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Ad #7639983
MLS #619668
Listing photo

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare

81801 Overseas Hwy # 729, Upper Matecumbe Key, FL 33036
$699,000
1Beds
1Baths
550Sqft
--Acres

About this property

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.

Property Features

1 Beds
1 Baths
550 Sqft
Built in 1988
0.000 Acres
Beachview
On Beachfront
Open
Siding: CBS
Concrete Roof
Has Swimming Pool
Central
$4,798 / yr property tax
Monroe County
Strattons (825) Community

Additional Photos

Additional listing photo 1
Additional listing photo 2
Additional listing photo 3
Additional listing photo 4

Contact Information

Ana G. Zalesky, P.A.

Coldwell Banker Schmitt Key Largo

305-394-1404

Location

Map
Listing Agent: Ana G. Zalesky, P.A. (License #: 3028693) 305-394-1404
Broker: Coldwell Banker Schmitt Key Largo 305-451-4422 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Aug 11, 2026

Photo Gallery

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 1
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 2
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 3
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 4
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 5
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 6
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 7
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 8
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 9
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 10
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 11
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 12
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 13
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 15
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 16
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 17
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 18
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 19
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 20
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 21
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 22
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 24
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 25
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 27
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 32
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 33
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 36
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Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 38
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 39
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 40
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 41
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 42
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 43
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 44
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 45
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 46
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 47
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 48
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 49
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 50

$699,000

1
Beds
1
Baths
550
Sqft

81801 Overseas Hwy # 729, Upper Matecumbe Key, FL 33036

By contacting this agent you agree to these Terms and Conditions.
Home Florida Upper Matecumbe Key
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 1
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 2
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 3
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 4
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare - photo 5
MLS# 619668
Home For Sale

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare

$699,000

81801 Overseas Hwy # 729, Upper Matecumbe Key, FL 33036

1
Beds
1
Baths
550
Sqft
--
Acres
$699,000
81801 Overseas Hwy # 729, Upper Matecumbe Key, FL 33036
1 Beds
1 Baths
550 Sqft
-- Acres
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.
105 days
on BeachHouse.com
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saves

Property Details

HOME DETAILS

1 Beds
1 Baths
550 Sqft
Built in 1988
0.000 Acres

BEACH & VIEW

Beachview
On Beachfront

EXTERIOR

Open
Siding: CBS
Concrete Roof
Has Swimming Pool

INTERIOR

Central

FINANCIAL & COMMUNITY

$4,798 / yr property tax
Monroe County
Strattons (825) Community
See More Details

Location

Map
Open in Google Maps

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Ad Statistics

Ad Number
7639983
Viewed
79 times
Listing Status
Active
Added
Apr 28, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM

Listing Information

Data Source
Florida Keys Board of REALTORS®
Source Property ID
619668
Listing Agent: Ana G. Zalesky, P.A. (License #: 3028693) 305-394-1404
Broker: Coldwell Banker Schmitt Key Largo 305-451-4422 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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By proceeding, you authorize Dream Home Network Inc., its service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners), its affiliates, and other real estate professionals that may not be associated with Dream Home Network, to contact you using the contact details you provided, via email, phone call, and text (SMS), including using automated dialing technology and prerecorded and artificial voice, for marketing or advertising purposes, including contacting you about your inquiry and other home-related matters. You understand that your consent to the foregoing is not a condition of any purchase. Message and data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what you are looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at csv@dreamhomenetwork.com.

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$735,000

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Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 1
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 2
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 3
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 4
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 5
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 6
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 7
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 8
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 9
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 10
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Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 12
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 13
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 14
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Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 16
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 17
Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 18
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By proceeding you authorize Dream Home Network Inc., its service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners), and its affiliates, to contact me using the contact details you provided, via phone call or text (SMS) using automated dialing technology for marketing or advertising purposes, including contacting me about my inquiry and other home-related matters. Not a condition for purchase. Message and data rates may apply.
This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what I am looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at  csv@dreamhomenetwork.com.
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SEARCH STATES
Alabama Alaska California Connecticut Delaware Florida Georgia Hawaii Louisiana Maine Maryland Mississippi New Hampshire New Jersey New York North Carolina Oregon Pennsylvania Rhode Island South Carolina Texas Virginia Washington
SERVICES
Buy Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com MountainHomes.com GolfHomes.com BarrierFreeHome.com
SUBSCRIBE
Receive notifications for new listings
Subscribe
X Facebook Instagram YouTube

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 BeachHouse.com
Part of Dream Home Network, Inc.
Last updated on 2026.08.11
Terms & Policy