Olde Cypress Real Estate

Welcome to Olde Cypress, a hidden gem nestled in the heart of Naples, Florida. This upscale community offers a perfect blend of luxury living and natural beauty, making it an ideal destination for families, retirees, and everyone in between. Known for its stunning landscapes and meticulously maintained properties, Olde Cypress is a place where tranquility meets elegance.

As you stroll through the tree-lined streets, you'll be captivated by the Mediterranean-inspired architecture that defines this charming neighborhood. Each home boasts unique designs and lush landscaping, creating a picturesque setting that feels both inviting and exclusive. With a variety of homes available, from sprawling estates to cozy villas, there’s something to suit every taste and lifestyle.

Olde Cypress is not just about beautiful homes; it’s also about community. Residents enjoy access to a magnificent golf course, designed to challenge players of all skill levels while providing breathtaking views of the surrounding nature. The community clubhouse serves as a social hub, offering a range of amenities including a fitness center, swimming pool, and dining options, perfect for mingling with neighbors or hosting special events.

Location is key, and Olde Cypress is conveniently situated near Naples' finest attractions. Just a short drive away, you'll find pristine beaches, upscale shopping at Waterside Shops, and a vibrant culinary scene that showcases the best of Florida’s dining. With its warm climate, friendly community, and an abundance of recreational activities, Olde Cypress truly embodies the essence of Florida living. Come discover your slice of paradise in this enchanting neighborhood!

Newest Listings in Olde Cypress

$749,900

3 Beds ⋅ 2 Baths ⋅ 226024092 MLS

This charming 3Br/2Ba detached villa offers the perfect blend of comfort and privacy situated on a private corner lot. This home features a spacious open-concept living and dining area. A bright kitchen with Raised panel Cherry cabinets, ample storage, offers granite countertops, tile backsplash, kitchen island w/ cook-top, wall oven & microwave, and breakfast bar. Great room features plantation shutters, tray ceiling w/ recessed lighting and French doors to the lanai pool area. The master bedroom offers a private door to a side patio, his & her walk-in closets, tray ceiling, walk-in shower, dual sinks and ladies seated vanity. Other features: Additional Guest room and second full bath with tub and shower. Neutral tile flooring and wood floors throughout main living area, private pool w/ privacy wall, expansive yard, volume ceilings, & recessed lighting. Olde Cypress is a low-density gated community with 550 single family homes, located in North Naples, the Social Membership allows residents to use the clubhouse facilities which include club activities, fine & casual dining, tennis, pickleball, swimming pool, fitness and meeting rooms. Residences of the community may enhance their privileges by upgrading to a Golf Membership on the prestigious P.B Dye 18-hole designed course. New renovated Clubhouse brings Olde Cypress to a class of it own. Olde Cypress is located just off I-75, allowing easy access to Fort Myers airport, numerous restaurants, beaches and shopping.

3155 Santorini CT, Naples

$1,995,000

3 Beds ⋅ 3 Baths ⋅ 226019476 MLS

Set against a picturesque golf course and lake backdrop with no homes in sight, this beautifully upgraded residence offers refined living in the sought-after community of Olde Cypress. Spanning approximately 2,800 square feet, the home features three bedrooms, a private study, and three full baths, thoughtfully designed for both everyday comfort and effortless entertaining. A grand interior unfolds with soaring 12- to 14-foot ceilings, expansive 9-foot sliders, and solid core 8-foot doors. Recent enhancements elevate the home with a new hurricane-rated front door, designer lighting and fixtures, architectural wood beam accents, luxury wood-look LVP flooring throughout the main living areas, and upgraded carpeting in the bedrooms. Crown molding and plantation shutters add timeless elegance, while a restored gas fireplace creates a warm focal point. The redesigned chef’s kitchen is a standout, featuring a brand-new LG stainless steel appliance package, double ovens with convection cooking, and a gas cooktop powered by a 250-gallon tank that also services the fireplace. Quartz countertops, custom cabinetry, a marble backsplash, and an oversized stainless-steel sink complete the space, while a large island with bar seating for four makes it ideal for gathering. The kitchen flows seamlessly into the family room, enhancing functionality and connection. The spacious primary suite offers tranquil golf course views, dual walk-in closets, and a well-appointed bath. All bathrooms have been tastefully updated with renovated vanities, granite countertops, and new fixtures for a clean, modern finish. Outdoor living is equally impressive, featuring a deep covered lanai with soaring ceilings alongside a sun-filled travertine pool deck. The pool has been fully upgraded with a new pebble finish, updated waterline tile, LED lighting, and brand-new equipment including pumps and a heater. A picture-frame enclosure has been re-screened and painted to maximize the stunning views. Additional upgrades include fresh exterior paint, sealed pavers, and refreshed landscaping. A newer roof (2021) and oversized garage with a dedicated golf cart bay add convenience. Located within Olde Cypress, residents enjoy a vibrant and active lifestyle with a mandatory social membership that provides access to a full suite of amenities. The community features a dynamic year-round social calendar, formal and informal dining with no food and beverage minimums, and exceptional recreational offerings including tennis, pickleball, bocce, a lap pool, and a state-of-the-art fitness center. Championship golf by P.B. Dye is optional, with both full and associate memberships available, offering flexibility to suit a variety of lifestyles. This premier North Naples community delivers the perfect balance of luxury, leisure, and convenience.

3105 Terramar DR, Naples

$3,390,000

4 Beds ⋅ 4.5 Baths ⋅ 226015132 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to an amazing opportunity in Da Vinci Estates at Olde Cypress—an exclusive DOUBLE-GATED community known for estate-sized homes and unparalleled privacy. This property has LAKE VIEWS, a RARE FIVE-CAR GARAGE and a GUEST HOUSE. Major 2025 upgrades include: NEW ROOF, GUTTERS, FULL EXTERIOR PAINT, AND HVAC. Designed for both luxury living and entertaining, the home features a chef’s kitchen with a Viking gas range, Bosch dishwasher and Fisher & Paykel double oven. Expansive pocketing sliding glass doors seamlessly retract into the walls, creating a complete indoor-outdoor living experience that leads to the HEATED POOL and GROTTO SPA. The main floor features a full East-Wing primary suite that has a cocktail/coffee bar, double vanities, free-standing bathtub, private shower room, oversized walk-in closet, and a sitting room that leads to a PRIVATE GARAGE ENTRY. The main floor also features an office, 2 living rooms, formal dining, laundry room, half bathroom, gourmet kitchen and 2 bedrooms with a jack & jill bathroom. The second-floor entertainment level has a MOVIE THEATER AND BILLIARDS ROOM with a half bath. The seperate guest house or in-law suite is 1 bed/1 bath with a wet bar and has beautiful lake views with sliding doors leading to the pool area. Located in a premier North Naples golf community with a P.B. Dye championship course, FULL and ASSOCIATE GOLF MEMBERSHIPS AVAILABLE, and a newly completed $17M CLUBHOUSE TRANSFORMATION (NO ASSESSMENTS & NO FOOD/BEVERAGE MIN).

3027 Mona Lisa BLVD, Naples

$1,630,000

4 Beds ⋅ 2.5 Baths ⋅ 226003848 MLS

Welcome to effortless Florida living in the prestigious Olde Cypress community, home to a celebrated P.B.Dye–designed golf course. This beautifully appointed fully turnkey Ruffino II residence allows you to simply arrive, unwind, and begin enjoying the lifestyle you’ve been waiting for—just bring your suitcase. Designed with both elegance and peace of mind, the light-filled interior features custom crown molding, plantation shutters throughout, and hurricane impact windows and doors, providing comfort, security, and energy efficiency year-round. The open-concept living space flows seamlessly into a stylish kitchen with stainless steel appliances, granite countertops, and solid wood cabinetry—ideal for entertaining or relaxed evenings at home. A private den offers flexible space for work or leisure, while the inviting bedrooms serve as peaceful retreats. The home also includes a spacious 3-car garage equipped with a storage lift, offering exceptional functionality for vehicles, bikes, golf gear, and seasonal storage. Step outside to your private outdoor oasis. The oversized lanai is thoughtfully designed for year-round enjoyment and features an upgraded Super Screen enclosure, allowing expansive views and refreshing breezes while keeping comfort top of mind. Complete with an outdoor kitchen, sparkling pool and spa, upgraded lighting, and a calming water feature, this space is perfect for morning coffee, afternoon relaxation, or sunset gatherings. Olde Cypress offers a vibrant social lifestyle with a mandatory social membership and optional golf memberships. Golf carts are welcome throughout the community, making it easy to cruise to the clubhouse, meet neighbors, or enjoy the laid-back Florida lifestyle. Conveniently located just minutes from I-75 and within 30 minutes of RSW, this home offers the ideal blend of accessibility and escape. Relaxed. Refined. Secure. Ready for you.

7352 Lantana WAY, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.