50 Valleywood Rd · Cos Cob, CT 06807

$1,050,000

4 bd · 2.0 ba · 1,954 sqft · SingleFamily public records · 32 Days on market

Built 1940 $537/sqft · 41% below area Est $1779k · 41% under

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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 +26.0/30.0
• ARV discount +15.0/15.0
• Appreciation +9.0/10.0
• DSCR +8.7/10.0
• Schools +6.6/10.0
• 1% rule +6.1/10.0
• Livability +3.7/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Fabulous opportunity to personalize this home & make it your own! Located on a coveted, tree lined street, with a charming, classic neighborhood feel! Close to beaches, parks, restaurants and shops! Minutes to train and I 95 for an easy commute/trip into NYC! This one has it all!

Key facts

• Close to parks
• Close to restaurants
• Tree lined street

Tags

• TREE LINED STREET
• CLOSE TO BEACHES
• CLOSE TO PARKS
• CLOSE TO RESTAURANTS
• CLOSE TO SHOPS
• EASY COMMUTE

Property features AI

Exterior

• Parking: Attached garage (1 car)
• Utilities: Public sewer; Utilities: see remarks
• Home design: Single-family residence
• Construction: Vinyl siding construction
• Exterior features: Vinyl siding; Not waterfront

Interior

• Kitchen: Microwave
• Bedrooms: Rooms total: 6
• Bathrooms: 2 full bathrooms
• Heating & cooling: Oil heating; Wall/window air conditioning units
• Interior features: First-floor bedroom; One fireplace

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $1.05M.

Deal economics

• At list price, monthly cash flow is $3k ($31k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($12k rent vs $1.05M).
• Recommended offer: $1.02M (3.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 73/100 on livability (#72 in CT) — a middle-class / working-renter tenant base. Strengths: schools A+, crime A+, employment A+; Watch: housing D+, amenities F, commute 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.
• Market conditions: 31 active listings in the ZIP; 21 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).

Forward outlook

• In year one you build about $90k of equity ($7k loan paydown + $83k appreciation (7.9% local appreciation)).
• At projected returns (7.9% appreciation + 3.0% rent growth), your $294k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$144k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 32 days — a 3% lower offer ($1.02M) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts 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.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major flood risk; major wind risk, 67% 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 $1,018,500 (3.0% below list)

Questions for the listing agent

1. It's been on market 32 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
5. 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.
6. 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.
7. 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: 1.11% ✓
• Cap rate: 9.26%
• Cash-on-cash: 10.61%
• DSCR: 1.47
• GRM: 7.5

CMA / ARV

• ARV (median comp): $1,779,174
• List price: $1,050,000
• Delta: -40.98%
• 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
52 Valleywood Rd	0.01mi	4/3.0	1,944 (-0%)	1mo	$1,855,000	$954	94
15 Ridge Rd	0.09mi	4/2.0	2,073 (+6%)	8mo	$1,420,000	$685	79
74 Valleywood Rd	0.13mi	4/2.5	1,858 (-5%)	10mo	$1,775,000	$955	75
53 Valleywood Rd	0.03mi	3/2.0 (-1)	1,840 (-6%)	12mo	$1,550,000	$842	74
68 Valleywood Rd	0.10mi	3/2.0 (-1)	2,096 (+7%)	8mo	$1,610,000	$768	72
10 Jackson St	0.11mi	3/3.0 (-1)	1,990 (+2%)	17mo	$1,175,000	$590	68
57 Orchard St	0.28mi	3/2.5 (-1)	1,836 (-6%)	11mo	$1,200,000	$654	61
4 Ponderosa Dr	0.42mi	4/3.0	1,856 (-5%)	11mo	$2,040,000	$1,099	59
39 Indian Field Rd	0.49mi	3/2.0 (-1)	1,791 (-8%)	5mo	$2,105,000	$1,175	55
42 Mead Ave	0.52mi	3/2.0 (-1)	1,833 (-6%)	7mo	$1,125,000	$614	54
11 Mill Pond Ct	0.42mi	3/3.0 (-1)	1,795 (-8%)	10mo	$2,000,000	$1,114	50
75 Loughlin Ave	0.67mi	4/3.5	2,230 (+14%)	10mo	$2,180,000	$978	31

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

Projected returns pro-forma

7.9% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 28.0%
• Equity multiple: 3.01×
• Total profit: $591,504
• Equity at exit: $790,880

10-year hold

• IRR: 25.2%
• Equity multiple: 6.42×
• Total profit: $1,592,443
• Equity at exit: $1,563,416

Cash invested: $294,000 (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 06807

• Home prices YoY: 4.3%
• Active inventory: 31
• Price-to-rent: 7.5×

Monthly cashflow live

• Estimated rent: $11,634 high
• Mortgage (P&I): −$5,506
• Tax from tax record: −$646 /mo · $7,756/yr
• Insurance: −$438
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,443
• Net cashflow: $2,600

Break-even live

Break-even rent $8,342

Max offer price $1,050,000

Occupancy floor 73%

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: $262,500
• Closing costs: $31,500
• Reserves months: —
• Total cash needed: —

Rent comps 21 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
11 Annjim Dr Greenwich, CT	5.0	4.0	2417	$19,500	$8.07	14d	1	0.14mi
9 Valleywood Rd Cos Cob, CT	5.0	3.0	2348	$13,500	$5.75	44d	1	0.23mi
14 Cos Cob Ave Unit 3 Cos Cob, CT	3.0	2.5	1900	$6,500	$3.42	44d	1	0.41mi
28 Pleasant St Cos Cob, CT	4.0	2.5	2140	$6,250	$2.92	12d	1	0.42mi
78 River Rd #15 Cos Cob, CT	3.0	2.5	2381	$12,000	$5.04	44d	1	0.52mi
78 River Rd #15 Cos Cob, CT	3.0	3.5	2381	$12,000	$5.04	44d	1	0.52mi
81 Cos Cob Ave Unit A Cos Cob, CT	3.0	2.0	1461	$5,900	$4.04	3d	1	0.62mi
3 River Rd Unit 3 Cos Cob, CT	3.0	1.0	1500	$3,150	$2.10	44d	1	0.69mi
18 Cary Rd Riverside, CT	3.0	2.0	1440	$6,950	$4.83	3d	1	0.79mi
45 Thornhill Rd Riverside, CT	3.0	2.0	1386	$6,500	$4.69	24d	1	0.89mi
17 Circle Dr Greenwich, CT	3.0	3.0	1911	$7,500	$3.92	14d	1	0.91mi
44 Riverside Ln Riverside, CT	3.0	3.5	2404	$19,000	$7.90	3d	1	0.92mi
15 Dandy Dr Cos Cob, CT	3.0	2.0	1762	$6,500	$3.69	21d	1	0.98mi
10 Miltiades Ave Riverside, CT	3.0	2.0	1477	$7,600	$5.15	14d	1	1.01mi
38 Sheephill Rd Riverside, CT	3.0	2.5	2600	$8,200	$3.15	44d	1	1.05mi
116 E Elm St Unit A Greenwich, CT	3.0	3.5	2150	$7,750	$3.60	3d	1	1.30mi
45 N Sound Beach Ave Riverside, CT	3.0	2.0	1344	$9,500	$7.07	24d	1	1.31mi
43 Church St Unit 1 Greenwich, CT	3.0	2.0	1319	$3,975	$3.01	21d	1	1.32mi
1 Ernel Dr Riverside, CT	5.0	3.5	2517	$13,000	$5.16	21d	1	1.36mi
8 Perry Pl Riverside, CT	4.0	3.0	2556	$11,500	$4.50	21d	1	1.44mi
257 Bruce Park Ave Unit B Greenwich, CT	3.0	3.5	2270	$11,750	$5.18	14d	1	1.49mi

Listing history 8 events

1. 2026-06-07
   statusdays on market $1,050,000 Pending 32 DOM
2. 2026-06-03
   days on market $1,050,000 Active 30 DOM
3. 2026-06-03
   days on market $1,050,000 Active 29 DOM
4. 2026-06-01
   days on market $1,050,000 Active 28 DOM
5. 2026-05-31
   days on market $1,050,000 Active 27 DOM
6. 2026-05-04
   listed $1,050,000 Active 284-char remark

   Show marketing remark (284 chars)

   Fabulous opportunity to personalize this home & make it your own! Located on a coveted, tree lined street, with a charming, classic neighborhood feel! Close to beaches, parks, restaurants and shops! Minutes to train and I 95 for an easy commute/trip into NYC! This one has it all!

7. 2026-05-04
   listed $1,050,000 Active 284-char remark

   Show marketing remark (284 chars)

   Fabulous opportunity to personalize this home & make it your own! Located on a coveted, tree lined street, with a charming, classic neighborhood feel! Close to beaches, parks, restaurants and shops! Minutes to train and I 95 for an easy commute/trip into NYC! This one has it all!

8. 2026-05-01
   listed $1,050,000 Active

   Show marketing remark (286 chars)

   Fabulous opportunity to personalize this home & make it your own! Located on a coveted, tree lined street, with a charming, classic neighborhood feel! Close to beaches, parks, restaurants and shops! Minutes to train and I 95 for an easy commute/trip into NYC! This one has it all!

ⓘ 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: $7,756 · $646/mo
• Projected year-2 tax: $15,113 · $1,259/mo
• Expected delta: +$7,357/yr (+$613/mo · 94.9%)

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

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone X (unshaded) · 69% 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 67% 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: $139,603
• − Mortgage interest: −$58,816
• − Property taxes: −$7,756
• − Insurance: −$5,250
• − Repairs & maintenance: −$11,168
• − Management: −$11,168
• − Depreciation: −$30,545
• Taxable income: $14,899
• Est. tax owed @ 24.0%: −$3,576
• After-tax cash flow: $27,629/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 — Cos Cob

• Score: 73/100
• State rank: #72
• US rank: #5178

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Cos Cob, CT
• City population: 7,667
• Population (ZIP): 7,667

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.58)
• Race & ethnicity: White 63% Two or more races 15% Hispanic / Latino 13% Asian 7% Black 4%
• Hispanic origin (detail): Puerto Rican 6% Dominican 1%
• Common ancestry: Romanian 4% Estonian 4% Italian 3%
• Foreign-born: 24% · Canada, China, Jamaica
• Languages at home: 76% English-only · Other Indo-European 9% Spanish 6% Other Asian/Pacific 5%

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: ▲ 7.90%
• Current HPI: 191.0957
• Rent YoY: —
• Metro: —
• 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

+0.0% since first listed

6 events — show timeline

• 2026-06-05 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-06-05 Pending — Smart MLS
• 2026-06-05 Pending — GMLS
• 2026-05-04 Listed $1,050,000 Smart MLS
• 2026-05-04 Listed $1,050,000 OneKey® MLS as Distributed by MLS Grid
• 2026-05-01 Listed $1,050,000 GMLS

Property tax history

+2.3%/yr

Latest (2023): $7,756 · +0.9% YoY. Source: county tax records.