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For sale
$5,495,000
4beds
3,982sqft

550 21ST AVE S, NAPLES, FL 34102

4beds
3,982sqft
Single Family Residence
Built in 2001
0.37 Acres Lot
$1,380/sqft

What's special

Exceptional privacyExpansive marble-tiled lanaiAdjacent to port royalFully equipped outdoor kitchenExquisite custom millworkElegant powder bathSoaring ceilings

An exceptional opportunity to own a beautifully crafted residence in one of Naples' most coveted waterfront neighborhoods, Five Hundred Fifty Twenty-First Avenue South captures the essence of effortless luxury in the heart of Aqualane Shores. Ideally positioned adjacent to Port Royal and just moments from the Gulf's pristine beaches, Third Street South, and Fifth Avenue South, this remarkable home offers an unrivaled blend of elegance, comfort, and location. Encompassing approximately Four Thousand square feet of thoughtfully designed single-level living, the residence is filled with natural light and showcases soaring ceilings, solid Eight-foot core doors, and exquisite custom millwork that reflect impeccable craftsmanship throughout. Designed for both intimate living and sophisticated entertaining, the open floor plan flows seamlessly between gracious interior spaces and spectacular outdoor living. The contemporary primary suite is a private sanctuary featuring multiple walk-in closets and a spa-inspired bath with dual vanities, a soaking tub, and a separate walk-in shower. Two additional ensuite guest bedrooms, a versatile fourth bedroom currently serving as a den, and an elegant powder bath provide exceptional comfort and flexibility for family and guests alike. Beyond the interiors, a true resort-inspired retreat awaits. The expansive marble-tiled lanai surrounds a heated pool with a cascading waterfall spa, while the fully equipped outdoor kitchen creates the perfect backdrop for elegant alfresco dining and unforgettable evenings under the stars. Lush, professionally designed landscaping provides exceptional privacy and a serene tropical setting. Whether enjoying a morning walk along the sugar-white sands of the Gulf, dining at Naples' finest restaurants, or browsing the boutiques and galleries of nearby Third Street South and Fifth Avenue South, this extraordinary residence offers the quintessential Naples lifestyle. Beautifully finished and offered move-in ready, this is luxury living at its finest.

93 days
377
19
Source: SWFLMLS,MLS#: 226026963MLS LogoOriginating MLS: Naples
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Chris Resop 239-231-6164,

The Agency Naples,

Kara Resop 239-280-8955,

The Agency Naples

Source: SWFLMLS,MLS#: 226026963MLS LogoOriginating MLS: Naples

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 5
  • Full bathrooms: 4
  • 1/2 bathrooms: 1
Rooms
  • Room types: Den - Study, Family Room, Office, Open Porch/Lanai, 4 Bed
Bedroom
  • Features: Split Bedrooms
Dining room
  • Features: Breakfast Bar, Breakfast Room, Formal
Kitchen
  • Features: Island, Pantry
Heating
  • Central
Cooling
  • Ceiling Fan(s), Central Air, Humidity Control, Whole House Fan, Zoned
Appliances
  • Included: Electric Cooktop, Dishwasher, Double Oven, Dryer, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Oven, Washer, Wine Cooler
  • Laundry: Inside, Laundry Tub
Features
  • Bar, Built-In Cabinets, Coffered Ceiling(s), Fireplace, Foyer, French Doors, Laundry Tub, Pantry, Pull Down Stairs, Smoke Detectors, Volume Ceiling, Walk-In Closet(s), Wet Bar, Window Coverings, Den - Study, Family Room, Home Office, Laundry in Residence, Open Porch/Lanai
  • Flooring: Carpet, Marble, Tile
  • Doors: French Doors
  • Windows: Window Coverings
  • Has fireplace: Yes
Interior area
  • Total structure area: 4,735
  • Total interior livable area: 3,982 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 3
  • Parking features: Attached
  • Attached garage spaces: 3
Features
  • Levels: Two
  • Stories: 2
  • Patio & porch: Open Porch/Lanai
  • Exterior features: Outdoor Kitchen
  • Has private pool: Yes
  • Pool features: Pool/Spa Combo, In Ground, Concrete, Electric Heat
  • Has spa: Yes
  • Spa features: In Ground, Concrete, Equipment Stays, Heated, Pool Integrated, Bath
  • Has view: Yes
  • View description: Landscaped Area
  • Waterfront features: None
Lot
  • Size: 0.37 Acres
  • Features: Regular
Details
  • Additional structures: Outdoor Kitchen
  • Parcel number: 18560520009

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Block, Stucco
  • Foundation: Concrete Block
  • Roof: Tile
Condition
  • New construction: No
  • Year built: 2001

Utilities & green energy

  • Gas: Propane
  • Water: Central

Community & HOA

Community
  • Features: Boating, Non-Gated
  • Security: Security System, Smoke Detector(s)
  • Subdivision: AQUALANE SHORES
HOA
  • Has HOA: No
  • Amenities included: None
Location
  • Region: Naples

Financial & listing details

  • Price per square foot: $1,380/sqft
  • Tax assessed value: $6,483,099
  • Annual tax amount: $27,918
  • Date on market: 7/23/2026
  • Lease term: Buyer Finance/Cash

Price history

DateEventPrice
7/23/2026Listed for sale$5,495,000-8.3%$1,380/sqft
Source: SWFLMLS #226026963 Report a problem
7/3/2026Listing removed$5,995,000$1,506/sqft
Source: BHHS broker feed #225072886 Report a problem
4/23/2026Price change$15,000-25%$4/sqft
Source: Zillow Rentals Report a problem
4/17/2026Price change$20,000-55.6%$5/sqft
Source: Zillow Rentals Report a problem
4/13/2026Listed for rent$45,000+7.1%$11/sqft
Source: Zillow Rentals Report a problem
4/2/2026Price change$5,995,000-7.1%$1,506/sqft
Source: SWFLMLS #225072886 Report a problem
12/23/2025Price change$6,450,000-7.2%$1,620/sqft
Source: SWFLMLS #225072886 Report a problem
10/4/2025Listed for sale$6,950,000-12%$1,745/sqft
Source: SWFLMLS #225072886 Report a problem
8/20/2025Listing removed$7,900,000$1,984/sqft
Source: SWFLMLS #225036471 Report a problem
4/23/2025Listed for sale$7,900,000+345.1%$1,984/sqft
Source: SWFLMLS #225036471 Report a problem
3/31/2025Listing removed$42,000$11/sqft
Source: Douglas Elliman Report a problem
2/20/2025Listed for rent$42,000+40%$11/sqft
Source: Douglas Elliman Report a problem
2/20/2025Listing removed$30,000$8/sqft
Source: NABOR FL #224050165 Report a problem
2/12/2025Listed for rent$30,000-28.6%$8/sqft
Source: NABOR FL #224050165 Report a problem
2/12/2025Listing removed$42,000$11/sqft
Source: NABOR FL #224051771 Report a problem
2/5/2025Price change$42,000+40%$11/sqft
Source: NABOR FL #224051771 Report a problem
10/4/2024Listed for rent$30,000-40%$8/sqft
Source: NABOR FL #224050165 Report a problem
10/1/2024Listing removed$50,000$13/sqft
Source: NABOR FL #224051771 Report a problem
9/27/2024Listed for rent$50,000+42.9%$13/sqft
Source: NABOR FL #224051771 Report a problem
9/18/2024Listing removed$35,000$9/sqft
Source: NABOR FL #224050165 Report a problem
9/13/2024Listed for rent$35,000-30%$9/sqft
Source: NABOR FL #224050165 Report a problem
9/10/2024Listing removed$50,000+42.9%$13/sqft
Source: NABOR FL #224051771 Report a problem
9/6/2024Listed for rent$35,000$9/sqft
Source: NABOR FL #224050165 Report a problem
9/1/2024Listing removed$35,000$9/sqft
Source: MIAMI #A11631872 Report a problem
7/11/2024Listed for rent$35,000$9/sqft
Source: NABOR FL #224050165 Report a problem
2/15/2002Sold$1,775,000+454.7%$446/sqft
Source: Public Record Report a problem
6/2/1994Sold$320,000+9.8%$80/sqft
Source: Public Record Report a problem
7/2/1993Sold$291,400$73/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$27,919 +2.2%$3,123,123 +2.9%
2024$27,319 +1.5%$3,035,105 +3%
2023$26,913 -2.8%$2,946,704 +3%
2022$27,676 -1.5%$2,860,878 +3%
2021$28,111 +2.5%$2,777,551 +1.4%
2020$27,425 +1.2%$2,739,202 +2.3%
2019$27,095 +2.1%$2,677,617 +1.9%
2018$26,533 $2,627,691 +2.1%
2017$26,533 +1.5%$2,573,644 -12.6%
2016$26,130 -13.2%$2,946,353 -5.1%
2015$30,097 -7.7%$3,103,772 +28.3%
2014$32,619 +35.1%$2,418,924 +10%
2013$24,141 +7.7%$2,199,022 +10%
2012$22,410 +11.8%$1,999,111 +10%
2011$20,043 -13.4%$1,817,374 -3.3%
2010$23,152 -8.1%$1,878,818 -11.9%
2009$25,188 $2,133,104 -13.8%
2008$25,188 -20.9%$2,474,448 -12.9%
2007$31,850 +18.7%$2,841,802 +1.8%
2006$26,837 $2,790,936 +25.6%
2005$26,837 +10.9%$2,221,904 +12.1%
2004$24,208 -1%$1,981,910 +1.3%
2003$24,455 +2.9%$1,955,701 +4.2%
2002$23,766 +99.4%$1,876,420 +308.8%
2001$11,917 +106%$459,000
2000$5,784 --
Find assessor info on the county website

Monthly payment

Est. payment
$32,779/mo
Principal & interest
$28337
Property taxes
$4442
More affordability toolsChevron Right

Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: Aqualane Shore

Nearby schools

Lake Park Elementary School
Grades PK-5 • 3 miles
10/10
GreatSchools® Rating
Test Score Rating
10/10
Student Progress Rating
10/10
Gulfview Middle School
Grades 6-8 • 1.6 miles
9/10
GreatSchools® Rating
Test Score Rating
9/10
Student Progress Rating
8/10
Naples High School
Grades PK,9-12 • 3.5 miles
6/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
6/10
Student Progress Rating
5/10

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