141 New Preston Hill Rd · New Preston, CT 06777

$424,900

3 bd · 1.0 ba · 1,800 sqft · SingleFamily public records · 5 Days on market

Built 1960 5.00 ac lot

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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 +24.3/30.0
• DSCR +7.9/10.0
• ARV discount +7.5/15.0
• Schools +6.3/10.0
• Appreciation +5.9/10.0
• 1% rule +5.6/10.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Welcome to this rare opportunity on New Preston Hill Road in the highly sought-after New Preston section of Washington, CT. Situated on 5 beautiful acres of mostly level, lightly wooded land, this unique property offers endless possibilities for investors, builders, renovators, or those looking to create their dream home in one of Litchfield County's most desirable locations. The existing single family structure features striking stone exterior construction, a circular driveway, hardwood flooring on the main level, an expansive attic, and a stunning oversized stone fireplace hearth that serves as the centerpiece of the home. The property currently requires installation of both a well and septic system, and all heating elements have been removed. A septic feasibility report done on April 21, 2026 confirms the property is septic ready, and a site plan is even available for review. Whether you choose to restore the existing home and preserve its character or take advantage of the exceptional setting to construct a new custom residence, this property presents a rare chance to unlock significant value in a premier Washington location. Bring your vision and imagination to this exceptional New Preston property and create something truly special. According to the town card, the home contains approximately 1,800 square feet; buyers are encouraged to perform their own due diligence regarding all property details.

Key facts

• Hardwood flooring
• Expansive attic
• Circular driveway

Tags

• 5 BEAUTIFUL ACRES
• STONE EXTERIOR CONSTRUCTION
• CIRCULAR DRIVEWAY
• HARDWOOD FLOORING
• EXPANSIVE ATTIC
• SEPTIC READY

Property features AI

Exterior

• Parking: Under-house garage; Driveway parking; 8 total parking spaces; 1 garage space
• Utilities: Well required for water; Septic required for sewage; Power available (standard connections)
• Home design: Single-family home
• Construction: Frame and stone construction; Shake and stone exterior siding; Asphalt shingle roof; Block and stone foundation
• Exterior features: Lightly wooded, level lot; Circular driveway

Interior

• Bedrooms: 3 bedrooms
• Bathrooms: 1 full bathroom
• Heating & cooling: No heat; No hot water
• Interior features: 5 total rooms; Wood-burning fireplace; Full basement with garage and interior access; dirt floor; Floored walk-up attic

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $425k.

Deal economics

• At list price, monthly cash flow is $859 ($10k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $425k).
• Cap rate 8.7% 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) — zoned schools average 25% FRL vs 8% district-wide (17 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 14 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).

Forward outlook

• In year one you build about $11k of equity ($3k loan paydown + $8k appreciation (1.9% local appreciation)).
• At projected returns (1.9% appreciation + 3.0% rent growth), your $119k cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 4, paydown + projected appreciation supports a ~$38k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• Only 5 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.

Recommended offer $424,900

Questions for the listing agent

1. Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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.
4. 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.
5. 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: 1.06% ✓
• Cap rate: 8.72%
• Cash-on-cash: 8.66%
• DSCR: 1.39
• GRM: 7.9

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: 12.7%
• Equity multiple: 1.68×
• Total profit: $81,233
• Equity at exit: $164,924

10-year hold

• IRR: 15.6%
• Equity multiple: 3.06×
• Total profit: $244,493
• Equity at exit: $235,461

Cash invested: $118,972 (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: 7.9×

Monthly cashflow live

• Estimated rent: $4,500 medium
• Mortgage (P&I): −$2,228
• Tax from tax record: −$291 /mo · $3,493/yr
• Insurance: −$177
• HOA: −$0
• Vacancy / Maint / Mgmt: −$945
• Net cashflow: $859

Break-even live

Break-even rent $3,413

Max offer price $424,900

Occupancy floor 76%

Sensitivity live

Price	-10% $1,099	-5% $979	+0% $859	+5% $738	+10% $618
Rent	-10% $503	-5% $681	+0% $859	+5% $1,036	+10% $1,214
Rate	-1.0pp $1,073	-0.5pp $967	base $859	+0.5pp $749	+1.0pp $637

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: $106,225
• Closing costs: $12,747
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
41 Frenchmans Rd New Milford, CT	3.0	2.0	1610	$4,500	$2.80	44d	1	1.15mi

Listing history 7 events

1. 2026-06-18
   status $424,900 Under Contract 5 DOM
2. 2026-06-18
   days on market $424,900 Active 5 DOM
3. 2026-06-17
   days on market $424,900 Active 4 DOM
4. 2026-06-16
   days on market $424,900 Active 3 DOM
5. 2026-06-15
   days on market $424,900 Active 2 DOM
6. 2026-06-14
   remarks 699-char remark
7. 2026-06-14
   listed $424,900 Active 1 DOM

ⓘ 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: $3,493 · $291/mo
• Projected year-2 tax: $6,293 · $524/mo
• Expected delta: +$2,800/yr (+$233/mo · 80.2%)

ⓘ 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 6 d/yr ≥94°F today · 12 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 17% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $54,000
• − Mortgage interest: −$23,801
• − Property taxes: −$3,493
• − Insurance: −$2,124
• − Repairs & maintenance: −$4,320
• − Management: −$4,320
• − Depreciation: −$12,361
• Taxable income: $3,581
• Est. tax owed @ 24.0%: −$859
• After-tax cash flow: $9,444/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

• Census place: New Preston, CT
• 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

+0.0% since first listed

2 events — show timeline

• 2026-06-13 Listed $424,900 Smart MLS
• 2026-06-13 Listed $424,900 Smart MLS

Property tax history

+0.2%/yr

Latest (2023): $3,493 · +0.0% YoY. Source: county tax records.