27 Litchfield Tpke · New Preston, CT 06777

$475,000

3 bd · 3.5 ba · 1,686 sqft · SingleFamily public records · 30 Days on market

Built 1982 5.83 ac lot $282/sqft · 32% below area Est $911k · 48% under

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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 +22.4/30.0
• ARV discount +15.0/15.0
• DSCR +7.2/10.0
• Schools +6.3/10.0
• Appreciation +5.9/10.0
• 1% rule +5.2/10.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Bring your imagination to 27 Litchfield Turnpike in New Preston. Turn this three-bedroom home on over 5.8 acres into your own. Home is being sold "As Is". In-law apartment over the garage. Plenty of open land and fields. The home is set off the main road to ensure some privacy. Close to Lake Waramaug, Hopkins Inn, Hopkins Vineyard, Washington Depot, New Preston, Marbledale and more. This is a great opportunity to revive this home and add great value.

Key facts

• In-law apartment
• Open land
• Privacy

Tags

• IN-LAW APARTMENT
• OPEN LAND
• PRIVACY
• CLOSE TO LAKE WARAMAUG
• CLOSE TO HOPKINS INN
• CLOSE TO HOPKINS VINEYARD

Property features AI

Finance

• Other: Property located in Connecticut, Litchfield County; Nearby amenities: golf course, lake, library, medical facilities, private schools

Exterior

• Parking: Attached garage; 2-car garage
• Utilities: Private well water; Septic sewage; Electric service
• Home design: Single-family home for sale
• Construction: Frame construction; Concrete foundation; Asphalt shingle roof; Aluminum siding
• Exterior features: Deck; Gutters; Lightly wooded, treed, level lot

Interior

• Kitchen: Oven/Range; Range hood; Refrigerator; Dishwasher
• Bedrooms: 3 bedrooms
• Bathrooms: 3 full bathrooms; 1 half bathroom
• Heating & cooling: Electric baseboard heat; Electric domestic hot water
• Interior features: 8 total rooms; Full, partially finished walk-out basement with concrete floor, interior and garage access, and heating; Has attic with access via hatch; In-law apartment possible with over-garage access; One fireplace
• Laundry & utility: Washer and dryer included; Laundry room on lower level

What this means for you Summary

Snapshot

• This is a 3-bed/3.5-bath single-family listed at $475k.

Deal economics

• At list price, monthly cash flow is $795 ($10k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $475k).
• Recommended offer: $468k (1.5% below list) — sets the bar for market timing.
• Cap rate 8.3% 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.
• Zoned schools: Washington Primary School (math 64% / reading 84%, grade A, #44 of 553 statewide, top 10%, 162 students, 25% FRL); Shepaug Valley School (math 61% / reading 76%, grade B, #23 of 194 statewide, top 12%, 494 students, 21% FRL) — zoned schools average 23% FRL vs 8% district-wide (15 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 14 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 $12k of equity ($3k loan paydown + $9k appreciation (1.9% local appreciation)).
• At projected returns (1.9% appreciation + 3.0% rent growth), your $133k cash investment doubles in ~6 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$31k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 30 days — a 2% lower offer ($468k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 29y 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.

Recommended offer $467,875 (1.5% below list)

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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.
3. 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.
4. 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: 1.02% ✓
• Cap rate: 8.30%
• Cash-on-cash: 7.18%
• DSCR: 1.32
• GRM: 8.2

CMA / ARV

• ARV (median comp): $910,599
• List price: $475,000
• Delta: -47.84%
• Verdict: UNDERPRICED
• Comps: 3 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
112 Christian St	0.42mi	3/2.5	1,848 (+10%)	23mo	$1,201,000	$650	42

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

1.88% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 11.3%
• Equity multiple: 1.60×
• Total profit: $80,332
• Equity at exit: $184,371

10-year hold

• IRR: 14.2%
• Equity multiple: 2.89×
• Total profit: $250,710
• Equity at exit: $263,225

Cash invested: $133,000 (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 06777

• Home prices YoY: 0.7%
• Active inventory: 14
• Price-to-rent: 8.2×

Monthly cashflow live

• Estimated rent: $4,833 medium
• Mortgage (P&I): −$2,491
• Tax from tax record: −$334 /mo · $4,010/yr
• Insurance: −$198
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,015
• Net cashflow: $795

Break-even live

Break-even rent $3,827

Max offer price $475,000

Occupancy floor 79%

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: $118,750
• Closing costs: $14,250
• Reserves months: —
• Total cash needed: —

Listing history 18 events

1. 2026-06-13
   statusdays on market $475,000 Under Contract 30 DOM
2. 2026-06-10
   days on market $475,000 Under Contract - Continue to Show 29 DOM
3. 2026-06-09
   days on market $475,000 Under Contract - Continue to Show 28 DOM
4. 2026-06-08
   days on market $475,000 Under Contract - Continue to Show 27 DOM
5. 2026-06-07
   days on market $475,000 Under Contract - Continue to Show 26 DOM
6. 2026-06-05
   days on market $475,000 Under Contract - Continue to Show 23 DOM
7. 2026-06-03
   days on market $475,000 Under Contract - Continue to Show 22 DOM
8. 2026-06-02
   days on market $475,000 Under Contract - Continue to Show 21 DOM
9. 2026-06-01
   days on market $475,000 Under Contract - Continue to Show 20 DOM
10. 2026-05-31
    days on market $475,000 Under Contract - Continue to Show 19 DOM
11. 2026-05-30
    days on market $475,000 Under Contract - Continue to Show 18 DOM
12. 2026-05-12
    listed $475,000 Active 464-char remark
13. 1999-07-07
    soldstatus $217,500
14. 1998-08-06
    listed $229,900
15. 1998-04-20
    historical
16. 1998-04-20
    historical
17. 1997-11-18
    listed $264,000
18. 1997-11-17
    listed $264,000

ⓘ 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: $4,010 · $334/mo
• Projected year-2 tax: $7,088 · $591/mo
• Expected delta: +$3,078/yr (+$256/mo · 76.7%)

ⓘ 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 17% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $58,000
• − Mortgage interest: −$26,607
• − Property taxes: −$4,010
• − Insurance: −$2,375
• − Repairs & maintenance: −$4,640
• − Management: −$4,640
• − Depreciation: −$13,818
• Taxable income: $1,910
• Est. tax owed @ 24.0%: −$458
• After-tax cash flow: $9,086/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): 1,802

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (85%)
• Race & ethnicity: White 85% Two or more races 11% Hispanic / Latino 10% Asian 3%
• Common ancestry: Romanian 9% Lithuanian 5% Slovak 2%
• Foreign-born: 8% · Canada, China
• Languages at home: 92% English-only · French/Haitian/Cajun 4% Other Asian/Pacific 3% Other Indo-European 1%

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: ▲ 1.88%
• Current HPI: 269.6504
• 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

+100.8% since first listed

10 events — show timeline

• 2026-06-12 Sold (MLS) $530,000 Smart MLS
• 2026-06-11 Pending — Smart MLS
• 2026-05-19 Contingent — Smart MLS
• 2026-05-12 Listed $475,000 Smart MLS
• 1999-07-07 Sold (MLS) $217,500 Smart MLS
• 1998-08-06 Listed $229,900 Smart MLS
• 1998-04-20 Listing Removed — Smart MLS
• 1998-04-20 Listing Removed — Smart MLS
• 1997-11-18 Listed $264,000 Smart MLS
• 1997-11-17 Listed $264,000 Smart MLS

Property tax history

+0.8%/yr

Latest (2023): $4,010 · +0.0% YoY. Source: county tax records.