119 Oak Grove Rd · Winter Park, FL 32789

$285,000

3 bd · 2.0 ba · 1,133 sqft · SingleFamily public records · 3 Days on market

Built 1994 3,557 sqft lot Est $309k · 8% under

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Why this score? — see what drove the C- 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 +17.8/30.0
• ARV discount +11.0/15.0
• DSCR +5.6/10.0
• Livability +4.2/5.0
• Schools +4.1/10.0
• 1% rule +3.4/10.0
• Rent growth +2.8/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

OPEN HOUSE CANCELLED. Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park—bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or entertaining. Conveniently located near shopping and dinning.

Key facts

• Private backyard
• 3,557 sq ft lot
• Garage

Tags

• PRIVATE BACKYARD

Property features AI

Finance

• Other: Property zoned RES
• Financial info: No lease restrictions; Homestead status indicated
• HOA & community: No association indicated

Exterior

• Parking: Attached garage (1 car)
• Utilities: Public water; Public sewer; Electricity connected; Cable available
• Home design: Single family residence; Residential property; One level; Facing east
• Construction: Concrete construction; Shingle roof; Concrete perimeter foundation; Building area about 1,396 square feet; Living area about 1,134 square feet
• Exterior features: Paved road access; Lot approximately 0.08 acres (under 1/4 acre)

Interior

• Kitchen: Dishwasher; Range; Refrigerator
• Bedrooms: 3 bedrooms
• Flooring: Carpet; Ceramic tile; Tile; Wood
• Bathrooms: 2 full bathrooms
• Heating & cooling: Central heating (electric); Central air conditioning
• Interior features: Eat-in kitchen; Seven total rooms
• Laundry & utility: Dedicated laundry room

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $285k.

Deal economics

• At list price, monthly cash flow is $237 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $241k (15.6% below list).
• Recommended offer: $241k (15.6% below list) — sets the bar for 1% rule.
• Cap rate 7.3% 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.
• Market conditions: Rents rising (+1.2%/yr); 337 active listings in the ZIP; 36 comparable units currently listed for rent nearby; rentals at typical pace (median 15d 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).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $9k 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

• Only 3 days on market — expect competitive offers; lowballing is unlikely to land.
• Current owner paid $92k; list at $285k implies a 210% gain — meaningful room to come down on a strong offer.

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 $240,604 (15.6% below list)

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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?
3. 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.
4. 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.
5. 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: 0.84% ✗
• Cap rate: 7.29%
• Cash-on-cash: 3.56%
• DSCR: 1.16
• GRM: 9.9

CMA / ARV

• ARV (on-the-fly): $309,309
• Comps found: 2

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
119 Oak Grove Rd	0.00mi	3/2.0	1,134 (+0%)	0mo	$287,500	$254	100
1132 Park Green Pl	0.25mi	3/2.0	1,282 (+13%)	22mo	$350,000	$273	49

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 · 1.22% rent growth · sell at horizon

5-year hold

• IRR: -12.5%
• Equity multiple: 0.56×
• Total profit: $-35,489
• Equity at exit: $42,494

10-year hold

• IRR: -6.0%
• Equity multiple: 0.64×
• Total profit: $-28,866
• Equity at exit: $24,642

Cash invested: $79,800 (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: 337
• Price-to-rent: 9.9×

Monthly cashflow live

• Estimated rent: $2,406 high
• Mortgage (P&I): −$1,495
• Tax from tax record: −$51 /mo · $608/yr
• Insurance: −$119
• HOA: −$0
• Vacancy / Maint / Mgmt: −$505
• Net cashflow: $237

Break-even live

Break-even rent $2,106

Max offer price $285,000

Occupancy floor 85%

Sensitivity live

Price	-10% $398	-5% $317	+0% $237	+5% $156	+10% $-266
Rent	-10% $47	-5% $142	+0% $237	+5% $332	+10% $427
Rate	-1.0pp $380	-0.5pp $309	base $237	+0.5pp $163	+1.0pp $88

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: $71,250
• Closing costs: $8,550
• Reserves months: —
• Total cash needed: —

Rent comps 36 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1701 Lee Rd Winter Park, FL	3.0	1.0–2.0	813	$2,172	$2.67	3d	18	0.13mi
1695 Lee Rd Winter Park, FL	1.0–2.0	1.0	759	$1,595	$2.10	3d	6	0.25mi
1305 Morgan Stanley Ave Winter Park, FL	3.0	1.0–3.0	1102	$3,866	$3.51	3d	23	0.38mi
100 Boucle Jeanne Cir Maitland, FL	1.0–3.0	1.0–2.0	1125	$3,857	$3.43	3d	9	0.41mi
304 Lake Ave Maitland, FL	1.0–3.0	1.0–3.0	1046	$3,201	$3.06	3d	20	0.47mi
200 S West St Maitland, FL	1.0–2.0	1.0	720	$1,395	$1.94	3d	1	0.50mi
921 S Orlando Ave Maitland, FL	1.0–3.0	1.0–2.0	1184	$3,037	$2.57	3d	40	0.67mi
1500 Gay Rd Unit Chateaux du Lac Winter Park, FL	2.0	2.0	1026	$1,850	$1.80	24d	1	0.75mi
2500 Lee Rd Winter Park, FL	1.0–2.0	1.0–2.0	800	$1,495	$1.87	24d	2	0.75mi
2500 Lee Rd Winter Park, FL	1.0–2.0	1.0–2.0	800	$1,495	$1.87	8d	3	0.75mi
301 Clark St Unit 2 Eatonville, FL	2.0	1.0	1100	$1,575	$1.43	22d	1	0.81mi
360 Eaton St Maitland, FL	3.0	1.0	962	$1,500	$1.56	24d	1	0.83mi
830 Carver St Winter Park, FL	3.0	1.0	1038	$1,995	$1.92	14d	1	0.86mi
821 Mulberry St Unit D Maitland, FL	2.0	1.0	920	$2,000	$2.17	24d	1	0.88mi
151 N Orlando Ave Winter Park, FL	2.0–3.0	1.0–2.0	1134	$2,750	$2.43	5d	3	0.92mi
151 N Orlando Ave Winter Park, FL	3.0	1.0–2.0	1500	$2,500	$1.67	24d	2	0.92mi
190 Ventris Ave W Maitland, FL	2.0	1.0	770	$1,550	$2.01	15d	1	0.94mi
1820 Rogers Ave Unit B 1 Maitland, FL	2.0	1.0	800	$1,300	$1.62	14d	1	0.95mi
114 Eaton St Unit 3 Eatonville, FL	2.0	1.0	750	$1,190	$1.59	3d	1	0.95mi
31 Bel Air St Maitland, FL	3.0	1.5	1015	$2,400	$2.36	18d	1	1.01mi
662 Callahan St Unit 1545989P Winter Park, FL	2.0	1.0	882	$2,097	$2.38	17d	1	1.01mi
16 Eaton St Maitland, FL	3.0	2.0	1323	$2,300	$1.74	14d	1	1.05mi
722 Baltimore Dr Orlando, FL	3.0	2.0	1453	$2,050	$1.41	8d	1	1.10mi
438 Lakeview Ave Winter Park, FL	2.0	1.0	1250	$3,200	$2.56	24d	1	1.16mi
503 Kilshore Ln Winter Park, FL	2.0	1.0	1125	$2,250	$2.00	18d	1	1.19mi
814 Malone Dr Orlando, FL	2.0	2.0	1211	$2,650	$2.19	24d	1	1.21mi
430 E Packwood Ave Maitland, FL	1.0–3.0	1.0–2.0	1130	$2,515	$2.23	2d	13	1.23mi
853 W Lyman Ave Winter Park, FL	3.0	1.0	820	$3,300	$4.02	24d	1	1.30mi
741 Clay St Winter Park, FL	2.0	1.0–2.0	860	$2,880	$3.35	3d	17	1.37mi
731 W Comstock Ave Winter Park, FL	3.0	1.5	1024	$1,950	$1.90	24d	1	1.41mi
400 N Orlando Ave Maitland, FL	1.0–3.0	1.0–2.0	1040	$2,937	$2.82	2d	16	1.43mi
5003 Adanson St Orlando, FL	2.0	2.0	875	$2,500	$2.86	24d	1	1.43mi
2500 Carver Ave Orlando, FL	3.0	1.0	1110	$1,875	$1.69	18d	1	1.44mi
4418 Eli St Orlando, FL	2.0	1.0	825	$1,600	$1.94	24d	1	1.44mi
735 Alton Ave Orlando, FL	3.0	2.0	1174	$1,800	$1.53	8d	1	1.45mi
912 Neuse Ave Orlando, FL	3.0	2.0	1388	$2,079	$1.50	8d	1	1.46mi

Listing history 5 events

1. 2026-04-11
   status Pending
2. 2026-04-09
   listed $285,000 Active
3. 2003-05-16
   soldstatus $92,000
4. 2000-03-06
   soldstatus $76,900
5. 1994-08-01
   soldstatus $73,900

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

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $608 · $51/mo
• Projected year-2 tax: $2,366 · $197/mo
• Expected delta: +$1,757/yr (+$146/mo · 288.8%)

ⓘ 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: $28,872
• − Mortgage interest: −$15,964
• − Property taxes: −$608
• − Insurance: −$1,425
• − Repairs & maintenance: −$2,310
• − Management: −$2,310
• − Depreciation: −$8,291
• Taxable loss: −$2,036
• Est. tax savings @ 24.0%: +$489
• After-tax cash flow: $3,330/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

+285.7% since first listed

5 events — show timeline

• 2026-04-11 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-04-09 Listed $285,000 Stellar MLS as Distributed by MLS Grid
• 2003-05-16 Sold (Public Records) $92,000 Public Records
• 2000-03-06 Sold (Public Records) $76,900 Public Records
• 1994-08-01 Sold (Public Records) $73,900 Public Records

Property tax history

+3.0%/yr

Latest (2025): $608 · +4.9% YoY. Source: county tax records.