37 Church Hill Rd · New Preston, CT 06794

$490,000

2 bd · 2.0 ba · 792 sqft · SingleFamily public records · 77 Days on market

Built 1962 0.69 ac lot $619/sqft · 36% above area Est $718k · 32% under

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Why this score? — see what drove the C+ 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 +18.2/30.0
• ARV discount +15.0/15.0
• Schools +6.3/10.0
• DSCR +5.7/10.0
• Appreciation +5.1/10.0
• 1% rule +3.8/10.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Welcome to 37 Church Hill Rd in Washington, a unique and versatile home set on a .69-acre lot offering flexible living space across two finished levels. The main level features an eat-in kitchen, a comfortable living room, 2 bedrooms, and a full bath, all designed for easy, functional living. The layout is bright and efficient, making the most of the space. The finished walk-out lower level provides excellent flexibility with a spacious family room, a half bathroom, and a 3rd bedroom or a guest space, home office, or hobby area. With its separate access, this level offers great potential. Outside, the property offers a detached carport for covered parking and a generously sized yard with plenty of room to enjoy the outdoors, garden, or entertain. Located in the desirable Washington area, this home presents a great opportunity for those seeking a manageable property with added living space and versatility in a peaceful setting. Schedule your showing today!

Key facts

• Detached carport
• Living room
• Eat-in kitchen

Tags

• EAT-IN KITCHEN
• LIVING ROOM
• FINISHED WALK-OUT LOWER LEVEL
• SPACIOUS FAMILY ROOM
• DETACHED CARPORT
• GENEROUSLY SIZED YARD

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath single-family listed at $490k.

Deal economics

• At list price, monthly cash flow is $444 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $429k (12.4% below list).
• Recommended offer: $429k (12.4% below list) — sets the bar for 1% rule.
• Cap rate 7.4% vs local median 4.0% in New Preston — 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 69/100 on livability (#105 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: 15 active listings in the ZIP; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).

Forward outlook

• In year one you build about $4k of equity ($3k loan paydown + $832 appreciation (0.2% local appreciation)).
• At projected returns (0.2% appreciation + 3.0% rent growth), your $137k cash investment doubles in ~9 years — after that, you're playing with house money.
• By year 7, paydown + projected appreciation supports a ~$34k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 77 days — a 6% lower offer ($461k) is reasonable based on typical stale-listing flexibility.
• 6 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 $423k; 16% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Recommended offer $429,329 (12.4% below list)

Questions for the listing agent

1. It's been on market 77 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1962 — 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: 0.88% ✗
• Cap rate: 7.38%
• Cash-on-cash: 3.88%
• DSCR: 1.17
• GRM: 9.5

CMA / ARV

• ARV (median comp): $718,298
• List price: $490,000
• Delta: -31.78%
• Verdict: UNDERPRICED
• Comps: 7 within 1.0 mi

Projected returns pro-forma

0.17% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 2.7%
• Equity multiple: 1.13×
• Total profit: $17,646
• Equity at exit: $146,453

10-year hold

• IRR: 7.9%
• Equity multiple: 1.87×
• Total profit: $119,672
• Equity at exit: $179,408

Cash invested: $137,200 (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 06794

• Home prices YoY: 0.1%
• Active inventory: 15
• Price-to-rent: 9.5×

Monthly cashflow live

• Estimated rent: $4,293 medium
• Mortgage (P&I): −$2,570
• Tax from tax record: −$174 /mo · $2,090/yr
• Insurance: −$204
• HOA: −$0
• Vacancy / Maint / Mgmt: −$902
• Net cashflow: $444

Break-even live

Break-even rent $3,732

Max offer price $490,000

Occupancy floor 85%

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: $122,500
• Closing costs: $14,700
• Reserves months: —
• Total cash needed: —

Listing history 30 events

1. 2026-06-19
   days on market $490,000 Active 77 DOM
2. 2026-06-18
   days on market $490,000 Active 76 DOM
3. 2026-06-17
   days on market $490,000 Active 75 DOM
4. 2026-06-16
   days on market $490,000 Active 74 DOM
5. 2026-06-15
   days on market $490,000 Active 73 DOM
6. 2026-06-14
   days on market $490,000 Active 71 DOM
7. 2026-06-13
   days on market $490,000 Active 70 DOM
8. 2026-06-10
   days on market $490,000 Active 68 DOM
9. 2026-06-09
   days on market $490,000 Active 67 DOM
10. 2026-06-08
    days on market $490,000 Active 66 DOM
11. 2026-06-07
    days on market $490,000 Active 65 DOM
12. 2026-06-05
    days on market $490,000 Active 62 DOM
13. 2026-06-03
    days on market $490,000 Active 61 DOM
14. 2026-06-02
    days on market $490,000 Active 60 DOM
15. 2026-06-01
    days on market $490,000 Active 59 DOM
16. 2026-05-31
    days on market $490,000 Active 58 DOM
17. 2026-05-30
    days on market $490,000 Active 57 DOM
18. 2026-04-20
    status Active 969-char remark

    Show marketing remark (969 chars)

    Welcome to 37 Church Hill Rd in Washington, a unique and versatile home set on a .69-acre lot offering flexible living space across two finished levels. The main level features an eat-in kitchen, a comfortable living room, 2 bedrooms, and a full bath, all designed for easy, functional living. The layout is bright and efficient, making the most of the space. The finished walk-out lower level provides excellent flexibility with a spacious family room, a half bathroom, and a 3rd bedroom or a guest space, home office, or hobby area. With its separate access, this level offers great potential. Outside, the property offers a detached carport for covered parking and a generously sized yard with plenty of room to enjoy the outdoors, garden, or entertain. Located in the desirable Washington area, this home presents a great opportunity for those seeking a manageable property with added living space and versatility in a peaceful setting. Schedule your showing today!

19. 2026-04-06
    status Under Contract 969-char remark

    Show marketing remark (969 chars)

    Welcome to 37 Church Hill Rd in Washington, a unique and versatile home set on a .69-acre lot offering flexible living space across two finished levels. The main level features an eat-in kitchen, a comfortable living room, 2 bedrooms, and a full bath, all designed for easy, functional living. The layout is bright and efficient, making the most of the space. The finished walk-out lower level provides excellent flexibility with a spacious family room, a half bathroom, and a 3rd bedroom or a guest space, home office, or hobby area. With its separate access, this level offers great potential. Outside, the property offers a detached carport for covered parking and a generously sized yard with plenty of room to enjoy the outdoors, garden, or entertain. Located in the desirable Washington area, this home presents a great opportunity for those seeking a manageable property with added living space and versatility in a peaceful setting. Schedule your showing today!

20. 2026-03-20
    listed $490,000 Active 969-char remark

    Show marketing remark (969 chars)

    Welcome to 37 Church Hill Rd in Washington, a unique and versatile home set on a .69-acre lot offering flexible living space across two finished levels. The main level features an eat-in kitchen, a comfortable living room, 2 bedrooms, and a full bath, all designed for easy, functional living. The layout is bright and efficient, making the most of the space. The finished walk-out lower level provides excellent flexibility with a spacious family room, a half bathroom, and a 3rd bedroom or a guest space, home office, or hobby area. With its separate access, this level offers great potential. Outside, the property offers a detached carport for covered parking and a generously sized yard with plenty of room to enjoy the outdoors, garden, or entertain. Located in the desirable Washington area, this home presents a great opportunity for those seeking a manageable property with added living space and versatility in a peaceful setting. Schedule your showing today!

21. 2024-05-13
    soldstatus $423,000 Closed 759-char remark

    Show marketing remark (759 chars)

    Highly sought after location (Church Street) less than 1 mile from town center. Fully updated, private location set back from the road and only 1 neighbor visible. Expansive composite deck for all those gatherings and quiet moments looking out over the tree tops. Plenty of parking to accommodate all those that visit &/or stay. Opportunity to remake the 2 car carport to something more. Original hardwood floors upstairs and lots of character for a 1962 home. Downstairs has been taken back to the studs and made livable and comfortable. Newer roof, well, mechanics, appliances, basement redone completely. It's all waiting for the person that wants something unique within walking distance to Washington Depot's quaint, sophisticated shops and eateries.

22. 2024-04-19
    historical Under Contract - Continue to Show 759-char remark

    Show marketing remark (759 chars)

    Highly sought after location (Church Street) less than 1 mile from town center. Fully updated, private location set back from the road and only 1 neighbor visible. Expansive composite deck for all those gatherings and quiet moments looking out over the tree tops. Plenty of parking to accommodate all those that visit &/or stay. Opportunity to remake the 2 car carport to something more. Original hardwood floors upstairs and lots of character for a 1962 home. Downstairs has been taken back to the studs and made livable and comfortable. Newer roof, well, mechanics, appliances, basement redone completely. It's all waiting for the person that wants something unique within walking distance to Washington Depot's quaint, sophisticated shops and eateries.

23. 2024-04-18
    listed $425,000 Active 759-char remark

    Show marketing remark (759 chars)

    Highly sought after location (Church Street) less than 1 mile from town center. Fully updated, private location set back from the road and only 1 neighbor visible. Expansive composite deck for all those gatherings and quiet moments looking out over the tree tops. Plenty of parking to accommodate all those that visit &/or stay. Opportunity to remake the 2 car carport to something more. Original hardwood floors upstairs and lots of character for a 1962 home. Downstairs has been taken back to the studs and made livable and comfortable. Newer roof, well, mechanics, appliances, basement redone completely. It's all waiting for the person that wants something unique within walking distance to Washington Depot's quaint, sophisticated shops and eateries.

24. 2023-11-16
    historical
25. 2023-10-18
    listed $425,000 Active
26. 2023-10-16
    historical
27. 2023-09-11
    listed $450,000 Active
28. 2019-04-29
    soldstatus $157,300
29. 2019-04-26
    soldstatus $157,300
30. 2018-09-24
    listed $169,000

ⓘ 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: $2,090 · $174/mo
• Projected year-2 tax: $6,288 · $524/mo
• Expected delta: +$4,198/yr (+$350/mo · 200.9%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥95°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 19% 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: $51,519
• − Mortgage interest: −$27,448
• − Property taxes: −$2,090
• − Insurance: −$2,450
• − Repairs & maintenance: −$4,122
• − Management: −$4,122
• − Depreciation: −$14,255
• Taxable loss: −$2,966
• Est. tax savings @ 24.0%: +$712
• After-tax cash flow: $6,037/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 — New Preston

• Score: 69/100
• State rank: #105
• US rank: #9031

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: 1,802
• Population (ZIP): 953

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (75%)
• Race & ethnicity: White 75% Hispanic / Latino 23% Two or more races 14%
• Hispanic origin (detail): Dominican 10%
• Common ancestry: Lithuanian 7% Romanian 6% Iranian 3%
• Foreign-born: 20% · Canada
• Languages at home: 69% English-only · Spanish 26% French/Haitian/Cajun 2% German/W. Germanic 2%

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: ▲ 0.17%
• Current HPI: 215.191
• 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

+189.9% since first listed

13 events — show timeline

• 2026-04-20 Relisted — Smart MLS
• 2026-04-06 Pending — Smart MLS
• 2026-03-20 Listed $490,000 Smart MLS
• 2024-05-13 Sold (MLS) $423,000 Smart MLS
• 2024-04-19 Contingent — Smart MLS
• 2024-04-18 Listed $425,000 Smart MLS
• 2023-11-16 Listing Removed — Smart MLS
• 2023-10-18 Listed $425,000 Smart MLS
• 2023-10-16 Listing Removed — Smart MLS
• 2023-09-11 Listed $450,000 Smart MLS
• 2019-04-29 Sold (Public Records) $157,300 Public Records
• 2019-04-26 Sold (MLS) $157,300 Smart MLS
• 2018-09-24 Listed $169,000 Smart MLS

Property tax history

+1.0%/yr

Latest (2023): $2,090 · +6.0% YoY. Source: county tax records.