Cypress Falls at the Woodlands

Cypress Falls at the Woodlands Homes for Sale – North Port, Florida 34289

Cypress Falls at the Woodlands is a North Port community for age 55-plus residents wherein new home construction regained vigor in the post-recession housing recovery. Its first offerings of Sarasota homes for sale were constructed in 2005 by Lennar Corp., one of the country’s largest home builder.

Lennar delivered approximately 148 homes in Cypress Falls up to 2008 after which further construction was halted up to 2011. Homebuilding in this community resumed in 2012 after the Del Webb senior housing unit of D.R. Horton, another U.S. homebuilding giant, took over its development.

2018 Expansion Okayed

The residences in Cypress Falls consist of a mix of garden villas, paired villas and single family homes. More choices of the latter residential types are forthcoming, as the North Port city commission approved in mid-February two expansion projects for this community.

Prior to the expansion approval, Del Webb opened in early February its Cypress Falls model park. It features two newly built and furnished single-family home designs both priced starting from the low $200s.

One of these designs has a floor area of 1,574‒2,333 square feet, while the other provides a floor plan of 1,861 to over 3,000 square. Their layouts provide two to five bedrooms and up to three and a half baths. All told, Del Webb offers six low-maintenance home designs at Cypress Falls which has sustained its growth under an active adult lifestyle theme.

Resale Choices

Existing pre-owned single family homes in this community can be offered on the market with asking prices in the $200s‒$300s range, featuring two to three bedrooms within floor areas ranging from 1,710 up to about 2,250 square feet.

For earlier builds of villas at Cypress Falls, price quotes typically start in the high $100s for residences with floor plans of between 1,350 and 1,500 square feet featuring two bedrooms and two baths.

Joys of Active Adult Lifestyle

A gated neighborhood, Cypress Falls provides all the facilities for an active lifestyle which age 55-plus residents would seek. The amenities which are available at the community’s spacious clubhouse include a state-of-the-art fitness center, a billiards facility, a library, and an Internet café.

Besides a heated resort-style pool, Cypress Falls provides a resistance pool for more challenging workouts. Residents’ yearning for sports, in addition, could be fulfilled in the community’s two tennis courts, four bocce ball courts, and putting green. A barbecue pit and gardening plots add flavor to the outdoor amenities of Cypress Falls.

A full-time activities director helps organize group events of the residents, which are varied and wide-ranging. These include weekly sessions on physical fitness, such as yoga, walk aerobics, and water aerobics. There are also regular neighborhood meets for round-robin tournaments on tennis, bocce ball, and ping-pong. Likewise popular amongst residents of Cypress Falls are mahjong, card games, and dominoes.

Owning a home in Cypress Falls, moreover, allows easy access to nearby Gulf Coast beaches, natural springs, and over 80 miles of freshwater canals. Nearby points of interest, like the Myakka State Forest, provide such delights as hiking, canoeing, kayaking and horse-riding. Venues for shopping, dining and healthcare are easily accessible too with the community just south of Interstate 75, a vital road corridor lending marketability to many of Sarasota’s community developments, old or new.

Cypress Falls at the Woodlands Homes for Sale

Below are the current real estate listings available at Cypress Falls at the Woodlands.

Please contact me if you would like to schedule a tour of any of the listed properties below.

MLS# O6296851 - Status: Active View Property Details Add to Favorites View Map

• 1427 HYSSOP LOOP
• Price: $510,000
• Zip Code: 34289
• 1996 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 3 Baths: 2
• PRIVATE POOL AND SPA ! - Welcome to This 2018 home is like new on an oversized lot with southwestern exposure. Equipped with hurricane impact windows, doors and zero corner sliding doors leading to the wrap around lanai with private pool and spa! - ... Read More
• Listing courtesy of: BLUE LIGHTHOUSE REALTY INC

MLS# D6146007 - Status: Active View Property Details Add to Favorites View Map

• 1596 HYSSOP LOOP
• Price: $499,000
• Zip Code: 34289
• 1997 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 3 Baths: 2
• NEW LISTING! WELCOME TO 1596 HYSSOP LOOP. This 1997 SQFT POOL HOME built in 2019, has a plethora of upgrades. This stunning 3-bedroom, 2 living areas 2-bathroom and 2 car garage haven is nestled in Del Webb Cypress Falls at the Woodlands, an exclusiv ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# D6145416 - Status: Active View Property Details Add to Favorites View Map

• 1445 HYSSOP LOOP
• Price: $499,000
• Zip Code: 34289
• 2004 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 3 Baths: 2
• Welcome to Cypress Falls at the Woodlands, an exclusive Del Webb 55+ gated active community where refined living meets resort-style amenities. This beautifully appointed Summerwood model offers 3 bedrooms, 2 baths, and a den across 2,004 square feet ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# D6145420 - Status: Active View Property Details Add to Favorites View Map

• 1721 HYSSOP LOOP
• Price: $485,000
• Zip Code: 34289
• 2100 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 3 Baths: 2
• LOOK AT THE NEW PRICE!! OPEN SUNDAY 2/15/26 1PM-3PM. Luxury Living in Cypress Falls at The WoodlandsPrepare to be dazzled. From the moment you arrive, the meticulous attention to detail is evident. Expertly manicured landscaping and custom curbing s ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# C7520763 - Status: Active View Property Details Add to Favorites View Map

• 1506 HYSSOP LOOP
• Price: $477,000
• Zip Code: 34289
• 1906 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 2 Baths: 2
• Turnkey and move-in ready, this beautifully upgraded home is located on a premium lake view lot in the desirable 55+ Del Webb community of Cypress Falls at the Woodlands. Built in 2020, the residence includes a model upgrades package valued at over $ ... Read More
• Listing courtesy of: KELLER WILLIAMS REALTY FT MYER

MLS# D6144752 - Status: Active View Property Details Add to Favorites View Map

• 2358 ARUGULA DR
• Price: $468,900
• Zip Code: 34289
• 1894 Square Feet
• Subdivision: CYPRESS FALLS PH 1D
• Bedrooms: 3 Baths: 2
• PRICE ADJUSTMENT!! BRING OFFERS!! Welcome to 2358 Arugula DriveLocated in the highly desirable Del Webb Cypress Falls at The Woodlands, this beautifully maintained home offers exceptional curb appeal with mature landscaping and a warm, inviting prese ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4669822 - Status: Active View Property Details Add to Favorites View Map

• 2633 DAISY DR
• Price: $457,000
• Zip Code: 34289
• 1815 Square Feet
• Subdivision: CYPRESS FALLS PH 2C
• Bedrooms: 2 Baths: 2
• Discover this meticulously maintained 2-bedroom, 2-bath home located in the highly sought-after Del Webb 55+ community of Cypress Falls. Built in 2021, this 1,815 sq ft gem features crown molding, recessed lighting, and a stylish open-concept layout. ... Read More
• Listing courtesy of: EXP REALTY LLC

MLS# C7521463 - Status: Active View Property Details Add to Favorites View Map

• 1712 HYSSOP LOOP
• Price: $440,000
• Zip Code: 34289
• 1789 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 2 Baths: 2
• Stunning home situated in Cypress Falls, a 55+ Del Webb resort style gated community! This 2021 built, water view, split/open floor plan, 1789sf, 2/2/2 with a Den/Study, added Sunroom, screened lanai/patio extension, and so many more updates, is wait ... Read More
• Listing courtesy of: FIVE STAR REALTY OF CHARLOTTE

MLS# N6135703 - Status: Active View Property Details Add to Favorites View Map

• 2539 BRASSICA DR
• Price: $407,000
• Zip Code: 34289
• 1575 Square Feet
• Subdivision: CYPRESS FALLS PH 2D
• Bedrooms: 3 Baths: 2
• BUILT IN 2021. HURRICANE PROTECTION. FURNISHED. Welcome to this stunning, move-in-ready 3-bedroom, 2-bathroom home, built in 2021, located in the desirable 55+ Cypress Falls gated community in North Port, FL. UPGRADES include LeafFilter gutter guards ... Read More
• Listing courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE

MLS# D6144286 - Status: Active View Property Details Add to Favorites View Map

• 2482 ARUGULA DR
• Price: $395,000
• Zip Code: 34289
• 1649 Square Feet
• Subdivision: CYPRESS FALLS PH 1A
• Bedrooms: 3 Baths: 2
• BIG PRICE IMPROVEMENT!! TAKE OTHER LOOK!! This charming home in Cypress Falls at the Woodland, a Del Webb 55+ gated community, offers 1,649 SQFT of living space with 3 bedrooms. The mature landscaping and screened front entry with a beautiful glass d ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# N6141439 - Status: Active View Property Details Add to Favorites View Map

• 1548 HYSSOP LOOP
• Price: $383,000
• Zip Code: 34289
• 1672 Square Feet
• Subdivision: CYPRESS FALLS
• Bedrooms: 2 Baths: 2
• Welcome to Cypress Falls at the Woodlands - North Port's Premier 55+ Lifestyle CommunityStep into this inviting 2-bedroom, 2-bathroom home with a versatile den/flex room, perfect for a home office, craft space, or cozy TV lounge. The open floor plan ... Read More
• Listing courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE

MLS# C7515754 - Status: Active View Property Details Add to Favorites View Map

• 2436 ARUGULA DR
• Price: $380,000
• Zip Code: 34289
• 1698 Square Feet
• Subdivision: CYPRESS FALLS PH 1D
• Bedrooms: 2 Baths: 2
• **HUGE PRICE IMPROVEMENT** Welcome to your dream home! Experience maintenance-free, comfortable living at its finest in the distinguished 55+ gated community of Del Webb at Cypress Falls. This stunning single-family residence features a 2.5-car garag ... Read More
• Listing courtesy of: RE/MAX PALM REALTY

MLS# TB8449586 - Status: Active View Property Details Add to Favorites View Map

• 1344 RASPBERRY DR
• Price: $365,000
• Zip Code: 34289
• 1412 Square Feet
• Subdivision: CYPRESS FALLS PH 2E
• Bedrooms: 2 Baths: 2
• Price improvement - turnkey furnished - move in ready! Enjoy effortless Florida living in this bright, upgraded turnkey furnished home with peaceful views of a wooded preserve from the rear lanai and a tranquil pond view from the front. Located at 1 ... Read More
• Listing courtesy of: MARK SPAIN REAL ESTATE

MLS# C7518777 - Status: Active View Property Details Add to Favorites View Map

• 1628 HYSSOP LOOP
• Price: $345,000
• Zip Code: 34289
• 1669 Square Feet
• Subdivision: CYPRESS FALLS PH 2A & 2B
• Bedrooms: 2 Baths: 2
• Welcome to your dream home!! Maintenance Free, Comfortable living at its best in the distinguished 55+ gated Community Del Webb of Cypress Falls. Step into this stunning, 2-bedroom, Den/Office, 2 bath single family home, with ALMOST 1,700 sq ft of l ... Read More
• Listing courtesy of: RE/MAX PALM REALTY

MLS# D6145195 - Status: Active View Property Details Add to Favorites View Map

• 2525 DAISY DR
• Price: $333,000
• Zip Code: 34289
• 1434 Square Feet
• Subdivision: CYPRESS FALLS PH 2C
• Bedrooms: 2 Baths: 2
• BONUS TO BUYERS AGENT!! MOTIVATED SELLER! BRING OFFERS! Welcome to this beautifully upgraded 2-bedroom, 2-bath with flex room. This home is Located in the highly desirable Del Webb 55+ community of Cypress Falls. Offering 1,434 sq ft of heated living ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# D6144792 - Status: Active View Property Details Add to Favorites View Map

• 2860 ARUGULA DR
• Price: $284,000
• Zip Code: 34289
• 1363 Square Feet
• Subdivision: CYPRESS FALLS PH 1C
• Bedrooms: 2 Baths: 2
• One or more of the pictures have been virtually stage. Welcome to 2860 Arugula Dr. this well-maintained 2-bedroom, 2-bath villa located in the desirable Del Webb Cypress Falls at The Woodlands, a premier 55+ active community in North Port. This spaci ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# C7517996 - Status: Active View Property Details Add to Favorites View Map

• 1393 KELP CT
• Price: $284,000
• Zip Code: 34289
• 1426 Square Feet
• Subdivision: CYPRESS FALLS PH 1A
• Bedrooms: 2 Baths: 2
• Lovely very well-maintained maintenance free villa in the sought after community of Cypress Falls at the Woodlands. This beautiful 2-bedroom plus den that can double as a 3-bedroom home has a newer ac, newer water heater, garage door opener, newly pa ... Read More
• Listing courtesy of: ANDERSON DAVIS REAL ESTATE INC

MLS# N6142833 - Status: Active View Property Details Add to Favorites View Map

• 2447 DAISY DR
• Price: $265,000
• Zip Code: 34289
• 1363 Square Feet
• Subdivision: CYPRESS FALLS PH 1C
• Bedrooms: 2 Baths: 2
• Welcome to this beautifully maintained Everglade floor plan villa located within the highly sought-after community of Cypress Falls at the Woodlands in North Port. Offering two bedrooms, two bathrooms, and a spacious two-car garage, this light-filled ... Read More
• Listing courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE