Sarasota Homes with Trail(s) Amenities

Sarasota Homes with Trail(s) Amenities

Welcome to Sarasota County, Florida, a vibrant gem nestled on the Gulf Coast that perfectly blends natural beauty with urban sophistication. Known for its stunning beaches, rich cultural scene, and lush landscapes, Sarasota is a paradise for those seeking a serene lifestyle without sacrificing modern conveniences. With its warm climate, diverse communities, and an array of recreational opportunities, Sarasota County is an ideal destination for families, retirees, and everyone in between.

One of the standout features of Sarasota is its exceptional homes with trail amenities. Imagine stepping out of your front door and onto a picturesque trail, perfect for morning jogs, evening strolls, or leisurely bike rides. These homes are designed for those who appreciate an active lifestyle and the great outdoors, offering direct access to a network of scenic pathways that wind through the county’s parks and nature reserves. Whether you’re exploring the breathtaking Myakka River State Park or enjoying the coastal views along the Legacy Trail, the opportunities for adventure are endless.

Sarasota is also home to a vibrant arts scene, with galleries, theaters, and music venues that showcase local talent and international acts alike. Dining options range from casual beachside eateries to upscale restaurants, ensuring that every culinary craving is satisfied. With its blend of natural beauty, cultural richness, and homes that embrace an active lifestyle, Sarasota County is not just a place to live—it's a place to thrive. Come discover your dream home in this enchanting coastal community!

Newest Sarasota Homes with Trail(s) Amenities

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 bathroom 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

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

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

Under Construction. Light, bright, and inviting, the Crystal Sand 2 paired villa offers easy, elegant living with a relaxed coastal feel. The open-concept great room and kitchen create a welcoming space for everyday living and entertaining, with pocket sliding glass doors opening to the covered lanai for seamless indoor-outdoor enjoyment. The primary suite features two closets, including a walk-in, while the primary bath offers dual vanities, a walk-in shower, and private water closet. An ideal retreat for a small family, seasonal getaway, or second home.

2345 Blue Mahoe Lane, Sarasota

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

Welcome to Windward at Lakewood Ranch, where modern design meets resort-style living. Built in 2024 by Neal Communities, this highly sought-after one-story Dream floorplan offers 3 bedrooms, 2 baths, a separate den, extended 2-car garage, and an impressive collection of builder and post-closing upgrades. The open-concept design centers around a beautifully appointed kitchen featuring Café appliances, marble backsplash, upgraded cabinetry with soft-close doors, pot drawers, taller upper cabinets, upgraded sink, pantry shelving, and a large center island overlooking the dining area and great room. Sliding glass doors extend the living space to an expanded lanai with a gas hookup for a future outdoor kitchen and a fenced backyard enhanced with upgraded landscaping, trees, rock beds, and smart-controlled landscape lighting. The private primary suite features two closets, dual vanities with Crate & Barrel mirrors, upgraded tile, walk-in shower with rain shower head, and built-in speakers. Two additional bedrooms, a full bath, den with glass doors, and laundry room complete the thoughtfully designed interior. Notable upgrades include hurricane-impact windows and doors, LVP flooring, crown molding, plantation shutters, custom Roman shades, designer lighting from Serena & Lily, Pottery Barn, and Crate & Barrel, five ceiling fans, dimmers throughout, LG washer and dryer, Culligan whole-home water filtration with reverse osmosis, HVAC UV light, whole-home surge protection, Guardian alarm system, built-in speakers, upgraded irrigation controls, additional recessed lighting, tall interior doors, and garage keypad access. Windward is one of Lakewood Ranch's premier gated communities, offering a resort-style pool, clubhouse, fitness center, pickleball and tennis courts, dog park, playground, walking trails, and numerous community parks. Ideally located near Waterside Place, University Town Center, downtown Sarasota, Gulf beaches, and SRQ Airport, this move-in-ready home combines the ease of newer construction with extensive upgrades already completed.

2545 Star Apple Way, Sarasota

3 Beds ⋅ 3 Baths ⋅ Windward At Lakewood Ranch Phase 2 SubDv. ⋅ 34240 Zip Code

Under Construction. Discover the Meadow Brook in Windward by Neal Communities, where style, comfort, and functionality come together. This spacious home offers 3 bedrooms, a den in place of a dining room, 2 full baths, a powder bath, and a 3-car garage. Impact-resistant windows and doors provide added peace of mind, while the well-appointed kitchen features a large island, corner walk-in pantry, and café area. The great room and primary suite showcase recessed ceilings for added architectural appeal. The primary suite also includes dual walk-in closets and a bath with a large walk-in shower and private water closet. Tile flooring throughout completes this thoughtfully designed home.

2460 Starapple Way, Sarasota

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