Quick Naples FL MLS Search

Browse All Tall Pines Properties for Sale

$1,500,000
6 Beds ⋅ 3.5 Baths ⋅ 226022940 MLS
Nestled beneath a canopy of mature trees in the desirable Tall Pines neighborhood, this expansive lakefront residence offers a rare combination of space, character and location. Situated on an oversized one-third-acre homesite with tranquil water views, the property is surrounded by lush tropical landscaping and enjoys a central Naples location within the highly rated Osceola Elementary, Pine Ridge Middle and Barron Collier High School zones. The home features seven bedrooms, three and one-half baths, multiple gathering spaces and a versatile upstairs bonus room, providing exceptional flexibility for guests, hobbies or home offices. Rich Brazilian hardwood floors add warmth and timeless appeal throughout much of the residence. From the moment you arrive, the home exudes a sense of charm and individuality that is increasingly difficult to find in today's market. Expansive lake views framed by mature trees create a picturesque backdrop, while the pool and outdoor living areas offer a peaceful setting for entertaining and everyday enjoyment. A long-lasting metal roof and three air conditioning systems provide a strong foundation for future enhancements. For buyers seeking something beyond the ordinary, this property presents a unique opportunity to own a home with personality, scale and enduring appeal. The setting, square footage and location combine to create exceptional long-term value in one of Naples convenient neighborhoods.

5731 Cypress Hollow WAY, Naples

Courtesy of Premier Sotheby's Int'l Realty.

$1,950,000
3 Beds ⋅ 3.5 Baths ⋅ 2026019839 MLS
Experience Lakeside Luxury Living at Its Finest — Welcome to this stunning custom lakeside estate at 5700 Waxmyrtle Way in the desirable Tall Pines community of North Naples, Florida. This meticulously upgraded 1995-built home sits on a rare 0.34-acre waterfront lot and offers 3 bedrooms plus a den, 3.5 baths of sophisticated living space. Completely transformed into a private resort, this move-in-ready Naples home boasts a brand-new pool and hot tub, an expansive screened lanai with panoramic views, and a charming detached guest cottage perfect for visitors, a poolside cabana, home office, or art studio. Wake up to tranquil lake vistas, lush landscaping, fruit trees, and an herb garden right in your backyard — the ultimate Florida lifestyle. Step inside to soaring ceilings, abundant natural light, and beautiful new flooring throughout. The show-stopping chef’s kitchen features dual islands, quartzite countertops, Sub-Zero refrigeration, a commercial-grade gas range with dual ovens, a dedicated drink cooler, ice maker, and ample storage — ideal for entertaining family and friends. Relax in the private second-floor primary suite with a versatile loft (perfect for a home office or den), spa-like bath with separate tub and shower, and generous walk-in closet. Additional highlights include four sets of French doors opening to the backyard oasis, two wood-burning fireplaces, zoned HVAC, tankless water heaters, and an extended 2-car garage with epoxy flooring. Unmatched Resiliency & Peace of Mind — This home is built like a fortress with a newer metal roof, impact-resistant windows, doors & skylights, a whole-house generator with buried propane tank, and a whole-house water filtration system. Low HOA fees make it even more appealing for full-time residents or seasonal snowbirds. Located in Tall Pines, a peaceful, non-gated North Naples neighborhood with low assessments and easy access to everything: world-class beaches, fine dining, shopping at Mercato, and top-rated schools — all just minutes away. Whether you're seeking a luxurious primary residence, a vacation retreat, or an incredible investment property with strong rental potential, this lakeside Naples pool home delivers unparalleled luxury, resilience, and lifestyle. Don’t miss this rare opportunity — homes like this on oversized waterfront lots don’t last long in North Naples. Schedule your private showing today and imagine your new life in paradise at 5700 Waxmyrtle Way! ***Please note there is a detached guest studio which has it's own full bathroom and is separate, but steps from the main house.*** Perfect for guests, pool house, office, art studio, etc. (3 + Den/2.1 in main house + 1/1 in detached guest studio)

5700 Waxmyrtle WAY, Naples

Courtesy of Redfin Corporation.

$938,000
3 Beds ⋅ 2 Baths ⋅ 225083898 MLS
In the heart of central Naples—minutes to the beach and located within one of the area’s most established neighborhoods and an X flood zone (no insurance required) — this fully renovated two-story pool home offers a rare combination of location, modern upgrades, and outdoor space. With over $400,000 in renovations in 2024, this move-in-ready property stands out as a unique offering in today’s market. The interior has been completely reimagined with a brand-new kitchen with induction cooktop, all-new bathrooms, updated flooring, upgraded lighting with LED accents, barn doors, and thoughtfully selected finishes throughout. Spacious bedrooms include new closet doors, custom built-ins, and closet organization systems. The main level features two guest bedrooms and a refreshed full bath, while the upper level offers a unique flex loft space, and a primary suite with tropical views and a spa-inspired bathroom with a custom walk-in shower. The home was updated with a brand new A/C system installed in 2026, new water heater (2025), new electric panel (2024), exterior paint (2024) and so much more! Outdoor living is highlighted by an east-facing, saltwater heated pool with sun shelf, overflow spa, and water features. Expansive impact sliders open to a two-story lanai, creating a seamless connection between indoor and outdoor spaces. The fully fenced, estate-sized yard and rear garage access enhance both privacy and functionality. The property is located in Tall Pines, a community known for its tight-knit community feel and calendar of resident-led neighborhood events held throughout the year. Conveniently situated in walking or biking distance to shopping, dining, and easy access to Naples beaches, this home offers an exceptional blend of location, upgrades, and lifestyle.

5900 Cypress Hollow WAY, Naples

Courtesy of KW Elevate Luxury.

Selling Office: Shawn Stuben Naples Properties.

$1,099,000
3 Beds ⋅ 2 Baths ⋅ 225082383 MLS
Welcome to 6161 Waxmyrtle Way—a beautifully refreshed pool home in one of Naples’ most sought-after neighborhoods. Freshly painted inside and out, this residence offers impact-resistant windows and doors, combining style with storm-ready peace of mind. The home features a spacious, light-filled layout centered around a private courtyard-style pool, providing the perfect backdrop for entertaining or relaxing in total privacy. High ceilings, oversized windows, and skylights invite natural light into every corner of the living space. This open floor plan includes generous guest rooms, a versatile den, and a large laundry room. The primary suite is its own retreat, complete with custom walk-in closets, dual vanities, a walk-in shower, and a freestanding soaking tub. An oversized garage offers extra space for storage or hobbies. Enjoy a fenced backyard ideal for pets, a newer roof and A/C system, and a low HOA of just $72/month. Perfectly situated just minutes from top-rated schools, Naples’ world-class beaches, fine dining, and shopping, this home is ideal for families, seasonal residents, or investors seeking long- or short-term rental potential. Homes in this quiet, centrally located community rarely hit the market—don’t miss your opportunity to own a move-in-ready home in the heart of Naples. No history of hurricane damage.

6161 Waxmyrtle WAY, Naples

Courtesy of John R Wood Properties.

$1,700,000
4 Beds ⋅ 3.5 Baths ⋅ 225080627 MLS
Beautifully renovated and set on an oversized 0.52-acre cul-de-sac lot with your very own private pickleball/basketball court, this fully furnished two-story estate blends high-end finishes, generous indoor-outdoor living, and an unbeatable central location. Inside, the open layout is filled with natural light and anchored by a coastal-inspired kitchen with teal shaker cabinetry, brass hardware, white quartz countertops, a farmhouse sink, and a rustic center island. Wide-plank, white oak floors flow throughout the living and dining areas, creating a warm, cohesive feel. The flexible floor plan includes two primary suites—one on each level. The first-floor suite offers a private exterior entrance ideal for guests or multigenerational living, while the upstairs suite enjoys a seating area and a balcony overlooking the peaceful, tropical yard. Outdoor living is a major highlight, with a full-length covered back porch, multiple seating and dining zones, and a hot tub overlooking the expansive backyard retreat. With its rare combination of privacy, location, and turnkey readiness, this home offers an exceptional lifestyle in one of Naples’ most coveted neighborhoods.

6260 Waxmyrtle WAY, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: John R Wood Properties.

$1,775,000
4 Beds ⋅ 3.5 Baths ⋅ 225063406 MLS
Welcome to 2761 Ardisia Lane, an exquisite lakefront sanctuary nestled in the charming and centrally located neighborhood of Tall Pines, Naples, FL. This stunning 4-bedroom, 3.5-bathroom residence, rebuilt from the ground up in 2014, offers modern luxury and comfort on an oversized private lot. Step inside this custom-designed home and be captivated by its elegant features and thoughtful layout. The living and formal dining room are artfully separated by a custom gas double-sided stone fireplace, creating warmth and ambiance. Your chef's kitchen is a masterpiece with a gas cooktop, double oven, and gleaming granite countertops, complemented by high-end stainless steel appliances. The main floor boasts a spacious master suite with dual walk-in closets, providing a serene retreat while the adjoining master bath offers luxury and relaxation. A mud room and expansive laundry room add to the home's functionality and charm. Ascend to the second floor to find a large suite with an en-suite bath, along with two additional bedrooms featuring a Jack and Jill bathroom. The airy game room/loft area invites a space for entertainment. A unique walk-in attic offers an additional 431 square feet of accessible storage space. As you make your way outside, you'll be delighted with the lakefront view complete with a refreshing pool and a relaxing hot tub. Sit outside on cool nights by your outdoor firepit. Whether you're hosting a weekend barbecue or enjoying a quiet evening under the stars, this outdoor oasis is sure to be a favorite gathering spot.

2761 Ardisia LN, Naples

Courtesy of Compass Florida LLC.

Selling Office: John R Wood Properties.

$795,000
5 Beds ⋅ 3 Baths ⋅ 225052133 MLS
Welcome to this charming two-story pool home nestled in the sought-after community of Tall Pines. Featuring a newer roof (2017), tile flooring (2017), air conditioning units (2017), and hot water heater (2025). This home boasts a bright open living space with high ceilings creating a warm and inviting atmosphere as well as generous bedrooms for the whole family. Enjoy beautiful views of the sunset from the private lanai and large pool- ideal for relaxing or hosting gatherings year-round. Located on a quiet cul-de-sac in a community with low HOA dues, this home combines privacy-with convenience-just minutes away from top-rated schools, shopping, dining, and Naples' pristine beaches.

6260 Cypress Hollow WAY, Naples

Courtesy of Realty One Group MVP.

Selling Office: Premiere Plus Realty Company.

$930,000
3 Beds ⋅ 3 Baths ⋅ 225001781 MLS
Only CONCRETE BLOCK home for sale in Tall Pines (all others wood frame) Exceptional family-centric floor plan in centrally located Tall Pines community. Outstanding curb appeal is accentuated by side-facing garage. With out without your garage door up, your housefront looks impeccable. A long paver driveway and a facade accented by functional plantation shutters in luxury black add to the visual charm. The exterior plantation shutters are hurricane rated and can be deadlocked for additional security on the front facing windows. Oversize impact glass front doors further define the entry and opulence of this beautiful home. The den or 4th room is enclosed and sound deadened. This space could be used as an infants room with its proximity to the master, an office, a workout room (currently equipped with a professional pull-up bar that is bolted to the trusses and virtually bullet proof) or a 4th bedroom with an additional full bathroom directly across the hall. Another unique room is the Mudroom / Storage off of laundry room. This is an enclosed separate room. Many upgrades have been completed during the current owners tenure. Most recently: new double oven '22, new AC in '23 and new dishwasher '24. Tall Pines is a highly desired neighborhood due to the location, low annual fees. proximity to schools and especially for the diversity of home styles and designs. Each home has a custom look without the "cookie-cutter" homes you see in most neighborhoods. Take a 2 mile lap within the community (as many do) or easily walk to Barron Collier High School, Osceola Elementary or Community School. Walk, run or cycle around the schools behind the community as the roads there are virtually car free and you have at least 5 miles to bike without worrying about traffic. Perfect for Families looking for a prime location within walking distance of many top area schools or empty nesters looking for a unique community close to everything.

5701 Waxmyrtle WAY, Naples

Courtesy of White Sands Realty.

Selling Office: Keller Williams Realty Naples.

$749,000
4 Beds ⋅ 2.5 Baths ⋅ 224039774 MLS
Spacious Home in Tall Pines – No Flood Zone, Low HOA Fees, and Huge Potential! Nestled in the desirable Tall Pines community, this 90x165-foot lot offers a rare opportunity to own a home in a NO FLOOD ZONE, saving you up to $3,500 a year on insurance. The property boasts a low annual HOA fee of just $850, making it even more affordable. Key Features: 4 Bedrooms, 2 Dens (potential 5th bedroom), and 2.5 Bathrooms 2,581 Sq Ft of living space with cozy nooks for work or relaxation Remodeled Master Bedroom (2005) and updated PGT hurricane impact windows (2015) Roof (2007) with 30-year shingles and AC units replaced (2012-2014) Brand new water heater Located in an A-rated school district Septic system for low water bills and high elevation for added peace of mind The first floor features the master bedroom and two dens, while the second floor includes three additional bedrooms and a desk nook. This charming home offers endless potential for personalization with its spacious layout and thoughtful updates. Don’t miss this gem in Tall Pines!

6100 Cypress Hollow WAY, Naples

Courtesy of VIP Realty Group, Inc..

Selling Office: Premiere Plus Realty Company.

$1,350,000
4 Beds ⋅ 3 Baths ⋅ 224030394 MLS
This stunning WATERFRONT POOL home was FULLY RENOVATED top to bottom with no expenses spared. One of a kind ENTERTAINER'S DREAM home with an open concept floor plan, tons of natural light, chef's dream kitchen & LUXURY OUTDOOR LIVING. Soaring ceilings and enormous light filled glass sliding doors, skylights, open great room with fireplace. Your divine and private master suite includes a walk-in shower, walk-in closet, dual sinks & a make-up counter. Master bedroom walks out to the lanai, perfect for your morning coffee. All is new: metal roof, outside and inside paint, impact windows & doors, cabinets, countertops, custom mirrors, designer light fixtures, custom made window treatments, landscaping, paver driveway... New epoxy flooring in freshly painted oversized 2-car garage with tons of brand-new shelving for extra storage. No detail was spared on the outdoor living: PANORAMIC pool cage, oversized new heated pool with spectacular waterfalls, new spa, new outdoor kitchen & fireplace. The amount of covered and uncovered outdoor space is unreal, allowing you to enjoy being outside all year round.

5891 Cypress Hollow WAY, Naples

Courtesy of Waterfront Realty Group Inc.

Selling Office: Compass Florida LLC.

$995,000
4 Beds ⋅ 3.5 Baths ⋅ 223054224 MLS
Well-maintained, traditional 2-story home offering 4 bedrooms + office + sunroom in very desirable Tall Pines. Privately tucked into a corner 1/2+ acre wooded lot make it a gardener’s paradise, on a low-traffic cul-de-sac street. Upgrades include wood flooring in main areas, French doors, plantation shutters, crown moldings, skylights, wine cooler, built-in bookcases, fireplace, track lighting and designer niches. First-floor owner's suite with private, walled courtyard off the owner's bath. Eat-in kitchen with stainless kitchen appliances including double oven, whole-house carbon water system with RO at kitchen sink. Sunroom with impact sliding doors lead out to an oversized, shaded, bi-level deck area for outdoor entertaining or relaxation. Separate office with complete built-in cabinets, counters and closets. Second floor offers three guest bedrooms, one with a sitting area, 2 full baths and walk-in attic storage. New roof in 2019. Tall Pines offers a very convenient location, great school district and low HOA fees.

6150 Cypress Hollow WAY, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Premiere Plus Realty Company.

$1,100,000
3 Beds ⋅ 2 Baths ⋅ 223043232 MLS
Welcome to a truly unique, fully renovated Entertainer’s Delight home in the heart of Naples. You will love the abundance of natural light flowing through HUGE floor-to-ceiling windows, doors and skylights. Spacious floor plan wraps around the courtyard with the pool offering tons of privacy. Completely renovated wood burning fireplace to create cozy memories gathering with friends and family. Desirable split floor plan: courtyard pool is visible from almost every part of the house, large bedrooms and a den, large laundry room and the oversized garage. Master suite features his and hers custom walk-in closets, stand alone tub, dual sinks and shower. No-stress living with newer roof, A/C, impact windows and doors, fenced in backyard perfect for pets! Centrally located in the heart of Naples: walking distance to shopping, fine dining, biking distance to the white sand beaches, and top rated school zone. HOA is 63/month! Don't miss out on this opportunity to own this beautiful home in one of the most desirable locations either for your family and/or short term/long term rental investment in a family friendly neighborhood where homes rarely come to the market. NO HURRICANE DAMAGE!

6161 Waxmyrtle WAY, Naples

Courtesy of LuxRe, LLC.

Selling Office: DomainRealty.com LLC.

$850,000
4 Beds ⋅ 3 Baths ⋅ 223028082 MLS
Located on a .36-acre corner lot, this spacious 4-bedroom, 3 full bath, 2 car side garage home with 2,756 sq. ft. of living space offers a separate private entrance to a lovely and spacious mother-in-law suite, ideal for a guest suite or a college student returning home. The charming front porch is complete with a two-person swing for lounging in the warm Florida breeze enjoying a glass of iced tea or a fine cocktail. Best of all the owner’s suite leads out to a stunning newly re-screened Western facing lanai filled with ample relaxing space, and a sparkling blue sun-shelf pool. Tall Pines is a non-gated, highly sought out community with low yearly HOA fee of only $750. Do not miss this fine opportunity to make this magnificent house your home, because truly, this is where you want to live!

5901 CYPRESS HOLLOW WAY, Naples

Courtesy of John R Wood Properties. 239-777-9574

Selling Office: EXP Realty LLC.

Start Your Search

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.

Tall Pines Real Estate & Homes