27 Park Ave · Old Greenwich, CT 06870

$1,795,000

4 bd · 1.0 ba · 1,080 sqft · SingleFamily public records · 6 Days on market

Built 1949 9,583 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 +9.7/10.0
• Cash flow +8.0/30.0
• ARV discount +7.5/15.0
• Schools +6.6/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.1/10.0
• 1% rule +1.5/10.0

Listing remarks MLS

Build your dream home on this lovely southwest-facing 0.22-acre lot, ideally located south of the Village in sought-after Old Greenwich. Just around the corner from the train, town, schools, Tod's Point beach, and Binney Park, the location is truly exceptional. Surrounded by beautiful homes and featuring advantageous setbacks, this property offers the perfect setting to create a custom new residence. Property to be sold in as-is condition. Survey available in the documents tab. Appointments are required to visit and walk the property. Please contact your Realtor to arrange access through the Listing Agent

Key facts

• 9,583 sq ft lot
• Built 1949
• Listed 6 days

Property features AI

Exterior

• Utilities: Public water
• Home design: Single-family residence; Built in 1949; Asphalt roof; Clapboard siding; Zoned R-12
• Construction: Clapboard construction; Asphalt roof; Built in 1949
• Exterior features: Level, park-like lot

Interior

• Bathrooms: 1 full bathroom
• Interior features: Full basement; No fireplaces

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $1.79M.

Deal economics

• At list price, monthly cash flow is $-2k ($-22k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.48M (17.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.17M (35.0% below list).
• Recommended offer: $1.17M (35.0% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 68/100 on livability (#108 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, commute F, 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: Old Greenwich School (math 72% / reading 82%, grade A, #28 of 553 statewide, top 7%, 406 students, 2% FRL); Eastern Middle School (math 75% / reading 81%, grade A+, #2 of 175 statewide, top 1%, 784 students, 6% FRL); Greenwich High School (math 59% / reading 78%, grade B, #23 of 194 statewide, top 12%, 2,668 students, 20% FRL) — zoned schools at 9% FRL track the district average.
• Market conditions: 49 active listings in the ZIP; 13 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• At $11,675/mo this rent would consume 56% of the median local household income ($250k/yr) (locally 143% 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 $181k of equity ($12k loan paydown + $169k appreciation (9.4% local appreciation)).
• By year 2, paydown + projected appreciation supports a ~$291k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• Only 6 days on market — expect competitive offers; lowballing is unlikely to land.
• 2 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 1949 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 72% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,167,516 (35.0% 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. Built in 1949 — 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. 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: 0.65% ✗
• Cap rate: 5.09%
• Cash-on-cash: -4.30%
• DSCR: 0.81
• GRM: 12.8

CMA / ARV

No comps found within radius.

Projected returns pro-forma

9.39% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 19.9%
• Equity multiple: 2.57×
• Total profit: $787,820
• Equity at exit: $1,537,909

10-year hold

• IRR: 18.3%
• Equity multiple: 5.76×
• Total profit: $2,391,585
• Equity at exit: $3,235,777

Cash invested: $502,600 (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 06870

• Home prices YoY: 4.8%
• Active inventory: 49
• Price-to-rent: 12.8×

Monthly cashflow live

• Estimated rent: $11,675 high
• Mortgage (P&I): −$9,413
• Tax from tax record: −$863 /mo · $10,357/yr
• Insurance: −$748
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,452
• Net cashflow: $-1,801

Break-even live

Break-even rent $13,955

Max offer price $1,476,881

Occupancy floor —

Sensitivity live

Price	-10% $-785	-5% $-1,293	+0% $-1,801	+5% $-2,309	+10% $-2,817
Rent	-10% $-2,723	-5% $-2,262	+0% $-1,801	+5% $-1,340	+10% $-878
Rate	-1.0pp $-897	-0.5pp $-1,344	base $-1,801	+0.5pp $-2,266	+1.0pp $-2,739

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: $448,750
• Closing costs: $53,850
• Reserves months: —
• Total cash needed: —

Rent comps 13 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
4 Highview Ave Old Greenwich, CT	3.0	2.5	1092	$10,000	$9.16	23d	1	0.18mi
143 Sound Beach Ave Old Greenwich, CT	1.0–3.0	1.0–3.0	1269	$12,985	$10.23	0d	1	0.30mi
51 Forest Ave Old Greenwich, CT	3.0	3.0	1737	$8,150	$4.69	5d	2	0.33mi
51 Benjamin St Old Greenwich, CT	3.0	1.5	1462	$8,500	$5.81	21d	1	0.39mi
30 Noble St Stamford, CT	3.0	1.5	1304	$5,500	$4.22	5d	1	0.83mi
39 Southfield Ave Unit A Stamford, CT	3.0	1.0	1000	$3,399	$3.40	45d	1	1.12mi
37 Southfield Ave Unit A Stamford, CT	3.0	1.0	1000	$3,199	$3.20	45d	1	1.12mi
37 Southfield Ave Stamford, CT	3.0	1.0	1000	$3,099	$3.10	25d	1	1.12mi
30 Mary Ln Riverside, CT	3.0	1.5	1255	$6,200	$4.94	16d	1	1.20mi
10 Miltiades Ave Riverside, CT	3.0	2.0	1477	$7,600	$5.15	16d	1	1.23mi
45 N Sound Beach Ave Riverside, CT	3.0	2.0	1344	$9,500	$7.07	25d	1	1.23mi
45 Thornhill Rd Riverside, CT	3.0	2.0	1386	$6,500	$4.69	25d	1	1.39mi
18 Cary Rd Riverside, CT	3.0	2.0	1440	$6,950	$4.83	5d	1	1.48mi

Listing history 5 events

1. 2026-06-03
   statusdays on market $1,795,000 Pending 6 DOM
2. 2026-06-01
   days on market $1,795,000 Active 5 DOM
3. 2026-05-31
   days on market $1,795,000 Active 4 DOM
4. 2026-05-22
   historical $1,795,000 689-char remark

   Show marketing remark (612 chars)

   Build your dream home on this lovely southwest-facing 0.22-acre lot, ideally located south of the Village in sought-after Old Greenwich. Just around the corner from the train, town, schools, Tod's Point beach, and Binney Park, the location is truly exceptional. Surrounded by beautiful homes and featuring advantageous setbacks, this property offers the perfect setting to create a custom new residence. Property to be sold in as-is condition. Survey available in the documents tab. Appointments are required to visit and walk the property. Please contact your Realtor to arrange access through the Listing Agent

5. 2026-05-22
   historical $1,795,000

   Show marketing remark (612 chars)

   Build your dream home on this lovely southwest-facing 0.22-acre lot, ideally located south of the Village in sought-after Old Greenwich. Just around the corner from the train, town, schools, Tod's Point beach, and Binney Park, the location is truly exceptional. Surrounded by beautiful homes and featuring advantageous setbacks, this property offers the perfect setting to create a custom new residence. Property to be sold in as-is condition. Survey available in the documents tab. Appointments are required to visit and walk the property. Please contact your Realtor to arrange access through the Listing Agent

ⓘ 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: $10,357 · $863/mo
• Projected year-2 tax: $24,385 · $2,032/mo
• Expected delta: +$14,028/yr (+$1,169/mo · 135.4%)

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

Climate risk First Street

• 🌊 Flood 3/10 Moderate FEMA zone X (unshaded) · 7% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥98°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 72% 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: $140,102
• − Mortgage interest: −$100,548
• − Property taxes: −$10,357
• − Insurance: −$8,975
• − Repairs & maintenance: −$11,208
• − Management: −$11,208
• − Depreciation: −$52,218
• Taxable loss: −$54,412
• Est. tax savings @ 24.0%: +$13,059
• After-tax cash flow: $-8,551/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 — Old Greenwich

• Score: 68/100
• State rank: #108
• US rank: #9415

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Old Greenwich, CT
• County: Fairfield County · 765,532 people
• City population: 7,903
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 7,864
• Household income: $250,001
• Rent vs Own: 16.1% rent · 83.9% own
• Severe rent burden: 143.0

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (75%)
• Race & ethnicity: White 75% Two or more races 10% Asian 9% Hispanic / Latino 8% Black 2%
• Hispanic origin (detail): Puerto Rican 2% Salvadoran 1%
• Common ancestry: Romanian 5% Slovak 3% Estonian 2%
• Foreign-born: 21% · Canada, China, Jamaica
• Languages at home: 82% English-only · Other Indo-European 7% Spanish 5% Chinese 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: ▲ 9.39%
• Current HPI: 205.9983
• Rent YoY: —
• 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

+0.0% since first listed

6 events — show timeline

• 2026-06-02 Pending — GMLS
• 2026-06-02 Pending — GMLS
• 2026-05-27 Listed $1,795,000 GMLS
• 2026-05-27 Listed $1,795,000 GMLS
• 2026-05-22 Coming Soon $1,795,000 GMLS
• 2026-05-22 Coming Soon $1,795,000 GMLS

Property tax history

+2.0%/yr

Latest (2023): $10,357 · +0.9% YoY. Source: county tax records.