32 Steep Hill Rd · Weston, CT 06883

$2,595,000

6 bd · 6.5 ba · 7,050 sqft · Other · 72 Days on market

Built 1750 3.92 ac lot $368/sqft · at area comps Est $2688k · at est.

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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 +27.5/30.0
• DSCR +9.6/10.0
• ARV discount +9.1/15.0
• Schools +7.5/10.0
• 1% rule +7.0/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

This restored, 6,100 sf-expanded 18th century antique commands a view of its 1.24 ac, brook-fed lake; expansive lawn; raised beds; and 450 ft. bleached stone driveway. Your vision--Big Tented Celebrations,Fabulous Local Tomatoes--is correct. The former NYC chef's professional kitchen, wet bar, and 2 eat-in dining areas are open to the 5 rooms that circle around this heartbeat, making large gatherings feel and taste delicious. The antique's original entrance to a home office + fireplace (cozy, authentic) complete the floor. The 2nd floor offers 4 secondary beds/baths, a superior primary suite, and has a 600-sf bonus room with its own entrance and full kitchen. Generous third-level space fronted by a viewing balcony becomes the game/exercise/screening room you choose. Windows are featured everywhere, in particular note the sunroom array and the sitting room's 28ft of windowed walls. The separate 1,100 sf, 1-2 BR COTTAGE has had just 4 long-term tenants in the owners' 28 years. The COTTAGE rental income and tax/financial advantages make your net purchase price and occupancy exceedingly comfortable. The owner has prepared for final approvals a survey,building plans, and rendering package of a pool and surrounding deck connected to the home's 500sf front terrace. The buyer wishing the design can move forward with confidence in the sellers' careful efforts. A 2025, 95% efficient,state-of-the art, Navien natural gas boiler and HW installation has proven to be a gas bill slayer.

Key facts

• 3.92 acre lot
• 2 garage spots
• Built 1750

What this means for you Summary

Snapshot

• This is a 6-bed/6.5-bath other listed at $2.60M.

Deal economics

• At list price, monthly cash flow is $8k ($92k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($31k rent vs $2.60M).
• Recommended offer: $2.44M (6.0% below list) — sets the bar for market timing.
• Cap rate 9.8% vs local median 3.1% in Weston — 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: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Weston School District (suburban): math 68% / reading 77% proficiency, ranked #4 of 153 in CT (top 3%) — strong family-tenant draw, lease renewals of 3-5y typical; only 1% free/reduced lunch — higher-income household profile.
• Market conditions: 73 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $18k of loan paydown is wiped out by about $78k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $727k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($2.44M) is reasonable based on typical stale-listing flexibility.
• 12 sale attempts since 31y 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 $372k; list at $2.60M implies a 598% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1750 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% 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 $2,439,300 (6.0% below list)

Questions for the listing agent

1. It's been on market 72 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1750 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 1.20% ✓
• Cap rate: 9.82%
• Cash-on-cash: 12.61%
• DSCR: 1.56
• GRM: 7.0

CMA / ARV

• ARV (median comp): $2,688,422
• List price: $2,595,000
• Delta: -3.47%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 2.3%
• Equity multiple: 1.09×
• Total profit: $65,506
• Equity at exit: $386,923

10-year hold

• IRR: 11.9%
• Equity multiple: 1.94×
• Total profit: $682,460
• Equity at exit: $224,368

Cash invested: $726,600 (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 06883

• Active inventory: 73
• Price-to-rent: 7.0×

Monthly cashflow live

• Estimated rent: $31,103 medium
• Mortgage (P&I): −$13,608
• Tax from tax record: −$2,249 /mo · $26,988/yr
• Insurance: −$1,081
• HOA: −$0
• Vacancy / Maint / Mgmt: −$6,532
• Net cashflow: $7,633

Break-even live

Break-even rent $21,441

Max offer price $2,595,000

Occupancy floor 70%

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: $648,750
• Closing costs: $77,850
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
37 Beaverbrook Rd Weston, CT	5.0	4.5	6734	$35,000	$5.20	43d	1	0.28mi
29 Rogues Rdg Weston, CT	6.0	6.5	7649	$17,000	$2.22	2d	1	0.99mi

Listing history 40 events

1. 2026-06-18
   days on market $2,595,000 Active 72 DOM
2. 2026-06-17
   days on market $2,595,000 Active 71 DOM
3. 2026-06-16
   days on market $2,595,000 Active 70 DOM
4. 2026-06-15
   days on market $2,595,000 Active 69 DOM
5. 2026-06-13
   days on market $2,595,000 Active 67 DOM
6. 2026-06-13
   days on market $2,595,000 Active 66 DOM
7. 2026-06-10
   days on market $2,595,000 Active 64 DOM
8. 2026-06-09
   days on market $2,595,000 Active 63 DOM
9. 2026-06-08
   days on market $2,595,000 Active 62 DOM
10. 2026-06-07
    days on market $2,595,000 Active 61 DOM
11. 2026-06-03
    days on market $2,595,000 Active 57 DOM
12. 2026-06-03
    days on market $2,595,000 Active 56 DOM
13. 2026-06-01
    days on market $2,595,000 Active 55 DOM
14. 2026-05-31
    days on market $2,595,000 Active 54 DOM
15. 2026-04-08
    listed $2,595,000 Active 1495-char remark

    Show marketing remark (1495 chars)

    This restored, 6,100 sf-expanded 18th century antique commands a view of its 1.24 ac, brook-fed lake; expansive lawn; raised beds; and 450 ft. bleached stone driveway. Your vision--Big Tented Celebrations,Fabulous Local Tomatoes--is correct. The former NYC chef's professional kitchen, wet bar, and 2 eat-in dining areas are open to the 5 rooms that circle around this heartbeat, making large gatherings feel and taste delicious. The antique's original entrance to a home office + fireplace (cozy, authentic) complete the floor. The 2nd floor offers 4 secondary beds/baths, a superior primary suite, and has a 600-sf bonus room with its own entrance and full kitchen. Generous third-level space fronted by a viewing balcony becomes the game/exercise/screening room you choose. Windows are featured everywhere, in particular note the sunroom array and the sitting room's 28ft of windowed walls. The separate 1,100 sf, 1-2 BR COTTAGE has had just 4 long-term tenants in the owners' 28 years. The COTTAGE rental income and tax/financial advantages make your net purchase price and occupancy exceedingly comfortable. The owner has prepared for final approvals a survey,building plans, and rendering package of a pool and surrounding deck connected to the home's 500sf front terrace. The buyer wishing the design can move forward with confidence in the sellers' careful efforts. A 2025, 95% efficient,state-of-the art, Navien natural gas boiler and HW installation has proven to be a gas bill slayer.

16. 2026-04-03
    historical $2,595,000 1495-char remark

    Show marketing remark (1495 chars)

    This restored, 6,100 sf-expanded 18th century antique commands a view of its 1.24 ac, brook-fed lake; expansive lawn; raised beds; and 450 ft. bleached stone driveway. Your vision--Big Tented Celebrations,Fabulous Local Tomatoes--is correct. The former NYC chef's professional kitchen, wet bar, and 2 eat-in dining areas are open to the 5 rooms that circle around this heartbeat, making large gatherings feel and taste delicious. The antique's original entrance to a home office + fireplace (cozy, authentic) complete the floor. The 2nd floor offers 4 secondary beds/baths, a superior primary suite, and has a 600-sf bonus room with its own entrance and full kitchen. Generous third-level space fronted by a viewing balcony becomes the game/exercise/screening room you choose. Windows are featured everywhere, in particular note the sunroom array and the sitting room's 28ft of windowed walls. The separate 1,100 sf, 1-2 BR COTTAGE has had just 4 long-term tenants in the owners' 28 years. The COTTAGE rental income and tax/financial advantages make your net purchase price and occupancy exceedingly comfortable. The owner has prepared for final approvals a survey,building plans, and rendering package of a pool and surrounding deck connected to the home's 500sf front terrace. The buyer wishing the design can move forward with confidence in the sellers' careful efforts. A 2025, 95% efficient,state-of-the art, Navien natural gas boiler and HW installation has proven to be a gas bill slayer.

17. 2025-06-05
    historical
18. 2025-04-28
    listed $2,495,000 Active
19. 2025-04-22
    historical
20. 2022-06-24
    historical
21. 2022-02-19
    listed $2,495,000 Active
22. 2022-02-15
    historical
23. 2021-11-23
    historical
24. 2021-09-16
    status Active
25. 2021-07-05
    historical
26. 2021-04-07
    listed $2,495,000 Active
27. 2016-10-27
    historical
28. 2016-10-26
    historical
29. 2016-04-15
    listed $2,295,000
30. 2016-04-15
    listed $2,295,000
31. 2015-11-15
    historical
32. 2015-03-14
    listed $2,350,000
33. 2015-01-18
    historical
34. 2014-10-03
    listed $2,395,000
35. 2006-12-14
    historical
36. 2006-10-07
    listed $2,595,000
37. 1997-11-30
    soldstatus $372,000
38. 1997-09-24
    listed $419,000
39. 1997-09-15
    historical
40. 1995-02-13
    listed $419,000

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $26,988 · $2,249/mo
• Projected year-2 tax: $41,260 · $3,438/mo
• Expected delta: +$14,272/yr (+$1,189/mo · 52.9%)

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 2/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥99°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 3 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $373,241
• − Mortgage interest: −$145,360
• − Property taxes: −$26,988
• − Insurance: −$12,975
• − Repairs & maintenance: −$29,859
• − Management: −$29,859
• − Depreciation: −$75,491
• Taxable income: $52,708
• Est. tax owed @ 24.0%: −$12,650
• After-tax cash flow: $78,946/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: Weston School District
• NCES district ID: 0905010
• Math proficiency: 68% ▼ -6.00%
• Reading proficiency: 77% ▼ -1.00%
• Median HH income: $194,414
• Composite: 75.21/100
• National rank: #137
• State rank: #4 of 153 in CT

Livability — Weston

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Population (ZIP): 10,335

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (78%)
• Race & ethnicity: White 78% Two or more races 10% Hispanic / Latino 9% Asian 5% Black 3%
• Hispanic origin (detail): Mexican 1% Puerto Rican 2% Dominican 1% Salvadoran 2%
• Common ancestry: Romanian 7% Scotch-Irish 5% Italian 5%
• Foreign-born: 16% · Canada, China, Dominican Republic
• Languages at home: 83% English-only · Spanish 5% Chinese 3% Other Indo-European 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: ▼ -316.44%
• Current HPI: 208.835
• 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

+519.3% since first listed

26 events — show timeline

• 2026-04-08 Listed $2,595,000 Smart MLS
• 2026-04-03 Coming Soon $2,595,000 Smart MLS
• 2025-06-05 Listing Removed — Smart MLS
• 2025-04-28 Listed $2,495,000 Smart MLS
• 2025-04-22 Coming Soon — Smart MLS
• 2022-06-24 Listing Removed — Smart MLS
• 2022-02-19 Listed $2,495,000 Smart MLS
• 2022-02-15 Coming Soon — Smart MLS
• 2021-11-23 Listing Removed — Smart MLS
• 2021-09-16 Relisted — Smart MLS
• 2021-07-05 Listing Removed — Smart MLS
• 2021-04-07 Listed $2,495,000 Smart MLS
• 2016-10-27 Delisted — GMLS
• 2016-10-26 Listing Removed — Smart MLS
• 2016-04-15 Listed $2,295,000 Smart MLS
• 2016-04-15 Listed $2,295,000 GMLS
• 2015-11-15 Listing Removed — Smart MLS
• 2015-03-14 Listed $2,350,000 Smart MLS
• 2015-01-18 Listing Removed — Smart MLS
• 2014-10-03 Listed $2,395,000 Smart MLS
• 2006-12-14 Listing Removed — Smart MLS
• 2006-10-07 Listed $2,595,000 Smart MLS
• 1997-11-30 Sold (MLS) $372,000 Smart MLS
• 1997-09-24 Listed $419,000 Smart MLS
• 1997-09-15 Listing Removed — Smart MLS
• 1995-02-13 Listed $419,000 Smart MLS

Property tax history

+1.2%/yr

Latest (2023): $26,988 · +0.3% YoY. Source: county tax records.