220 Painter Hill Rd · Bethlehem Village, CT 06783

$2,895,000

4 bd · 4.5 ba · 3,870 sqft · SingleFamily public records · 65 Days on market

Built 2007 4.68 ac lot $748/sqft · 16% above area Est $2958k · at est.

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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).

• Cash flow +12.9/30.0
• ARV discount +8.5/15.0
• Schools +6.3/10.0
• DSCR +3.9/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +2.4/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

Key facts

• Three story elevator
• Walk in pantry
• Oversized island

Tags

• THREE STORY ELEVATOR
• DEDICATED GAME MEDIA ROOM
• CHEF'S KITCHEN
• WALK IN PANTRY
• OVERSIZED ISLAND
• SPACIOUS SCREENED PORCH

What this means for you Summary

Snapshot

• This is a 4-bed/4.5-bath single-family listed at $2.90M.

Deal economics

• At list price, monthly cash flow is $-196 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $2.86M (1.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $2.15M (25.6% below list).
• Recommended offer: $2.15M (25.6% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 68/100 on livability (#107 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Regional School District 12 (rural): math 64% / reading 77% proficiency, ranked #20 of 153 in CT (top 13%) — strong family-tenant draw, lease renewals of 3-5y typical; only 8% free/reduced lunch — higher-income household profile.
• Market conditions: 48 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $20k of loan paydown is wiped out by about $87k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 65 days — a 6% lower offer ($2.72M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 8y 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 $700k; list at $2.90M implies a 314% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: moderate wind risk, 25% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $2,153,754 (25.6% 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. It's been on market 65 days. Have you received any prior offers? Is the seller open to a 26% concession, seller financing, or rate buy-down credit?
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. Schools are B-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?
6. 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?
7. 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.
8. 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.
9. 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: 0.74% ✗
• Cap rate: 6.21%
• Cash-on-cash: -0.29%
• DSCR: 0.99
• GRM: 11.2

CMA / ARV

• ARV (median comp): $2,957,942
• List price: $2,895,000
• Delta: -2.13%
• Verdict: FAIR
• Comps: 4 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: -16.8%
• Equity multiple: 0.40×
• Total profit: $-482,988
• Equity at exit: $431,654

10-year hold

• IRR: -8.8%
• Equity multiple: 0.45×
• Total profit: $-442,308
• Equity at exit: $250,307

Cash invested: $810,600 (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 06783

• Home prices YoY: -24.7%
• Active inventory: 48
• Price-to-rent: 11.2×

Monthly cashflow live

• Estimated rent: $21,538 medium
• Mortgage (P&I): −$15,182
• Tax from tax record: −$823 /mo · $9,872/yr
• Insurance: −$1,206
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,523
• Net cashflow: $-196

Break-even live

Break-even rent $21,786

Max offer price $2,860,384

Occupancy floor 96%

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: $723,750
• Closing costs: $86,850
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
45 Moosehorn Rd Roxbury, CT	3.0	3.5	4251	$30,900	$7.27	43d	1	0.60mi
18 Bear Burrow Rd Roxbury, CT	4.0	2.5	3026	$7,500	$2.48	43d	1	0.78mi

Listing history 32 events

1. 2026-06-19
   days on market $2,895,000 Active 65 DOM
2. 2026-06-18
   days on market $2,895,000 Active 64 DOM
3. 2026-06-17
   days on market $2,895,000 Active 63 DOM
4. 2026-06-16
   days on market $2,895,000 Active 62 DOM
5. 2026-06-15
   days on market $2,895,000 Active 61 DOM
6. 2026-06-14
   days on market $2,895,000 Active 59 DOM
7. 2026-06-13
   days on market $2,895,000 Active 58 DOM
8. 2026-06-10
   days on market $2,895,000 Active 56 DOM
9. 2026-06-09
   days on market $2,895,000 Active 55 DOM
10. 2026-06-08
    days on market $2,895,000 Active 54 DOM
11. 2026-06-07
    days on market $2,895,000 Active 53 DOM
12. 2026-06-05
    days on market $2,895,000 Active 50 DOM
13. 2026-06-03
    days on market $2,895,000 Active 49 DOM
14. 2026-06-02
    days on market $2,895,000 Active 48 DOM
15. 2026-06-01
    days on market $2,895,000 Active 47 DOM
16. 2026-05-31
    days on market $2,895,000 Active 46 DOM
17. 2026-05-30
    days on market $2,895,000 Active 45 DOM
18. 2026-04-15
    listed $2,895,000 Active 1505-char remark

    Show marketing remark (1505 chars)

    Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

19. 2023-06-16
    historical
20. 2023-05-28
    price $2,695,000
21. 2023-04-26
    listed $2,795,000 Active
22. 2021-05-20
    soldstatus $700,000
23. 2020-09-01
    soldstatus $650,000
24. 2020-08-28
    soldstatus $650,000 Closed
25. 2020-06-03
    historical Under Contract - Continue to Show
26. 2020-05-18
    status Active
27. 2020-05-13
    historical
28. 2020-03-05
    price $685,000
29. 2020-03-05
    status Active
30. 2019-03-26
    historical
31. 2019-02-06
    price $795,000
32. 2018-06-20
    listed $875,000 Active

ⓘ 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: $9,872 · $823/mo
• Projected year-2 tax: $35,912 · $2,993/mo
• Expected delta: +$26,040/yr (+$2,170/mo · 263.8%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 3/10 Moderate 7 d/yr ≥95°F today · 15 d/yr by 30 yrs out
• 💨 Wind 5/10 Major 25% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $258,450
• − Mortgage interest: −$162,165
• − Property taxes: −$9,872
• − Insurance: −$14,475
• − Repairs & maintenance: −$20,676
• − Management: −$20,676
• − Depreciation: −$84,218
• Taxable loss: −$53,632
• Est. tax savings @ 24.0%: +$12,872
• After-tax cash flow: $10,520/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: Regional School District 12
• NCES district ID: 0903530
• Math proficiency: 64% ▼ -9.00%
• Reading proficiency: 77% ▬ 0.00%
• Median HH income: $86,065
• Composite: 63.18/100
• National rank: #638
• State rank: #20 of 153 in CT

Livability — Bethlehem Village

• Score: 68/100
• State rank: #107
• US rank: #9178

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 3,398
• Population (ZIP): 2,184

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (84%)
• Race & ethnicity: White 84% Black 7% Hispanic / Latino 5% Two or more races 3% Asian 3%
• Common ancestry: Slovak 8% Romanian 7% Hispanic 5%
• Foreign-born: 14% · Canada
• Languages at home: 82% English-only · French/Haitian/Cajun 6% Other Indo-European 4% Spanish 3%

Political lean MEDSL · Northwest Hills

• 2024 margin: Toss-up / Even · D 48.6% · R 49.9% · Other 1.6%
• All cycles: 2024: R+1.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -55.80%
• Current HPI: 170.3789
• 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

+230.9% since first listed

15 events — show timeline

• 2026-04-15 Listed $2,895,000 Smart MLS
• 2023-06-16 Listing Removed — Smart MLS
• 2023-05-28 Price Changed $2,695,000 Smart MLS
• 2023-04-26 Listed $2,795,000 Smart MLS
• 2021-05-20 Sold (Public Records) $700,000 Public Records
• 2020-09-01 Sold (Public Records) $650,000 Public Records
• 2020-08-28 Sold (MLS) $650,000 Smart MLS
• 2020-06-03 Contingent — Smart MLS
• 2020-05-18 Relisted — Smart MLS
• 2020-05-13 Listing Removed — Smart MLS
• 2020-03-05 Price Changed $685,000 Smart MLS
• 2020-03-05 Relisted — Smart MLS
• 2019-03-26 Listing Removed — Smart MLS
• 2019-02-06 Price Changed $795,000 Smart MLS
• 2018-06-20 Listed $875,000 Smart MLS

Property tax history

-1.9%/yr

Latest (2023): $9,872 · +14.8% YoY. Source: county tax records.