1029 Tranquil Brook Dr · Winding Cypress, FL 34114

$439,999

4 bd · 4.0 ba · 1,496 sqft · SingleFamily public records · 37 Days on market

Built 2023 Fair condition

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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 +18.3/30.0
• ARV discount +7.5/15.0
• DSCR +5.7/10.0
• Schools +5.0/10.0
• 1% rule +4.5/10.0
• Appreciation +4.3/10.0
• Rent growth +3.3/5.0
• Livability +2.5/5.0
• Condition / age +2.2/5.0

Listing remarks MLS

Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

Key facts

• Gated community
• Led lighting
• Plantation shutters

Tags

• GATED COMMUNITY
• HURRICANE WINDOWS AND DOORS
• PLANTATION SHUTTERS
• CERAMIC TILE PLANK FLOORING
• CROWN MOLDING
• LED LIGHTING

Property features AI

Exterior

• Home design: Built in 2023
• Construction: Living area of 1,854; Newer construction (2023)
• Exterior features: Located in the South Naples subdivision

What this means for you Summary

Snapshot

• This is a 4-bed/4.0-bath single-family listed at $440k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $-25 ($-304/yr) — negative.
• To cash-flow at today's rent, offer at most $436k (1.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $417k (5.2% below list).
• Recommended offer: $417k (5.2% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Collier (suburban): math 60% / reading 56% proficiency, ranked #16 of 73 in FL (top 22%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents rising (+3.2%/yr); 900 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).
• At $4,169/mo this rent would consume 56% of the median local household income ($89k/yr) (locally 550% 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 (-1.5%/yr); year-one equity from $3k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Collier County population projected at +30% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 37 days — a 3% lower offer ($427k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 4y 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

• Watch-outs: flood insurance adds $427/mo.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 99% chance of damaging wind over 30y; moderate wildfire risk; extreme-heat days projected 7→28/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $416,933 (5.2% 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 37 days. Have you received any prior offers? Is the seller open to a 5% concession, seller financing, or rate buy-down credit?
3. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
4. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 0.95% ✗
• Cap rate: 7.39%
• Cash-on-cash: 3.91%
• DSCR: 1.17
• GRM: 8.8

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-1.48% appreciation · 3.21% rent growth · sell at horizon

5-year hold

• IRR: -8.4%
• Equity multiple: 0.65×
• Total profit: $-43,086
• Equity at exit: $96,146

10-year hold

• IRR: -0.8%
• Equity multiple: 0.93×
• Total profit: $-8,707
• Equity at exit: $92,615

Cash invested: $123,200 (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 34114

• Home prices YoY: -0.6%
• Rents YoY: 3.2%
• Active inventory: 900
• Price-to-rent: 8.8×

Monthly cashflow live

• Estimated rent: $4,169 high
• Mortgage (P&I): −$2,307
• Tax from tax record: −$402 /mo · $4,822/yr
• Insurance: −$183
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$876
• Net cashflow: $-25

Break-even live

Break-even rent $4,201

Max offer price $435,528

Occupancy floor 96%

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: $110,000
• Closing costs: $13,200
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
2000 Rookery Bay Dr Naples, FL	1.0–3.0	1.0–2.0	929	$2,020	$2.17	23d	9	0.10mi
158 Rookery Rd Naples, FL	3.0	2.0	1456	$2,450	$1.68	23d	1	0.37mi
4650 Hawks Nest Way Unit M202 Naples, FL	3.0	2.0	1840	$9,600	$5.22	14d	1	0.96mi
3955 Deer Crossing Ct #103 Naples, FL	3.0	2.0	1812	$7,500	$4.14	23d	1	0.97mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	14d	1	1.08mi
1414 Oceania Dr S Naples, FL	3.0	2.0	1572	$5,000	$3.18	23d	1	1.26mi
163 Indies Dr E #206 Naples, FL	3.0	2.0	1698	$6,000	$3.53	23d	1	1.45mi
163 Indies Dr E #106 Naples, FL	3.0	2.0	1698	$7,500	$4.42	23d	1	1.45mi

Listing history 31 events

1. 2026-06-18
   days on market $439,999 Active 37 DOM
2. 2026-06-17
   days on market $439,999 Active 36 DOM
3. 2026-06-16
   days on market $439,999 Active 35 DOM
4. 2026-06-15
   days on market $439,999 Active 34 DOM
5. 2026-06-10
   days on market $439,999 Active 29 DOM
6. 2026-06-09
   days on market $439,999 Active 28 DOM
7. 2026-06-08
   days on market $439,999 Active 27 DOM
8. 2026-06-07
   days on market $439,999 Active 26 DOM
9. 2026-06-02
   days on market $439,999 Active 21 DOM
10. 2026-06-01
    days on market $439,999 Active 20 DOM
11. 2026-05-31
    days on market $439,999 Active 19 DOM
12. 2026-05-30
    days on market $439,999 Active 18 DOM
13. 2026-05-12
    listed $439,999 Active
14. 2026-01-14
    soldstatus $390,000
15. 2026-01-09
    soldstatus $390,000 Sold 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

16. 2025-12-12
    status Pending With Contingencies 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

17. 2025-11-20
    status Active 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

18. 2025-11-07
    status Pending With Contingencies 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

19. 2025-10-10
    price $424,900 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

20. 2025-08-21
    listed $434,900 Active 1799-char remark

    Show marketing remark (1799 chars)

    Welcome to a stunning Carrington model villa in the desirable Enbrook community—perfect for the savvy investor or anyone seeking the ideal Southwest Florida lifestyle. This newer construction villa offers exceptional investment potential for long-term or seasonal rentals. Investors appreciate the lower upkeep costs and better energy efficiency that come with a newer build. The low HOA fees are a major advantage, allowing you to maximize your return on investment. This home offers a perfect blend of modern style and comfortable living, starting with its inviting open-concept floor plan. The heart of the home is the gourmet kitchen, a chef's delight featuring custom-designed cabinetry, solid-surface countertops, and a handy breakfast bar for casual dining. This desirable villa includes two bedrooms, a spacious den, two full bathrooms, and a two-car garage. The versatile den is perfect as a home office, media room, or a second living space. Step out to the screened-in lanai to relax and enjoy the beautiful Florida weather year-round. This home has been thoughtfully upgraded throughout with premium features like plantation shutters, updated light fixtures, and ceiling fans. Enjoy optimal storage with custom closets and peace of mind from impact-resistant windows and upgraded flooring. Enbrook provides a true resort-style lifestyle with fantastic amenities, including a clubhouse with a large social room and catering kitchen, a fitness center, a sparkling resort-style pool, and courts for tennis, bocce, and pickleball. You're just a short drive from the shopping and dining of Downtown 5th Avenue, Marco Island, and pristine Gulf beaches. Don't miss this opportunity to own an exceptional property offering the best of Southwest Florida living. Schedule your showing today!

21. 2023-06-05
    soldstatus $445,000
22. 2023-06-02
    soldstatus $445,000 Sold 874-char remark

    Show marketing remark (874 chars)

    Brand New never lived in!! This stylish Carrington model Villa located at Enbrook has great amenities and so much to offer! From open-concept living to a kitchen crafted with custom designed cabinetry, ample solid surface counter space and a breakfast bar, there is so much to love! Featuring 2 bedrooms plus a den that is large enough to be a second living room, 2 bathrooms, 2 car garage and a screened in lanai this property checks many boxes! Just a short drive to downtown Olde Naples or to Marco Island the location is just right! Upgraded impact windows and flooring make this Villa a desirable home! As a resident of Enbrook you would have access to enjoy the club house with a large social room, Fitness center, resort-style swimming pool, tennis, bocce, pickle ball and a catering kitchen! This community has low HOA fees and easy living so schedule a showing now!

23. 2023-04-30
    status Pending 874-char remark

    Show marketing remark (874 chars)

    Brand New never lived in!! This stylish Carrington model Villa located at Enbrook has great amenities and so much to offer! From open-concept living to a kitchen crafted with custom designed cabinetry, ample solid surface counter space and a breakfast bar, there is so much to love! Featuring 2 bedrooms plus a den that is large enough to be a second living room, 2 bathrooms, 2 car garage and a screened in lanai this property checks many boxes! Just a short drive to downtown Olde Naples or to Marco Island the location is just right! Upgraded impact windows and flooring make this Villa a desirable home! As a resident of Enbrook you would have access to enjoy the club house with a large social room, Fitness center, resort-style swimming pool, tennis, bocce, pickle ball and a catering kitchen! This community has low HOA fees and easy living so schedule a showing now!

24. 2023-04-18
    price $469,000 874-char remark

    Show marketing remark (874 chars)

    Brand New never lived in!! This stylish Carrington model Villa located at Enbrook has great amenities and so much to offer! From open-concept living to a kitchen crafted with custom designed cabinetry, ample solid surface counter space and a breakfast bar, there is so much to love! Featuring 2 bedrooms plus a den that is large enough to be a second living room, 2 bathrooms, 2 car garage and a screened in lanai this property checks many boxes! Just a short drive to downtown Olde Naples or to Marco Island the location is just right! Upgraded impact windows and flooring make this Villa a desirable home! As a resident of Enbrook you would have access to enjoy the club house with a large social room, Fitness center, resort-style swimming pool, tennis, bocce, pickle ball and a catering kitchen! This community has low HOA fees and easy living so schedule a showing now!

25. 2023-03-30
    price $499,000 874-char remark

    Show marketing remark (874 chars)

    Brand New never lived in!! This stylish Carrington model Villa located at Enbrook has great amenities and so much to offer! From open-concept living to a kitchen crafted with custom designed cabinetry, ample solid surface counter space and a breakfast bar, there is so much to love! Featuring 2 bedrooms plus a den that is large enough to be a second living room, 2 bathrooms, 2 car garage and a screened in lanai this property checks many boxes! Just a short drive to downtown Olde Naples or to Marco Island the location is just right! Upgraded impact windows and flooring make this Villa a desirable home! As a resident of Enbrook you would have access to enjoy the club house with a large social room, Fitness center, resort-style swimming pool, tennis, bocce, pickle ball and a catering kitchen! This community has low HOA fees and easy living so schedule a showing now!

26. 2023-01-18
    listed $553,500 Active 874-char remark

    Show marketing remark (874 chars)

    Brand New never lived in!! This stylish Carrington model Villa located at Enbrook has great amenities and so much to offer! From open-concept living to a kitchen crafted with custom designed cabinetry, ample solid surface counter space and a breakfast bar, there is so much to love! Featuring 2 bedrooms plus a den that is large enough to be a second living room, 2 bathrooms, 2 car garage and a screened in lanai this property checks many boxes! Just a short drive to downtown Olde Naples or to Marco Island the location is just right! Upgraded impact windows and flooring make this Villa a desirable home! As a resident of Enbrook you would have access to enjoy the club house with a large social room, Fitness center, resort-style swimming pool, tennis, bocce, pickle ball and a catering kitchen! This community has low HOA fees and easy living so schedule a showing now!

27. 2022-03-14
    historical
28. 2022-03-09
    price $506,420
29. 2022-03-02
    price $503,420
30. 2022-02-25
    listed $499,420 Active
31. 2021-12-17
    soldstatus $1,582,400

ⓘ 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: $4,822 · $402/mo
• Projected year-2 tax: $4,822 · $402/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 10/10 Extreme 7 d/yr ≥108°F today · 28 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $50,032
• − Mortgage interest: −$24,647
• − Property taxes: −$4,822
• − Insurance: −$7,318
• − Repairs & maintenance: −$4,003
• − Management: −$4,003
• − Depreciation: −$12,800
• Taxable loss: −$7,560
• Est. tax savings @ 24.0%: +$1,814
• After-tax cash flow: $1,511/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 · 1 photo

Fair 45/100 Cosmetic rehab

This home is in fair condition with a good kitchen and bathrooms. It needs minor cosmetic updates, such as painting interior walls and replacing flooring, to improve its resale and rental value.

Value-add opportunities

• Both Paint interior walls — Fresh paint can improve the home's appearance and curb appeal.
• Both Replace flooring in bathrooms — New flooring can enhance the home's aesthetic and value.
• Both Install new windows — New windows can improve energy efficiency and increase the home's value.
• Both Upgrade HVAC system — A new HVAC system can improve comfort and energy efficiency, boosting both resale and rental value.
• Both Landscaping and curb appeal — A well-maintained exterior can significantly increase the home's curb appeal and value.

Renovation cost estimate screening

Value-add ROI direction

• Both Paint interior walls — Fresh paint can improve the home's appearance and curb appeal. ↑
• Both Replace flooring in bathrooms — New flooring can enhance the home's aesthetic and value. ↑
• Both Install new windows — New windows can improve energy efficiency and increase the home's value. ↑
• Both Upgrade HVAC system — A new HVAC system can improve comfort and energy efficiency, boosting both resale and rental value. ↑
• Both Landscaping and curb appeal — A well-maintained exterior can significantly increase the home's curb appeal and value. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Collier
• NCES district ID: 1200330
• Math proficiency: 60% ▼ -4.00%
• Reading proficiency: 56% ▼ -2.00%
• Median HH income: $58,275
• Composite: 50.23/100
• National rank: #1892
• State rank: #16 of 73 in FL

Livability — Winding Cypress

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• County: Collier County · 396,295 people
• Metro: Naples-Marco Island, FL
• Population (ZIP): 23,559
• Household income: $89,334
• Rent vs Own: 15.3% rent · 84.7% own
• Severe rent burden: 550.0

Population outlook (Collier County) Hauer SSP2

• Today (2025): 420,858 people
• By 2030: 450,054 · +6.9%
• By 2040: 502,232 · +19.3%
• By 2050: 544,932 · +29.5%
• By 2075: 627,203 · +49.0%
• By 2100: 659,015 · +56.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (72%)
• Race & ethnicity: White 72% Hispanic / Latino 17% Two or more races 13% Black 7%
• Hispanic origin (detail): Mexican 7% Puerto Rican 1% Cuban 3%
• Common ancestry: Hispanic 5% Romanian 4% Lithuanian 1%
• Foreign-born: 21% · Canada, Jamaica
• Languages at home: 75% English-only · Spanish 15% French/Haitian/Cajun 5% Other Indo-European 4%

Political lean MEDSL · Collier

• 2024 margin: Solid R (+33.1) · D 33.1% · R 66.2%
• 2008→2024 swing: -10.6pp toward R · 2008: -22.5pp · 2024: -33.1pp
• All cycles: 2024: R+33.1 2020: R+24.7 2016: R+26.0 2012: R+30.1 2008: R+22.5

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1.48%
• Current HPI: 266.5545
• Rent YoY: ▲ 3.21%
• Metro: Naples-Marco Island, 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

-72.2% since first listed

19 events — show timeline

• 2026-05-12 Listed $439,999 FSBO.com
• 2026-01-14 Sold (Public Records) $390,000 Public Records
• 2026-01-09 Sold (MLS) $390,000 NAPLESMLS
• 2025-12-12 Pending — NAPLESMLS
• 2025-11-20 Relisted — NAPLESMLS
• 2025-11-07 Pending — NAPLESMLS
• 2025-10-10 Price Changed $424,900 NAPLESMLS
• 2025-08-21 Listed $434,900 NAPLESMLS
• 2023-06-05 Sold (Public Records) $445,000 Public Records
• 2023-06-02 Sold (MLS) $445,000 NAPLESMLS
• 2023-04-30 Pending — NAPLESMLS
• 2023-04-18 Price Changed $469,000 NAPLESMLS
• 2023-03-30 Price Changed $499,000 NAPLESMLS
• 2023-01-18 Listed $553,500 NAPLESMLS
• 2022-03-14 Listing Removed — NAPLESMLS
• 2022-03-09 Price Changed $506,420 NAPLESMLS
• 2022-03-02 Price Changed $503,420 NAPLESMLS
• 2022-02-25 Listed $499,420 NAPLESMLS
• 2021-12-17 Sold (Public Records) $1,582,400 Public Records

Property tax history

+29.4%/yr

Latest (2025): $4,822 · +1.2% YoY. Source: county tax records.