37 California Ave · Middletown, NY 10940

$319,000

3 bd · 1.0 ba · 1,152 sqft · SingleFamily public records · 19 Days on market

Built 1926 0.25 ac lot $277/sqft · 21% below area Est $406k · 21% 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 +7.5/30.0
• Rent growth +4.6/5.0
• Schools +4.2/10.0
• Livability +4.1/5.0
• Condition / age +2.5/5.0
• 1% rule +2.3/10.0
• DSCR +1.6/10.0
• Appreciation +0.0/10.0

Listing remarks

MLS Listing Description: Charming 3-bedroom, 1-bath traditional two-story home featuring a spacious, enclosed backyard—perfect for outdoor enjoyment and entertaining. The first floor offers an oversized living room, an open dining area, and a functional kitchen layout ideal for everyday living. Upstairs, you’ll find three comfortable bedrooms and a full bath. A walk-up attic provides convenient additional storage space. The basement includes laundry area, and walk-out access to the backyard, adding flexibility and potential for extended living or recreation space. Conveniently located near a local park and a variety of restaurants, this home offers both comfort and accessibilit

Key facts

• Open dining area
• Finished basement
• Walk-up attic

Tags

• ENCLOSED BACKYARD
• OVERSIZED LIVING ROOM
• OPEN DINING AREA
• FUNCTIONAL KITCHEN LAYOUT
• WALK-UP ATTIC
• FINISHED BASEMENT

Property features AI

Exterior

• Parking: Driveway
• Utilities: Electricity connected (Orange & Rockland); Natural gas connected; Public water; Public sewer; Trash collection (public)
• Home design: Single family residence; Living area recorded from public records
• Construction: Frame construction
• Exterior features: Frame construction; Not waterfront; No additional parcels

Interior

• Kitchen: Gas range
• Bathrooms: 1 full bathroom
• Heating & cooling: Baseboard heating; Natural gas heating; No central cooling
• Interior features: Ceiling fans; Washer/dryer hookup; Full basement with partial finish, storage space and walk-out access; Attic with stairs, storage and unfinished space; 8 total rooms
• Laundry & utility: Washer; Dryer; Washer/dryer hookup

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $319k.

Deal economics

• At list price, monthly cash flow is $-395 ($-5k/yr) — negative.
• To cash-flow at today's rent, offer at most $249k (21.8% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $234k (26.7% below list).
• Recommended offer: $234k (26.7% below list) — sets the bar for 1% rule.
• Cap rate 4.8% vs local median 3.3% in Middletown — 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 (#79 in NY, #1,219 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, housing A+, health & safety A+; Watch: commute C-.
• Middletown City School District (suburban): math 41% / reading 55% proficiency, ranked #411 of 590 in NY (top 70%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; 61% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: Maple Hill Elementary School (math 32% / reading 38%, grade F, #1,569 of 2,108 statewide, top 75%, 1,012 students, 80% FRL); Monhagen Middle School (math 16% / reading 39%, grade F, #576 of 729 statewide, top 79%, 817 students, 75% FRL); Middletown High School (math 90% / reading 92%, grade A+, #203 of 1,100 statewide, top 20%, 2,523 students, 71% FRL).
• Market conditions: Rents rising fast (+8.2%/yr); 273 active listings in the ZIP; 31 comparable units currently listed for rent nearby; rentals at typical pace (median 25d on market — plan ~3-4 weeks tenant-placement turnaround); 45% of comp listings sitting > 30 days — soft ceiling on asking rent; solid renter incomes; 1,746 units permitted in Orange County in 2024 (1,265 in 5+ unit buildings).
• This rent runs 32% of the median local income ($87k/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 $10k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 19 days — a 2% lower offer ($314k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 23y 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 $142k; list at $319k implies a 124% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1926 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $233,860 (26.7% 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. Built in 1926 — 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 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. 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: 0.73% ✗
• Cap rate: 4.81%
• Cash-on-cash: -5.30%
• DSCR: 0.76
• GRM: 11.4

CMA / ARV

• ARV (median comp): $406,046
• List price: $319,000
• Delta: -21.22%
• 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
37 Hanford St	0.41mi	3/1.0	1,144 (-1%)	4mo	$285,000	$249	76
240 W Main St	0.16mi	3/2.0	1,170 (+2%)	15mo	$380,000	$325	73
242 1/2 W Main St	0.18mi	3/1.5	1,080 (-6%)	8mo	$265,000	$245	73
26 Chestnut St	0.31mi	2/1.0 (-1)	1,151 (-0%)	16mo	$260,000	$226	67
53 Richmond Pl	0.59mi	3/1.0	1,144 (-1%)	6mo	$345,000	$302	66
14 Mercer St	0.23mi	3/1.0	1,044 (-9%)	10mo	$400,000	$383	65
12 State St	0.40mi	2/1.5 (-1)	1,222 (+6%)	6mo	$383,000	$313	59
72 Hanford St	0.31mi	3/1.5	1,251 (+9%)	15mo	$274,000	$219	57
75-79 Madison Ave	0.61mi	3/1.5	1,149 (-0%)	15mo	$399,000	$347	56
20 Columbia Ave	0.60mi	3/1.0	1,232 (+7%)	10mo	$290,000	$235	52
15 Independence Ave	0.69mi	3/1.5	1,320 (+15%)	10mo	$310,000	$235	33
9 Grandview Ave	0.69mi	2/1.0 (-1)	1,324 (+15%)	8mo	$363,740	$275	31

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: -19.8%
• Equity multiple: 0.28×
• Total profit: $-64,401
• Equity at exit: $47,564

10-year hold

• IRR: -4.5%
• Equity multiple: 0.64×
• Total profit: $-31,946
• Equity at exit: $27,581

Cash invested: $89,320 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 15 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City: — inherits STATE

NYC rent stabilization (~1M units); 2019 HSTPA strengthened tenant rights; courts deeply backlogged.

Methodology + full state rankings →

ZIP-level market 10940

• Home prices YoY: -18.7%
• Rents YoY: 8.2%
• Active inventory: 273
• Price-to-rent: 11.4×

Monthly cashflow live

• Estimated rent: $2,339 high
• Mortgage (P&I): −$1,673
• Tax from tax record: −$436 /mo · $5,235/yr
• Insurance: −$133
• HOA: −$0
• Vacancy / Maint / Mgmt: −$491
• Net cashflow: $-395

Break-even live

Break-even rent $2,838

Max offer price $249,309

Occupancy floor —

Sensitivity live

Price	-10% $-214	-5% $-304	+0% $-395	+5% $-485	+10% $-575
Rent	-10% $-579	-5% $-487	+0% $-395	+5% $-302	+10% $-210
Rate	-1.0pp $-234	-0.5pp $-313	base $-395	+0.5pp $-477	+1.0pp $-561

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: $79,750
• Closing costs: $9,570
• Reserves months: —
• Total cash needed: —

Rent comps 31 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
203 W Main St Unit 2 Middletown, NY	2.0	1.0	784	$1,700	$2.17	45d	1	0.05mi
128 W Main St Unit 2 Middletown, NY	3.0	2.0	880	$2,500	$2.84	45d	1	0.42mi
126 W Main St Middletown, NY	3.0	1.0	900	$2,200	$2.44	22d	1	0.43mi
126 W Main St Unit 2 Middletown, NY	3.0	1.0	700	$2,200	$3.14	45d	1	0.43mi
39 Crescent Pl Middletown, NY	3.0	1.0	1278	$2,500	$1.96	25d	1	0.45mi
11 Knapp Ave Apt 2 Middletown, NY	2.0	1.0	950	$2,500	$2.63	45d	1	0.46mi
118 W Main St Unit 1 Middletown, NY	3.0	1.0	1158	$2,350	$2.03	22d	1	0.46mi
26 Mill St Unit 2 Middletown, NY	3.0	2.0	1300	$2,600	$2.00	45d	1	0.50mi
26 Mill St Middletown, NY	3.0	2.0	1300	$2,600	$2.00	25d	1	0.50mi
31 Liberty St Middletown, NY	2.0	1.0	1090	$2,000	$1.83	15d	1	0.54mi
151 Tall Oaks Dr Middletown, NY	1.0–3.0	1.0	920	$1,607	$1.75	15d	1	0.57mi
102 Wawayanda Ave Unit 1 Middletown, NY	2.0	1.0	750	$1,950	$2.60	45d	1	0.60mi
38 Richmond Pl Unit 1B Middletown, NY	2.0	1.0	950	$2,400	$2.53	15d	1	0.61mi
23 Wawayanda Ave Middletown, NY	3.0	2.0	1072	$2,150	$2.01	45d	1	0.61mi
225 Monhagen Ave Middletown, NY	3.0	1.0	1466	$2,700	$1.84	15d	1	0.71mi
28 North St #1 Middletown, NY	2.0	2.0	1200	$2,000	$1.67	45d	1	0.73mi
2 E Main St #5 Middletown, NY	3.0	1.0	1200	$1,850	$1.54	15d	1	0.75mi
17 Academy Ave Unit 2 Middletown, NY	2.0	1.0	750	$1,850	$2.47	45d	1	0.95mi
184 Highland Ave Middletown, NY	4.0	2.0	1486	$3,500	$2.36	25d	1	1.19mi
31 Beattie Ave #2 Middletown, NY	2.0	1.0	718	$2,000	$2.79	45d	1	1.19mi
90 Montgomery St Unit Upper Middletown, NY	2.0	1.0	900	$2,400	$2.67	25d	1	1.20mi
32 Palmer Ave Unit 5 Middletown, NY	2.0	1.0	1100	$2,000	$1.82	45d	1	1.28mi
1 Ruth Ct Middletown, NY	2.0	1.0	984	$2,200	$2.24	25d	1	1.30mi
56 Wisner Ave Middletown, NY	3.0	1.0	1144	$2,500	$2.19	25d	1	1.31mi
139 Ruth Ct Middletown, NY	2.0	2.0	880	$2,000	$2.27	25d	1	1.32mi
260 Ruth Ct Middletown, NY	2.0	2.0	900	$2,025	$2.25	25d	1	1.38mi
63 Broad St Middletown, NY	3.0	1.0	1088	$2,700	$2.48	25d	1	1.39mi
1 Dewitt St Middletown, NY	3.0	1.0	1127	$2,100	$1.86	45d	1	1.39mi
132 Prospect Ave Middletown, NY	3.0	1.0	1240	$2,300	$1.85	45d	1	1.41mi
268 Ruth Ct Middletown, NY	2.0	2.0	1125	$2,375	$2.11	45d	1	1.41mi
2 Underhill Rd Middletown, NY	1.0–2.0	1.0–1.5	727	$2,260	$3.11	15d	25	1.49mi

Listing history 36 events

1. 2026-06-18
   days on market $319,000 Active 19 DOM
2. 2026-06-17
   days on market $319,000 Active 18 DOM
3. 2026-06-16
   days on market $319,000 Active 17 DOM
4. 2026-06-15
   days on market $319,000 Active 16 DOM
5. 2026-06-14
   days on market $319,000 Active 14 DOM
6. 2026-06-13
   days on market $319,000 Active 13 DOM
7. 2026-06-10
   days on market $319,000 Active 11 DOM
8. 2026-06-09
   days on market $319,000 Active 10 DOM
9. 2026-06-08
   days on market $319,000 Active 9 DOM
10. 2026-06-07
    days on market $319,000 Active 8 DOM
11. 2026-06-05
    days on market $319,000 Active 5 DOM
12. 2026-06-03
    days on market $319,000 Active 4 DOM
13. 2026-06-02
    days on market $319,000 Active 3 DOM
14. 2026-06-01
    days on market $319,000 Active 2 DOM
15. 2026-05-31
    pricedays on marketlisting id $319,000 Active 1 DOM
16. 2026-05-14
    listed $339,900 Active 730-char remark
17. 2026-04-19
    price $365,900
18. 2026-04-02
    listed $379,900 Active
19. 2018-10-10
    soldstatus $142,500
20. 2018-10-03
    soldstatus $142,500 Sold
21. 2018-08-24
    historical Pending
22. 2018-05-31
    price $149,900
23. 2018-04-16
    listed $139,900 Active
24. 2017-11-08
    historical
25. 2017-10-05
    listed $139,900 Active
26. 2017-08-22
    historical
27. 2017-08-21
    status Active
28. 2017-05-25
    historical Pending
29. 2017-05-11
    listed $139,900 Active
30. 2006-07-25
    soldstatus $234,100
31. 2004-01-20
    soldstatus $160,000
32. 2003-11-05
    soldstatus $160,000
33. 2003-10-23
    historical
34. 2003-10-23
    price $164,900
35. 2003-06-12
    listed $160,000
36. 1986-03-05
    soldstatus $58,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $5,235 · $436/mo
• Projected year-2 tax: $5,313 · $443/mo
• Expected delta: +$78/yr (+$7/mo · 1.5%)

ⓘ 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 ≥98°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 10% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $28,063
• − Mortgage interest: −$17,869
• − Property taxes: −$5,235
• − Insurance: −$1,595
• − Repairs & maintenance: −$2,245
• − Management: −$2,245
• − Depreciation: −$9,280
• Taxable loss: −$10,405
• Est. tax savings @ 24.0%: +$2,497
• After-tax cash flow: $-2,237/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: Middletown City School District
• NCES district ID: 3619320
• Math proficiency: 41% ▼ -2.00%
• Reading proficiency: 55% ▲ 19.00%
• Median HH income: $54,612
• Composite: 41.52/100
• National rank: #3453
• State rank: #411 of 590 in NY

Livability — Middletown

• Score: 82/100
• State rank: #79
• US rank: #1219

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Middletown, NY
• County: Orange County · 267,004 people
• City population: 68,033
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• Population (ZIP): 53,611
• Household income: $87,080
• Rent vs Own: 38.4% rent · 61.6% own
• Severe rent burden: 1846.0

Population outlook (Orange County) Hauer SSP2

• Today (2025): 379,830 people
• By 2030: 378,955 · -0.2%
• By 2040: 375,444 · -1.2%
• By 2050: 369,311 · -2.8%
• By 2075: 354,233 · -6.7%
• By 2100: 318,150 · -16.2%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Highly diverse neighborhood (Simpson 0.70)
• Race & ethnicity: White 39% Hispanic / Latino 32% Black 20% Two or more races 13% Asian 4% Native American 3%
• Hispanic origin (detail): Mexican 9% Puerto Rican 13% Dominican 3%
• Common ancestry: Romanian 3% Italian 1% Iranian 1%
• Foreign-born: 18% · Canada, China, Jamaica
• Languages at home: 72% English-only · Spanish 21% Other Indo-European 2% Chinese 1%

Political lean MEDSL · Orange

• 2024 margin: Lean R (+8.4) · D 45.8% · R 54.2%
• 2008→2024 swing: -12.5pp toward R · 2008: 4.1pp · 2024: -8.4pp
• All cycles: 2024: R+8.4 2020: R+0.2 2016: R+6.5 2012: D+5.2 2008: D+4.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -71.68%
• Current HPI: 311.5969
• Rent YoY: ▲ 8.23%
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+450.0% since first listed

23 events — show timeline

• 2026-05-30 Listed $319,000 OneKey® MLS as Distributed by MLS Grid
• 2026-05-23 Price Changed $319,900 OneKey® MLS as Distributed by MLS Grid
• 2026-05-14 Listed $339,900 OneKey® MLS as Distributed by MLS Grid
• 2026-04-19 Price Changed $365,900 OneKey® MLS as Distributed by MLS Grid
• 2026-04-02 Listed $379,900 OneKey® MLS as Distributed by MLS Grid
• 2018-10-10 Sold (Public Records) $142,500 Public Records
• 2018-10-03 Sold (MLS) $142,500 OneKey® MLS as Distributed by MLS Grid
• 2018-08-24 Contingent — OneKey® MLS as Distributed by MLS Grid
• 2018-05-31 Price Changed $149,900 OneKey® MLS as Distributed by MLS Grid
• 2018-04-16 Listed $139,900 OneKey® MLS as Distributed by MLS Grid
• 2017-11-08 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2017-10-05 Listed $139,900 OneKey® MLS as Distributed by MLS Grid
• 2017-08-22 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2017-08-21 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2017-05-25 Contingent — OneKey® MLS as Distributed by MLS Grid
• 2017-05-11 Listed $139,900 OneKey® MLS as Distributed by MLS Grid
• 2006-07-25 Sold (Public Records) $234,100 Public Records
• 2004-01-20 Sold (Public Records) $160,000 Public Records
• 2003-11-05 Sold (MLS) $160,000 HGMLS
• 2003-10-23 Price Changed $164,900 HGMLS
• 2003-10-23 Delisted — HGMLS
• 2003-06-12 Listed $160,000 HGMLS
• 1986-03-05 Sold (Public Records) $58,000 Public Records

Property tax history

+1.0%/yr

Latest (2025): $5,235 · -0.3% YoY. Source: county tax records.