Olde Cypress Homes for Sale in Naples, Florida

Olde Cypress is a private gated golf community in North Naples offering custom estate homes, luxury detached residences and villa-style properties surrounding the P.B. Dye-designed championship golf course, lakes, preserves and mature tropical landscaping.

The community contains nine distinct residential neighborhoods, and buyers benefit from comparing properties within the correct housing category. A custom residence in Da Vinci Estates competes in a different segment from an Egret Cove or Santorini villa, while newer Lantana construction may appeal to a different buyer than an established home of similar size elsewhere in Olde Cypress.

9 Residential Neighborhoods • Private Golf Community • P.B. Dye Championship Golf • Custom Estates • Single-Family Pool Homes • Villa-Style Homes • Golf, Lake & Preserve Views

Estate Homes Da Vinci Estates, Wild Orchid and Biscayne Place provide larger luxury-home and custom-estate opportunities.

Detached Homes Lantana, Santa Rosa, Strada Bella and Terramar offer distinctive single-family residential choices.

Villa Living Egret Cove and Santorini Villas provide smaller-scale alternatives within the private-club setting.

Private Club Golf membership is separate from simply owning an Olde Cypress residence, with current membership categories and availability subject to Club terms.

Explore All 9 Olde Cypress Neighborhoods

Custom Estate & Larger Luxury Homes

Detached Single-Family Homes

Villa-Style Homes

Olde Cypress Real Estate by Home Type

Olde Cypress provides more residential variety than its single gated-community identity might suggest. Buyers can move from manageable villa-style homes to conventional luxury pool residences and substantial individually designed estates.

Biscayne Place A very low-density enclave of larger executive-style residences where limited turnover can make same-neighborhood comparable sales scarce.

Da Vinci Estates The signature double-gated custom-estate section, where architecture, parcel quality, guest accommodations and garage capacity deserve significant weight.

Egret Cove Detached villa-style homes offering a smaller-scale alternative with private outdoor living and neighborhood-specific maintenance considerations.

Lantana A newer generation of Olde Cypress single-family construction with contemporary floor plans and comparatively newer major systems.

Santa Rosa Detached residences where lake and golf-course orientation can play an important role in value and outdoor living.

Santorini Villas Villa-style residences appealing to buyers seeking a more manageable footprint within Olde Cypress.

Strada Bella Luxury detached pool homes where floor plan, view, garage and renovation are important comparison factors.

Terramar Courtyard and conventional single-family homes with private pools and golf, lake or landscaped settings represented.

Wild Orchid Custom luxury residences where individual architecture, homesite and golf-course relationship can create substantial property-to-property differences.

Custom Estates & Larger Luxury Homes

Da Vinci Estates and select Wild Orchid residences represent the upper end of Olde Cypress real estate, with individually designed homes, substantial outdoor living, larger garages and premium golf or lake settings.

Estate valuation requires more than a broad price-per-square-foot calculation. Parcel quality, architecture, builder, floor-plan function, ceiling volume, guest accommodations, garage capacity, pool environment, view, roof, storm protection and mechanical systems should be analyzed together.

Biscayne Place occupies its own niche as an exceptionally small enclave of larger executive homes. When neighborhood turnover is limited, comparable analysis may need to expand carefully to similar Olde Cypress properties after accounting for scarcity and homesite quality.

Detached Single-Family Homes

Lantana, Santa Rosa, Strada Bella and Terramar provide several interpretations of luxury single-family ownership.

Lantana is particularly relevant to buyers seeking a newer construction generation. Santa Rosa, Strada Bella and Terramar offer established residences where golf, lake, preserve or landscaped positioning, private pools, renovations and major capital improvements can strongly influence value.

Egret Cove & Santorini Villa Living

Egret Cove and Santorini Villas provide a more manageable alternative to Olde Cypress's larger residences while retaining the gated private-club environment.

Villa buyers should verify the precise maintenance structure of the property. Roof replacement, exterior painting, landscaping, irrigation, insurance, pool maintenance and structural responsibilities should be determined from current governing documents rather than inferred from the word villa.

Golf, Lake & Preserve Homesites

Homesite quality is one of Olde Cypress's most durable real-estate characteristics. Properties may face fairways, greens, tees, lakes, preserves or mature landscaping, and the quality of the view can vary considerably within the same neighborhood.

A broad lake-to-golf panorama may compete differently from direct fairway frontage. Buyers should consider golf-ball exposure, cart paths, landing zones, neighboring rooflines, water width, vegetation and the view from the great room, primary bedroom and lanai.

Golf Frontage Evaluate the exact hole, tee, fairway, green, cart path and active-play relationship.

Lake View Compare water width, shoreline angle, golf beyond the water and neighboring sightlines.

Preserve Consider vegetation, privacy, protected boundaries and long-term sightlines.

Rear Exposure Compare morning light, southern pool sun and western sunset exposure.

Private Pools & Outdoor Living

Private pools and screened outdoor environments are strongly represented throughout Olde Cypress. Depending upon the home, outdoor areas may include spas, deep covered lanais, summer kitchens, fireplaces, television areas, landscaped courtyards and large picture-window screens.

Buyers should inspect pool finish, heater, pumps, filtration, automation, spa equipment, screen enclosure, pavers and drainage. The amount of roof-covered lanai space is particularly important because it determines how comfortably the outdoor area can be used during sun and rain.

P.B. Dye Golf & Olde Cypress Membership

The private P.B. Dye-designed championship course is central to the Olde Cypress identity. The course underwent substantial renovation work in 2021, including improvements to greens, teeing areas, bunkers, drainage and practice facilities.

Residential ownership and golf access should nevertheless be evaluated separately. Current Club materials describe multiple membership options, including Full Golf and Associate Golf, while a resident Social category serves homeowners who do not maintain a higher golf category.

Golf buyer guidance: verify current membership availability, joining requirements, dues, golf privileges, cart programs and guest policies directly with The Club at Olde Cypress before making a home purchase dependent upon a particular membership.

Olde Cypress Clubhouse & Amenities

The Club at Olde Cypress provides a broad private-club lifestyle in addition to golf, with dining and social spaces, fitness and wellness facilities, swimming, tennis, pickleball, bocce and organized activities.

The Club has also made substantial recent investments in its clubhouse and dining environment. Current hours, programs, guest privileges and access should be confirmed through the Club because facilities and policies can evolve.

HOA, Villa & Ownership Costs

Olde Cypress ownership expenses can include master-community obligations, neighborhood-specific maintenance and private Club costs depending upon the residence and membership selected.

Buyers should identify exactly which services are included with the property, especially landscaping, irrigation, exterior painting, roofing, structural insurance and other maintenance items in villa-oriented neighborhoods.

Master Community Review recurring HOA expenses, reserves, security and common-area responsibilities.

Neighborhood Costs Determine whether an additional neighborhood association applies.

Villa Maintenance Confirm roof, exterior, landscaping, irrigation and structural responsibilities.

Club Costs Consider the current Social, Associate Golf or Full Golf membership selected or required.

Roof, HVAC & Storm Protection

Olde Cypress spans multiple construction periods, so two similarly priced homes may carry very different future capital requirements.

Buyers should review roof installation date and permits, HVAC equipment, water heaters, electrical systems, plumbing, generators, impact-resistant windows and doors, shutters, storm screens, garage doors, pool systems and irrigation.

A newly renovated kitchen improves appearance, but a newer roof, impact protection, modern HVAC equipment and updated pool systems may have greater significance to future ownership cost.

What Olde Cypress Buyers Should Compare

Neighborhood Begin with Biscayne Place, Da Vinci Estates, Egret Cove, Lantana, Santa Rosa, Santorini Villas, Strada Bella, Terramar or Wild Orchid.

Property Type Custom estate, detached luxury home or villa-style residence.

Homesite Golf, lake, preserve, interior or landscaped position.

Living Area Compare similar size and functional floor-plan arrangements.

Outdoor Living Pool, spa, covered lanai, outdoor kitchen and rear exposure.

Garage Evaluate actual capacity, golf-cart space and storage.

Major Systems Roof, HVAC, plumbing, electrical, generator and pool equipment.

Membership Confirm current Social or golf membership structure and expenses.

How to Evaluate Olde Cypress Home Values

Olde Cypress should not be valued as one undifferentiated subdivision. The individual neighborhood and property type establish the strongest starting point.

A Santorini villa should not be directly compared with a Da Vinci Estates custom residence, and newer Lantana construction may compete with a different group of homes than an established residence elsewhere in Olde Cypress.

Olde Cypress valuation sequence: neighborhood → property type → living area & floor plan → construction generation → homesite → golf/lake/preserve position → rear exposure → pool & outdoor living → garage → roof & major systems → renovation → association responsibilities → relevant comparable sales.

Olde Cypress Homes, Map Search & Market Report

Use the OLDE CYPRESS Homes For Sale circle at the top of this page to review current MLS inventory throughout the community.

The OLDE CYPRESS Map Search helps compare individual properties with the golf course, lakes, preserves and individual neighborhoods.

The dedicated OLDE CYPRESS Market Report provides current active and recent sold-property activity. Because one custom-estate transaction can materially affect community-wide averages, buyers and sellers should narrow the report to the appropriate neighborhood and property type.

Selling an Olde Cypress Home

Olde Cypress sellers should position the residence within its exact neighborhood and housing category before relying on broad community statistics.

Permanent characteristics such as homesite, golf or lake orientation, rear exposure, garage capacity and property type should be established first. Roof age, storm protection, HVAC, generator, pool improvements, renovations and outdoor living can then demonstrate how the home differs from competing properties.

Custom estates should emphasize architecture, parcel quality and scarcity, while villas should clearly explain maintenance responsibilities and lock-and-leave advantages where applicable.

Olde Cypress Location in North Naples

Olde Cypress provides a private-club residential setting in North Naples with convenient access to major roads, shopping, dining, healthcare and Gulf beaches.

Buyers comparing private golf communities may also explore TwinEagles , Greyhawk , Mediterra , Quail West and the complete Naples Luxury Golf Communities directory.

Explore Olde Cypress With Schulz Realty

Schulz Realty helps buyers and sellers compare all nine Olde Cypress neighborhoods by property type, construction generation, floor plan, golf and lake orientation, rear exposure, private pool, garage, roof, storm protection, major systems, neighborhood maintenance responsibilities, current Club membership choices and relevant comparable sales.

Contact Schulz Realty for Olde Cypress Listings & Private Tours

Call David Schulz at (239) 682-5800.

Olde Cypress neighborhood characteristics, property features, homeowner and neighborhood association fees, maintenance responsibilities, reserves, assessments, insurance requirements, rental provisions, Club membership categories, membership availability, joining requirements, annual dues, golf privileges, guest policies and amenities may change or vary. Buyers should verify material information for the specific property through current governing documents, association budgets, official Club information, inspections, surveys, insurance professionals, permits, public records, title documentation and other appropriate qualified professionals before purchasing.

Olde Cypress Naples Golf Resort Homes for Sale

$3,390,000

4 Beds ⋅ 4.5 Baths ⋅ 226015132 MLS ⋅ ACTIVE Status ⋅ 15,246 Sqft. Lot ⋅ 0.35000000000000003 Acres

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

$1,995,000

3 Beds ⋅ 3 Baths ⋅ 226019476 MLS ⋅ ACTIVE Status ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres

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

$1,790,000

4 Beds ⋅ 4 Baths ⋅ 226031255 MLS ⋅ ACTIVE Status ⋅ 11,761 Sqft. Lot ⋅ 0.27 Acres

Experience refined Naples living at 7491 Treeline Dr, an impressive 4-bedroom-plus-den residence with 4 full bathrooms and 3,350 square feet of beautifully designed living space. Set within the Olde Cypress community, this home offers a thoughtful blend of elegant finishes, warm architectural details, and inviting indoor-outdoor living. The interior is rich with custom detail. Crown moldings throughout the home add a timeless, finished look, while tray ceilings bring dimension and visual interest to the main living areas and bedrooms. The great room makes a memorable statement with a cedar wood ceiling that adds warmth, texture, and a sense of craftsmanship. This central living space is designed to feel open, comfortable, and elevated, with details that draw the eye without feeling overdone.The outdoor living area continues the same level of care and style. The patio features a cedar wood ceiling, creating a seamless connection between interior and exterior spaces. A summer kitchen with a wet bar and refrigerator makes outdoor entertaining feel effortless. The infinity-edge pool creates a beautiful resort-style focal point, while the trellis adds architectural beauty and a graceful finish to the space. The floor plan offers 4 bedrooms, a den, and 4 full bathrooms, giving the home both comfort and flexibility. Each room has its own sense of purpose, and each bathroom reflects the attention to detail found throughout the property. This is a home that cannot be fully captured in words alone. You have to see it in person to appreciate the beauty, finish work, and thoughtful design that went into each and every room and bathroom. Olde Cypress offers an exceptional collection of amenities, including a clubhouse, business center, community pool, community room, spa/hot tub, exercise room, attended fitness center, golf course, internet access, pickleball, private membership options, putting green, restaurant, sauna, sidewalks, streetlights, and tennis courts. From the cedar ceiling details to the infinity-edge pool and beautifully finished interiors, 7491 Treeline Dr offers a polished Naples lifestyle with comfort, style, and standout design.

7491 Treeline DR, Naples

$1,669,900

3 Beds ⋅ 3 Baths ⋅ 226031879 MLS ⋅ ACTIVE Status ⋅ 11,326 Sqft. Lot ⋅ 0.26 Acres

Comfort and craftsmanship await you in this North Naples' distinguished, low-density community of Olde Cypress. Offering 3,255 square feet of beautifully curated living space, this custom residence features 4 bedrooms, 3 full bathrooms, a 3-car garage, and a newer roof. The updated gourmet eat-in kitchen boasts an oversized quartz counter-height island, top-tier finishes, and newer appliances. Designed for effortless indoor-outdoor living, the expansive open great room and dining spaces showcase volume ceilings, detailed crown molding, upgraded solid-core doors, transoms, and pocketing sliding glass doors that flood the interior with natural light. The primary suite offers a tastefully redesigned bath, while a separate dedicated guest cabana provides total privacy for visitors, in-laws, or a remote workspace. Step outside to a massive screened tropical courtyard featuring a propane-heated pool and spillover spa. Nestled on 540+ acres of natural preserve with just 550 homes, residents enjoy a newly renovated clubhouse with dining options (no food/beverage minimums or assessments), a PB Dye championship golf course (optional golf membership), Har-Tru tennis, pickleball, bocce, a putting green, driving range, and a state-of-the-art fitness center. Mandatory social membership applies.

3137 Terramar DR, Naples

$749,900

3 Beds ⋅ 2 Baths ⋅ 226024092 MLS ⋅ ACTIVE Status ⋅ 21,780 Sqft. Lot ⋅ 0.5 Acres

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

$630,000

2 Beds ⋅ 2 Baths ⋅ 225081090 MLS ⋅ ACTIVE Status ⋅ 7,035 Sqft. Lot ⋅ 0.1615 Acres

FRESHLY UPDATED & READY TO IMPRESS. Welcome to 3134 Santorini Ct, a beautifully refreshed 2-bedroom + den, 2-bath villa with a private screened pool in the gated Santorini enclave of Olde Cypress. Recently transformed with High-End LVP Flooring throughout and a complete interior repaint in Sherwin-Williams Greek Villa, this home now offers the fresh, light and sophisticated feel today’s Naples buyers are looking for. Step inside and the difference is immediate. The new flooring flows seamlessly throughout the home, while the warm, soft-white interior complements soaring ceilings, architectural details and an open-concept floor plan filled with natural light. The spacious great room opens directly to the screened lanai and pool, creating effortless indoor-outdoor living with a peaceful green backdrop. At the heart of the home, the kitchen features abundant cabinetry, generous counter space, stainless steel appliances and breakfast seating while remaining open to the main living areas—ideal for both everyday living and entertaining. The private primary suite offers direct lanai access, a spacious walk-in closet and ensuite bath with dual sinks and a walk-in shower. A separate guest bedroom provides privacy for visitors, while the spacious den with closet, custom built-ins and plantation shutters offers exceptional flexibility as a home office, media room or additional guest space. Outside, the private screened pool and lanai create your own Florida retreat. Enjoy morning coffee, an afternoon swim or evenings outdoors surrounded by tropical landscaping and tranquil green views. Olde Cypress offers an exceptional North Naples lifestyle with a beautifully appointed clubhouse, fitness center, tennis, pickleball and bocce, along with the P.B. Dye-designed championship golf course with OPTIONAL GOLF MEMBERSHIP. Ideally located with convenient access to shopping, dining, I-75 and Naples’ renowned Gulf beaches, 3134 Santorini Ct combines location, lifestyle and the advantage of major interior updates already completed. New floors. Fresh paint. Private pool. A fresh opportunity in Olde Cypress. Come see the transformation for yourself.

3134 Santorini CT, 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.