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Sold for $938,000
    • $938,000

    5900 Cypress Hollow WAY, NAPLES, FL 34109

    3beds
    2,600sqft
    Single Family Residence
    Built in 1985
    0.34 Acres Lot
    $937,800 Zestimate®
    $361/sqft
    $4,801 Estimated rent

    Home value

    $937,800

    $844,000 - $1.04M

    $4,801/mo

    Zestimate® history
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    What's special

    Overflow spaThoughtfully selected finishes throughoutUnique flex loft spaceSpacious bedroomsCustom built-insExterior paintAll-new bathrooms
    In the heart of central Naples—minutes to the beach and located within one of the area’s most established neighborhoods and an X flood zone (no insurance required) — this fully renovated two-story pool home offers a rare combination of location, modern upgrades, and outdoor space. With over $400,000 in renovations in 2024, this move-in-ready property stands out as a unique offering in today’s market. The interior has been completely reimagined with a brand-new kitchen with induction cooktop, all-new bathrooms, updated flooring, upgraded lighting with LED accents, barn doors, and thoughtfully selected finishes throughout. Spacious bedrooms include new closet doors, custom built-ins, and closet organization systems. The main level features two guest bedrooms and a refreshed full bath, while the upper level offers a unique flex loft space, and a primary suite with tropical views and a spa-inspired bathroom with a custom walk-in shower. The home was updated with a brand new A/C system installed in 2026, new water heater (2025), new electric panel (2024), exterior paint (2024) and so much more! Outdoor living is highlighted by an east-facing, saltwater heated pool with sun shelf, overflow spa, and water features. Expansive impact sliders open to a two-story lanai, creating a seamless connection between indoor and outdoor spaces. The fully fenced, estate-sized yard and rear garage access enhance both privacy and functionality. The property is located in Tall Pines, a community known for its tight-knit community feel and calendar of resident-led neighborhood events held throughout the year. Conveniently situated in walking or biking distance to shopping, dining, and easy access to Naples beaches, this home offers an exceptional blend of location, upgrades, and lifestyle.

    Zillow last checked:

    Listing updated:

    Listed by:

    Jessica Powell 630-800-9944,

    KW Elevate Luxury,

    Diane Hawran 239-249-8832,

    KW Elevate Luxury

    Bought with:

    Shawn Stuben

    Shawn Stuben Naples Properties

    Source: SWFLMLS,MLS#: 225083898MLS LogoOriginating MLS: Naples

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 2
    • Full bathrooms: 2
    Rooms
    • Room types: Den - Study, Family Room, Loft, Screened Lanai/Porch, 3 Bedrooms Plus Den
    Bedroom
    • Features: First Floor Bedroom, Master BR Upstairs
    Dining room
    • Features: Dining - Family, Eat-in Kitchen
    Kitchen
    • Features: Island, Pantry
    Heating
    • Central
    Cooling
    • Central Air
    Appliances
    • Included: Electric Cooktop, Disposal, Double Oven, Dryer, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Washer
    • Laundry: Inside, Laundry Tub
    Features
    • Foyer, Laundry Tub, Pantry, Pull Down Stairs, Smoke Detectors, Volume Ceiling, Walk-In Closet(s), Window Coverings, Den - Study, Family Room, Laundry in Residence, Loft, Screened Lanai/Porch
    • Flooring: Carpet, Tile, Vinyl, Wood
    • Doors: Impact Resistant Doors
    • Windows: Skylight(s), Window Coverings, Impact Resistant Windows, Shutters - Manual
    • Has fireplace: No
    Interior area
    • Total structure area: 3,900
    • Total interior livable area: 2,600 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Driveway, Attached
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Screened Lanai/Porch
    • Has private pool: Yes
    • Pool features: Pool/Spa Combo, In Ground, Concrete, Custom Upgrades, Equipment Stays, Electric Heat, Salt Water, Screen Enclosure
    • Has spa: Yes
    • Spa features: In Ground, Concrete, Equipment Stays, Heated, Pool Integrated, Screened
    • Fencing: Fenced
    • Has view: Yes
    • View description: Trees/Woods
    • Waterfront features: None
    Lot
    • Size: 0.34 Acres
    • Features: Regular
    Details
    • Parcel number: 76363040003

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Frame, Wood Siding
    • Roof: Metal
    Condition
    • New construction: No
    • Year built: 1985

    Utilities & green energy

    • Sewer: Septic Tank
    • Water: Central

    Community & HOA

    Community
    • Features: Non-Gated
    • Security: Smoke Detector(s)
    • Subdivision: TALL PINES
    HOA
    • Has HOA: Yes
    • Amenities included: Underground Utility
    • HOA fee: $875 annually
    Location
    • Region: Naples

    Financial & listing details

    • Price per square foot: $361/sqft
    • Tax assessed value: $855,400
    • Annual tax amount: $8,102
    • Date on market: 12/18/2025
    • Lease term: Buyer Finance/Cash,FHA,VA
    • Contingency: Financing

    Price history

    DateEventPrice
    5/28/2026Sold$938,000-1.2%$361/sqft
    Source: SWFLMLS #225083898 Report a problem
    4/14/2026Pending sale$949,000$365/sqft
    Source: SWFLMLS #225083898 Report a problem
    4/1/2026Price change$949,000-2.6%$365/sqft
    Source: SWFLMLS #225083898 Report a problem
    2/27/2026Price change$974,000-2.5%$375/sqft
    Source: SWFLMLS #225083898 Report a problem
    12/18/2025Listed for sale$999,000-9.2%$384/sqft
    Source: SWFLMLS #225083898 Report a problem
    7/28/2025Listing removed$1,100,000$423/sqft
    Source: SWFLMLS #225025571 Report a problem
    6/20/2025Price change$1,100,000-8.3%$423/sqft
    Source: SWFLMLS #225025571 Report a problem
    3/8/2025Listed for sale$1,200,000$462/sqft
    Source: SWFLMLS #225025571 Report a problem
    12/10/2024Listing removed$1,200,000$462/sqft
    Source: SWFLMLS #224086705 Report a problem
    11/1/2024Listed for sale$1,200,000+48.1%$462/sqft
    Source: SWFLMLS #224086705 Report a problem
    2/8/2022Sold$810,000-4.7%$312/sqft
    Source: Public Record Report a problem
    12/23/2021Pending sale$849,900$327/sqft
    Source: SWFLMLS #221075707 Report a problem
    10/26/2021Listed for sale$849,900+84.8%$327/sqft
    Source: SWFLMLS #221075707 Report a problem
    5/9/2018Sold$460,000-1.6%$177/sqft
    Source: Public Record Report a problem
    3/23/2018Pending sale$467,500$180/sqft
    Source: ADDvantage Real Estate #218018825 Report a problem
    3/7/2018Price change$467,500-1.6%$180/sqft
    Source: Altru Realty,LLC #218018825 Report a problem
    1/18/2018Listed for sale$475,000+8.9%$183/sqft
    Source: Owner Report a problem
    6/13/2016Sold$436,000-10.1%$168/sqft
    Source: Public Record Report a problem
    2/19/2016Listing removed$485,000$187/sqft
    Source: Premier Sotheby's International Realty #215064501 Report a problem
    1/21/2016Pending sale$485,000$187/sqft
    Source: Premier Sotheby's International Realty #215064501 Report a problem
    11/18/2015Listed for sale$485,000+106.4%$187/sqft
    Source: Premier Sotheby's International Realty #215064501 Report a problem
    8/23/2012Sold$235,000-6%$90/sqft
    Source: Public Record Report a problem
    7/11/2012Price change$249,900-3.8%$96/sqft
    Source: Weichert Realtors on Gulf #212017013 Report a problem
    6/11/2012Price change$259,900-3.7%$100/sqft
    Source: Naples - WEICHERT, REALTORS - On the Gulf #212017013 Report a problem
    5/23/2012Listed for sale$269,900$104/sqft
    Source: WEICHERT, REALTORS On The Gulf #212017013 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$8,103 +0%$855,400 +0.6%
    2024$8,103 +2.2%$850,140 +6.3%
    2023$7,930 +205.2%$799,881 +180.6%
    2022$2,599 -1.1%$285,108 +3%
    2021$2,628 +2.4%$276,804 +1.4%
    2020$2,566 +1.8%$272,982 +2.3%
    2019$2,520 -21.2%$266,845 -18.8%
    2018$3,197 -6.3%$328,494 +2.1%
    2017$3,410 +1.5%$321,738 +43.4%
    2016$3,358 +48.5%$224,302 +0.7%
    2015$2,261 -0.8%$222,743 +30.3%
    2014$2,279 +9.2%$170,975 +1.9%
    2013$2,087 +335.1%$167,709 +479.1%
    2012$480 +6.8%$28,962 +8.6%
    2011$449 +9.6%$26,662 +4.4%
    2010$410 +6.5%$25,529 +2.1%
    2009$385 $25,000 -66%
    2008$385 -72%$73,470 -73.3%
    2007$1,375 -2.4%$275,606 +98%
    2006$1,408 $139,179 +3%
    2005$1,408 +2.5%$135,125 +3%
    2004$1,374 -0.2%$131,189 +1.9%
    2003$1,377 +1.5%$128,743 +2.4%
    2002$1,356 -50.1%$125,726 +1.6%
    2001$2,719 +103.6%$123,746
    2000$1,335 --
    Find assessor info on the county website

    Neighborhood: 34109

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    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: OSCEOLA
    • Middle: PINE RIDGE
    • High: BARRON COLLIER

    Source: SWFLMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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