Sarasota Homes with Trail(s) Amenities

Sarasota Homes with Trail(s) Amenities

Welcome to Sarasota County, Florida, a sun-kissed paradise known for its stunning coastal beauty, vibrant arts scene, and a lifestyle that perfectly blends relaxation and recreation. Nestled along the Gulf of Mexico, Sarasota boasts pristine beaches, lush parks, and an array of outdoor activities that cater to nature enthusiasts and adventure seekers alike.

One of the standout features of Sarasota County is its diverse selection of homes, many of which come with exceptional trail amenities. Imagine stepping out of your front door and onto a scenic pathway that winds through picturesque landscapes, allowing you to explore the natural beauty of the area. Whether you enjoy leisurely strolls, invigorating jogs, or biking adventures, the trail systems in Sarasota provide the perfect backdrop for an active lifestyle.

Sarasota is also renowned for its rich cultural offerings, including the renowned Ringling Museum of Art, the vibrant local theater scene, and a variety of galleries showcasing both local and international artists. The community is infused with a sense of camaraderie, making it easy to connect with neighbors and participate in local events.

With year-round sunshine, a temperate climate, and an abundance of recreational opportunities, Sarasota County is more than just a place to live; it's a lifestyle. Explore homes with trail amenities that invite you to embrace the outdoors and experience the charm of this remarkable region. Discover your dream home in Sarasota County today, where every day feels like a vacation!

Newest Sarasota Homes with Trail(s) Amenities

2 Beds ⋅ 2 Baths ⋅ Arbor Oaks At The Woodlands SubDv. ⋅ 34289 Zip Code

4782 W Blue Star Court, North Port

3 Beds ⋅ 3 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code

Experience unrivaled luxury, views and value at Penshurst Park! Spacious elegance, exquisite finishes and breathtaking pond and golf views come together in The Meadows’ premier maintenance-free enclave, a park-like oasis in a phenomenal location. Ideally positioned on the developer’s choice lot, this exceptional residence welcomes you along a picturesque, tree-canopied street to a paver driveway and private courtyard. Inside, soaring ceilings, abundant natural light and expansive living spaces create an immediate sense of being home. A meticulous $300K top-to-bottom renovation blends timeless sophistication with modern comfort. The showstopping chef’s kitchen features solid-wood soft-close shaker cabinetry, gleaming Laguna quartz countertops, a striking hammered-copper sink, premium KitchenAid stainless-steel appliances and a dazzling stone-and-glass mosaic backsplash. Retreat to the sumptuous primary suite with a custom walk-in closet and spa-inspired bath with dual vanities, a luxurious Jacuzzi tub and a frameless walk-in shower clad in marble. Beyond the fabulous interior, mesmerizing lake and golf views steal the show, accompanied by spectacular sunsets and a daily parade of birds. All this beauty and tranquility, yet just five minutes from 93 restaurants and all the fun The Meadows has to offer. Set on 1,600 park-like acres, The Meadows is a resort-style community just 15 minutes from downtown. Enjoy 14 miles of scenic trails and, for a low fee, access to a fitness center, Junior Olympic pool, pickleball, golf, and Har-Tru tennis. You’ll be minutes to award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, Mote SEA Aquarium, the 31-mile Legacy (bike) Trail, the future Sarasota Orchestra, and University Town Center: a favorite shopping, dining and entertainment destination. CANNOT BE REPRODUCED AT THIS PRICE. 2023 water heater, 20212 hurricane garage door, 2011 A/C, 2006 tile roof (HOA’s responsibility), above flood plain in zone X

4060 Penshurst Park, Sarasota

4 Beds ⋅ 2 Baths ⋅ Avanti At Waterside SubDv. ⋅ 34240 Zip Code

Welcome to Avanti at Waterside, where easy living and convenient location meet at this stunning residence at 6524 Silverstar Drive. Just a mile from Waterside Place which is overflowing with year-round events, Farmer’s Market, shopping and dining; providing an ultimate location. Showcasing picturesque views of Blue Heron Lake, every day is a Florida paradise. Brimming with smart and stylish upgrades, this home was originally built in 2023 and completely reimagined design-wise in 2025 to exude a comfortable, upscale style that is far above and beyond the standard builder grade finishes that you will find in other homes. Plus, IMPACT windows and doors provide added peace of mind. You’re welcomed home amidst manicured landscaping with grounds maintenance included in your HOA dues, to a charming front entry along the paver drive and walkway. The long foyer provides an elegant entry, as well as functionality with a convenient coat closet. The open floor plan is ideal for modern living with a spacious great room, formal dining space, and chef’s kitchen all with luxury vinyl flooring and upgraded interior paint in Swiss Coffee, plus impact sliding glass doors so your entertaining can spill out onto the lanai. The great room is adorned with custom wall molding, designer chandelier, and in-ceiling speakers. The formal dining space showcases lake views framed by window treatments around the sliders, and custom wall molding. The executive kitchen features refinished cabinetry in Galapagos Green, upgraded designer hardware in brushed gold, picket subway tile backsplash, quartz counters, single basin sink with upgraded faucet, triple designer pendant lights above the island and stainless-steel appliance suite. The upgraded design details continue throughout the whole residence with all the door handles and hinges upgraded with designer hardware for a refined and cohesive style. Your primary suite is perfectly poised to take-in sparkling lake views from sunrise to sunset; and is enhanced by custom limewashed walls, wall moldings to set off the headboard space, modern ceiling fan, custom window treatments, and an expansive walk-in closet for all of your wardrobe needs. The primary bath has also been meticulously upgraded with refinished cabinetry in Birchwood, quartz counters, new cabinetry hardware, new sink faucets, and a new seamless glass shower door installed August 2026. The inviting space also includes dual sinks, stone counters, framed vanity mirror, designer light fixture, and built-in shower bench. Guests will find comfort in three guest bedrooms outfitted with plush carpeting and spacious closets. One of the bedrooms features elegant upgrades with designer wallpaper, custom wainscotting, and a designer chandelier light fixture. The full guest bathroom has the same sophisticated design appeal with a long vanity, upgraded cabinetry hardware, new faucet, quartz counters, framed mirror, designer vanity light, painted stripe detailing, and shower with tub combination. Even the laundry room exudes style with an accent wall, convenient utility tub, and Whirlpool washer and dryer. The garage is expanded for great storage and car space. And just a 5-minute drive from Waterside Place, you’ll have shopping, dining, events, playground, volleyball courts, walking trails, and more all at your fingertips. Lakewood Ranch is the top multi-generational community in the country for 9 years in a row with plentiful shopping, dining, parks and nearby beaches.

6524 Silverstar Drive, Sarasota

3 Beds ⋅ 3 Baths ⋅ Arbor Oaks At The Woodlands SubDv. ⋅ 34289 Zip Code

1626 Pepper Grass Drive Sw, North Port

3 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code

Virtually Staged. Enchanting opportunity in The Meadows, a park-like oasis in a phenomenal location! Cocooned in a lush Old Florida preserve, this very private pool home offers the ease of maintenance-free living and the seclusion of a remote forest retreat yet remains remarkably close to everything Sarasota has to offer. Inside, high ceilings and tall walls of glass fill the home with natural light and adorn it with serene, lush preserve views from nearly every room. The ideal great-room floor plan offers comfortable living with no wasted space. The open kitchen features white cabinetry, Silver Pearl granite countertops and stainless appliances. A split-bedroom design provides privacy, with the spacious primary suite on one side and two guest bedrooms on the other. Surrounded by mature trees and tropical vegetation, the home feels like a hidden treehouse in the forest. All this tranquility, yet just five minutes from 93 restaurants and all the fun The Meadows has to offer. Set on 1,600 park-like acres, The Meadows is a resort-style community just 15 minutes from downtown. Enjoy 14 miles of scenic trails and, for a low fee, access to a fitness center, Junior Olympic pool, pickleball, golf and Har-Tru tennis. You’ll be minutes to award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, Mote SEA Aquarium, the 31-mile Legacy (bike) Trail, the future Sarasota Orchestra and University Town Center: a favorite shopping, dining and entertainment destination. 2025 water heater, 2023 A/C, 2010 tile roof, maintenance-free, pool needs new surface ($10K), above flood plain in zone X.

2929 Sandringham Place, Sarasota

3 Beds ⋅ 3 Baths ⋅ Gran Paradiso SubDv. ⋅ 34293 Zip Code

This 2016 Custom-Built Home sits on a "Premium" lot with a Preserve View and is located in the "Resort Style" Community of "Gran Paradiso" at Wellen Park, Venice, FL! The "Napoli" floorplan design by Sam Rodgers, offers 2,808 sq. ft. of "SPACIOUS" living space, 3-bedroom 3-bathroom with a bonus room and 3-car garage. Premium Upgrades and Quality finishes with architectural details inside and out. Extra-wide plantation shutters and upgraded light fixtures add to the elegance of this home. A true Chef's kitchen with Quartz counter-tops, stainless steel appliances, built-in wall oven and microwave, closet pantry, abundant cabinet storage, 42" cabinets, soft close drawers, under cabinet lights, tile back splash, cooktop, and "Natural Quartzite" kitchen island for entertaining! You will love the oversized owner's suite that offers views of the pool and private preserve and features an en-suite bath with a custom closet, dual-sinks, private water closet, soaking tub, and frameless glass walk-in tile shower. Step outside to your Tropical Oasis lounge area and undercover space that overlooks the serene preserve while featuring an extended lanai with a clear view-panoramic screen, Heated "SALTWATER POOL," and outdoor kitchen. LUSH LANDSCAPING has been added all around the outside of the home to provide EXTRA PRIVACY! Gran Paradiso offers a lifestyle with amenities that include: an activities director, resort style pool, Tuscan-Inspired clubhouse, fitness center, billards room, large fitness facility, pickleball, tennis & basketball courts, walking paths, and so much more! Only minutes from the new "Downtown Wellen Park" with restaurants, shopping AND "Cool Today Park" the home of the Atlanta Braves spring training facility. Venice's beautiful beaches, historic downtown, shopping, and restaurants are only a few miles away! Sit back, relax, and enjoy the peace & tranquility while enjoying the Florida sunshine! Live the Florida lifestyle & make this your home!

13440 Campanile Court, Venice

3 Beds ⋅ 3 Baths ⋅ Skye Ranch Neighborhood Four North SubDv. ⋅ 34241 Zip Code

Where luxury meets lifestyle, discover an extraordinary opportunity to own one of the finest residences in Esplanade at Skye Ranch. Perfectly positioned on a premium preserve homesite within this coveted gated community, this exceptional Taylor Morrison Pallazio model offers over 3,000 square feet of thoughtfully designed living space with 3 bedrooms, 3 bathrooms, a private office/den, and an extended two-car garage with custom built in cabinetry. Enhanced with an extensive collection of designer upgrades and custom finishes, this home offers a level of quality that surpasses new construction. Inside, soaring tray and vaulted ceilings, elegant crown molding, designer lighting, and abundant natural light create a warm yet inviting atmosphere. The open-concept design flows effortlessly from the spacious living area to the chef-inspired kitchen featuring custom solid wood cabinetry, quartz countertops, premium stainless-steel appliances, expansive prep space, an oversized center island, and a stylish dry bar. Expansive sliding glass doors seamlessly connect the kitchen and living room to the covered lanai, creating the ultimate indoor-outdoor lifestyle. The owner’s suite is a private retreat with peaceful preserve views, a spa-inspired bath with dual vanities and an oversized walk-in shower, plus a custom Closet. Two guest suites add privacy and comfort, while the dedicated office provides the perfect workspace or quiet retreat. Additional upgrades include custom Closets throughout, designer window treatments, refined bathroom finishes, premium cabinetry, architectural details, and upgraded lighting throughout. The expansive covered lanai is a true extension of the home, overlooking a serene nature preserve with no rear neighbors—perfect for morning coffee, evening cocktails, or simply enjoying Florida’s natural beauty. Residents enjoy exclusive access to Esplanade’s resort-style amenities, including a pool and spa, Bahama Bar, pickleball and bocce courts, fire pit gathering areas, dog park, state-of-the-art fitness center, wellness programs, and a full-time Lifestyle Director. Owners also enjoy full access to the Skye Ranch HUB, featuring multiple pools, a fitness center, indoor gymnasium, basketball, tennis and pickleball courts, volleyball, sports fields, playgrounds, scenic walking and biking trails, dog parks, and year-round recreation. Ideally located near top-rated schools, including the new Skye Ranch K-8 STEM Academy, premier shopping, dining, healthcare, and just minutes from the world-famous sands of Siesta Key Beach. Why wait to build? One of the finest Pallazio homes in Esplanade at Skye Ranch, this exceptional residence is move-in ready with every luxury upgrade already completed. Schedule your private showing today and experience the difference. Luxury lives here.

10342 Morning Mist Lane, Sarasota

3 Beds ⋅ 3 Baths ⋅ Lakewood Ranch SubDv. ⋅ 34240 Zip Code

Better than new and impossible to duplicate at this price. Situated on a premium corner lot in the highly sought-after Windward at Waterside, this exceptional residence combines luxury finishes, over $100,000 in post-closing upgrades, and one of the most private outdoor living spaces in the community. From the moment you step outside, you'll understand what makes this home special. The expansive screened lanai was designed for year-round Florida living and features a sparkling saltwater pool, spa, fully equipped outdoor kitchen, and generous covered entertaining space. Extensive professionally designed landscaping with custom lighting creates an incredible sense of privacy while preserving peaceful water views—a rare combination that's difficult to find. Inside, the home continues to impress with thoughtful, high-end improvements throughout. Custom built-in shelving in the pantry, laundry room, and primary closet, pull-out kitchen shelving, plantation shutters, automated WiFi-controlled draperies, designer lighting, fireplace with custom media wall, framed mirrors, whole-house water treatment with reverse osmosis, whole-house surge protection, UV air purification, and an extended HVAC warranty are just a few of the upgrades that elevate this home well beyond builder standards. Ceiling fans, upgraded electrical, and countless finishing touches complete the package. Originally built with premium features including impact glass, GE Café appliances, quartz countertops, pocketing sliding glass doors, a three-car garage, and smart home technology, this home has since been transformed into a truly exceptional residence. If you've been considering new construction but don't want the time, expense, and hassle of adding a pool, landscaping, window treatments, storage systems, and outdoor living after closing, 2469 Paradise Plum delivers it all today. Simply move in and enjoy one of Waterside's finest homes.

2469 Paradise Plum Drive, Sarasota

3 Beds ⋅ 4 Baths ⋅ Shellstone At Waterside SubDv. ⋅ 34240 Zip Code

Some Photos Digitally Staged. Just completed and never occupied, this exceptional CUSTOM Camber plan offers a rare opportunity to enjoy new construction without the wait. Perfectly positioned on a premium 200-acre lakefront homesite with breathtaking long-water views, every detail of this thoughtfully designed home was created to maximize both stunning views and everyday livability. A double door entry welcomes you to an expanded great room & dining room with soaring ceilings, floor to ceiling windows and expansive 22-foot sliding glass doors to frame spectacular water views from the moment you arrive. At the heart of the home, the chef's kitchen is a beautifully appointed with abundant cabinetry, a walk-in pantry with custom built-ins, and a Butler's pantry complete with wine refrigerator. Unlike the standard Camber plan, this custom-designed home provides a private en-suite bath for every bedroom, creating exceptional comfort for family and guests alike. The spacious flex room, featuring a closet with custom built-ins is located adjacent to a full pool bath and offers endless possibilities as a home office, media room and additional guest space. The owner's retreat is a peaceful sanctuary featuring a custom designed walk in closet with mirrored doors and generous storage and a spa-inspired bath with dual vanities and an oversized walk-in shower. Designed with convenience in mind, the mud room offers custom built in cabinetry and benches while providing seamless access to the laundry room, butler's pantry and kitchen. Step outside to an expansive covered lanai featuring a custom outdoor kitchen, elegant salt pool and spa with sun shelf, and stunning panoramic lake views that create the perfect backdrop for entertaining or relaxing. Additional upgrades include custom closets throughout, impact windows and doors, dual HVAC systems, floor to ceiling glass pocket door off flex room to lanai, and a finished 3-car garage. Shellstone residents enjoy numerous community sponsored events as well as the use to two amenity centers that include a resort style pool, spa & cabanas, fitness center, club house, tennis, pickleball, basket ball, tot lot and more. Conveniently located near the outstanding restaurants and shops at Waterside Place.

812 Blue Shell Loop, Sarasota

2 Beds ⋅ 2 Baths ⋅ Windward At Lakewood Ranch Phase 2 SubDv. ⋅ 34240 Zip Code

This move-in ready villa offers 1,530 square feet of thoughtfully designed living space with wood-look tile flooring throughout. The open great room features a recessed ceiling and pocket sliding glass doors that extend the living area onto the spacious lanai, complete with a gas stub for a future outdoor grill and peaceful preserve views. The well-appointed kitchen showcases quartz countertops, brushed gold hardware, soft-close cabinetry, and a gas slide-in range. Impact-resistant windows provide added peace of mind while complementing the low-maintenance lifestyle of villa ownership. Residents enjoy an impressive collection of community amenities, including a clubhouse with a full-time activities coordinator, two resort-style swimming pools, dog parks, a tot lot, and more than five miles of scenic walking trails.

2373 Blue Mahoe Lane, Sarasota

4 Beds ⋅ 3 Baths ⋅ Arbor Oaks At The Woodlands SubDv. ⋅ 34289 Zip Code

Welcome to the 2025 community of the year. Come see why Arbor Oaks won this honor. The community has pickle ball, tennis, bocce, swimming pool, and gym.

4415 Lakeside Grove, North Port

3 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code

Soul-nurturing pond views framed by an Old Florida preserve create a serene setting in one of The Meadows desirable enclaves, a park-like oasis in a phenomenal location. Meandering, canopied streets, a paver driveway and gated courtyard welcome you home. Inside, high ceilings, abundant natural light, hardwood floors in the great room and a shimmering Marina glass-mosaic fireplace set the stage, while tranquil pond and preserve views provide a beautiful backdrop to everyday living. The primary suite is a relaxing retreat with a shaker-style dual vanity topped with Bianco Carrara quartz, a glass-enclosed step-in shower and a generous walk-in closet with a custom organizer system. The Florida room may quickly become your favorite spot, ideal for relaxing, entertaining or simply enjoying the peaceful views and daily parade of birds. Truly special! On 1,600 lush acres just 15 minutes from downtown Sarasota, The Meadows offers a resort lifestyle with 14 miles of scenic trails, an active social calendar, and at a reasonable fee, a fitness center, Junior Olympic pool, 10 pickleball courts, two 18-hole golf courses and a top-notch tennis complex. Ideally near award-winning beaches, cultural attractions, Nathan Benderson Park, Mote SEA Aquarium, Whole Foods, Trader Joe’s, the Legacy Trail and The Mall at University Town Center, a world-class destination for shopping, dining and entertainment. A fabulous Florida lifestyle awaits. A 2023 air-conditioning system, 2018 re-plumbing, 2007 tile roof, which is the condominium’s responsibility, and above flood plain in zone X.

3331 Hadfield Greene Unit 49, Sarasota

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