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 ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

Welcome to your fully furnished, TURNKEY water view condo. Simply move-in and take in the tranquil Little Sarasota Bay and marvel at the dolphins, manatees, birds, and other wildlife. This remodeled 2 bed/2 bath condo features soaring cathedral ceilings, clerestory windows, generous open floor plan and luxury vinyl flooring throughout. This bright and peaceful second-floor unit is centrally located within the 75-acre, botanic garden-like setting of Pelican Cove. Across the way is the private picturesque 87-boat slip harbor. Boat and kayak to Midnight Pass and have direct access to the gulf. Residents gain entry to the unique blend of natural habitats, miles of scenic trails, a fitness room, multiple heated pools and hot tub. There are six new pickle-ball courts and resurfaced tennis courts with active clubs for play. Many more recreational and cultural events are hosted year around. Robust live music, art and culture, and educational seminars are abundant in season. The community is also conveniently located with shopping and restaurants nearby. Siesta Key and downtown Sarasota are in very close proximity as well.

1519 Pelican Point Drive Unit 288, Sarasota

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

Wonderfully connected to nature! Be surrounded by mesmerizing tropical views and absolute calm in The Highlands, the crown jewel of The Meadows - a park-like oasis in a phenomenal location. Canopied streets, a paver driveway and gated courtyard welcome you to this spotless maintenance-free villa. Inside, you will love the natural light, ideal split-plan with high ceilings, coastal wood-look tile floors, and walls of sliders overlooking majestic oaks, native palms and a glimpse of the golf course in the distance. The setting feels private, tranquil and wonderfully connected to nature. The spacious kitchen features a breakfast nook, grilling patio and a high opening to admire the view. All just half a block to the heated community pool, near all the fun The Meadows has to offer and a 5-minute ride to 90+ restaurants. Set on 1,600 lush acres just 15 minutes from Downtown Sarasota, The Meadows combines resort living with the beauty of untouched nature. Enjoy 14 miles of scenic trails, an active social calendar, new fitness center, Junior Olympic pool, 10 pickleball courts, two 18-hole golf courses, and 15 Har-Tru tennis courts. Ideally located 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. Features a 2023 Trane A/C with 10-year transferable warranty, 2023 water heater, 2009 re-plumbing, 2007 tile roof which is the condo’s responsibility, fully-funded condo association, and above flood plain in zone X

3477 Hadfield Greene Unit 2, Sarasota

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

2 Beds ⋅ 3 Baths ⋅ 1000 Boulevard Of The Arts SubDv. ⋅ 34236 Zip Code

Virtually Staged. Pre-Construction. To be built. Residence 2007 presents elevated harbor views, overlooking Quay Harbor, the Ringling Bridge and coastal horizons beyond. As part of the Harbor residence collection, this home captures the energy of the marina and the dramatic light of Sarasota sunsets. The interior features a contemporary open layout with floor to-ceiling glass, a refined kitchen with European cabinetry and premium appliances, and a private terrace oriented toward the harbor. The primary suite offers a spa-like bath and walk-in closet, while an additional bedroom and a den provide flexible living options. Within 1000 Boulevard of the Arts, residents enjoy a vibrant waterfront lifestyle with access to resort-style amenities, concierge services, and immediate proximity to dining, arts and marina experiences.

1000 Boulevard Of The Arts Unit 2007, Sarasota

3 Beds ⋅ 2 Baths ⋅ Venetian Golf & River Club SubDv. ⋅ 34275 Zip Code

Imagine ending each day on your private screened lanai, watching the sun set over the lake and fountain. This spacious second-floor carriage home in the Venetian Golf & River Club offers more than 2,300 square feet of beautifully designed living space, with the convenience of a private elevator and an attached side-entry two-car garage. The light-filled open floor plan brings together the great room, dining area and kitchen, creating an inviting setting for both quiet evenings and entertaining. The kitchen features granite countertops, 42-inch wood cabinetry with soft-close doors and pullouts, under-cabinet lighting, a walk-in pantry, breakfast bar and casual dining area. The private primary suite enjoys tranquil water views, lanai access, a walk-in closet with built-in organization and a generous walk-in shower. Two additional bedrooms, a full guest bath and a separate den provide flexibility for visiting family, a home office or hobbies. Crown molding, plantation shutters, engineered hardwood and tile flooring, high ceilings, storm-rated windows and sliding glass doors add to the home’s comfort and appeal. An interior laundry room with cabinetry and a utility sink completes the thoughtful layout. Residents of this gated community enjoy resort-style and lap pools, tennis, pickleball, a fitness center, clubhouse, tiki bar, nature trails and a lively calendar of social activities. All of this is conveniently located near I-75, Sarasota Memorial Hospital-Venice, Nokomis Beach and historic downtown Venice.

137 Bella Vista Terrace Unit 33C, Nokomis

2 Beds ⋅ 2 Baths ⋅ Foxwood SubDv. ⋅ 34223 Zip Code

Welcome to this beautifully updated 2-bedroom, 2-bath, 2-care garage condo in the desirable Foxwood community, featuring a newer roof, recently painted exterior, and located in an X flood zone (no Flood Insurance required!). Offered turnkey furnished, this home is truly move-in ready, with furnishings, décor, dishes, linens, towels, and more all included. Inside, you’ll find all-tile flooring with no carpet, hurricane-impact windows, updated lighting and ceiling fans, and attractive blinds and window treatments throughout. The beautifully updated kitchen features KraftMaid white cabinetry with all-wood construction and no particle board, granite countertops, and convenient pull-out cabinet storage. Appliances include a Bosch oven, cooktop, and dishwasher, along with a Frigidaire refrigerator and a beverage refrigerator conveniently located beneath the bar counter. The primary bedroom offers a comfortable and stylish retreat, furnished with a genuine vintage Henry Link bedroom set, complemented by a new, never-used Sealy Posturepedic queen mattress, all new bedding including pillows, a queen cotton percale sheet set, and a quilted bedspread with matching shams. The primary bathroom features the highly desirable dual-sink vanity. The guest bedroom is thoughtfully furnished with a Murphy bed, providing a comfortable space for guests while maintaining flexibility for an office or additional living area. Both bathrooms feature Toto bath fixtures, including a luxuriously deep Toto “Clayton” soaking tub in the guest bathroom—a wonderful place to unwind after a day in the Florida sunshine. Additional features include a large freezer in the garage for added storage and thoughtful updates throughout the home. Everything has been carefully selected to provide a comfortable, polished, and truly turnkey experience. Life at Foxwood offers an abundance of amenities and activities, including a community pool and spa, walking trails, pickleball and tennis courts, and a clubhouse with billiards. The community also offers numerous activities and social events, providing plenty of opportunities to stay active, meet neighbors, and enjoy the Florida lifestyle. With its newer roof, X flood zone, hurricane-impact windows, updated kitchen and baths, quality finishes, extensive furnishings, close proximity to the beautiful gulf beaches and exceptional community amenities, this Foxwood condo is ready to be enjoyed from the moment you arrive. Just bring your suitcase!

306 Persimmon Street Unit 208, Englewood

2 Beds ⋅ 2 Baths ⋅ Grand Palm SubDv. ⋅ 34293 Zip Code

THIS is what Florida is all about, a true show stopper! PANORAMIC SCREEN VIEWS - Welcome to one of the most upgraded Tidewater Villas available in Grand Palm, where maintenance-free living, exceptional lake views, and thoughtful improvements come together in one of Venice's most sought-after resort communities. Beautifully maintained and meticulously updated, this villa offers the peace of mind buyers are looking for with a WHOLE-HOUSE GENERAC GENERATOR and ANDERSEN IMPACT-RESISTANT WINDOWS, while elegant interior upgrades and premium outdoor enhancements make this home truly move-in ready. Inside, the open-concept Tidewater floor plan lives like a single-family home while offering the convenience of maintenance-free villa living. High ceilings, crown molding, abundant natural light, NEW LVP FLOORING, and NEW BEDROOM CARPETING create an inviting atmosphere throughout the spacious great room, dining area, and kitchen. The beautifully updated kitchen features solid wood cabinetry, BRAND-NEW QUARTZ COUNTERTOPS, ALL NEW APPLIANCES, natural gas cooking, and a large center island with additional seating, creating the perfect space for entertaining or everyday living. A private office/den at the front of the home provides the ideal work-from-home space, while the split-bedroom layout offers outstanding privacy for owners and guests. The spacious primary suite features two walk-in closets, dual vanities with NEW SINKS AND FAUCETS, a walk-in shower, NEW PRIMARY TOILET, and a private water closet. The guest bathroom has also been refreshed with NEW SINKS AND FAUCETS, while the NEW HOT WATER HEATER adds another valuable system upgrade. The extended screened lanai is the true centerpiece of the home, overlooking one of the community's most peaceful lake settings. Pocket sliding glass doors create seamless indoor-outdoor living, while Storm Smart pull-down screens, an electronic retractable awning, and a professionally installed paver grilling patio provide the perfect setting for entertaining or enjoying spectacular Florida sunsets. The FRESHLY PAINTED LANAI, NEW REAR SCREEN, upgraded landscaping, paver edging, French drain system, and LeafGuard gutters complete this exceptional outdoor retreat. Even the garage has been thoughtfully upgraded with premium cabinetry, a PROFESSIONALLY FINISHED EPOXY FLOOR, additional lighting, and outstanding storage, creating a space equally suited for vehicles, hobbies, or workshop projects. Villa owners enjoy their own private neighborhood pool, spa, grilling area, and shaded lounge spaces, while Grand Palm offers one of Venice's premier resort lifestyles with three heated pools, a splash park, fitness center, tennis and pickleball courts, bocce, dog parks, miles of walking and biking trails, Exploration Park, a full-time lifestyle director, and Grand Palm's signature private island with fishing piers and scenic nature trails. Perfectly located in Venice, Grand Palm provides convenient access to Downtown Wellen Park, CoolToday Park, Venice Island, world-renowned Gulf beaches, shopping, dining, medical facilities, and I-75. With extensive upgrades, breathtaking lake views, exceptional outdoor living, and one of Grand Palm's most desirable villa floor plans, this home presents a rare opportunity to enjoy resort-style living with the comfort, quality, and peace of mind that today's buyers are searching for. Schedule your private showing today.

21620 Avon Park Court, Venice

2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34238 Zip Code

Welcome to resort-style living in this maintenance-free, immaculate and very well cared for home, turn-key furnished and ready for you! This 2 bedroom, 2 bath with DEN and EXTRA Florida room home has one of the largest lots on Forest Hills Cir. Not to mention one of the largest driveways for room to entertain guests, and is literally across the street from the community heated pool to socialize with neighbors or join a water aerobics class! Soaring ceilings, crown molding, plantation shutters and an abundance of natural light add to this impressive villa. The kitchen features beautiful granite counters, eat on bar, lots of cabinetry for storage, closet pantry, and a roomy dinette overlooking the front screened in lanai. Both bathrooms have updated walk-in showers and granite top, raised vanities. Den/office has a built in desk/shelving, and 2 tall windows for lots of sunshine. The bonus Florida room gives you the option to enjoy the private back yard and private preserve from the comfort of air conditioning or relax and grill on your screened in lanai and take in all the nature and your own tropical paradise! The 2 car garage has a workbench, utility sink, shelving/storage and plenty of room for all your beach toys and golf gear. New tile roof in 2021. Stoneybrook Golf and Country Club is in sought after Palmer Ranch, is gated and boasts a vibrant and active community. They just completed their new 18 hole golf course designed by Arthur Hills and Kipp Schulties and is said to be one of the best on the West Coast! Other top-notch amenities include Lighted Har-Tru tennis/pickleball courts, pro-shop, well-equipped fitness center, bocce court, putting greens, driving range, fitness studio, sharing library, additional heated pool/spa, full service restaurant/bar, meeting rooms, catering facility, outdoor dining patio, walking/biking trails, fishing, planned activities like yoga, mahjong, line dancing, and so much more! Stoneybrook Golf and Country Club is a prime location close to the Legacy Trail, beaches, Costco, Lowes, restaurants, a newly planned Whole Foods, Trader Joe's and all Sarasota and Venice has to enjoy! WELCOME HOME to an easy, carefree Sarasota lifestyle!

9413 Forest Hills Circle, Sarasota

2 Beds ⋅ 2 Baths ⋅ Sarasota National SubDv. ⋅ 34293 Zip Code

Experience resort-style living at its finest in this meticulously maintained home located within the sought-after gated community of Sarasota National. Enjoy this furnished home, which showcases an impressive list of high-end enhancements, featuring an extended lanai complete with a private hot tub and automated electric storm shades. The seller has modified this home to remove the carpeting. Inside, enjoy the elegance of new luxury vinyl and tile flooring throughout, stylish plantation shutters, and a hurricane-rated front door insert. Enjoy a stunning kitchen featuring upgraded quartz countertops and an improved appliance package for next-level cooking enjoyment. Comfort and peace of mind are fully prioritized with a brand-new AC system, upgraded garage attic insulation, a customized primary closet system, and comprehensive storm protection including side accordion shutters, front roll-down shutters, and motorized lanai shades. Take advantage of the spare room for reading or office use. Beyond your front door, Sarasota National offers an unmatched suite of amenities—including an on-site 18-hole championship golf course currently undergoing a stunning full renovation, a massive resort pool with swimming lanes and zero-entry, a vibrant tiki bar, and the top-rated Palm Club restaurant. Stay active with Har-Tru tennis, pickleball, bocce, and a modern fitness center, or unwind with a community library, a coffee lounge, and a dedicated dog park. This is more than a home; it’s an active, upscale Florida lifestyle waiting for you. This home does not include a golf membership, but owners can pay and play. Remember, lawn care, landscaping, and irrigation are included with this property. This home is part of the Wellen Park neighborhood with the Cool Today Park stadium, many restaurants, shopping, and beaches close by.

10393 Crooked Creek Drive, Venice

2 Beds ⋅ 2 Baths ⋅ Wedgewood Lake SubDv. ⋅ 34235 Zip Code

WELCOME TO EASY FLORIDA LIVING IN THE MEADOWS! This inviting FIRST-FLOOR, 2-bedroom, 2-bath condominium is located in Wedgewood Lake, a charming enclave within the highly desirable Meadows community of Sarasota. Featuring UPDATED PORCELAIN TILE FLOORING THROUGHOUT, a split-bedroom floor plan, front and rear outdoor living spaces, and views of the beautifully landscaped courtyard and community pool, this light-filled residence is ideal for year-round living or a seasonal Florida retreat. Recent improvements include an A/C IN 2023, WASHER AND DRYER IN 2025, AND WATER HEATER IN 2025. A covered front entry welcomes you home, framed by mature landscaping and colorful tropical plantings. Just outside the kitchen, a private covered patio provides a charming spot for morning coffee, reading, or relaxing in the Florida sunshine. Inside, abundant natural light enhances the spacious living and dining area, creating a comfortable setting for everyday living and entertaining. Large sliding glass doors open to the screened rear lanai, where peaceful courtyard and pool views provide an attractive backdrop. The updated kitchen features sleek cabinetry with abundant storage, generous counter space, a decorative tile backsplash, stainless-steel appliances, recessed lighting, and a breakfast bar overlooking the living and dining areas. Sliding glass doors at the opposite end of the kitchen provide direct access to the front patio, offering convenient indoor-outdoor flow. The split-bedroom design provides privacy for owners and guests. The spacious primary suite is filled with natural light and features private sliding-door access to the rear lanai, a generous walk-in closet, vanity/dressing area with additional storage, and a private bath with a walk-in shower. On the opposite side of the condo, the nice-sized guest bedroom features a built-in closet and convenient access to the second full bathroom. A dedicated laundry room is located just off the guest bath hallway and includes the washer and dryer. Additional conveniences include assigned and guest parking and easy access to the Wedgewood Lake community pool. This pet-friendly community is surrounded by the mature landscaping and natural beauty for which The Meadows is known, with miles of walking and biking trails to enjoy. Optional membership opportunities at The Meadows Country Club additional golf, tennis, pickleball, fitness, dining, and recreational amenities. Ideally situated near downtown Sarasota, UTC shopping and dining, St. Armands Circle, cultural attractions, and Gulf Coast beaches, this first-floor condo offers a wonderful combination of comfortable living, inviting outdoor spaces, community amenities, and a desirable Sarasota location.

5209 Wedgewood Lane Unit 17, Sarasota

3 Beds ⋅ 3 Baths ⋅ Nokomis Sub SubDv. ⋅ 34275 Zip Code

Welcome to 5901 Biscotti Street in Vinterra Townhomes, a beautifully maintained gated community in the heart of Nokomis! This thoughtfully designed townhome offers a smart, functional floor plan with modern finishes and low-maintenance Florida living. The bright white kitchen is a standout, featuring quartz countertops, stainless steel appliances, and plenty of cabinetry, creating a clean, timeless space that flows effortlessly into the main living and dining areas. Step outside to your private rear patio—perfect for morning coffee, outdoor dining or simply relaxing in the Florida sunshine. The attached one-car garage features an epoxy-coated floor and offers convenient parking plus additional storage. Vinterra is a gated Sarasota County community with a resort-style pool and cabanas, dog park, butterfly garden, and it's ideally located with easy access to the Legacy Trail, making it simple to enjoy miles of walking and biking. Spend your weekends at beautiful Nokomis Beach and Casey Key, explore nearby parks, or enjoy the shopping, restaurants, and entertainment of both Venice and Sarasota. With its convenient location, modern finishes, and smart floor plan, 5901 Biscotti Street is an ideal full-time residence, seasonal retreat, or investment opportunity. Some furnishings are available on a separate purchase. Come see why this Nokomis location makes it easy to enjoy the best of the Florida lifestyle!

5901 Biscotti Street, Nokomis

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