106 Orchard St · Cos Cob, CT 06807

$2,450,000

5 bd · 4.5 ba · 2,939 sqft · SingleFamily public records · 11 Days on market

Built 2008 0.40 ac lot Est $2316k · 6% over

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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 +9.0/10.0
• Schools +6.6/10.0
• Cash flow +6.1/30.0
• ARV discount +4.9/15.0
• Livability +3.7/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.4/10.0
• DSCR +0.4/10.0

Listing remarks

With open plan, high ceilings, and abundant natural light, this 5-bedroom home offers the best in convenience and privacy. Sidewalks connect the home to Cos Cob village restaurants & shops, and elementary, middle & high schools. Simply cross the street to the 170 acre Pomerance Park and Montgomery Pinetum nature preserves. Only minutes to I-95 & train but no highway or rail noise impact. Gourmet kitchen w/ Fr. doors to deck & flat, private backyard. 1st floor guest suite w/ full bath, kitchenette & separate entrance. On the 2nd floor is a luxurious primary suite w/ tub, separate shower, walk-in closet & balcony. 3 more bedrooms & hall bath w/ tub

Key facts

• Separate entrance
• Private backyard
• Gourmet kitchen

Tags

• HIGH CEILINGS
• ABUNDANT NATURAL LIGHT
• GOURMET KITCHEN
• PRIVATE BACKYARD
• GUEST SUITE
• SEPARATE ENTRANCE

Property features AI

Exterior

• Parking: 2-car garage with garage door opener
• Utilities: Public water
• Home design: Single family residence; Built in 2008 (effective year 2016); Asphalt roof; Vinyl siding; Architect-reported building area approximately 3539
• Construction: Vinyl siding construction; Asphalt roof; Finished full basement
• Exterior features: Balcony; Deck; Shed(s); Backlot; Level lot

Interior

• Kitchen: Eat-in kitchen
• Bathrooms: Four full bathrooms; One half bathroom (total 4.5 bathrooms)
• Heating & cooling: Central air conditioning; Natural gas heating with forced air
• Interior features: Eat-in kitchen; Separate shower; Whirlpool tub; Double-pane windows; Finished full basement; One fireplace

What this means for you Summary

Snapshot

• This is a 5-bed/4.5-bath single-family listed at $2.45M.

Deal economics

• At list price, monthly cash flow is $-5k ($-56k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.63M (33.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.31M (46.5% below list).
• Recommended offer: $1.31M (46.5% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 73/100 on livability (#72 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety B; 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.
• Zoned schools: Cos Cob School (math 62% / reading 67%, grade B, #118 of 553 statewide, top 23%, 337 students, 13% FRL); Central Middle School (math 60% / reading 71%, grade A-, #26 of 175 statewide, top 16%, 506 students, 18% FRL).
• Market conditions: 31 active listings in the ZIP; 20 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 $211k of equity ($17k loan paydown + $194k appreciation (7.9% local appreciation)).
• By year 2, paydown + projected appreciation supports a ~$337k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• Only 11 days on market — expect competitive offers; lowballing is unlikely to land.
• 12 sale attempts since 20y 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 $750k; list at $2.45M implies a 227% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo.
• Climate carrying-cost: severe 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 $1,310,834 (46.5% 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. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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. 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?
6. 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.
7. 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.
8. 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: 0.54% ✗
• Cap rate: 4.04%
• Cash-on-cash: -8.06%
• DSCR: 0.64
• GRM: 15.6

CMA / ARV

• ARV (on-the-fly): $2,315,932
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
44 Bote Rd	0.23mi	4/4.5 (-1)	2,916 (-1%)	9mo	$2,605,000	$893	75
108 Orchard St	0.02mi	4/3.5 (-1)	2,802 (-5%)	11mo	$2,300,000	$821	73
71 Valleywood Rd	0.25mi	4/3.5 (-1)	2,965 (+1%)	13mo	$2,000,000	$675	67
85 Valleywood Rd	0.18mi	4/3.5 (-1)	3,272 (+11%)	13mo	$2,105,000	$643	53
64 Orchard St	0.29mi	5/3.5	3,254 (+11%)	14mo	$1,953,000	$600	53
99 Stanwich Rd	0.39mi	4/3.5 (-1)	2,720 (-8%)	10mo	$2,850,000	$1,048	52
24 Valley Rd	0.54mi	4/4.5 (-1)	3,221 (+10%)	4mo	$2,400,000	$745	50
19 Pond Pl	0.75mi	5/4.0	3,023 (+3%)	10mo	$2,410,000	$797	50
113 Stanwich Rd	0.49mi	4/2.5 (-1)	2,824 (-4%)	11mo	$1,750,000	$620	49
4 Miami Ct	0.64mi	4/3.0 (-1)	2,765 (-6%)	3mo	$1,885,000	$682	47
1 Arrowhead Ln	0.52mi	4/3.5 (-1)	3,120 (+6%)	13mo	$2,460,000	$788	46
12 River Ln	0.68mi	4/2.5 (-1)	2,653 (-10%)	17mo	$2,225,000	$839	24

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: 13.6%
• Equity multiple: 2.02×
• Total profit: $696,337
• Equity at exit: $1,845,387

10-year hold

• IRR: 13.7%
• Equity multiple: 4.26×
• Total profit: $2,238,474
• Equity at exit: $3,647,971

Cash invested: $686,000 (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: 15.6×

Monthly cashflow live

• Estimated rent: $13,108 high
• Mortgage (P&I): −$12,848
• Tax from tax record: −$1,094 /mo · $13,124/yr
• Insurance: −$1,021
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,753
• Net cashflow: $-4,663

Break-even live

Break-even rent $19,010

Max offer price $1,626,346

Occupancy floor —

Sensitivity live

Price	-10% $-3,276	-5% $-3,969	+0% $-4,663	+5% $-5,356	+10% $-6,049
Rent	-10% $-5,698	-5% $-5,180	+0% $-4,663	+5% $-4,145	+10% $-3,627
Rate	-1.0pp $-3,429	-0.5pp $-4,039	base $-4,663	+0.5pp $-5,297	+1.0pp $-5,943

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: $612,500
• Closing costs: $73,500
• Reserves months: —
• Total cash needed: —

Rent comps 20 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
11 Osee Pl Cos Cob, CT	5.0	4.0	3112	$12,000	$3.86	44d	1	0.10mi
28 Pleasant St Cos Cob, CT	4.0	2.5	2140	$6,250	$2.92	12d	1	0.24mi
11 Annjim Dr Greenwich, CT	5.0	4.0	2417	$19,500	$8.07	15d	1	0.28mi
41 Grove St Cos Cob, CT	5.0	3.5	2787	$12,000	$4.31	44d	1	0.31mi
9 Valleywood Rd Cos Cob, CT	5.0	3.0	2348	$13,500	$5.75	44d	1	0.58mi
1 Cary Rd Riverside, CT	4.0	3.5	3300	$13,500	$4.09	44d	1	0.81mi
40 Mianus View Ter Cos Cob, CT	5.0	3.5	2895	$14,500	$5.01	4d	1	0.90mi
40 Mianus View Ter Cos Cob, CT	4.0	3.5	2895	$14,500	$5.01	12d	1	0.90mi
25 Buxton Ln Riverside, CT	5.0	3.5	2780	$12,995	$4.67	24d	1	0.98mi
30 Bayside Ter Riverside, CT	4.0	3.5	3730	$25,000	$6.70	44d	1	1.06mi
24 Juniper Ln Riverside, CT	4.0	3.5	2843	$14,000	$4.92	4d	1	1.14mi
4 Wescott Ct Riverside, CT	4.0	4.5	3950	$15,000	$3.80	24d	1	1.19mi
15 Lancer Rd Riverside, CT	4.0	2.5	3031	$8,889	$2.93	24d	1	1.25mi
18 Cornelia Dr Greenwich, CT	4.0	3.5	2656	$12,250	$4.61	4d	1	1.34mi
1 Ernel Dr Riverside, CT	5.0	3.5	2517	$13,000	$5.16	22d	1	1.35mi
8 Perry Pl Riverside, CT	4.0	3.0	2556	$11,500	$4.50	22d	1	1.36mi
14 Rainbow Dr Riverside, CT	5.0	3.5	3510	$16,000	$4.56	24d	1	1.41mi
63 Sherwood Pl #63 Greenwich, CT	5.0	5.5	3072	$17,500	$5.70	4d	1	1.42mi
146 E Elm St Unit B Greenwich, CT	4.0	3.5	2809	$9,700	$3.45	19d	1	1.46mi
1 Crawford Ter Riverside, CT	4.0	4.0	2819	$18,000	$6.39	22d	1	1.48mi

Listing history 8 events

1. 2026-06-15
   statusdays on market $2,450,000 Pending 11 DOM
2. 2026-06-13
   days on market $2,450,000 Active 10 DOM
3. 2026-06-10
   days on market $2,450,000 Active 7 DOM
4. 2026-06-09
   days on market $2,450,000 Active 6 DOM
5. 2026-06-08
   days on market $2,450,000 Active 5 DOM
6. 2026-06-07
   days on market $2,450,000 Active 4 DOM
7. 2026-06-03
   remarks 671-char remark
8. 2026-06-03
   listed $2,450,000 Active 1 DOM

ⓘ 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: $13,124 · $1,094/mo
• Projected year-2 tax: $32,777 · $2,731/mo
• Expected delta: +$19,653/yr (+$1,638/mo · 149.7%)

ⓘ 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 (unshaded) · 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 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: $157,300
• − Mortgage interest: −$137,238
• − Property taxes: −$13,124
• − Insurance: −$12,916
• − Repairs & maintenance: −$12,584
• − Management: −$12,584
• − Depreciation: −$71,273
• Taxable loss: −$102,419
• Est. tax savings @ 24.0%: +$24,581
• After-tax cash flow: $-31,370/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

+236.1% since first listed

25 events — show timeline

• 2026-06-03 Listed $2,450,000 GMLS
• 2024-07-22 Listing Removed — Smart MLS
• 2024-07-19 Rental Removed $11,500 GMLS
• 2024-06-25 Listed for Rent $11,500 GMLS
• 2024-05-31 Listed $1,995,000 Smart MLS
• 2024-05-29 Listed $1,995,000 GMLS
• 2021-07-13 Listing Removed — Smart MLS
• 2021-07-13 Delisted — GMLS
• 2021-06-28 Listed $1,895,000 Smart MLS
• 2021-06-16 Listed $1,895,000 GMLS
• 2017-08-25 Delisted — GMLS
• 2017-08-24 Listing Removed — Smart MLS
• 2017-08-24 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2017-03-03 Listed $1,725,000 OneKey® MLS as Distributed by MLS Grid
• 2017-03-02 Listed $1,725,000 Smart MLS
• 2017-02-24 Listed $1,725,000 GMLS
• 2014-08-26 Listing Removed — Smart MLS
• 2014-08-15 Delisted — GMLS
• 2014-02-28 Listed $1,695,000 Smart MLS
• 2014-02-28 Listed $1,695,000 GMLS
• 2007-10-31 Sold (Public Records) $750,000 Public Records
• 2007-05-10 Sold (Public Records) $615,000 Public Records
• 2007-05-10 Sold (Public Records) $615,000 Public Records
• 2007-05-09 Sold (MLS) $615,000 GMLS
• 2006-10-16 Listed $729,000 GMLS

Property tax history

+0.1%/yr

Latest (2023): $13,124 · +0.9% YoY. Source: county tax records.