Ole Homes with Two Story Style

Welcome to Ole, a vibrant and picturesque subdivision nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming community is renowned for its stunning architecture, lush landscapes, and an array of amenities that cater to a lifestyle of comfort and leisure.

Ole is a delightful blend of Mediterranean-inspired homes and modern conveniences, making it an ideal choice for families, retirees, and anyone seeking a serene yet active lifestyle. One of the standout features of this community is its selection of two-story homes, which offer both spacious living and the perfect backdrop for creating lasting memories. These homes are designed with elegance in mind, boasting open floor plans, high ceilings, and abundant natural light.

As you step into a two-story residence in Ole, you’ll be greeted by inviting living spaces that seamlessly connect to gourmet kitchens, perfect for entertaining friends and family. The upper levels often feature generous bedrooms, including luxurious master suites, providing a private retreat for relaxation. Many homes also come with outdoor spaces, allowing residents to enjoy the beautiful Florida weather year-round.

Beyond the homes, Ole offers a wealth of amenities that enhance the community experience. Residents can enjoy a resort-style clubhouse, a sparkling pool, fitness facilities, and scenic walking trails, all within a friendly neighborhood atmosphere. With its prime location in Naples, you’ll also have easy access to pristine beaches, upscale shopping, and exquisite dining options.

Experience the charm and elegance of Ole, where your dream home awaits!

Newest Ole Homes with Two Story Style

$449,000

3 Beds ⋅ 2.5 Baths ⋅ 226029087 MLS ⋅ Ole BLDG.

Discover this beautifully renovated fully furnished 3-bedroom, 2.5-bath Santa Ana in the highly desirable Ole at Lely Resort. Ideally located just 0.5 miles from the Ole Village Center, this light-filled residence offers a private covered front entry, an open-concept floor plan with spacious living and dining areas, soaring ceilings, 8-foot doors, a convenient half bath, and a well-appointed kitchen featuring light gray wood cabinetry, granite countertops, stainless steel appliances, and a generous walk-in pantry. Enjoy the privacy with peaceful landscaped views .Upstairs you’ll find all three bedrooms, a versatile loft with a built-in desk, a laundry room, and two full baths. The primary suite and one guest bedroom feature walk-in closets, while the third bedroom includes a standard closet. Hurricane Impact windows and doors provide added peace of mind, and a private attached new epoxy two-car garage. Residents enjoy exceptional resort-style amenities at the Ole Village Center, including a resort-style pool, children’s pool, fitness center, movie theater, pub and restaurant, café, ice cream parlor, library, business center, tennis, pickleball, bocce, basketball, beach volleyball, and a variety of social activities. Conveniently located approximately 9 miles from Downtown Naples and 5 miles to Marco Island, and within walking distance of restaurants and grocery stores, this home offers easy access to beaches, shopping, dining, and entertainment. Whether you’re looking for a primary residence, seasonal retreat, or investment opportunity, this property is an excellent choice, with rentals permitted up to 12 times per year with a 30-day minimum lease, and comes turnkey ready to enjoy.

9108 Capistrano ST S Unit 7405, Naples

$419,000

3 Beds ⋅ 2.5 Baths ⋅ 226031124 MLS ⋅ Ole BLDG.

Imagine being next to the clubhouse and on the most desired street in Ole. Image living on Rialto with all the wonderful fountains across from your front door, plus a semiprivate quad pool outside your back door. Tucked away in the heart of Ole at Lely Resort, this charming Santa Ana End Unit townhome feels more like a private retreat than a typical condo. With three spacious bedrooms, two and a half baths, and an open, inviting layout, it’s the perfect place to call home—whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity. The kitchen features granite countertops, a walk-in pantry, and sleek stainless-steel appliances (owner is installing), all opening up to a bright and airy living space where you can unwind or entertain with ease. Upstairs, the primary suite is your own personal sanctuary, complete with a walk-in closet and an en-suite bath that boasts dual sinks, a soaking tub, and a separate shower. Two additional bedrooms offer plenty of space for family, guests, or even a home office. A large two-car garage provides extra storage, and impact-resistant windows offer peace of mind. One of the best parts? You’re just a short walk from the Village Center, where you can grab a drink at the pub, catch a movie in the private theater, lounge by the resort-style pool, or get a workout in at the fitness center. The community also offers tennis, basketball, bocce, and volleyball courts, plus miles of bike and walking trails to soak in the Florida sunshine. And with Naples' famous beaches, Marco Island, and the shopping and dining of Fifth Avenue South just minutes away, you’ll have the best of Southwest Florida right at your fingertips. This home is more than just a place to live—it’s a lifestyle. Come see it for yourself!

9092 Capistrano ST S Unit 6401, Naples

$293,900

2 Beds ⋅ 2 Baths ⋅ 2026035371 MLS ⋅ Ole BLDG.

SELLER SAYS SELL! BEST-PRICED 2-BEDROOM IN OLE AT LELY RESORT! Move-in ready and fully furnished, this 2-bedroom, 2-bath home with a 2-car garage offers an excellent opportunity to enjoy the Ole lifestyle at an exceptional value. The spacious primary suite features a walk-in closet and large shower. The second bedroom is located on the opposite side of the home for added privacy and also offers a walk-in closet and tub/shower combination. Separate laundry room for added convenience. The owner resides outside the country and has used the property only a few weeks over the past several years. Offered fully furnished for an easy transition—bring your suitcase and start enjoying Naples and all that Ole at Lely Resort has to offer. Easy to show.

9064 Capistrano ST N Unit 5004, Naples

$425,000

3 Beds ⋅ 2.5 Baths ⋅ 226028444 MLS ⋅ Ole BLDG.

Experience the ultimate Southwest Florida lifestyle in this beautifully maintained Santa Clarita end-unit, perfectly positioned within the desirable Ole’ at Lely Resort community. This stylish residence offers enhanced privacy and an ideal location between the world-class beaches of Marco Island and the upscale shopping, dining, and entertainment of downtown Naples. Inside, you’ll find a bright and inviting open-concept layout designed for modern living. The spacious kitchen features granite countertops, stainless-steel appliances, a breakfast bar, and white cabinetry, seamlessly flowing into the living and dining areas—perfect for everyday living or entertaining. The home offers three comfortable bedrooms and two-and-a-half baths, including a luxurious primary suite with dual vanities, a soaking tub, separate shower, and a large walk-in closet. A flexible lower-level den provides extra space for a home office, gym, or guest area. Ole’ at Lely Resort is known for its award-winning amenities, where residents enjoy a resort-style lagoon pool with cabanas and poolside service, a spa, fitness center, movie theater, pub and café, library, and courts for pickleball, tennis, basketball, and volleyball. The community is also pet-friendly and offers access to two public championship golf courses, scenic walking paths, and lush green spaces. This turnkey-furnished home has been thoughtfully updated with a new roof (2024) and new AC (2023)—providing peace of mind and move-in readiness. Whether you’re seeking a full-time residence, a seasonal retreat, or an investment with flexible rental options, this property combines comfort, elegance, and convenience in one exceptional package.

9114 Capistrano ST S Unit 8501, Naples

$430,000

3 Beds ⋅ 2.5 Baths ⋅ 226026015 MLS ⋅ Ole BLDG.

Discover this beautifully furnished 3-bedroom, 2.5-bath Santa Ana end-unit in the highly desirable Ole at Lely Resort. Ideally located just 0.5 miles from the Ole Village Center, this light-filled residence offers a private covered front entry, an open-concept floor plan with spacious living and dining areas, soaring ceilings, 8-foot doors, a convenient half bath, and a well-appointed kitchen featuring wood cabinetry, granite countertops, stainless steel appliances, and a generous walk-in pantry. Enjoy the privacy of an end unit with peaceful landscaped views and no buildings directly behind. Upstairs you’ll find all three bedrooms, a versatile loft with a built-in desk, a laundry room, and two full baths. The primary suite and one guest bedroom feature walk-in closets, while the third bedroom includes a standard closet. Hurricane shutters provide added peace of mind, and a private attached two-car garage with a tennis court directly across the street adds to the home’s appeal. Residents enjoy exceptional resort-style amenities at the Ole Village Center, including a resort-style pool, children’s pool, fitness center, movie theater, pub and restaurant, café, ice cream parlor, library, business center, tennis, pickleball, bocce, basketball, beach volleyball, and a variety of social activities. Conveniently located approximately 10 miles from Downtown Naples and 12 miles from Marco Island, and within walking distance of restaurants and grocery stores, this home offers easy access to beaches, shopping, dining, and entertainment. Whether you’re looking for a primary residence, seasonal retreat, or investment opportunity, this property is an excellent choice, with rentals permitted up to 12 times per year with a 30-day minimum lease, and furnishings are negotiable.

9163 Delano ST Unit 10006, Naples

$364,000

2 Beds ⋅ 2.5 Baths ⋅ 226022280 MLS ⋅ Ole BLDG.

Lowest-Priced Cordova Casita in Award-Winning Lely Resort! Only One owner and no flood insurance required! This 2 bedroom, 2.5 bath home with dual en-suites and a two-car garage with extra storage is a perfect blend of privacy, luxury, and location. Recent updates include a new roof (2024, paid through special assessment), new dryer and new dishwasher. Ideally situated on sought after Chula Vista Street, this home enjoys one of the community's most private settings, nestled beside a beautifully landscaped preserve. The bright eat-in kitchen features granite countertops, while the spacious upstairs layout includes a private primary suite, a second en-suite bedroom, and a dedicated office nook with granite desk across from the laundry area. Just a short walk to the Lely Resort Village Center with resort-style pool, fitness center, movie theater, pub, coffee shop, and restaurant. Optional memberships available for The Players Club and golf, including 2 public and 1 private course within the community. Located between Naples and Marco Island, minutes from 5th Avenue, beaches, dining, and shopping. Perfect for full-time living, vacationing, or rental income.

9118 Chula Vista ST Unit 12002, Naples

$470,000

3 Beds ⋅ 2.5 Baths ⋅ 226020009 MLS ⋅ Ole BLDG.

This listing has it all! Ideally near wonderful shopping and restaurants and offered move-in ready with designer decorations that elevate every space, this beautifully maintained residence delivers effortless luxury living. Bright natural lighting fills the home from top to bottom, enhancing the airy, open atmosphere and highlighting the thoughtful layout and finishes. In the desirable Ole community in Lely Resort, this three-bedroom, two-full-bath plus one-half-bath home with a two-car garage offers comfort, style and easy Florida living. Ideally positioned within the community, the residence is conveniently located near the main clubhouse, resort-style pool and fitness center. The main living areas are located on the upper level, where the kitchen, dining room and living room flow seamlessly together alongside the primary suite. This space is enhanced by tile and laminate flooring and abundant natural light. The living room features glass French doors leading to a small balcony, creating a charming outdoor connection and inviting fresh air into the space. Impact doors and windows provide valuable storm protection and added peace of mind. The kitchen is designed for function and style, featuring custom cabinetry, recessed lighting and a full suite of appliances, including a microwave, electric range, dishwasher and refrigerator/freezer with an icemaker. The dining area sits adjacent to the kitchen and living space, creating an open environment ideal for everyday living and entertaining. A screened, covered lanai extends off the kitchen, offering a private outdoor retreat ideal for morning coffee or evening relaxation. The primary suite is privately situated upstairs and offers a peaceful escape with laminate flooring, a ceiling fan and generous natural light. The en-suite bath includes dual sinks, a soaking tub, an enclosed walk-in glass shower and a private water closet, along with a spacious walk-in closet. A dedicated laundry area with washer and dryer is also conveniently located on this level. On the first floor, two guest bedrooms provide comfortable accommodations, both with laminate flooring and ceiling fans and one with a walk-in closet. A full guest bath with dual sinks and a shower/tub combo serves this level. A flexible sitting and dining area adds additional functionality for guests or casual use. Residents of Ole enjoy a vibrant resort-style lifestyle with a tropical pool, fitness center, 80-seat movie theater, café, pub, ice cream parlor and inviting social spaces. Outdoor amenities include bocce, pickleball, tennis, basketball, sand volleyball and scenic recreational and biking paths. Lely Resort also offers three championship golf courses and the optional Players Club & Spa for an elevated experience with golf, spa, dining and social membership opportunities. Ideally located just minutes from Naples and Marco Island beaches, this home delivers the ideal blend of resort living and coastal convenience.

9066 Albion LN N Unit 5101, Naples

$419,000

3 Beds ⋅ 2.5 Baths ⋅ 226017987 MLS ⋅ Ole BLDG.

Perfectly positioned within the highly sought-after Lely Resort community of Olé at Lely Resort, this beautifully updated and impeccably maintained Casita-Capistrano floorplan model townhouse at 9128 Delano Street #89-2 offers the comfort and spaciousness of a single-family home paired with the ease of maintenance-free resort living. Guests are welcomed through a charming arched entry framed by lush jasmine-covered wrought iron arbor and picturesque paver walkways, creating a warm and inviting arrival experience. Inside, the residence showcases a fresh, sophisticated aesthetic with gorgeous lighter hardwood flooring flowing throughout both levels, crisp neutral interiors, and abundant natural light. The open-concept kitchen has been tastefully updated with white cabinetry, sleek black granite countertops, subway tile backsplash, center island, and newer stainless-steel Samsung appliances including a French-door refrigerator, dishwasher, microwave, and electric range. A spacious walk-in pantry with shelving and additional utility storage adds exceptional functionality, while a cozy breakfast nook offers the perfect setting for morning coffee or evening cocktails. The expansive great room seamlessly combines comfortable living and dining spaces and opens to a private outdoor patio and courtyard ideal for entertaining or relaxing in the Florida sunshine. A stylish first-floor powder bath features a pedestal sink and bidet toilet. Upstairs, all three generously sized bedrooms feature hardwood flooring, walk-in closets, and neutral finishes and blinds. The spacious guest suites are connected by an oversized Jack-and-Jill bath with dual vanities, separate water closet, and private shower/tub area, while the luxurious owner’s suite offers a spa-inspired bath complete with dual sinks, soaking tub, walk-in shower, and tiled flooring. The oversized two-car garage, accessed from the rear of the townhome with a side street entrance, provides abundant storage space rarely found in townhome living at this price point. Offered completely furnished, this barely lived-in residence is move-in ready—simply bring your suitcase and begin enjoying the exceptional Olé lifestyle. Residents enjoy access to an unmatched amenity-rich environment featuring a spectacular resort-style pool with food and beverage service, fitness center, pub, bistro, private movie theater, ice cream parlor, library, tennis, pickleball, bocce, basketball, volleyball, miles of scenic biking and walking paths throughout Lely Resort. Ideally located just minutes from Downtown Naples, world-class dining and shopping along Fifth Avenue South, pristine Gulf beaches, and Marco Island, this extraordinary residence delivers the very best of Southwest Florida resort-style living.

9128 Delano ST Unit 89-2, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 226017452 MLS

INVEST, ESCAPE, or LIVE the RESORT LIFESTYLE year-round in this beautifully maintained 3-bedroom, 2-bath residence located in the vibrant community of Olé at Lely Resort. Offering the highly desirable San Pablo floor plan, with a PRIVATE TWO-CAR GARAGE, this home is designed for both comfort and convenience with all main living areas situated on the upper level. The interior welcomes you with LIGHT, NEUTRAL TONES, abundant NATURAL LIGHT, and an open-concept layout that feels both spacious and inviting. The main living area is enhanced by LIGHT TILE FLOORING and flows seamlessly into the dining space and kitchen—creating an ideal setting for entertaining or relaxed everyday living. The kitchen features timeless WOOD CABINETRY, GRANITE COUNTERTOPS, and a generous island perfect for casual meals, hosting guests, or gathering with family and friends. Just beyond, enjoy indoor-outdoor living with access to a PRIVATE BALCONY—ideal for morning coffee or unwinding in the evening. The thoughtfully designed SPLIT FLOOR PLAN offers privacy for residents and guests alike. The primary suite provides a peaceful retreat with ample natural light, while guest bedrooms offer flexibility for visitors, seasonal living, or rental potential. Set within the charming, MEDITERRANEAN-INSPIRED community of Olé, residents enjoy a truly unmatched AMENITY-RICH lifestyle. The impressive 20,000-SQUARE-FOOT VILLAGE CENTER features a RESORT-STYLE POOL, POOLSIDE BISTRO, PRIVATE MOVIE THEATER, FITNESS CENTER, and lively social spaces. Outdoor enthusiasts will appreciate access to TENNIS, PICKLEBALL, basketball, and scenic walking paths—all complemented by a full SOCIAL CALENDAR. Ideally located just minutes from DOWNTOWN NAPLES and the white-sand beaches of Marco Island, this home offers easy access to renowned dining, shopping, and coastal attractions. With STRONG RENTAL APPEAL and LOW-MAINTENANCE ownership, this property presents an exceptional opportunity for investment, seasonal use, or full-time living.

9140 Delano ST Unit 9302, Naples

$359,500

2 Beds ⋅ 2.5 Baths ⋅ 226015827 MLS ⋅ Ole BLDG.

Welcome to the ultimate Casita lifestyle in the heart of Olé at Lely Resort, where you get the privacy and space of a single-family home with the effortless maintenance of a luxury condo. This rarely available two-story residence is a standout, boasting an attached two-car garage and a bright, open floor plan that feels incredibly expansive from the moment you walk through the door. Offered unfurnished and ready for your personal touch, the home features a modern kitchen finished with sleek stainless-steel appliances and a large center island that’s perfect for casual morning coffee or hosting friends before a night out. The layout is thoughtfully designed for flexibility, featuring two generous bedrooms and a massive upstairs loft that is the true "wild card" of the property. Since the closet is already in place, this space can easily be converted into a third bedroom, a high-end home office, or a media room depending on your needs. With two and a half bathrooms and a private patio for enjoying the Florida breeze, this home offers a level of comfort and utility that is hard to find in this price point. Location is everything in Olé, and this property hits the sweet spot. Tucked away in a quiet, private position on Chula Vista Street, you escape the noise of the main thoroughfares, yet you are still just a three-minute stroll from the legendary Olé Village Center. You’ll have the main resort-style pool, the pub, the bistro, and the 80-seat movie theater almost at your doorstep, allowing you to enjoy world-class amenities without the need to ever get in your car. Beyond the boundaries of Olé, you are perfectly positioned to take advantage of the quintessential Naples and Marco Island lifestyle. Whether you’re heading to the sugar-sand beaches for sunset, hitting the designer boutiques on Fifth Avenue South, or exploring the vibrant dining scene nearby, everything is just a short drive away. This is more than just a home; it’s an invitation to join one of Southwest Florida’s most active and sought-after communities.

9080 Chula Vista ST Unit 10401, Naples

$295,000

2 Beds ⋅ 2.5 Baths ⋅ 226014518 MLS ⋅ Ole BLDG.

Welcome to Olé at Lely Resort, intentionally built to transport residents to a walkable, Mediterranean-inspired small town. This beautifully landscaped community is designed to be inspiring, whether taking in a concert at the bandstand, sharing coffee at the café, or unwinding at the massive resort-style pool. This charming 2 bedroom and 2.5 bath Santa Isabella townhome with a new roof offers the best of Southwest Florida, featuring a beautifully tiled living area that flows into a gourmet kitchen complete with brand new appliances, granite counters, and shaker cabinets. Upstairs, a grand staircase leads to a master suite that is sure to impress, with brand new carpet, a large walk-in closet, double vanity, and walk-in shower. Enjoy the perfect nook for work and study or invite guests over in the spacious spare bedroom with full bath. Unlike most homes in Olé, this residence is part of an exclusive QUAD, offering a luxurious pool, patio, and grilling area for privacy and escape. Meanwhile, your HOA also grants full access to the 20,000 sq. ft. Village Center’s pub, restaurant, gym, movie theater, and tennis and pickleball courts. Located just 15 minutes from Marco Island’s beaches and 20 minutes from the world-class dining of Naples’ 5th Avenue South, this home includes an attached one-car garage and impact-resistant windows for total peace of mind.

9098 Capistrano ST S Unit 7103, Naples

$369,000

3 Beds ⋅ 2 Baths ⋅ 226009552 MLS ⋅ Ole BLDG.

Near the Village Center of Ole at Lely Resort, this San Pablo townhome offers a refined residential experience. Featuring three generously sized bedrooms and two spacious baths, the residence is designed with an open layout that enhances comfort and functionality. The kitchen is equipped with granite countertops and black appliances, seamlessly connecting to a bright living area ideal for relaxing or entertaining. The entire living space is upstairs. The primary suite provides a tranquil retreat, including a walk-in closet and an en-suite bath with dual sinks, a soaking tub and separate shower. The two additional bedrooms provide generous accommodation for family members or guests, complemented by a built-in desk conveniently between them. The spacious two-car garage adds valuable storage space, while impact-resistant windows enhance security and comfort. One of the greatest benefits is being just a short distance from the Village Center, where you can enjoy a drink at the pub, watch a film in the old-time theater, relax by the resort-style pool or exercise in the fitness center. The community also features tennis, basketball, bocce and volleyball courts, as well as scenic bike and recreational trails ideal for enjoying the Florida sunshine. With Naples renowned beaches, Marco Island, and the shopping and dining options of Fifth Avenue South only minutes away, you can easily experience everything Southwest Florida has to offer. This property isn't simply a home, it's a way of life. Discover it for yourself! Please note the home is unfurnished. The images provided include actual photographs of the property and virtually staged pictures to assist with visualization.

9037 Alturas ST Unit 3702, 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.