726/720 N Pennsylvania Ave · Winter Park, FL 32789

$1,185,999

3 bd · 2.0 ba · 1,167 sqft · MultiFamily public records · 53 Days on market

Built 2015 4,091 sqft lot

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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 +9.6/30.0
• ARV discount +7.5/15.0
• Livability +4.2/5.0
• Schools +4.1/10.0
• Rent growth +2.8/5.0
• DSCR +2.7/10.0
• Condition / age +2.5/5.0
• 1% rule +1.8/10.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 4 units. confirmed

Listing remarks

Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, a

Key facts

• Custom cabinetry
• Stone countertops
• Open-concept layouts

Tags

• MINUTES FROM ROLLINS COLLEGE
• OPEN-CONCEPT LAYOUTS
• STONE COUNTERTOPS
• STAINLESS STEEL APPLIANCES
• CUSTOM CABINETRY
• WOOD AND TILE FLOORING

Property features AI

Finance

• Other: Zoned R-2
• Financial info: Gross annual income reported at $84,000; Annual net income reported at $55,000; Pro forma rent listed at $3,500 per unit for each 3-bedroom unit
• HOA & community: No HOA association

Exterior

• Parking: No parking information provided
• Security: No security features listed
• Utilities: Public water; Septic tank sewer; Cable, electricity, and water connected
• Home design: Residential income property (duplex); Two total buildings
• Construction: Block construction; Metal roof; Block foundation; Built area reported as 2,282 square feet
• Exterior features: Asphalt road access; Property includes additional parcels; Two lots (total acreage between 0 and 1/4 acre)

Interior

• Kitchen: No specific kitchen appliances listed
• Bedrooms: Six bedrooms total; Two separate 3-bedroom units (each with 3 bedrooms)
• Flooring: No flooring information provided
• Bathrooms: Each unit has 2 bathrooms
• Heating & cooling: Central heating; Central air conditioning
• Interior features: No notable interior features listed
• Laundry & utility: Laundry located inside

What this means for you Summary

Snapshot

• This is a 4 × 3-bed/2.0-bath units multifamily listed at $1.19M.

Deal economics

• At list price, monthly cash flow is $-801 ($-10k/yr) — negative. Per door: $-200/mo.
• To cash-flow at today's rent, offer at most $1.04M (11.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $803k (32.3% below list).
• Recommended offer: $803k (32.3% below list) — sets the bar for 1% rule.
• Cap rate 5.5% vs local median 1.8% in Winter Park — 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 83/100 on livability (#44 in FL, #852 nationally) — a professional / high-income tenant draw. Strengths: commute A+, employment A+, health & safety A+; Watch: cost of living F.
• Orange (suburban): math 46% / reading 51% proficiency, ranked #43 of 73 in FL (top 59%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Lakemont Elementary (math 57% / reading 60%, grade B-, #735 of 2,144 statewide, top 35%, 611 students, 43% FRL); Winter Park High (math 42% / reading 64%, grade C-, #148 of 667 statewide, top 23%, 3,369 students, 37% FRL) — zoned schools average 40% FRL vs 56% district-wide (17 pts lower); this property's tenant base skews higher-income than the district average.
• Market conditions: Rents rising (+1.2%/yr); 339 active listings in the ZIP; 22 comparable units currently listed for rent nearby; rentals at typical pace (median 17d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 8,053 units permitted in Orange County in 2024 (3,133 in 5+ unit buildings).
• At $8,030/mo this rent would consume 90% of the median local household income ($107k/yr) (locally 1178% of renters already pay >50% of income on rent) — 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 $8k of loan paydown is wiped out by about $36k of value loss. Plan a longer hold.
• Orange County population projected at +52% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 53 days — a 3% lower offer ($1.15M) is reasonable based on typical stale-listing flexibility.
• 19 sale attempts since 8y 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.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→22/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $803,000 (32.3% 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 53 days. Have you received any prior offers? Is the seller open to a 32% concession, seller financing, or rate buy-down credit?
3. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
4. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Schools are B-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?
7. 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?
8. 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.
9. 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.
10. 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: 0.68% ✗
• Cap rate: 5.48%
• Cash-on-cash: -2.89%
• DSCR: 0.87
• GRM: 12.3

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 1.22% rent growth · sell at horizon

5-year hold

• IRR: -22.9%
• Equity multiple: 0.22×
• Total profit: $-257,842
• Equity at exit: $176,836

10-year hold

• IRR: -22.0%
• Equity multiple: -0.05×
• Total profit: $-348,282
• Equity at exit: $102,544

Cash invested: $332,080 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Florida: 87 Strongly Landlord-Friendly · R+3
• County: — inherits STATE
• City: — inherits STATE

3-day pay-or-quit; preempts local rent control; landlord-friendly statutes. Court speed varies by county.

Methodology + full state rankings →

ZIP-level market 32789

• Rents YoY: 1.2%
• Active inventory: 339
• Price-to-rent: 49.2×

Monthly cashflow live

• Estimated rent: $8,030 medium
• Mortgage (P&I): −$6,220
• Tax from tax record: −$431 /mo · $5,170/yr
• Insurance: −$494
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,686
• Net cashflow: $-801

Break-even live

Break-even rent $9,044

Max offer price $1,044,535

Occupancy floor —

Sensitivity live

Price	-10% $-129	-5% $-465	+0% $-801	+5% $-1,136	+10% $-1,472
Rent	-10% $-1,435	-5% $-1,118	+0% $-801	+5% $-484	+10% $-166
Rate	-1.0pp $-204	-0.5pp $-499	base $-801	+0.5pp $-1,108	+1.0pp $-1,421

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

Units	Beds	Baths	Est. rent
▸ 4× units	3	2	$8,032
Total (4 units)			$8,030

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: $296,500
• Closing costs: $35,580
• Reserves months: —
• Total cash needed: —

Rent comps 22 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
662 Callahan St Unit 1545989P Winter Park, FL	2.0	1.0	882	$2,097	$2.38	17d	1	0.08mi
830 Carver St Winter Park, FL	3.0	1.0	1038	$1,995	$1.92	15d	1	0.17mi
151 N Orlando Ave Winter Park, FL	2.0–3.0	1.0–2.0	1134	$2,750	$2.43	5d	3	0.61mi
151 N Orlando Ave Winter Park, FL	3.0	1.0–2.0	1500	$2,500	$1.67	25d	2	0.61mi
1305 Morgan Stanley Ave Winter Park, FL	3.0	1.0–3.0	1102	$3,866	$3.51	3d	23	0.65mi
853 W Lyman Ave Winter Park, FL	3.0	1.0	820	$3,300	$4.02	25d	1	0.66mi
731 W Comstock Ave Winter Park, FL	3.0	1.5	1024	$1,950	$1.90	25d	1	0.68mi
301 W Comstock Ave Winter Park, FL	2.0	2.5	1500	$6,000	$4.00	25d	1	0.69mi
540 W Comstock Ave Winter Park, FL	3.0	1.0	1056	$2,900	$2.75	23d	1	0.70mi
1500 Gay Rd Unit Chateaux du Lac Winter Park, FL	2.0	2.0	1026	$1,850	$1.80	25d	1	0.73mi
747 Maryland Ave Winter Park, FL	3.0	2.0	786	$2,500	$3.18	18d	1	0.87mi
1701 Lee Rd Winter Park, FL	3.0	1.0–2.0	813	$2,172	$2.67	3d	18	0.90mi
438 Lakeview Ave Winter Park, FL	2.0	1.0	1250	$3,200	$2.56	25d	1	0.96mi
1695 Lee Rd Winter Park, FL	1.0–2.0	1.0	759	$1,595	$2.10	3d	6	0.97mi
503 Kilshore Ln Winter Park, FL	2.0	1.0	1125	$2,250	$2.00	18d	1	1.05mi
100 Boucle Jeanne Cir Maitland, FL	1.0–3.0	1.0–2.0	1125	$3,857	$3.43	3d	9	1.06mi
1137 S Pennsylvania Ave Winter Park, FL	3.0	2.0	1500	$2,995	$2.00	5d	1	1.06mi
304 Lake Ave Maitland, FL	1.0–3.0	1.0–3.0	1046	$3,201	$3.06	4d	20	1.15mi
921 S Orlando Ave Maitland, FL	1.0–3.0	1.0–2.0	1184	$3,037	$2.57	3d	40	1.17mi
925 Mead Ave Winter Park, FL	2.0	1.0	800	$2,095	$2.62	25d	1	1.33mi
741 Clay St Winter Park, FL	2.0	1.0–2.0	860	$2,880	$3.35	3d	17	1.34mi
190 Ventris Ave W Maitland, FL	2.0	1.0	770	$1,550	$2.01	15d	1	1.48mi

Listing history 50 events

1. 2026-06-21
   days on market $1,185,999 Active 53 DOM
2. 2026-06-18
   days on market $1,185,999 Active 50 DOM
3. 2026-06-17
   days on market $1,185,999 Active 49 DOM
4. 2026-06-16
   days on market $1,185,999 Active 48 DOM
5. 2026-06-15
   days on market $1,185,999 Active 47 DOM
6. 2026-06-13
   days on market $1,185,999 Active 45 DOM
7. 2026-06-13
   days on market $1,185,999 Active 44 DOM
8. 2026-06-09
   days on market $1,185,999 Active 41 DOM
9. 2026-06-08
   days on market $1,185,999 Active 40 DOM
10. 2026-06-07
    days on market $1,185,999 Active 39 DOM
11. 2026-06-04
    days on market $1,185,999 Active 36 DOM
12. 2026-06-03
    days on market $1,185,999 Active 35 DOM
13. 2026-06-02
    days on market $1,185,999 Active 34 DOM
14. 2026-06-02
    days on market $1,185,999 Active 33 DOM
15. 2026-05-31
    days on market $1,185,999 Active 32 DOM
16. 2026-04-29
    listed $1,185,999 Active
17. 2025-09-15
    price $1,215,000
18. 2025-09-15
    price $1,215,000
19. 2025-09-15
    price $695,000
20. 2025-08-14
    status Active
21. 2025-08-14
    status Active
22. 2025-08-14
    status Active
23. 2025-08-13
    historical
24. 2025-08-13
    historical
25. 2025-08-13
    historical
26. 2025-02-19
    listed $1,275,000 Active
27. 2025-02-19
    listed $1,275,000 Active
28. 2025-02-19
    listed $750,000 Active
29. 2024-10-14
    historical
30. 2024-08-20
    listed $700,000 Active
31. 2022-12-31
    historical
32. 2022-11-01
    price $1,375,000
33. 2022-09-06
    status Active
34. 2022-07-31
    historical
35. 2022-07-09
    status Active
36. 2022-06-09
    status Pending
37. 2022-04-23
    price $700,000
38. 2022-04-23
    price $1,400,000
39. 2022-04-08
    price $600,000
40. 2022-04-08
    listed $1,200,000 Active
41. 2022-04-04
    status Active
42. 2022-03-31
    listed $500,000
43. 2022-03-31
    historical
44. 2021-02-16
    historical
45. 2020-09-08
    listed $439,000 Active
46. 2020-08-28
    historical
47. 2020-06-16
    listed $439,000 Active
48. 2018-06-04
    historical
49. 2018-06-03
    status Active
50. 2018-05-28
    historical

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

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $5,170 · $431/mo
• Projected year-2 tax: $9,844 · $820/mo
• Expected delta: +$4,674/yr (+$389/mo · 90.4%)

ⓘ 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 9/10 Extreme 7 d/yr ≥107°F today · 22 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $96,360
• − Mortgage interest: −$66,434
• − Property taxes: −$5,170
• − Insurance: −$5,930
• − Repairs & maintenance: −$7,709
• − Management: −$7,709
• − Depreciation: −$34,502
• Taxable loss: −$31,094
• Est. tax savings @ 24.0%: +$7,462
• After-tax cash flow: $-2,147/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: Orange
• NCES district ID: 1201440
• Math proficiency: 46% ▼ -9.00%
• Reading proficiency: 51% ▼ -2.00%
• Median HH income: $49,350
• Composite: 41.47/100
• National rank: #3461
• State rank: #43 of 73 in FL

Livability — Winter Park

• Score: 83/100
• State rank: #44
• US rank: #852

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winter Park, FL
• County: Orange County · 1,471,359 people
• City population: 80,764
• Metro: Orlando-Kissimmee-Sanford, FL
• Population (ZIP): 27,788
• Household income: $106,671
• Rent vs Own: 35.6% rent · 64.4% own
• Severe rent burden: 1178.0

Population outlook (Orange County) Hauer SSP2

• Today (2025): 1,618,226 people
• By 2030: 1,787,404 · +10.5%
• By 2040: 2,125,621 · +31.4%
• By 2050: 2,454,016 · +51.6%
• By 2075: 3,173,711 · +96.1%
• By 2100: 3,607,781 · +122.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (73%)
• Race & ethnicity: White 73% Hispanic / Latino 13% Two or more races 10% Asian 5% Black 5%
• Hispanic origin (detail): Mexican 1% Puerto Rican 5% Cuban 3%
• Common ancestry: Slovak 4% Romanian 3% Italian 3%
• Foreign-born: 12% · Canada, China, Jamaica
• Languages at home: 83% English-only · Spanish 9% Other Indo-European 3% German/W. Germanic 1%

Political lean MEDSL · Orange

• 2024 margin: D (+13.6) · D 56.1% · R 42.5% · Other 1.3%
• 2008→2024 swing: -5.0pp toward R · 2008: 18.6pp · 2024: 13.6pp
• All cycles: 2024: D+13.6 2020: D+23.1 2016: D+24.6 2012: D+18.2 2008: D+18.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1111.99%
• Current HPI: 342.0935
• Rent YoY: ▲ 1.22%
• Metro: Orlando-Kissimmee-Sanford, FL
• State GDP YoY: ▲ 3.28%
• F500 in state: 36

Industry mix (Fortune 500 HQ in FL)

Industry	F500 HQs	Revenue
▸Industrial Technology	2	$29B
▸Insurance	2	$17B
▸Retail	1	$60B
▸Technology Distribution	1	$58B
▸Homebuilding	1	$35B
▸Technology Manufacturing	1	$35B

Price history

+69.5% since first listed

41 events — show timeline

• 2026-04-29 Listed $1,185,999 Stellar MLS as Distributed by MLS Grid
• 2025-09-15 Price Changed $1,215,000 Stellar MLS as Distributed by MLS Grid
• 2025-09-15 Price Changed $1,215,000 Stellar MLS as Distributed by MLS Grid
• 2025-09-15 Price Changed $695,000 Stellar MLS as Distributed by MLS Grid
• 2025-08-14 Relisted — Stellar MLS as Distributed by MLS Grid
• 2025-08-14 Relisted — Stellar MLS as Distributed by MLS Grid
• 2025-08-14 Relisted — Stellar MLS as Distributed by MLS Grid
• 2025-08-13 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-08-13 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-08-13 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-02-19 Listed $750,000 Stellar MLS as Distributed by MLS Grid
• 2025-02-19 Listed $1,275,000 Stellar MLS as Distributed by MLS Grid
• 2025-02-19 Listed $1,275,000 Stellar MLS as Distributed by MLS Grid
• 2024-10-14 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2024-08-20 Listed $700,000 Stellar MLS as Distributed by MLS Grid
• 2022-12-31 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-11-01 Price Changed $1,375,000 Stellar MLS as Distributed by MLS Grid
• 2022-09-06 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-07-31 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-07-09 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-06-09 Pending — Stellar MLS as Distributed by MLS Grid
• 2022-04-23 Price Changed $700,000 Stellar MLS as Distributed by MLS Grid
• 2022-04-23 Price Changed $1,400,000 Stellar MLS as Distributed by MLS Grid
• 2022-04-08 Price Changed $600,000 Stellar MLS as Distributed by MLS Grid
• 2022-04-08 Listed $1,200,000 Stellar MLS as Distributed by MLS Grid
• 2022-04-04 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-03-31 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-03-31 Listed $500,000 Stellar MLS as Distributed by MLS Grid
• 2021-02-16 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2020-09-08 Listed $439,000 Stellar MLS as Distributed by MLS Grid
• 2020-08-28 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2020-06-16 Listed $439,000 Stellar MLS as Distributed by MLS Grid
• 2018-06-04 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2018-06-03 Relisted — Stellar MLS as Distributed by MLS Grid
• 2018-05-28 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2018-05-25 Relisted — Stellar MLS as Distributed by MLS Grid
• 2018-05-07 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2018-05-06 Relisted — Stellar MLS as Distributed by MLS Grid
• 2018-04-26 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2018-04-23 Price Changed $599,900 Stellar MLS as Distributed by MLS Grid
• 2018-04-11 Listed $699,900 Stellar MLS as Distributed by MLS Grid

Property tax history

+12.4%/yr

Latest (2025): $5,170 · +4.2% YoY. Source: county tax records.