187 Old Toll Rd. Rd · Guilford Center, CT 06443

$579,000

3 bd · 2.5 ba · 2,034 sqft · SingleFamily public records · 26 Days on market

Built 1972 2.34 ac lot $285/sqft · 19% above area Est $760k · 24% under

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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).

• ARV discount +15.0/15.0
• Cash flow +6.8/30.0
• Schools +6.6/10.0
• Livability +4.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +1.5/10.0
• DSCR +1.1/10.0
• Appreciation +0.0/10.0

Listing remarks

Originally built in the 1970's, this home has been thoughtfully transformed over time with extensive additions and updates that make it hard to imagine it's the same house. Newer mechanicals, Anderson windows, new interior doors and beautifully renovated kitchen & baths ensure a truly turnkey experience. Set well back from the road on 2.34 landscaped acres, this property offers privacy with expansive front and rear yards perfect for entertaining, recreation or simply enjoying the outdoors. The lower level provides a FR, a half bath and large mud room, equally suited as an office, featuring generous storage and space for custom built-ins. The fireplaced family room and Sunroom feature

Key facts

• 2.34 acre lot
• 2 garage spots
• Built 1972

Property features AI

Exterior

• Parking: Attached garage (2-car); Paved driveway; Off-street parking; Total of about 6 parking spaces
• Utilities: Private well water; Septic system; Oil fuel (tank in basement)
• Home design: Single-family home; Frame construction; Tan exterior; Clapboard and vinyl siding; Asphalt shingle roof; Shared paved driveway
• Construction: Concrete foundation
• Exterior features: Deck; Shed; Gutters; Garden area; Exterior lighting; Professionally landscaped yard; Lightly wooded, level lot with some wetlands

Interior

• Kitchen: Electric range; Range hood; Refrigerator; Dishwasher
• Bedrooms: 3 bedrooms
• Bathrooms: 2 full bathrooms; 1 half bathroom
• Heating & cooling: Central air conditioning; Oil-fired hot water/baseboard heat with zoned heating; 65-gallon hot water tank; Fireplace insert
• Interior features: Auto garage door opener; Pre-wired for cable; Open floor plan; Possible in-law apartment with separate lower-level entry; Mud room; Solarium; One fireplace; Has attic with pull-down stairs and storage
• Laundry & utility: Laundry on lower level next to family room; Lower-level laundry room

What this means for you Summary

Snapshot

• This is a 3-bed/2.5-bath single-family listed at $579k.

Deal economics

• At list price, monthly cash flow is $-889 ($-11k/yr) — negative.
• To cash-flow at today's rent, offer at most $422k (27.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $375k (35.2% below list).
• Recommended offer: $375k (35.2% below list) — sets the bar for 1% rule.
• Cap rate 4.5% vs local median 3.1% in Guilford Center — 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 82/100 on livability (#10 in CT, #1,186 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, health & safety A+; Watch: cost of living F.
• Madison School District (suburban): math 69% / reading 75% proficiency, ranked #10 of 153 in CT (top 6%) — strong family-tenant draw, lease renewals of 3-5y typical; only 3% free/reduced lunch — higher-income household profile.
• Zoned schools: Daniel Hand High School (math 69% / reading 86%, grade A-, #8 of 194 statewide, top 4%, 828 students, 5% FRL) — zoned schools at 5% FRL track the district average.
• Market conditions: 107 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $17k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 26 days — a 2% lower offer ($570k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Climate carrying-cost: major flood risk; major wind risk, 67% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $375,000 (35.2% 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. Built in 1972 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. Schools are A-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?
5. 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?
6. 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.
7. 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.
8. 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: 0.65% ✗
• Cap rate: 4.45%
• Cash-on-cash: -6.58%
• DSCR: 0.71
• GRM: 12.9

CMA / ARV

• ARV (median comp): $760,039
• List price: $579,000
• Delta: -23.82%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
71 Old Toll Rd	0.43mi	3/3.0	2,092 (+3%)	10mo	$505,000	$241	65
5 Dover Ln	0.56mi	4/2.5 (+1)	2,096 (+3%)	10mo	$670,000	$320	56
12 Rustic Ln	0.69mi	4/2.0 (+1)	1,849 (-9%)	1mo	$620,000	$335	45
106 Bradley Corners Rd	0.69mi	4/2.5 (+1)	2,080 (+2%)	18mo	$510,000	$245	44
4 Sheffield Ln	0.66mi	4/2.5 (+1)	2,312 (+14%)	12mo	$730,000	$316	32

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: -27.7%
• Equity multiple: 0.07×
• Total profit: $-150,464
• Equity at exit: $86,331

10-year hold

• IRR: -26.2%
• Equity multiple: -0.26×
• Total profit: $-204,054
• Equity at exit: $50,061

Cash invested: $162,120 (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 06443

• Active inventory: 107
• Price-to-rent: 12.9×

Monthly cashflow live

• Estimated rent: $3,750 medium
• Mortgage (P&I): −$3,036
• Tax from tax record: −$574 /mo · $6,884/yr
• Insurance: −$241
• HOA: −$0
• Vacancy / Maint / Mgmt: −$788
• Net cashflow: $-889

Break-even live

Break-even rent $4,875

Max offer price $421,998

Occupancy floor —

Sensitivity live

Price	-10% $-561	-5% $-725	+0% $-889	+5% $-1,053	+10% $-1,217
Rent	-10% $-1,185	-5% $-1,037	+0% $-889	+5% $-741	+10% $-593
Rate	-1.0pp $-597	-0.5pp $-741	base $-889	+0.5pp $-1,039	+1.0pp $-1,191

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: $144,750
• Closing costs: $17,370
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1281 Durham Rd Madison, CT	4.0	2.0	2192	$3,750	$1.71	3d	1	1.35mi

Listing history 12 events

1. 2026-06-13
   status $579,000 Under Contract 26 DOM
2. 2026-06-12
   days on market $579,000 Under Contract - Continue to Show 26 DOM
3. 2026-06-09
   days on market $579,000 Under Contract - Continue to Show 23 DOM
4. 2026-06-08
   days on market $579,000 Under Contract - Continue to Show 22 DOM
5. 2026-06-07
   days on market $579,000 Under Contract - Continue to Show 21 DOM
6. 2026-06-04
   days on market $579,000 Under Contract - Continue to Show 17 DOM
7. 2026-06-02
   days on market $579,000 Under Contract - Continue to Show 16 DOM
8. 2026-06-01
   days on market $579,000 Under Contract - Continue to Show 15 DOM
9. 2026-05-31
   days on market $579,000 Under Contract - Continue to Show 14 DOM
10. 2026-05-31
    days on market $579,000 Under Contract - Continue to Show 13 DOM
11. 2026-05-18
    listed $579,000 Active 1510-char remark
12. 2026-05-14
    historical $579,000 1510-char remark

ⓘ 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: $6,884 · $574/mo
• Projected year-2 tax: $9,637 · $803/mo
• Expected delta: +$2,753/yr (+$229/mo · 40.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone X (shaded) · 74% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 6/10 Major 7 d/yr ≥94°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 67% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $45,000
• − Mortgage interest: −$32,433
• − Property taxes: −$6,884
• − Insurance: −$2,895
• − Repairs & maintenance: −$3,600
• − Management: −$3,600
• − Depreciation: −$16,844
• Taxable loss: −$21,256
• Est. tax savings @ 24.0%: +$5,101
• After-tax cash flow: $-5,564/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: Madison School District
• NCES district ID: 0902280
• Math proficiency: 69% ▲ 1.00%
• Reading proficiency: 75% ▲ 2.00%
• Median HH income: $103,788
• Composite: 66.15/100
• National rank: #435
• State rank: #10 of 153 in CT

Livability — Guilford Center

• Score: 82/100
• State rank: #10
• US rank: #1186

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 17,577

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Two or more races 5% Asian 4% Hispanic / Latino 3%
• Common ancestry: Romanian 5% Lithuanian 3% Slovak 2%
• Foreign-born: 9% · Canada, China
• Languages at home: 92% English-only · Other Indo-European 2% Spanish 2% German/W. Germanic 1%

Political lean MEDSL · South Central Connecticut

• 2024 margin: Strong D (+20.1) · D 59.0% · R 38.9% · Other 2.1%
• All cycles: 2024: D+20.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -375.58%
• Current HPI: 242.8467
• 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

4 events — show timeline

• 2026-06-12 Pending — Smart MLS
• 2026-05-21 Contingent — Smart MLS
• 2026-05-18 Listed $579,000 Smart MLS
• 2026-05-14 Coming Soon $579,000 Smart MLS

Property tax history

+2.1%/yr

Latest (2023): $6,884 · +1.9% YoY. Source: county tax records.