188 Settlers Hill Rd · Southbury, CT 06488

$965,000

5 bd · 4.5 ba · 4,473 sqft · MultiFamily public records · 42 Days on market

Built 1978 3.89 ac lot $216/sqft · at area comps Est $933k · at est.

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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).

• Cash flow +11.3/30.0
• ARV discount +6.0/15.0
• Schools +5.4/10.0
• DSCR +3.3/10.0
• 1% rule +3.1/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks MLS

Times have changed and this home is perfect for the buyer who needs separate home office space, extra room for family and friends or potential rental income. The solution is a 1500 sf attached 2 bedroom, 2 bath legally approved apartment with separate entrance. The light-filled main house features a living room with fireplace, formal dining room, a spacious new kitchen with granite counters and new appliances. There are 3 BR, 2.5 baths. The setting is private with a gracious driveway at the end of a cul-de-sac. The grounds are beautifully landscaped with a free form salt water pool, Roxbury granite patio, a cabana/changing room, and extensive decking and gardens. Convenient to shopping, restaurants in Southbury and access to I 84. List of recent upgrades and improvements available.

Key facts

• 3.89 acre lot
• 3 garage spots
• Pool

Property features AI

Finance

• Other: In-ground heated saltwater pool with pool house

Exterior

• Parking: Under-house garage; Driveway parking; 3-car garage (total garage spaces 3); Total parking for 6 vehicles
• Utilities: Private well water; Septic system; Radon mitigation (air)
• Home design: Single-family home; Paved driveway
• Construction: Frame construction; Clapboard siding; Asphalt shingle roof; Concrete foundation; Light green exterior color
• Exterior features: Shed; Awnings; Deck; Garden area; Professionally landscaped; Secluded, lightly wooded and rolling grounds; Sloping lot on a cul-de-sac

Interior

• Kitchen: Electric cooktop; Gas cooktop; Wall oven; Microwave; Refrigerator; Dishwasher
• Bedrooms: 5 bedrooms
• Bathrooms: 4 full bathrooms; 1 half bathroom
• Heating & cooling: Hot water heating (oil-fired; fuel tank in basement); Attic fan; Central air; Split system
• Interior features: Auto garage door opener; In-law apartment with separate entry and over-garage access; Two fireplaces; Full basement; Attic with pull-down stairs; Laundry room (lower level); Workshop
• Laundry & utility: Washer; Dryer; 50-gallon hot water tank

What this means for you Summary

Snapshot

• This is a 5-bed/4.5-bath multifamily listed at $965k.

Deal economics

• At list price, monthly cash flow is $-351 ($-4k/yr) — negative.
• To cash-flow at today's rent, offer at most $903k (6.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $783k (18.9% below list).
• Recommended offer: $783k (18.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• Regional School District 15 (suburban): math 56% / reading 64% proficiency, ranked #46 of 153 in CT (top 30%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 4% free/reduced lunch — higher-income household profile.
• Zoned schools: Long Meadow Elementary School (math 62% / reading 66%, grade B, #129 of 553 statewide, top 23%, 515 students, 10% FRL); Pomperaug Regional High School (math 54% / reading 74%, grade B-, #37 of 194 statewide, top 19%, 1,039 students, 14% FRL).
• Market conditions: 156 active listings in the ZIP; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $7k of loan paydown is wiped out by about $29k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 42 days — a 3% lower offer ($936k) is reasonable based on typical stale-listing flexibility.
• 8 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.
• Current owner paid $695k; 39% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Climate carrying-cost: moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $782,900 (18.9% 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. It's been on market 42 days. Have you received any prior offers? Is the seller open to a 19% concession, seller financing, or rate buy-down credit?
3. Built in 1978 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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 apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 0.81% ✗
• Cap rate: 5.86%
• Cash-on-cash: -1.56%
• DSCR: 0.93
• GRM: 10.3

CMA / ARV

• ARV (median comp): $932,982
• List price: $965,000
• Delta: 3.43%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: -18.9%
• Equity multiple: 0.34×
• Total profit: $-178,695
• Equity at exit: $143,885

10-year hold

• IRR: -11.4%
• Equity multiple: 0.32×
• Total profit: $-184,248
• Equity at exit: $83,436

Cash invested: $270,200 (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 06488

• Active inventory: 156
• Price-to-rent: 30.8×

Monthly cashflow live

• Estimated rent: $7,829 high
• Mortgage (P&I): −$5,061
• Tax from tax record: −$1,073 /mo · $12,880/yr
• Insurance: −$402
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,644
• Net cashflow: $-351

Break-even live

Break-even rent $8,273

Max offer price $902,982

Occupancy floor 99%

3-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
1× unit	3	2	$2,610
▸ 2× units	2	1	$5,220
Total (3 units)			$7,829

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: $241,250
• Closing costs: $28,950
• Reserves months: —
• Total cash needed: —

Listing history 36 events

1. 2026-06-18
   days on market $965,000 Active 42 DOM
2. 2026-06-17
   days on market $965,000 Active 41 DOM
3. 2026-06-16
   days on market $965,000 Active 40 DOM
4. 2026-06-15
   days on market $965,000 Active 39 DOM
5. 2026-06-14
   days on market $965,000 Active 37 DOM
6. 2026-06-13
   days on market $965,000 Active 36 DOM
7. 2026-06-10
   days on market $965,000 Active 34 DOM
8. 2026-06-09
   days on market $965,000 Active 33 DOM
9. 2026-06-08
   pricedays on market $965,000 Active 32 DOM
10. 2026-06-07
    days on market $990,000 Active 31 DOM
11. 2026-06-03
    days on market $990,000 Active 27 DOM
12. 2026-06-03
    days on market $990,000 Active 26 DOM
13. 2026-06-01
    days on market $990,000 Active 25 DOM
14. 2026-05-31
    days on market $990,000 Active 24 DOM
15. 2026-05-08
    listed $990,000 Active 1478-char remark
16. 2026-05-05
    historical $990,000 1478-char remark
17. 2020-11-12
    soldstatus $695,000
18. 2020-11-10
    soldstatus $695,000 Closed 792-char remark

    Show marketing remark (792 chars)

    Times have changed and this home is perfect for the buyer who needs separate home office space, extra room for family and friends or potential rental income. The solution is a 1500 sf attached 2 bedroom, 2 bath legally approved apartment with separate entrance. The light-filled main house features a living room with fireplace, formal dining room, a spacious new kitchen with granite counters and new appliances. There are 3 BR, 2.5 baths. The setting is private with a gracious driveway at the end of a cul-de-sac. The grounds are beautifully landscaped with a free form salt water pool, Roxbury granite patio, a cabana/changing room, and extensive decking and gardens. Convenient to shopping, restaurants in Southbury and access to I 84. List of recent upgrades and improvements available.

19. 2020-10-11
    historical Under Contract - Continue to Show 792-char remark

    Show marketing remark (792 chars)

    Times have changed and this home is perfect for the buyer who needs separate home office space, extra room for family and friends or potential rental income. The solution is a 1500 sf attached 2 bedroom, 2 bath legally approved apartment with separate entrance. The light-filled main house features a living room with fireplace, formal dining room, a spacious new kitchen with granite counters and new appliances. There are 3 BR, 2.5 baths. The setting is private with a gracious driveway at the end of a cul-de-sac. The grounds are beautifully landscaped with a free form salt water pool, Roxbury granite patio, a cabana/changing room, and extensive decking and gardens. Convenient to shopping, restaurants in Southbury and access to I 84. List of recent upgrades and improvements available.

20. 2020-09-22
    price $720,000 792-char remark

    Show marketing remark (792 chars)

    Times have changed and this home is perfect for the buyer who needs separate home office space, extra room for family and friends or potential rental income. The solution is a 1500 sf attached 2 bedroom, 2 bath legally approved apartment with separate entrance. The light-filled main house features a living room with fireplace, formal dining room, a spacious new kitchen with granite counters and new appliances. There are 3 BR, 2.5 baths. The setting is private with a gracious driveway at the end of a cul-de-sac. The grounds are beautifully landscaped with a free form salt water pool, Roxbury granite patio, a cabana/changing room, and extensive decking and gardens. Convenient to shopping, restaurants in Southbury and access to I 84. List of recent upgrades and improvements available.

21. 2020-08-03
    listed $745,000 Active 792-char remark

    Show marketing remark (792 chars)

    Times have changed and this home is perfect for the buyer who needs separate home office space, extra room for family and friends or potential rental income. The solution is a 1500 sf attached 2 bedroom, 2 bath legally approved apartment with separate entrance. The light-filled main house features a living room with fireplace, formal dining room, a spacious new kitchen with granite counters and new appliances. There are 3 BR, 2.5 baths. The setting is private with a gracious driveway at the end of a cul-de-sac. The grounds are beautifully landscaped with a free form salt water pool, Roxbury granite patio, a cabana/changing room, and extensive decking and gardens. Convenient to shopping, restaurants in Southbury and access to I 84. List of recent upgrades and improvements available.

22. 2015-08-12
    soldstatus $622,500

    Show marketing remark (1137 chars)

    Stunning park-like setting for this peaceful country retreat. Beautiful property with free form in-ground heated salt-water pool, pool house and lushly landscaped level yard with stone walls. Entertain on your expansive ground level mahogany deck or relax poolside on surrounding Roxbury granite patio. This home offers comfortable and easy living with formal and informal light filled rooms. Features include wideboard flooring, crown moulding, recessed lighting and four zone HVAC. The spacious kitchen has granite counters, island/breakfast bar and stainless steel appliances including two wall ovens, two side-by-side refrigerators, microwave, gas cook top, wine chiller and ample Woodmode cabinets. The main floor master has a full bath and three walk-in closets. A large home office on the main floor could function as a library/den or music room. An additional 4 bedrooms and three full baths complete the second floor. The finished lower level is not included in the sq. ft. All this located at the end of a cul-de-sac just minutes from I-84 and 90 minutes from New York City. A very special home just waiting for you to enjoy!

23. 2015-08-12
    soldstatus $637,500

    Show marketing remark (1137 chars)

    Stunning park-like setting for this peaceful country retreat. Beautiful property with free form in-ground heated salt-water pool, pool house and lushly landscaped level yard with stone walls. Entertain on your expansive ground level mahogany deck or relax poolside on surrounding Roxbury granite patio. This home offers comfortable and easy living with formal and informal light filled rooms. Features include wideboard flooring, crown moulding, recessed lighting and four zone HVAC. The spacious kitchen has granite counters, island/breakfast bar and stainless steel appliances including two wall ovens, two side-by-side refrigerators, microwave, gas cook top, wine chiller and ample Woodmode cabinets. The main floor master has a full bath and three walk-in closets. A large home office on the main floor could function as a library/den or music room. An additional 4 bedrooms and three full baths complete the second floor. The finished lower level is not included in the sq. ft. All this located at the end of a cul-de-sac just minutes from I-84 and 90 minutes from New York City. A very special home just waiting for you to enjoy!

24. 2015-07-17
    historical

    Show marketing remark (1137 chars)

    Stunning park-like setting for this peaceful country retreat. Beautiful property with free form in-ground heated salt-water pool, pool house and lushly landscaped level yard with stone walls. Entertain on your expansive ground level mahogany deck or relax poolside on surrounding Roxbury granite patio. This home offers comfortable and easy living with formal and informal light filled rooms. Features include wideboard flooring, crown moulding, recessed lighting and four zone HVAC. The spacious kitchen has granite counters, island/breakfast bar and stainless steel appliances including two wall ovens, two side-by-side refrigerators, microwave, gas cook top, wine chiller and ample Woodmode cabinets. The main floor master has a full bath and three walk-in closets. A large home office on the main floor could function as a library/den or music room. An additional 4 bedrooms and three full baths complete the second floor. The finished lower level is not included in the sq. ft. All this located at the end of a cul-de-sac just minutes from I-84 and 90 minutes from New York City. A very special home just waiting for you to enjoy!

25. 2015-05-01
    listed $637,500

    Show marketing remark (1137 chars)

    Stunning park-like setting for this peaceful country retreat. Beautiful property with free form in-ground heated salt-water pool, pool house and lushly landscaped level yard with stone walls. Entertain on your expansive ground level mahogany deck or relax poolside on surrounding Roxbury granite patio. This home offers comfortable and easy living with formal and informal light filled rooms. Features include wideboard flooring, crown moulding, recessed lighting and four zone HVAC. The spacious kitchen has granite counters, island/breakfast bar and stainless steel appliances including two wall ovens, two side-by-side refrigerators, microwave, gas cook top, wine chiller and ample Woodmode cabinets. The main floor master has a full bath and three walk-in closets. A large home office on the main floor could function as a library/den or music room. An additional 4 bedrooms and three full baths complete the second floor. The finished lower level is not included in the sq. ft. All this located at the end of a cul-de-sac just minutes from I-84 and 90 minutes from New York City. A very special home just waiting for you to enjoy!

26. 2007-09-07
    historical
27. 2007-06-04
    listed $899,000
28. 2002-05-24
    soldstatus $570,000
29. 2002-05-24
    soldstatus $570,000
30. 2002-03-18
    historical
31. 2001-12-27
    listed $595,000
32. 2001-09-19
    listed $595,000
33. 1998-06-15
    historical
34. 1998-02-09
    listed $595,000
35. 1997-10-15
    historical
36. 1997-10-04
    listed $645,000

ⓘ 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: $12,880 · $1,073/mo
• Projected year-2 tax: $16,766 · $1,397/mo
• Expected delta: +$3,886/yr (+$324/mo · 30.2%)

ⓘ 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 (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥97°F today · 14 d/yr by 30 yrs out
• 💨 Wind 5/10 Major 26% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $93,948
• − Mortgage interest: −$54,055
• − Property taxes: −$12,880
• − Insurance: −$4,825
• − Repairs & maintenance: −$7,516
• − Management: −$7,516
• − Depreciation: −$28,073
• Taxable loss: −$20,916
• Est. tax savings @ 24.0%: +$5,020
• After-tax cash flow: $807/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 15
• NCES district ID: 0903537
• Math proficiency: 56% ▼ -15.00%
• Reading proficiency: 64% ▼ -11.00%
• Median HH income: $84,697
• Composite: 54.36/100
• National rank: #1361
• State rank: #46 of 153 in CT

Livability — Southbury

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Population (ZIP): 19,973

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (83%)
• Race & ethnicity: White 83% Hispanic / Latino 9% Two or more races 7% Asian 3% Black 2%
• Hispanic origin (detail): Puerto Rican 4%
• Common ancestry: Romanian 5% Lithuanian 3% Scotch-Irish 2%
• Foreign-born: 8% · China, Canada, Jamaica
• Languages at home: 89% English-only · Spanish 4% Chinese 2% Other Indo-European 2%

Political lean MEDSL · Naugatuck Valley

• 2024 margin: Lean R (+7.4) · D 45.6% · R 53.0% · Other 1.4%
• All cycles: 2024: R+7.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -124.35%
• Current HPI: 165.0514
• 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

+49.6% since first listed

23 events — show timeline

• 2026-06-07 Price Changed $965,000 Smart MLS
• 2026-05-08 Listed $990,000 Smart MLS
• 2026-05-05 Coming Soon $990,000 Smart MLS
• 2020-11-12 Sold (Public Records) $695,000 Public Records
• 2020-11-10 Sold (MLS) $695,000 Smart MLS
• 2020-10-11 Contingent — Smart MLS
• 2020-09-22 Price Changed $720,000 Smart MLS
• 2020-08-03 Listed $745,000 Smart MLS
• 2015-08-12 Sold (Public Records) $637,500 Public Records
• 2015-08-12 Sold (MLS) $622,500 Smart MLS
• 2015-07-17 Listing Removed — Smart MLS
• 2015-05-01 Listed $637,500 Smart MLS
• 2007-09-07 Listing Removed — Smart MLS
• 2007-06-04 Listed $899,000 Smart MLS
• 2002-05-24 Sold (Public Records) $570,000 Public Records
• 2002-05-24 Sold (MLS) $570,000 Smart MLS
• 2002-03-18 Listing Removed — Smart MLS
• 2001-12-27 Listed $595,000 Smart MLS
• 2001-09-19 Listed $595,000 Smart MLS
• 1998-06-15 Listing Removed — Smart MLS
• 1998-02-09 Listed $595,000 Smart MLS
• 1997-10-15 Listing Removed — Smart MLS
• 1997-10-04 Listed $645,000 Smart MLS

Property tax history

+2.6%/yr

Latest (2023): $12,880 · +5.3% YoY. Source: county tax records.