Olde Cypress Homes For Sale

Olde Cypress, an upscale single-family development featuring stunning estate homes and villas, is located in North Naples within 10 minutes of cultural activities, world-class shopping and fine dining. The natural environment with ancient cypress and pine forests create exquisite views whether you’re playing golf or relaxing on your lanai. Olde Cypress homes for sale are located around the esteemed Club At Olde Cypress. A high-end lifestyle hub, this prestigious private club is defined by its legendary golf course, state-of-the-art athletic facilities, and rich social life complemented by exclusive events and fine dining.

Search all Olde Cypress homes for sale by browsing the listings below — or, discover all there is to know about this elegant golf community! Get in touch with our team for expert advice about Olde Cypress homes for sale and buying a luxury home in Naples, FL. We look forward to helping you find your perfect home.

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25 16th Ave S, NAPLES

$88,000,000 - 6 Beds, 9 Baths, 11,279 Sf

MLS® # 223041209

William Raveis Real Estate

4550 Gordon Dr, NAPLES

$63,000,000 - 1 Acres

MLS® # 223062658

John R Wood Properties

25 5th Ave S, NAPLES

$40,000,000

MLS® # 223030086

William Raveis Real Estate

600 Galleon Dr, NAPLES

$39,950,000 - 5 Beds, 9 Baths, 7,195 Sf

MLS® # 223069997

DomainRealty.com LLC

1601 Gulf Shore Blvd N Penthouse 1, NAPLES

$35,000,000 - 5 Beds, 6 Baths, 7,010 Sf

MLS® # 223075755

Ronto Realty

3880 Rum Row, NAPLES

$34,995,000 - 5 Beds, 8 Baths, 8,466 Sf

MLS® # 223001372

William Raveis Real Estate

New Listing

3093 Fort Charles Dr, NAPLES

$33,500,000 - 6 Beds, 9 Baths, 11,912 Sf

MLS® # 223086554

William Raveis Real Estate

3631 Rum Row, NAPLES

$31,900,000 - 6 Beds, 7 Baths, 6,308 Sf

MLS® # 223024314

William Raveis Real Estate

5580 Estero Blvd, FORT MYERS BEACH

$30,000,000

MLS® # 223082128

LSI Companies Inc.

5580 Estero Blvd, FORT MYERS BEACH

$30,000,000 - 3 Acres

MLS® # 223080122

LSI Companies Inc.

2999 Rum Row, NAPLES

$29,950,000 - 5 Beds, 7 Baths, 7,326 Sf

MLS® # 223085261

Gulf Coast International Prop

1365 Spyglass Ln, NAPLES

$29,750,000 - 6 Beds, 8 Baths, 6,736 Sf

MLS® # 223081582

Alfred Robbins Realty Group

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Explore Olde Cypress Real Estate

Olde Cypress real estate is in a class of its own. There are over 550 homes in this upscale country club community; these are made up of stunning Mediterranean villa homes, single-family estates, and custom homes, crafted to fit buyer needs. Currently listed homes on the Olde Cypress real estate market start at approximately $500,000 and peak at just under $2,000,000. With expansive lots, lush green surroundings, and an idyllic blend of privacy and communal culture, this neighborhood is truly the cream of the crop of gated Naples living.

World Class Amenities At Olde Cypress

Olde Cypress is a dynamic community, home to an 18-hole championship P.B. Dye designed golf course with elevated tees. Har-Tru tennis courts and an expanding tennis program provide players a chance to meet for Round Robins and mixers. A remodeled 4,100 square foot fitness facility offers everything you would expect from a world-class health club: personal trainers, classes, and state-of-the-art equipment, all designed to help you create your own individual fitness program. As a social member, you will enjoy amenities such as private cooking demonstrations, dinner parties, and book clubs where your neighbors become your lifelong friends. A recently expanded outdoor dining area is perfect for sunset cocktails and a late dinner. Olde Cypress’ mix of landscape, natural surroundings and world class amenities make it a sought after, luxurious lifestyle community.