Browse All Cypress Woods Estates Properties for Sale

5 Beds ⋅ 3.5 Baths ⋅ 226021919 MLS

An exceptional, newly constructed custom residence, never before occupied, offering a rare blend of luxury, privacy, and sophisticated coastal living in the heart of Naples, Florida. Designed with an open-concept floor plan and soaring ceilings, this extraordinary home features five true bedrooms, or alternatively four bedrooms plus a private office, along with 3.5 beautifully appointed bathrooms. The seamless flow between the living, dining, and entertaining spaces creates an inviting atmosphere ideal for both everyday living and hosting guests. The gourmet chef's kitchen is equipped with top-of-the-line integrated appliances discreetly concealed behind custom cabinetry, creating a sleek and elegant aesthetic throughout the main living areas. Rich French oak engineered wood flooring extends throughout the home, while the bathrooms and wet areas showcase custom high-end tile finishes. Step outside to your private resort-style courtyard retreat, where a sparkling swimming pool and spa await, complete with LED lighting, therapeutic jets, and a temperature-controlled heating system. The highly sought-after southern exposure provides abundant natural sunlight throughout the day, enhancing the outdoor living experience year-round. Additional premium features include hurricane-impact windows and doors, a spacious walk-in pantry, and an oversized three-car garage with durable non-slip epoxy flooring. Every detail of this residence has been thoughtfully curated to create a warm, earthy, spa-inspired ambiance that exudes comfort and refinement. Perfectly positioned in one of Naples' most desirable locations, this one-of-a-kind property is within walking, biking, or golf-cart distance to the area's world-famous white sand beaches, upscale shopping, fine dining, entertainment, and other premier destinations. A truly rare opportunity to own a brand-new luxury residence in one of Southwest Florida's most desired locations.

1364 Cypress Woods DR, Naples

Courtesy of Realty One Group MVP.

$717,500

2 Beds ⋅ 2 Baths ⋅ 2026008858 MLS

Charming, completely renovated Old Florida home. Light, bright and comfortable. Fabulous location in central Naples. Just a block away from Tamiami Trail and directly across from Park Shore, Venetian Village and lovely quiet white sand beaches. The stop light at Cypress Woods Dr and 41 is a real plus making is easy to head south to Downtown and 5th Ave or right to North Naples, Mercato and Vanderbilt Beach. Easy access to Goodlette if you want to avoid traffic on 41! Venetian Village and the Park Shore beaches are just 3 minutes away by car and 10 minutes by bike! Very private home and fully fenced yard, wonderful neighbors and a new firepit and pavers. Much more spacious than it looks from the street. Currently operating as a short term rental with 5 star review for the home, amenities and location! Cant ask for a better central Naples location!

1051 Cypress Woods DR, Naples

Courtesy of LISTWITHFREEDOM.COM.

Selling Office: John R Wood Properties.

$2,700,000

4 Beds ⋅ 4.5 Baths ⋅ 225076400 MLS

This exceptional new construction home is located in one of the best areas with no flood concerns. Designed with an open-concept layout and soaring ceilings, this residence features 4 bedrooms plus a dedicated office, 4 full bathrooms, and an inviting outdoor oasis complete with a pool and spa. The gourmet kitchen showcases quartz countertops, sleek modern cabinetry, a spacious center island, double oven, and a beverage cooler—perfect for entertaining. The expansive primary suite includes dramatic 90-degree sliders that open directly to the pool area. The luxurious en-suite bathroom features a freestanding tub, oversized shower, dual vanities, and two walk-in closets. One of the front bedrooms offers direct access to a charming front porch terrace, providing a private outdoor retreat. Additional highlights include impact-resistant windows, tile roof, 3-car garage, abundant natural light, and Lutron dimmer switches throughout the home for customizable lighting and ambiance.

1317 Cypress Woods DR, Naples

Courtesy of John R Wood Properties.

$990,000

3 Beds ⋅ 2 Baths ⋅ 225060051 MLS

Stunning Remodeled 3-Bedroom Home in Naples, FL. Discover this beautifully renovated 3-bedroom, 2-bathroom home situated on a premium 100-foot-wide lot with southern exposure in the sought-after Cypress Woods Estates. Located just across US 41 from Park Shore Drive, this home is only about a mile from the pristine Naples beaches. This residence boasts a fully fenced backyard, featuring a brand-new pool surrounded by exquisite landscaping, perfect for embracing the luxurious Florida lifestyle. Inside, the modern kitchen shines with Bosch appliances, sleek quartz countertops, and a spacious island ideal for entertaining. Plantation shutters adorn every window, offering both elegance and privacy, while durable luxury vinyl wood flooring flows seamlessly throughout the home. Attention to detail is evident with solid core doors and premium hardware upgrades. Stay secure with hurricane protection for peace of mind during storm season. Cypress Woods Estates offers the freedom of no HOA or restrictions, allowing you to live life on your terms. Note: Owners are licensed real estate brokers.

1132 Cypress Woods DR, Naples

Courtesy of Compass Florida LLC.

Selling Office: Compass Florida LLC.

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 224103899 MLS

Experience this enchanting Key West-Style Home in the Heart of Naples! Built in 2004, this stunning home is offered turnkey furnished and features 1,900 square feet of living space, including 3 spacious bedrooms and 2 well-appointed bathrooms. As you arrive, a charming front porch with double entrance doors welcomes you into a bright and airy open-plan living area. The centerpiece is a striking 20-foot central cupola, flooding the space with natural light and adding a sense of grandeur. The living area seamlessly connects the lounge, kitchen, and dining spaces, creating an ideal setting for both relaxation and entertaining. The kitchen is a chef’s delight, boasting new cabinetry, stainless steel appliances, granite countertops, and a pantry to meet all your culinary needs. The master suite offers a serene retreat with dual sinks, a tiled walk-in shower, and a luxurious soaking tub. Additional interior highlights include wood and tile flooring, soaring ceilings, and custom window coverings. Step outside to enjoy the screened rear porch and wooden deck, perfect for soaking in the Naples lifestyle. The detached two-car garage provides ample storage, while the beautifully landscaped yard, complete with raised garden beds, exudes the charm of an English cottage garden. Located less than 2 miles from premier shopping at The Village Shops on Venetian Bay and the pristine sands of Park Shore Beach, this home offers the perfect blend of convenience and tranquility. Whether you’re seeking a peaceful personal oasis or a lucrative short-term rental investment, 1367 Cypress Woods Drive is an exceptional opportunity to embrace the quintessential Naples lifestyle!

1367 Cypress Woods DR, Naples

Courtesy of John R Wood Properties. 860-839-3424

Selling Office: Dalton Wade Inc.

$1,075,500

3 Beds ⋅ 2 Baths ⋅ 223064728 MLS

Don't miss out on this large, Southern exposure, building lot on a beautiful, tree lined street in the downtown Naples area! Nestled amongst new, multi-million dollar homes. This beautiful property features: - Large, 0.37 acre, 118' wide x 135' deep lot - Existing 2,030 sf, 3 Bedroom, 2 Bath, 2 Car home can be remodeled and has approved plans and permits in place - Southern exposure - Beautiful, mature landscaping - Downtown Naples location - City and Reclaimed water - Located in a quiet location, half way between Goodlette and 41

1200 Cypress Woods DR, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: Premiere Plus Realty Company.

$1,132,500

3 Beds ⋅ 2 Baths ⋅ 223021572 MLS

H9463 - Listings of this caliber on Cypress Woods Drive are a rarity. Outstanding location directly across US 41 from Park Shore Drive, approx 1 mile to beach w/access to everything in all directions. 3BR+den 2Ba on 75’x135’ lot, flanked by new homes on both sides (one under construction). Well maintained by original owners, this CBS home features newer updates from new roof (Nov. 2018), to kitchen & guest bath (2020), to acacia hardwood floors in BRs/walk-in (2014-21), exterior paint (2022), all appliances (2020-21), & water heater (2019). Hurricane panels (some clear) and circuit for generator. Floor plan easily reconfigured should more open layout be desired. Highly sought school district. The long-projected spillover from the Park Shore neighborhood to northern NA15’s BEST street has commenced in earnest, with multiple multi-million dollar new builds currently under construction on the street due to relative affordability. A great place to live, with accelerating lot values in the area (proximate lots 50x135 - 76x137 currently available in NA15 range from $599K to $1.5M) rendering this an exceptional investment opportunity as well. AGENTS, SEE CONFIDENTIAL REMARKS.

1335 Cypress Woods DR, Naples

Courtesy of John R Wood Properties. 239-370-0880

Selling Office: Compass Florida LLC.

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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.

Cypress Woods Estates Real Estate & Homes