9506 Rolling Cir · San Antonio, FL 33576

$294,900

3 bd · 3.0 ba · 1,577 sqft · SingleFamily public records · 215 Days on market

Built 2006 5,130 sqft lot Est $339k · 13% under $358/mo HOA · 17% of rent

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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 +13.4/15.0
• Cash flow +6.8/30.0
• Schools +4.3/10.0
• Appreciation +3.8/10.0
• Livability +3.5/5.0
• Rent growth +2.6/5.0
• Condition / age +2.5/5.0
• 1% rule +2.3/10.0
• DSCR +1.0/10.0

Listing remarks

BRAND NEW ROOF!!! This "rare" Cayman Courtyard home is hard to find and awaiting your updates. It boasts a main house with large Master BR. Master Bath includes a double vanity, large garden tub, and separate walk-in shower, 2nd BR with a full bath, and an "In-Law or Guest Suite" with a full bath, on the other side of the courtyard. The kitchen features solid wood cabinets, granite countertops and stainless-steel appliances. Total 3, BR, 3 baths, 2 car garage. Large (12 "X 16") brick paver courtyard separates the main house from the guest house. Very rare home, only 5 were built in the community. TBG & CC has two incredible golf courses, the 18-hole Champio

Key facts

• 5,130 sq ft lot
• 2 garage spots
• Community pool

Tags

• CAYMAN COURTYARD HOME
• IN-LAW OR GUEST SUITE
• BRICK PAVER COURTYARD
• TWO INCREDIBLE GOLF COURSES
• 18-HOLE CHAMPIONSHIP COURSE
• 9-HOLE EXECUTIVE COURSE

Property features AI

Finance

• Other: Lease restrictions apply; Homestead exemption indicated
• Financial info: Total monthly fees and association fees apply
• HOA & community: Has HOA (monthly/quarterly fees required); Monthly HOA amount listed; Association amenities include clubhouse, fitness center, pool, spa/hot tub, tennis courts, pickleball courts, shuffleboard, recreation facilities, golf course access, dog park, gated entry, street lights, and cable TV; Buyer/association approval required; Deed restrictions; Golf carts allowed; Vehicle restrictions and fence restrictions

Exterior

• Parking: Attached garage; 2 garage spaces
• Security: Gated community
• Utilities: Public water; Public sewer; Cable connected; BB/HS internet available; Electricity connected; Phone available; Underground utilities; Water connected; Sewer connected
• Home design: Single family residence; One story; Faces east; Completed condition
• Construction: Block and stucco construction; Shingle roof; Slab foundation; Built by Transeastern (Caymen Courtyard model)
• Exterior features: Patio; Porch; Rain gutters; Near golf course; Paved lot; Private lot; Trees and landscaped yard; Private maintained road

Interior

• Kitchen: Dishwasher; Disposal; Microwave; Range; Refrigerator
• Bedrooms: 3 bedrooms
• Flooring: Carpet; Ceramic tile
• Bathrooms: 3 full bathrooms
• Heating & cooling: Electric heating; Reverse cycle heating; Central air conditioning
• Interior features: Ceiling fans; Thermostat
• Laundry & utility: Laundry inside; Dryer

What this means for you Summary

Snapshot

• This is a 3-bed/3.0-bath single-family listed at $295k.

Deal economics

• At list price, monthly cash flow is $-457 ($-5k/yr) — negative.
• To cash-flow at today's rent, offer at most $214k (27.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $216k (26.6% below list).
• Recommended offer: $214k (27.4% below list) — sets the bar for cash-flow.
• Cap rate 4.4% vs local median 3.4% in San Antonio — 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 69/100 on livability (#454 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, cost of living A; Watch: schools D, amenities F, commute F.
• Pasco (suburban): math 50% / reading 52% proficiency, ranked #32 of 73 in FL (top 44%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents flat; 365 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals leasing fast (median 11d on market — plan ~1-2 weeks tenant-placement turnaround); solid renter incomes; 6,765 units permitted in Pasco County in 2024 (1,250 in 5+ unit buildings).
• This rent runs 34% of the median local income ($76k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-2.3%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Pasco County population projected at +29% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 215 days — a 12% lower offer ($260k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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; moderate wildfire risk; extreme-heat days projected 7→26/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $214,233 (27.4% 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 215 days. Have you received any prior offers? Is the seller open to a 27% concession, seller financing, or rate buy-down credit?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
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. 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 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: 4.43%
• Cash-on-cash: -6.64%
• DSCR: 0.70
• GRM: 11.4

CMA / ARV

• ARV (on-the-fly): $339,055
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
29549 Tee Shot Dr	0.09mi	3/2.0	1,554 (-2%)	1mo	$312,000	$201	88
9534 Rolling Cir	0.04mi	2/2.0 (-1)	1,489 (-6%)	3mo	$299,900	$201	77
9617 Rolling Cir	0.11mi	2/2.0 (-1)	1,521 (-4%)	6mo	$333,000	$219	75
29702 Tee Shot Dr	0.07mi	2/2.0 (-1)	1,489 (-6%)	6mo	$263,000	$177	73
9952 Gap Wedge Dr	0.35mi	3/2.0	1,707 (+8%)	6mo	$350,000	$205	60
10242 Chatuge Dr	0.59mi	2/2.0 (-1)	1,538 (-2%)	4mo	$330,000	$215	56
29109 Enniscrone Dr	0.62mi	3/2.0	1,707 (+8%)	2mo	$370,000	$217	52
10131 Old Tampa Bay Dr	0.74mi	2/2.0 (-1)	1,554 (-2%)	5mo	$345,000	$222	50
9911 Saunton Dr	0.63mi	3/2.0	1,707 (+8%)	7mo	$435,000	$255	47
10150 Old Tampa Bay Dr	0.69mi	2/2.0 (-1)	1,489 (-6%)	4mo	$310,000	$208	46
29129 Enniscrone Dr	0.60mi	4/2.0 (+1)	1,731 (+10%)	4mo	$360,000	$208	43
10232 Buncombe Way	0.63mi	3/2.0	1,397 (-11%)	9mo	$350,000	$251	40

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-2.32% appreciation · 0.37% rent growth · sell at horizon

5-year hold

• IRR: -25.0%
• Equity multiple: 0.11×
• Total profit: $-73,861
• Equity at exit: $52,991

10-year hold

• IRR: -25.9%
• Equity multiple: -0.40×
• Total profit: $-115,603
• Equity at exit: $41,266

Cash invested: $82,572 (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 33576

• Home prices YoY: -0.8%
• Rents YoY: 0.4%
• Active inventory: 365
• Price-to-rent: 11.4×

Monthly cashflow live

• Estimated rent: $2,165 high
• Mortgage (P&I): −$1,546
• Tax from tax record: −$139 /mo · $1,673/yr
• Insurance: −$123
• HOA: −$358
• Vacancy / Maint / Mgmt: −$455
• Net cashflow: $-457

Break-even live

Break-even rent $2,743

Max offer price $214,233

Occupancy floor —

Sensitivity live

Price	-10% $-290	-5% $-373	+0% $-457	+5% $-540	+10% $-624
Rent	-10% $-628	-5% $-542	+0% $-457	+5% $-371	+10% $-286
Rate	-1.0pp $-308	-0.5pp $-382	base $-457	+0.5pp $-533	+1.0pp $-611

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: $73,725
• Closing costs: $8,847
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
9751 Rolling Cir Unit 1 San Antonio, FL	3.0	2.0	1772	$1,850	$1.04	2d	1	0.16mi
10326 Hyannisport Loop San Antonio, FL	3.0	2.0	2008	$1,900	$0.95	2d	1	0.59mi
8824 Overlook Dr Wesley Chapel, FL	3.0	3.0	1200	$1,900	$1.58	25d	1	1.18mi
8351 Greenway Ave Wesley Chapel, FL	4.0	3.0	2017	$2,495	$1.24	25d	1	1.42mi
10225 Fieldstone Myrtle Way San Antonio, FL	4.0	3.0	1985	$2,800	$1.41	11d	1	1.46mi

HOA detail

• Monthly dues: $358 · $4,296/yr

Listing history 19 events

1. 2026-06-18
   days on market $294,900 Active 215 DOM
2. 2026-06-17
   days on market $294,900 Active 214 DOM
3. 2026-06-16
   days on market $294,900 Active 213 DOM
4. 2026-06-15
   days on market $294,900 Active 212 DOM
5. 2026-06-13
   days on market $294,900 Active 210 DOM
6. 2026-06-09
   days on market $294,900 Active 206 DOM
7. 2026-06-08
   days on market $294,900 Active 205 DOM
8. 2026-06-07
   days on market $294,900 Active 204 DOM
9. 2026-06-04
   days on market $294,900 Active 201 DOM
10. 2026-06-03
    days on market $294,900 Active 200 DOM
11. 2026-06-02
    days on market $294,900 Active 199 DOM
12. 2026-06-01
    days on market $294,900 Active 198 DOM
13. 2026-05-31
    days on market $294,900 Active 197 DOM
14. 2026-04-20
    price $294,900
15. 2026-04-20
    price $249,900
16. 2025-11-26
    status Active
17. 2025-11-06
    status Pending
18. 2025-10-26
    listed $299,900 Active
19. 2006-04-07
    soldstatus $2,856,000

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

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $1,673 · $139/mo
• Projected year-2 tax: $2,448 · $204/mo
• Expected delta: +$774/yr (+$65/mo · 46.3%)

ⓘ 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 5/10 Major
• 🌡 Heat 9/10 Extreme 7 d/yr ≥108°F today · 26 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $25,977
• − Mortgage interest: −$16,519
• − Property taxes: −$1,673
• − Insurance: −$1,474
• − Repairs & maintenance: −$2,078
• − Management: −$2,078
• − HOA: −$4,296
• − Depreciation: −$8,579
• Taxable loss: −$10,721
• Est. tax savings @ 24.0%: +$2,573
• After-tax cash flow: $-2,907/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: Pasco
• NCES district ID: 1201530
• Math proficiency: 50% ▼ -10.00%
• Reading proficiency: 52% ▼ -5.00%
• Median HH income: $45,039
• Composite: 43.14/100
• National rank: #3074
• State rank: #32 of 73 in FL

Livability — San Antonio

• Score: 69/100
• State rank: #454
• US rank: #8221

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Pasco County · 524,098 people
• City population: 6,273
• Metro: Tampa-St. Petersburg-Clearwater, FL
• Population (ZIP): 6,273
• Household income: $76,388
• Rent vs Own: 4.5% rent · 95.5% own
• Severe rent burden: 31.0

Population outlook (Pasco County) Hauer SSP2

• Today (2025): 570,045 people
• By 2030: 605,844 · +6.3%
• By 2040: 674,806 · +18.4%
• By 2050: 736,022 · +29.1%
• By 2075: 862,900 · +51.4%
• By 2100: 906,364 · +59.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (81%)
• Race & ethnicity: White 81% Hispanic / Latino 12% Two or more races 5% Black 5%
• Hispanic origin (detail): Mexican 3% Puerto Rican 5%
• Common ancestry: Romanian 5% Lithuanian 3% Slovak 2%
• Foreign-born: 7% · Canada
• Languages at home: 91% English-only · Spanish 6% Other Indo-European 1%

Political lean MEDSL · Pasco

• 2024 margin: Strong R (+25.2) · D 36.9% · R 62.1% · Other 1.0%
• 2008→2024 swing: -21.6pp toward R · 2008: -3.6pp · 2024: -25.2pp
• All cycles: 2024: R+25.2 2020: R+20.1 2016: R+21.6 2012: R+6.7 2008: R+3.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -2.32%
• Current HPI: 281.7138
• Rent YoY: ▲ 0.37%
• Metro: Tampa-St. Petersburg-Clearwater, 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

-89.7% since first listed

6 events — show timeline

• 2026-04-20 Price Changed $294,900 Stellar MLS as Distributed by MLS Grid
• 2026-04-20 Price Changed $249,900 Stellar MLS as Distributed by MLS Grid
• 2025-11-26 Relisted — Stellar MLS as Distributed by MLS Grid
• 2025-11-06 Pending — Stellar MLS as Distributed by MLS Grid
• 2025-10-26 Listed $299,900 Stellar MLS as Distributed by MLS Grid
• 2006-04-07 Sold (Public Records) $2,856,000 Public Records

Property tax history

+1.1%/yr

Latest (2025): $1,673 · +3.0% YoY. Source: county tax records.