical
26. 2013-10-17
    listed $750,000
27. 2013-10-05
    listed $750,000
28. 1997-05-02
    soldstatus $240,000
29. 1997-03-10
    soldstatus
30. 1996-08-30
    listed $269,000
31. 1990-03-30
    soldstatus $192,500

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $7,352 · $613/mo
• Projected year-2 tax: $21,855 · $1,821/mo
• Expected delta: +$14,503/yr (+$1,209/mo · 197.3%)

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

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone X (shaded) · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥98°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 60% chance of damaging wind over 30 yrs
• 🫁 Air quality 6/10 Major 9 unhealthy d/yr today · 13 by 30 yrs out

Taxation est. · year 1

• Rental income: $120,216
• − Mortgage interest: −$95,170
• − Property taxes: −$7,352
• − Insurance: −$9,162
• − Repairs & maintenance: −$9,617
• − Management: −$9,617
• − Depreciation: −$49,425
• Taxable loss: −$60,128
• Est. tax savings @ 24.0%: +$14,431
• After-tax cash flow: $-14,029/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: Greenwich School District
• NCES district ID: 0901710
• Math proficiency: 64% ▼ -7.00%
• Reading proficiency: 73% ▼ -5.00%
• Median HH income: $129,257
• Composite: 65.67/100
• National rank: #461
• State rank: #12 of 153 in CT

Livability — Greenwich

• Score: 80/100
• State rank: #23
• US rank: #1655

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Greenwich, CT
• County: Fairfield County · 765,532 people
• City population: 47,954
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 24,880
• Household income: $146,654
• Rent vs Own: 42.6% rent · 57.4% own
• Severe rent burden: 1088.0

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.55)
• Race & ethnicity: White 64% Hispanic / Latino 18% Two or more races 10% Asian 6% Black 5%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1% Dominican 1%
• Common ancestry: Romanian 3% Lithuanian 2% Scotch-Irish 2%
• Foreign-born: 24% · Canada, Jamaica, China
• Languages at home: 72% English-only · Spanish 12% Other Indo-European 5% Russian/Polish/Slavic 3%

Political lean MEDSL · Western Connecticut

• 2024 margin: D (+19.1) · D 58.8% · R 39.7% · Other 1.6%
• All cycles: 2024: D+19.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 6.89%
• Current HPI: 173.5938
• Rent YoY: ▲ 3.36%
• Metro: Bridgeport-Stamford-Norwalk, CT
• State GDP YoY: ▲ 1.06%
• F500 in state: 38

Industry mix (Fortune 500 HQ in CT)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$38B
▸Insurance	3	$71B
▸Financial Services	2	$25B
▸Transportation / Logistics	2	$18B
▸Healthcare	1	$247B
▸Telecommunications	1	$55B

Price history

+782.6% since first listed

17 events — show timeline

• 2026-05-21 Listed $1,699,000 GMLS
• 2020-05-26 Delisted — GMLS
• 2020-03-13 Listed $1,150,000 GMLS
• 2015-04-10 Sold (Public Records) $695,000 Public Records
• 2015-04-10 Sold (MLS) $695,000 Smart MLS
• 2015-03-27 Listing Removed — Smart MLS
• 2015-03-25 Listing Removed — Smart MLS
• 2015-01-20 Listed $699,000 Smart MLS
• 2015-01-09 Listed $699,000 Smart MLS
• 2014-09-17 Listing Removed — Smart MLS
• 2014-09-17 Listing Removed — Smart MLS
• 2013-10-17 Listed $750,000 Smart MLS
• 2013-10-05 Listed $750,000 Smart MLS
• 1997-05-02 Sold (Public Records) $240,000 Public Records
• 1997-03-10 Sold (MLS) — GMLS
• 1996-08-30 Listed $269,000 GMLS
• 1990-03-30 Sold (Public Records) $192,500 Public Records

Property tax history

+6.8%/yr

Latest (2023): $7,352 · +0.9% YoY. Source: county tax records.