29 Esther Ave · Waterbury, CT 06708

$245,000

3 bd · 1.0 ba · 1,287 sqft · SingleFamily public records · 87 Days on market

Built 1940 8,276 sqft lot $190/sqft · 22% below area Est $316k · 22% under

---

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
• Rent growth +4.9/5.0
• Livability +4.0/5.0
• 1% rule +2.9/10.0
• Condition / age +2.5/5.0
• Schools +1.5/10.0
• DSCR +1.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

This 3-bedroom home offers flexibility, with the option of a 4th bedroom or home office to suit your needs. Inside, you'll find hardwood floors, ceiling fans for added comfort, and a functional layout with an eat-in kitchen. The bathroom has been updated, and portions of the living space have seen improvements over time. Step outside to a deck overlooking the rear yard, perfect for relaxing or entertaining. The home is equipped with gas heat, gas hot water, and central air for year-round comfort. With solid fundamentals and room to personalize, this property presents a great opportunity to build equity while enjoying everyday living. Conveniently located near local amenities.

Key facts

• Gas hot water
• Gas heat
• Eat-in kitchen

Tags

• HARDWOOD FLOORS
• EAT-IN KITCHEN
• UPDATED BATHROOM
• DECK OVERLOOKING REAR YARD
• GAS HEAT
• GAS HOT WATER

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $245k.

Deal economics

• At list price, monthly cash flow is $-385 ($-5k/yr) — negative.
• To cash-flow at today's rent, offer at most $177k (27.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $194k (21.0% below list).
• Recommended offer: $177k (27.7% below list) — sets the bar for cash-flow.
• Cap rate 4.4% vs local median 3.6% in Waterbury — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.

Location & tenants

• Location reads 79/100 on livability (#32 in CT, #2,205 nationally) — a middle-class / working-renter tenant base. Strengths: commute A+, cost of living A+, housing A+; Watch: schools D+, crime D, employment D.
• Waterbury School District (suburban): math 12% / reading 23% proficiency, ranked #148 of 153 in CT (top 97%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 73% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: Rents rising fast (+9.8%/yr); 121 active listings in the ZIP; 35 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 63% of comp listings sitting > 30 days — soft ceiling on asking rent; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).
• This rent runs 34% of the median local income ($67k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 87 days — a 6% lower offer ($230k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 19y ago; this cycle's ask has dropped $30k (11%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $190k; 29% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: property tax is 2.6% of price; built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $177,076 (27.7% 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 87 days. Have you received any prior offers? Is the seller open to a 28% concession, seller financing, or rate buy-down credit?
3. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Property tax is high relative to price — has the assessment been appealed recently, and will the sale trigger a re-assessment?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. 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?
8. Crime grade is D in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
9. 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?
10. 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.
11. 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.
12. 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: 0.79% ✗
• Cap rate: 4.41%
• Cash-on-cash: -6.73%
• DSCR: 0.70
• GRM: 10.5

CMA / ARV

• ARV (median comp): $316,077
• List price: $245,000
• Delta: -22.49%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
375 Bradley Ave	0.25mi	3/2.5	1,292 (+0%)	2mo	$395,000	$306	80
239 Fairfield Ave	0.29mi	3/2.5	1,248 (-3%)	1mo	$371,000	$297	75
372 Anna Ave	0.18mi	3/1.0	1,440 (+12%)	6mo	$287,000	$199	67
46 Greenview Dr	0.51mi	3/1.0	1,200 (-7%)	2mo	$310,000	$258	63
25 Greenview Dr	0.54mi	3/2.0	1,200 (-7%)	1mo	$380,000	$317	59
207 Nichols Dr	0.54mi	4/1.0 (+1)	1,362 (+6%)	2mo	$210,000	$154	58
197 Hickory Hill Dr	0.61mi	3/1.5	1,200 (-7%)	4mo	$350,000	$292	55
17 Hickory Hill Dr	0.49mi	3/1.5	1,440 (+12%)	1mo	$245,000	$170	55
24 Polk Ave	0.69mi	3/2.0	1,176 (-9%)	2mo	$350,000	$298	48
48 Macnamara St	0.50mi	2/1.5 (-1)	1,156 (-10%)	5mo	$270,000	$234	48
43 Taft Pt	0.66mi	3/2.0	1,188 (-8%)	6mo	$365,000	$307	48
35 Rosemount Ave	0.61mi	3/3.5	1,386 (+8%)	4mo	$360,000	$260	46

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 · 8.0% rent growth · sell at horizon

5-year hold

• IRR: -21.6%
• Equity multiple: 0.22×
• Total profit: $-53,792
• Equity at exit: $36,530

10-year hold

• IRR: -5.7%
• Equity multiple: 0.55×
• Total profit: $-31,131
• Equity at exit: $21,183

Cash invested: $68,600 (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 06708

• Rents YoY: 9.8%
• Active inventory: 121
• Price-to-rent: 10.5×

Monthly cashflow live

• Estimated rent: $1,936 high
• Mortgage (P&I): −$1,285
• Tax from tax record: −$527 /mo · $6,327/yr
• Insurance: −$102
• HOA: −$0
• Vacancy / Maint / Mgmt: −$407
• Net cashflow: $-385

Break-even live

Break-even rent $2,423

Max offer price $177,076

Occupancy floor —

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: $61,250
• Closing costs: $7,350
• Reserves months: —
• Total cash needed: —

Rent comps 35 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
173 Bradley Ave Waterbury, CT	2.0	1.0	900	$1,850	$2.06	3d	1	0.19mi
174 Lucille St Unit 2 Waterbury, CT	2.0	1.0	875	$1,600	$1.83	43d	1	0.26mi
14 Elmview Cir Unit 3 Waterbury, CT	2.0	1.0	900	$1,450	$1.61	23d	1	0.38mi
1101 Highland Ave Waterbury, CT	2.0	1.5	1380	$1,800	$1.30	23d	1	0.46mi
1101 Highland Ave Waterbury, CT	2.0	1.5	1180	$1,800	$1.53	43d	1	0.46mi
219 Nichols Dr Waterbury, CT	2.0	1.5	1060	$1,550	$1.46	3d	1	0.48mi
44 Taft St Unit 9 Waterbury, CT	2.0	1.5	1200	$2,100	$1.75	43d	1	0.50mi
91 Taft St Unit 11 Waterbury, CT	2.0	1.5	1320	$2,600	$1.97	43d	1	0.51mi
95 Hawthorne Ave Unit 2 Waterbury, CT	3.0	1.0	1300	$1,800	$1.38	23d	1	0.56mi
925 Oronoke Rd Unit 12C Waterbury, CT	2.0	1.5	1330	$2,200	$1.65	43d	1	0.61mi
925 Oronoke Rd Unit 30L Waterbury, CT	2.0	1.5	1042	$1,995	$1.91	11d	1	0.61mi
67 Avon Ave Unit 2 Waterbury, CT	2.0	1.0	887	$1,700	$1.92	23d	1	0.62mi
905 Oronoke Rd #13 Waterbury, CT	3.0	2.5	1614	$3,000	$1.86	2d	1	0.62mi
124 Geddes Ter Unit Left Waterbury, CT	3.0	1.5	1255	$2,300	$1.83	43d	1	0.63mi
124 Geddes Ter Waterbury, CT	3.0	2.0	1255	$2,300	$1.83	43d	1	0.64mi
654 Highland Ave Unit 2 Waterbury, CT	2.0	1.0	1000	$1,400	$1.40	44d	1	0.66mi
468 Congress Ave Unit third floor Waterbury, CT	3.0	1.0	1250	$1,500	$1.20	23d	1	0.76mi
1585 Highland Ave Waterbury, CT	2.0	1.5	1050	$1,875	$1.79	43d	1	0.90mi
124 Charles St Unit 2 Waterbury, CT	2.0	1.0	1012	$1,800	$1.78	43d	1	0.93mi
241 Congress Ave Unit 1st Floor Waterbury, CT	2.0	1.0	909	$1,300	$1.43	43d	1	0.95mi
41 Lawlor St Waterbury, CT	3.0	1.0	1750	$2,000	$1.14	14d	1	1.01mi
143 Congress Ave Unit 2 Waterbury, CT	4.0	1.0	1050	$1,800	$1.71	43d	1	1.04mi
127 Congress Ave Unit 1 Waterbury, CT	3.0	1.0	1200	$2,300	$1.92	43d	1	1.06mi
72 Chambers St Unit 2 Waterbury, CT	3.0	1.0	1540	$1,750	$1.14	43d	1	1.12mi
59 Green St Waterbury, CT	3.0	1.0	900	$1,650	$1.83	43d	1	1.19mi
85 Draher St Unit 1 Waterbury, CT	2.0	1.0	1200	$1,600	$1.33	43d	1	1.19mi
203 Alder St Unit 1st floor Waterbury, CT	2.0	1.0	1060	$1,600	$1.51	43d	1	1.23mi
29 Madison St Unit 2 Waterbury, CT	4.0	1.0	1010	$1,900	$1.88	43d	1	1.32mi
113 Southview St Waterbury, CT	2.0	1.0	1860	$1,250	$0.67	23d	1	1.32mi
1120 Baldwin St Waterbury, CT	3.0	1.0	1100	$1,750	$1.59	43d	1	1.33mi
75 Vernon St Waterbury, CT	2.0	1.0	1000	$1,450	$1.45	43d	1	1.35mi
59 Baldwin Ave Waterbury, CT	3.0	1.0	1200	$2,350	$1.96	43d	1	1.42mi
150 Mohican Ave Unit 4 Waterbury, CT	2.0	1.5	1024	$1,650	$1.61	23d	1	1.46mi
182 Jersey St #2 Waterbury, CT	3.0	1.0	1200	$1,800	$1.50	43d	1	1.48mi
182 Jersey St #2 Waterbury, CT	3.0	1.0	1200	$1,800	$1.50	11d	1	1.48mi

Listing history 25 events

1. 2026-06-18
   days on market $245,000 Active 87 DOM
2. 2026-06-17
   days on market $245,000 Active 86 DOM
3. 2026-06-16
   days on market $245,000 Active 85 DOM
4. 2026-06-15
   days on market $245,000 Active 84 DOM
5. 2026-06-14
   statusdays on market $245,000 Active 82 DOM
6. 2026-06-13
   days on market $245,000 Under Contract - Continue to Show 81 DOM
7. 2026-06-10
   days on market $245,000 Under Contract - Continue to Show 79 DOM
8. 2026-06-09
   days on market $245,000 Under Contract - Continue to Show 78 DOM
9. 2026-06-08
   days on market $245,000 Under Contract - Continue to Show 77 DOM
10. 2026-06-07
    days on market $245,000 Under Contract - Continue to Show 76 DOM
11. 2026-06-05
    days on market $245,000 Under Contract - Continue to Show 73 DOM
12. 2026-06-03
    days on market $245,000 Under Contract - Continue to Show 72 DOM
13. 2026-06-03
    days on market $245,000 Under Contract - Continue to Show 71 DOM
14. 2026-06-01
    days on market $245,000 Under Contract - Continue to Show 70 DOM
15. 2026-05-31
    days on market $245,000 Under Contract - Continue to Show 69 DOM
16. 2026-04-25
    status Active 684-char remark

    Show marketing remark (684 chars)

    This 3-bedroom home offers flexibility, with the option of a 4th bedroom or home office to suit your needs. Inside, you'll find hardwood floors, ceiling fans for added comfort, and a functional layout with an eat-in kitchen. The bathroom has been updated, and portions of the living space have seen improvements over time. Step outside to a deck overlooking the rear yard, perfect for relaxing or entertaining. The home is equipped with gas heat, gas hot water, and central air for year-round comfort. With solid fundamentals and room to personalize, this property presents a great opportunity to build equity while enjoying everyday living. Conveniently located near local amenities.

17. 2026-04-21
    historical Under Contract - Continue to Show 684-char remark

    Show marketing remark (684 chars)

    This 3-bedroom home offers flexibility, with the option of a 4th bedroom or home office to suit your needs. Inside, you'll find hardwood floors, ceiling fans for added comfort, and a functional layout with an eat-in kitchen. The bathroom has been updated, and portions of the living space have seen improvements over time. Step outside to a deck overlooking the rear yard, perfect for relaxing or entertaining. The home is equipped with gas heat, gas hot water, and central air for year-round comfort. With solid fundamentals and room to personalize, this property presents a great opportunity to build equity while enjoying everyday living. Conveniently located near local amenities.

18. 2026-04-16
    price $265,000 684-char remark

    Show marketing remark (684 chars)

    This 3-bedroom home offers flexibility, with the option of a 4th bedroom or home office to suit your needs. Inside, you'll find hardwood floors, ceiling fans for added comfort, and a functional layout with an eat-in kitchen. The bathroom has been updated, and portions of the living space have seen improvements over time. Step outside to a deck overlooking the rear yard, perfect for relaxing or entertaining. The home is equipped with gas heat, gas hot water, and central air for year-round comfort. With solid fundamentals and room to personalize, this property presents a great opportunity to build equity while enjoying everyday living. Conveniently located near local amenities.

19. 2026-03-23
    listed $275,000 Active 684-char remark

    Show marketing remark (684 chars)

    This 3-bedroom home offers flexibility, with the option of a 4th bedroom or home office to suit your needs. Inside, you'll find hardwood floors, ceiling fans for added comfort, and a functional layout with an eat-in kitchen. The bathroom has been updated, and portions of the living space have seen improvements over time. Step outside to a deck overlooking the rear yard, perfect for relaxing or entertaining. The home is equipped with gas heat, gas hot water, and central air for year-round comfort. With solid fundamentals and room to personalize, this property presents a great opportunity to build equity while enjoying everyday living. Conveniently located near local amenities.

20. 2022-08-10
    soldstatus $190,000
21. 2022-08-05
    soldstatus $190,000 Closed 440-char remark

    Show marketing remark (440 chars)

    BEAUTIFUL CAPE COD IN WATERBURY IS THE PERFECT PLACE TO CALL HOME!Don't miss out on this 4 bedroom cape with private backyard! Enjoy 2 bedrooms & full bath on the main level and an additional 2 bedrooms upstairs.Freshly painted & hardwood floors throughout this well maintained and ready for you to move in! This property also has a great spacious unfinished basement with plenty of storage.Quick access to the highway and shopping!

22. 2022-06-24
    listed $175,000 Active 440-char remark

    Show marketing remark (440 chars)

    BEAUTIFUL CAPE COD IN WATERBURY IS THE PERFECT PLACE TO CALL HOME!Don't miss out on this 4 bedroom cape with private backyard! Enjoy 2 bedrooms & full bath on the main level and an additional 2 bedrooms upstairs.Freshly painted & hardwood floors throughout this well maintained and ready for you to move in! This property also has a great spacious unfinished basement with plenty of storage.Quick access to the highway and shopping!

23. 2007-12-03
    soldstatus $170,000
24. 2007-11-30
    soldstatus $170,000
25. 2007-07-21
    listed $179,900

ⓘ 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: $6,327 · $527/mo
• Projected year-2 tax: $6,327 · $527/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $23,235
• − Mortgage interest: −$13,724
• − Property taxes: −$6,327
• − Insurance: −$1,225
• − Repairs & maintenance: −$1,859
• − Management: −$1,859
• − Depreciation: −$7,127
• Taxable loss: −$8,886
• Est. tax savings @ 24.0%: +$2,133
• After-tax cash flow: $-2,481/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: Waterbury School District
• NCES district ID: 0904830
• Math proficiency: 12% ▼ -7.00%
• Reading proficiency: 23% ▼ -8.00%
• Median HH income: $40,040
• Composite: 14.85/100
• National rank: #9380
• State rank: #148 of 153 in CT

Livability — Waterbury

• Score: 79/100
• State rank: #32
• US rank: #2205

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Waterbury, CT
• County: New Haven County · 688,236 people
• City population: 115,012
• Metro: New Haven-Milford, CT
• Population (ZIP): 29,594
• Household income: $67,364
• Rent vs Own: 40.7% rent · 59.3% own
• Severe rent burden: 1276.0

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.68)
• Race & ethnicity: White 43% Hispanic / Latino 33% Black 17% Two or more races 13% Asian 2%
• Hispanic origin (detail): Puerto Rican 17% Dominican 8%
• Common ancestry: Romanian 2% Russian 2% Estonian 2%
• Foreign-born: 20% · Canada, Jamaica, China
• Languages at home: 64% English-only · Spanish 23% Other Indo-European 8% French/Haitian/Cajun 1%

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: ▼ -297.81%
• Current HPI: 281.1446
• Rent YoY: ▲ 9.75%
• Metro: New Haven-Milford, CT
• 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

+47.3% since first listed

10 events — show timeline

• 2026-04-25 Relisted — Smart MLS
• 2026-04-21 Contingent — Smart MLS
• 2026-04-16 Price Changed $265,000 Smart MLS
• 2026-03-23 Listed $275,000 Smart MLS
• 2022-08-10 Sold (Public Records) $190,000 Public Records
• 2022-08-05 Sold (MLS) $190,000 Smart MLS
• 2022-06-24 Listed $175,000 Smart MLS
• 2007-12-03 Sold (Public Records) $170,000 Public Records
• 2007-11-30 Sold (MLS) $170,000 Smart MLS
• 2007-07-21 Listed $179,900 Smart MLS

Property tax history

+2.0%/yr

Latest (2023): $6,327 · +47.6% YoY. Source: county tax records.