20 John St · Middletown, NY 10940

$575,000

3 bd · 3.0 ba · 5,157 sqft · MultiFamily · 86 Days on market

Built 1900 Fair condition 4,700 sqft lot $111/sqft · 36% below area Est $893k · 36% 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 +26.5/30.0
• ARV discount +15.0/15.0
• DSCR +9.1/10.0
• 1% rule +7.1/10.0
• Schools +5.1/10.0
• Rent growth +4.6/5.0
• Livability +4.1/5.0
• Condition / age +2.2/5.0
• 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

For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential. Property Overview: First Floor: Spacious 2,000 sq. ft.

Key facts

• Multi purpose room
• Mixed use building
• Private parking lot

Tags

• INCOME PRODUCING
• MIXED USE BUILDING
• COMMERCIAL SPACE
• MULTI PURPOSE ROOM
• PRIVATE PARKING LOT
• DOWNTOWN LOCATION

What this means for you Summary

Snapshot

• This is a 3-bed/3.0-bath multifamily listed at $575k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $2k ($18k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $575k).
• Recommended offer: $540k (6.0% below list) — sets the bar for market timing.
• Cap rate 9.5% vs local median 3.7% 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); 465 active listings in the ZIP; 29 comparable units currently listed for rent nearby; rentals lingering (median 119d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 72% 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).
• At $6,964/mo this rent would consume 96% of the median local household income ($87k/yr) — very limited rent-growth headroom before tenants either downsize or default.

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.
• At projected returns (-3.0% appreciation + 8.0% rent growth), your $161k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• It's been on market 86 days — a 6% lower offer ($540k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $540,500 (6.0% below list)

Questions for the listing agent

1. It's been on market 86 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
3. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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.
8. 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.
9. 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: 1.21% ✓
• Cap rate: 9.48%
• Cash-on-cash: 11.39%
• DSCR: 1.51
• GRM: 6.9

CMA / ARV

• ARV (median comp): $893,417
• List price: $575,000
• Delta: -35.64%
• Verdict: UNDERPRICED
• Comps: 7 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
26 Paglia Dr	0.22mi	5/4.0 (+2)	3,718 (-28%)	49mo	$895,000	$241	31
22 Oak Ridge Rd	1.11mi	5/4.0 (+2)	5,304 (+3%)	45mo	$600,000	$113	26
148 Highland Ave	0.51mi	4/3.5 (+1)	3,617 (-30%)	46mo	$429,780	$119	24
54 Highrose Ridge Way	1.87mi	3/4.5	3,647 (-29%)	17mo	$525,000	$144	20
529 Route 17m #531	1.42mi	4/1.5 (+1)	4,240 (-18%)	12mo	$1,300,000	$307	19
150 Highland Ave	0.52mi	5/3.5 (+2)	3,921 (-24%)	52mo	$505,000	$129	19
14 Lincoln Ter	1.25mi	5/4.5 (+2)	3,642 (-29%)	6mo	$665,000	$183	19
1 Wawayanda Pl	0.93mi	5/3.0 (+2)	3,890 (-25%)	14mo	$595,000	$153	18
27 Oak Ridge Rd	1.11mi	4/3.0 (+1)	3,988 (-23%)	49mo	$745,000	$187	15
18-20 Randall Hts	0.78mi	4/3.5 (+1)	3,953 (-23%)	37mo	$505,000	$128	13
25 Pilgrim Corners Rd	1.56mi	5/3.5 (+2)	5,980 (+16%)	29mo	$830,000	$139	8
59 Webb Rd	1.28mi	5/5.5 (+2)	3,960 (-23%)	42mo	$570,000	$144	0

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: 6.2%
• Equity multiple: 1.25×
• Total profit: $41,044
• Equity at exit: $85,734

10-year hold

• IRR: 19.6%
• Equity multiple: 3.04×
• Total profit: $328,976
• Equity at exit: $49,715

Cash invested: $161,000 (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: 465
• Price-to-rent: 20.2×

Monthly cashflow live

• Estimated rent: $6,964 high
• Mortgage (P&I): −$3,015
• Tax est. 1.5%: −$719 /mo · $8,625/yr
• Insurance: −$240
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,462
• Net cashflow: $1,528

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

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$4,734
1× unit	0	1	$2,230
Total (3 units)			$6,964

Break-even live

Break-even rent $5,030

Max offer price $575,000

Occupancy floor 73%

Sensitivity live

Price	-10% $1,925	-5% $1,727	+0% $1,528	+5% $1,329	+10% $1,130
Rent	-10% $978	-5% $1,253	+0% $1,528	+5% $1,803	+10% $2,078
Rate	-1.0pp $1,817	-0.5pp $1,674	base $1,528	+0.5pp $1,379	+1.0pp $1,227

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: $143,750
• Closing costs: $17,250
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
91 North St Unit 204 Middletown, NY	1.0	1.0	828	$1,700	$2.05	6d	1	0.06mi
108 North St Apt 302 Middletown, NY	3.0	2.0	750	$1,900	$2.53	6d	1	0.06mi
108 North St Unit 303 Middletown, NY	1.0	1.0	550	$1,450	$2.64	6d	1	0.06mi
44 John St Unit 3 Middletown, NY	1.0	1.0	650	$1,500	$2.31	139d	1	0.09mi
48 North St Middletown, NY	1.0–2.0	1.0–2.0	834	$3,145	$3.77	0d	10	0.11mi
28 North St #1 Middletown, NY	2.0	2.0	1200	$2,000	$1.67	139d	1	0.15mi
30 E Main St Unit 4 Middletown, NY	1.0	1.0	—	$1,500	—	3d	1	0.20mi
30 E Main St Unit 4 Middletown, NY	1.0	1.0	600	$1,500	$2.50	139d	1	0.20mi
23 W Main St Unit 1 Middletown, NY	1.0	1.0	770	$1,900	$2.47	139d	1	0.20mi
23 County Highway 108 Middletown, NY	1.0–2.0	1.0–2.0	1023	$2,761	$2.70	0d	6	0.21mi
2 E Main St #5 Middletown, NY	3.0	1.0	1200	$1,850	$1.54	109d	1	0.22mi
2 E Main St Unit 4 Middletown, NY	1.0	1.0	1000	$1,650	$1.65	139d	1	0.22mi
8 Roberts St Unit 2-A Middletown, NY	2.0	1.0	2132	$2,000	$0.94	119d	1	0.22mi
22 Cottage St Unit 3B Middletown, NY	1.0	1.0	1250	$2,000	$1.60	119d	1	0.23mi
118 W Main St Unit 1 Middletown, NY	3.0	1.0	1158	$2,350	$2.03	116d	1	0.27mi
77 Linden Ave Middletown, NY	1.0	1.0	742	$1,675	$2.26	139d	1	0.29mi
31 Liberty St Middletown, NY	2.0	1.0	1090	$2,000	$1.83	109d	1	0.30mi
17 Academy Ave Unit 2 Middletown, NY	2.0	1.0	750	$1,850	$2.47	139d	1	0.30mi
126 W Main St Unit 2 Middletown, NY	3.0	1.0	700	$2,200	$3.14	139d	1	0.30mi
126 W Main St Middletown, NY	3.0	1.0	900	$2,200	$2.44	116d	1	0.30mi
11 Knapp Ave Apt 2 Middletown, NY	2.0	1.0	950	$2,500	$2.63	139d	1	0.30mi
26 Mill St Unit 2 Middletown, NY	3.0	2.0	1300	$2,600	$2.00	139d	1	0.31mi
26 Mill St Middletown, NY	3.0	2.0	1300	$2,600	$2.00	119d	1	0.31mi
128 W Main St Unit 2 Middletown, NY	3.0	2.0	880	$2,500	$2.84	139d	1	0.31mi
36 Wallkill Ave Unit 36 Middletown, NY	2.0	1.0	500	$2,050	$4.10	109d	1	0.31mi
14 Smith St Middletown, NY	3.0	2.0	1852	$3,600	$1.94	109d	1	0.35mi
26 Washington St Unit 2 Middletown, NY	3.0	1.0	2274	$2,100	$0.92	139d	1	0.36mi
125 Wickham Ave Unit 3B Middletown, NY	2.0	1.0	650	$2,000	$3.08	6d	1	0.37mi
25 Knapp Ave #2 Middletown, NY	2.0	1.0	984	$2,200	$2.24	0d	1	0.38mi
30 Knapp Ave Middletown, NY	2.0	1.0	1532	$1,800	$1.17	139d	1	0.39mi
39 Crescent Pl Middletown, NY	3.0	1.0	1278	$2,500	$1.96	119d	1	0.40mi
20 Benton Ave Middletown, NY	3.0	2.0	1504	$2,900	$1.93	6d	1	0.41mi
89 Cottage St Unit 1466615P Middletown, NY	1.0	1.0	—	$2,889	—	119d	1	0.44mi
23 Wawayanda Ave Middletown, NY	3.0	2.0	1072	$2,150	$2.01	139d	1	0.45mi
31 Beattie Ave #2 Middletown, NY	2.0	1.0	718	$2,000	$2.79	139d	1	0.46mi
90 Montgomery St Unit Upper Middletown, NY	2.0	1.0	900	$2,300	$2.56	6d	1	0.48mi
54 Sprague Ave Unit 1 Middletown, NY	2.0	1.0	—	$1,400	—	119d	1	0.49mi
44 Broad St Middletown, NY	1.0	1.0	1684	$1,700	$1.01	139d	1	0.58mi
63 Broad St Middletown, NY	3.0	1.0	1088	$2,500	$2.30	6d	1	0.66mi
1 Dewitt St Middletown, NY	3.0	1.0	1127	$2,100	$1.86	139d	1	0.66mi

Property features AI

Exterior

• Parking: Three parking spacesOff-street, private parking lot
• Utilities: Electric service by Orange & RocklandPublic sewerElectricity available
• Home design: Triplex
• Construction: Frame constructionBrick/mortar and stone foundation
• Exterior features: Level lot

Interior

• Bedrooms: One 1-bedroom unitOne 2-bedroom unit
• Bathrooms: Three full bathrooms (total)
• Heating & cooling: Baseboard heatingNatural gas heatingOther heating
• Interior features: Other interior features

Listing history 50 events

1. 2026-09-05
   days on market $575,000 Active 86 DOM
2. 2026-09-04
   days on market $575,000 Active 85 DOM
3. 2026-09-03
   days on market $575,000 Active 84 DOM
4. 2026-08-31
   days on market $575,000 Active 81 DOM
5. 2026-08-30
   days on market $575,000 Active 80 DOM
6. 2026-08-29
   days on market $575,000 Active 79 DOM
7. 2026-08-28
   days on market $575,000 Active 78 DOM
8. 2026-08-06
   days on market $575,000 Active 77 DOM
9. 2026-08-05
   days on market $575,000 Active 76 DOM
10. 2026-08-04
    days on market $575,000 Active 75 DOM
11. 2026-08-03
    days on market $575,000 Active 74 DOM
12. 2026-07-31
    days on market $575,000 Active 71 DOM
13. 2026-07-30
    days on market $575,000 Active 70 DOM
14. 2026-07-29
    days on market $575,000 Active 69 DOM
15. 2026-07-27
    days on market $575,000 Active 67 DOM
16. 2026-07-25
    days on market $575,000 Active 65 DOM
17. 2026-07-23
    days on market $575,000 Active 63 DOM
18. 2026-07-22
    days on market $575,000 Active 62 DOM
19. 2026-07-21
    days on market $575,000 Active 61 DOM
20. 2026-07-18
    days on market $575,000 Active 58 DOM
21. 2026-07-16
    days on market $575,000 Active 56 DOM
22. 2026-07-16
    days on market $575,000 Active 55 DOM
23. 2026-07-14
    days on market $575,000 Active 54 DOM
24. 2026-07-14
    days on market $575,000 Active 53 DOM
25. 2026-07-12
    days on market $575,000 Active 52 DOM
26. 2026-07-11
    days on market $575,000 Active 51 DOM
27. 2026-07-10
    days on market $575,000 Active 50 DOM
28. 2026-07-09
    days on market $575,000 Active 49 DOM
29. 2026-07-08
    days on market $575,000 Active 48 DOM
30. 2026-07-07
    days on market $575,000 Active 47 DOM
31. 2026-07-06
    days on market $575,000 Active 46 DOM
32. 2026-07-05
    days on market $575,000 Active 45 DOM
33. 2026-07-04
    days on market $575,000 Active 44 DOM
34. 2026-07-03
    days on market $575,000 Active 43 DOM
35. 2026-07-02
    days on market $575,000 Active 42 DOM
36. 2026-07-01
    days on market $575,000 Active 41 DOM
37. 2026-06-30
    days on market $575,000 Active 40 DOM
38. 2026-06-29
    days on market $575,000 Active 39 DOM
39. 2026-06-28
    days on market $575,000 Active 38 DOM
40. 2026-06-28
    days on market $575,000 Active 37 DOM
41. 2026-06-27
    days on market $575,000 Active 36 DOM
42. 2026-06-25
    days on market $575,000 Active 34 DOM
43. 2026-06-23
    days on market $575,000 Active 32 DOM
44. 2026-06-22
    days on market $575,000 Active 31 DOM
45. 2026-06-18
    days on market $575,000 Active 28 DOM
46. 2026-06-17
    days on market $575,000 Active 27 DOM
47. 2026-06-16
    days on market $575,000 Active 26 DOM
48. 2026-06-15
    days on market $575,000 Active 25 DOM
49. 2026-06-14
    days on market $575,000 Active 23 DOM
50. 2026-06-13
    days on market $575,000 Active 22 DOM

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

Taxation est. · year 1

• Rental income: $83,568
• − Mortgage interest: −$32,209
• − Property taxes: −$8,625
• − Insurance: −$2,875
• − Repairs & maintenance: −$6,685
• − Management: −$6,685
• − Depreciation: −$16,727
• Taxable income: $9,761
• Est. tax owed @ 24.0%: −$2,343
• After-tax cash flow: $15,992/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.

Condition & rehab AI · 12 photos

Fair 45/100 Moderate rehab Est. rehab $128,925–$232,065 screening

This mixed-use property requires significant updates to its exterior, interior, and HVAC system to improve its condition and value. The property has potential for rental or resale, but the current state detracts from its appeal.

Repairs flagged

• Major Paint — Peeling paint on exterior and interior
• Major Siding — Worn and peeling
• Major Flooring — Worn carpet and outdated tile
• Major Kitchen cabinets — Outdated and worn
• Major Bathroom fixtures — Outdated and worn
• Major HVAC system — Outdated and cluttered

Value-add opportunities

• Both Paint and update interior decor — Enhances curb appeal and interior aesthetics ↑
• Both Replace flooring — Improves comfort and appearance ↑
• Both Replace kitchen cabinets and appliances — Modernizes the space and improves functionality ↑
• Both Replace bathroom fixtures and tiles — Enhances functionality and appearance ↑
• Both Replace HVAC system — Improves comfort and energy efficiency ↑

ⓘ Rehab cost is a screening estimate — Moderate scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

D Composite school gradezoned avg 51/100

Zoned Schools

Elementary Maple Hill Elementary School F NY #1,569/2,108 Nat'l #22,904/41,679 Middle Monhagen Middle School F NY #576/729 Nat'l #9,659/14,009 High Middletown High School A+ NY #203/1,100 Nat'l #335/17,239

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

A Composite livability gradescore 82/100

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 · 379,830 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: 12% of renters

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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%

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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%

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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

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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

Property features AI

Exterior

• Parking: Three parking spacesOff-street, private parking lot
• Utilities: Electric service by Orange & RocklandPublic sewerElectricity available
• Home design: Triplex
• Construction: Frame constructionBrick/mortar and stone foundation
• Exterior features: Level lot

Interior

• Bedrooms: One 1-bedroom unitOne 2-bedroom unit
• Bathrooms: Three full bathrooms (total)
• Heating & cooling: Baseboard heatingNatural gas heatingOther heating
• Interior features: Other interior features

Price history

1 event — show timeline

• 2026-05-21 Listed $575,000 OneKey® MLS as Distributed by MLS Grid