233 Southbury Rd · Heritage Village, CT 06783

$1,795,000

5 bd · 6.0 ba · 5,447 sqft · SingleFamily public records · 170 Days on market

Built 1988 15 ac lot $330/sqft · 29% below area Est $2525k · 29% 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 +30.0/30.0
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +6.3/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

Key facts

• In-law suite
• Expansive lawn
• Remodeled kitchen

Tags

• OPEN-CONCEPT LIVING
• PROTECTED BROOKSIDE LAND
• GRAND CIRCULAR DRIVEWAY
• REMODELED KITCHEN
• IN-LAW SUITE
• EXPANSIVE LAWN

What this means for you Summary

Snapshot

• This is a 5-bed/6.0-bath single-family listed at $1.79M.

Deal economics

• At list price, monthly cash flow is $16k ($192k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($35k rent vs $1.79M).
• Recommended offer: $1.58M (12.0% below list) — sets the bar for market timing.
• Cap rate 17.0% vs local median 3.0% in Heritage Village — 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 68/100 on livability (#112 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, health & safety A+; Watch: schools D+, employment D, amenities 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; 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

• Local home prices are declining (-3.0%/yr); year-one equity from $12k of loan paydown is wiped out by about $54k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $503k cash investment doubles in ~4 years — after that, you're playing with house money.

Negotiation context

• It's been on market 170 days — a 12% lower offer ($1.58M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 33y 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.

Risks & watch-outs

• Climate carrying-cost: moderate wind risk, 23% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,579,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 170 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
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: 1.95% ✓
• Cap rate: 16.97%
• Cash-on-cash: 38.15%
• DSCR: 2.70
• GRM: 4.3

CMA / ARV

• ARV (median comp): $2,525,216
• List price: $1,795,000
• Delta: -28.92%
• Verdict: UNDERPRICED
• Comps: 4 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
30 Hickory Ln	0.68mi	4/5.5 (-1)	4,721 (-13%)	8mo	$1,400,000	$297	33

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

Projected returns pro-forma

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

5-year hold

• IRR: 34.2%
• Equity multiple: 2.45×
• Total profit: $726,884
• Equity at exit: $267,640

10-year hold

• IRR: 41.1%
• Equity multiple: 4.87×
• Total profit: $1,943,689
• Equity at exit: $155,199

Cash invested: $502,600 (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: 4.3×

Monthly cashflow live

• Estimated rent: $35,000 medium
• Mortgage (P&I): −$9,413
• Tax from tax record: −$1,510 /mo · $18,126/yr
• Insurance: −$748
• HOA: −$0
• Vacancy / Maint / Mgmt: −$7,350
• Net cashflow: $15,978

Break-even live

Break-even rent $14,774

Max offer price $1,795,000

Occupancy floor 49%

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: $448,750
• Closing costs: $53,850
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
34 Old Roxbury Rd Roxbury, CT	4.0	4.5	3996	$35,000	$8.76	43d	1	1.09mi

Listing history 20 events

1. 2026-06-19
   days on market $1,795,000 Active 170 DOM
2. 2026-06-18
   days on market $1,795,000 Active 169 DOM
3. 2026-06-17
   days on market $1,795,000 Active 168 DOM
4. 2026-06-16
   days on market $1,795,000 Active 167 DOM
5. 2026-06-15
   days on market $1,795,000 Active 166 DOM
6. 2026-06-14
   days on market $1,795,000 Active 164 DOM
7. 2026-06-13
   days on market $1,795,000 Active 163 DOM
8. 2026-06-10
   days on market $1,795,000 Active 161 DOM
9. 2026-06-09
   days on market $1,795,000 Active 160 DOM
10. 2026-06-08
    days on market $1,795,000 Active 159 DOM
11. 2026-06-07
    days on market $1,795,000 Active 158 DOM
12. 2026-06-05
    days on market $1,795,000 Active 155 DOM
13. 2026-06-03
    days on market $1,795,000 Active 154 DOM
14. 2026-06-02
    days on market $1,795,000 Active 153 DOM
15. 2026-06-01
    days on market $1,795,000 Active 152 DOM
16. 2026-05-31
    days on market $1,795,000 Active 151 DOM
17. 2026-05-30
    days on market $1,795,000 Active 150 DOM
18. 2025-12-30
    listed $1,795,000 Active 1407-char remark

    Show marketing remark (1407 chars)

    Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

19. 1993-12-30
    historical
20. 1993-06-30
    listed $750,000

ⓘ 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: $18,126 · $1,510/mo
• Projected year-2 tax: $28,270 · $2,356/mo
• Expected delta: +$10,144/yr (+$845/mo · 56.0%)

ⓘ 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 ≥96°F today · 16 d/yr by 30 yrs out
• 💨 Wind 5/10 Major 23% 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: $420,000
• − Mortgage interest: −$100,548
• − Property taxes: −$18,126
• − Insurance: −$8,975
• − Repairs & maintenance: −$33,600
• − Management: −$33,600
• − Depreciation: −$52,218
• Taxable income: $172,933
• Est. tax owed @ 24.0%: −$41,504
• After-tax cash flow: $150,237/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 — Heritage Village

• Score: 68/100
• State rank: #112
• US rank: #9662

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 19,973
• 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

+139.3% since first listed

3 events — show timeline

• 2025-12-30 Listed $1,795,000 Smart MLS
• 1993-12-30 Listing Removed — Smart MLS
• 1993-06-30 Listed $750,000 Smart MLS

Property tax history

+1.3%/yr

Latest (2023): $18,126 · -0.3% YoY. Source: county tax records.