Skip main navigation
Pending
$2,800,000
4beds
3,286sqft

21640 Overseas Hwy, Cudjoe Key, FL 33042

4beds
3,286sqft
Single Family Residence
Built in 1985
1.17 Acres Lot
$2,588,600 Zestimate®
$852/sqft

What's special

Private poolMassive parcelOversized windowsGenerous bedroom suitesSandy beach areaMature tropical groundsOpen-water backdrop

SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

192 days
49
3
Source: FLKMLS,MLS#: 619615MLS Logo
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Dan R Serban 305-797-2352,

Key West Luxury Real Estate Inc (KW)

Source: FLKMLS,MLS#: 619615MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 3
  • Full bathrooms: 3
Cooling
  • Central Air, Heat Pump, Ceiling Fans(s), Attic Fan
Appliances
  • Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Disposal, Freezer
Features
  • Built-in Features, Granite Counters, Dade County Pine, Walk-in Closet(s)
  • Flooring: Combination
  • Furnished: Yes
Interior area
  • Total structure area: 3,286
  • Total interior livable area: 3,286 sqft

Property

Parking
  • Parking features: RV Carport
  • Has garage: Yes
  • Has carport: Yes
Features
  • Patio & porch: Deck, Patio, Screened Patio
  • Exterior features: Chickee Hut, Sandy Beach, Storage
  • Has private pool: Yes
  • Pool features: In Ground
  • Has spa: Yes
  • Spa features: Heated
  • Fencing: Privacy
  • On waterfront: Yes
Lot
  • Size: 1.17 Acres
Details
  • Additional structures: Airplane Hangar
  • Parcel number: 00174830000000
  • Zoning: URM - Urban Res Mobile Home District

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Hardi Board Siding
Condition
  • Updated/Remodeled
  • New construction: No
  • Year built: 1985

Community & HOA

Community
  • Subdivision: Sacarma (21.0)
HOA
  • Has HOA: No
  • Services included: None
Location
  • Region: Cudjoe Key

Financial & listing details

  • Price per square foot: $852/sqft
  • Tax assessed value: $2,243,932
  • Annual tax amount: $17,431
  • Date on market: 4/23/2026

Price history

DateEventPrice
9/5/2026Listing removed$8,500$3/sqft
Source: FLKMLS #616553 Report a problem
9/3/2026Price change$8,500-32%$3/sqft
Source: FLKMLS #616553 Report a problem
8/25/2026Pending sale$2,800,000$852/sqft
Source: FLKMLS #619615 Report a problem
8/13/2026Listed for rent$12,500$4/sqft
Source: FLKMLS #616553 Report a problem
4/23/2026Listed for sale$2,800,000+115.4%$852/sqft
Source: FLKMLS #619615 Report a problem
11/30/2015Sold$1,300,000-25.7%$396/sqft
Source: FLKMLS #553740 Report a problem
10/9/2015Pending sale$1,749,000$532/sqft
Source: Coldwell Banker Schmitt Real Estate Co. #553740 Report a problem
2/18/2015Listed for sale$1,749,000+12.9%$532/sqft
Source: Coldwell Banker Schmitt Real Estate Co. #553740 Report a problem
4/10/2013Listed for sale$1,549,000+3.3%$471/sqft
Source: Coldwell Banker Schmitt Real Estate Co. #553740 Report a problem
7/27/2012Listed for sale$1,500,000-24.6%$456/sqft
Source: Coldwell Banker Schmitt Real Estate Co #553740 Report a problem
3/7/2012Listing removed$1,990,000$606/sqft
Source: Homes.com #550189 Report a problem
3/6/2012Listed for sale$1,990,000+32.7%$606/sqft
Source: Homes.com #550189 Report a problem
12/15/2011Listing removed$1,500,000$456/sqft
Source: Coldwell Banker Schmitt Real Estate Co. #553740 Report a problem
12/28/2010Listed for sale$1,500,000-20.6%$456/sqft
Source: Coldwell Banker Schmitt R.E. - Mar #553740 Report a problem
11/8/2010Listing removed$1,890,000$575/sqft
Source: Addvantage Real Estate Service #550189 Report a problem
5/23/2010Listed for sale$1,890,000-5%$575/sqft
Source: Addvantage Real Estate Service #550189 Report a problem
11/8/2009Listed for sale$1,990,000-11.6%$606/sqft
Source: Coldwell Banker Schmitt Real Estate #550189 Report a problem
12/8/2008Listed for sale$2,250,000-10%$685/sqft
Source: Coldwell Banker Schmitt Real Estate #550189 Report a problem
1/10/2008Listed for sale$2,500,000+1036.4%$761/sqft
Source: Number1Expert #543286 Report a problem
12/11/1997Sold$220,000$67/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$17,432 +0.2%$1,745,290 +10%
2024$17,398 +10.2%$1,586,627 +10%
2023$15,784 +28%$1,442,388 +10%
2022$12,328 +3.8%$1,311,262 +10%
2021$11,882 +11.1%$1,192,056 +10%
2020$10,699 $1,083,687 -22.8%
2019$10,699 -22%$1,404,616 -0.4%
2018$13,713 +0.1%$1,410,374 +15%
2017$13,702 +12%$1,226,879 +11%
2016$12,233 +6.6%$1,105,543 +77.2%
2015$11,471 $623,899
Find assessor info on the county website

Monthly payment

Est. payment
$16,933/mo
Principal & interest
$15020
Property taxes
$1913
More affordability toolsChevron Right

Estimated market value

$2,588,600

$2.46M - $2.72M

$7,305/mo

Climate risks

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

Neighborhood: 33042

Nearby schools

Sugarloaf School
Grades PK-8 • 2.1 miles
6/10
GreatSchools® Rating
Test Score Rating
5/10
Student Progress Rating
6/10
Key West High School
Grades 9-12 • 19.2 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
College Readiness Rating
5/10
Student Progress Rating
2/10