South Sarasota Homes with Trail(s) Amenities

South Sarasota Homes with Trail(s) Amenities

Welcome to South Sarasota, Florida—a vibrant community nestled in the heart of Sarasota County, where the sun shines brightly and the lifestyle is as inviting as the warm Gulf breeze. Known for its picturesque landscapes, South Sarasota offers a perfect blend of suburban charm and coastal allure. Residents enjoy easy access to stunning beaches, lush parks, and a variety of recreational activities, making it an ideal destination for families, retirees, and everyone in between.

One of the standout features of South Sarasota is its array of homes that come with exceptional trail amenities. Imagine stepping out of your door and onto a scenic trail that winds through beautiful natural landscapes, perfect for morning jogs, evening strolls, or leisurely bike rides. These trails not only promote a healthy lifestyle but also foster a sense of community among neighbors who share a love for the outdoors.

The homes in South Sarasota are designed with comfort and convenience in mind, often featuring spacious layouts, modern finishes, and ample outdoor spaces. Whether you’re looking for a cozy single-family home or a luxurious estate, you’ll find options that cater to your unique needs and preferences.

In addition to the natural beauty and trail amenities, South Sarasota boasts a vibrant local culture with an array of dining, shopping, and entertainment options. From charming boutiques to gourmet restaurants, there’s always something new to explore.

Discover your dream home in South Sarasota, where the trails lead to a lifestyle full of adventure, community, and endless sunshine!

Newest South Sarasota Homes with Trail(s) Amenities

$390,000
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
It's easy to enjoy the beauty of coastal waterfront living in Pelican Cove and this 3-bedroom end unit condo is centrally located within the complex. Everything in this condo is exquisitely done and no expense was spared with new flooring, new lighting, updated bathrooms, new kitchen with all new appliances, sink, lighting, counters and backsplash. Enjoy volume ceilings and the open floor plan that this three-bedroom unit provides. Pelican Cove is a magical place with lush landscaping that sits on gorgeous acres overlooking the Little Sarasota Bay. This is what Florida living is all about, stroll to the Pelican Point Observation deck, the bird sanctuary or the through the gardens. This community is a boaters dream with more than 87 boat harbor slips with each slip having water and electric. There are six heated pools to choose from, pickle ball, kayak and canoe launch and storage, gym, 4 lighted tennis courts, shuffleboard, basketball, 5 miles of amazing walking trails and Musical concerts. Pelican University offers classes and clubs for all including woodworking, photography, and clay sculpture, to name a few.

1508 Pelican Cove Road Unit 235, Sarasota
$598,000
3 Beds ⋅ 2 Baths ⋅ Eagles Point At The Landings SubDv. ⋅ 34231 Zip Code
Experience relaxed elegance in Eagles Point at The Landings, where waterfront surroundings, vibrant amenities, and colorful sunsets create a true year-round retreat. This light and inviting second-floor corner residence offers three bedrooms, spacious living areas, all hurricane-rated windows, and an enclosed Florida room with hurricane-rated sliders and western exposure for enjoying beautiful evening skies. The open living and dining areas flow seamlessly together, while the kitchen features a granite-topped island, stainless steel appliances, and an eat-in area. The owners suite opens to the Florida room and includes a fitted walk-in closet, dual-sink vanity, soaking tub, and separate shower. Two guest bedrooms enjoy eastern exposure and morning light. Additional features include a spacious laundry room with utility sink, secure garage parking, private storage, and pet-friendly living up to 25 pounds. Eagles Point residents enjoy a private pool and grilling area, while The Landings offers gated security, a vibrant social atmosphere, Racquet Club membership included in monthlies with Har-Tru tennis, pickleball, fitness, pool and spa, library, community room, kayak storage and launch, and a scenic trail to the Intracoastal fishing pier. Whether full-time or seasonal, Unit 206 offers an exceptional opportunity to enjoy The Landings lifestyle.

5420 Eagles Point Circle Unit 206, Sarasota
$769,000
3 Beds ⋅ 3 Baths ⋅ Eagles Point At The Landings SubDv. ⋅ 34231 Zip Code
Experience penthouse living in Eagles Point at The Landings, where expansive water views, vibrant amenities, and colorful sunsets create a true year-round retreat. This light and inviting top floor 3-bedroom residence offers spacious living areas, an additional foot of ceiling height, and an enclosed Florida room with hurricane-rated sliders and western exposure for enjoying sweeping views and beautiful evening skies. The open living and dining areas flow seamlessly together, while the kitchen features a granite-topped island, stainless steel appliances, and an eat-in area. The owner's suite opens to the Florida room and includes a fitted walk-in closet, dual-sink vanity, soaking tub, and separate shower. Two additional guest bedrooms enjoy eastern exposure and morning light, while the rare additional half bath not found in many other Eagles Point residences adds extra convenience for guests. Additional features include a spacious laundry room with utility sink, private storage, and two assigned parking spaces in the secure garage, a valuable benefit reserved for top-floor residences. Eagles Point residents enjoy a private pool and grilling area, while The Landings offers gated security, a vibrant social atmosphere, Racquet Club membership with Har-Tru tennis, pickleball, fitness, pool and spa, library, community room, kayak storage and launch, and a scenic trail to the Intracoastal fishing pier. Whether full-time or seasonal, Unit 406 offers an exceptional opportunity to enjoy penthouse views and The Landings lifestyle.

5420 Eagles Point Circle Unit 406, Sarasota
$449,000
3 Beds ⋅ 2 Baths ⋅ The Landings SubDv. ⋅ 34231 Zip Code
SIGNIFICANT PRICE IMPROVEMENT - Welcome to one of The Landings' best-kept secrets and now its most compelling value. This Carriage House residence has just been reduced by $50,000, making it the lowest-priced Carriage House currently available in The Landings. Opportunities like this don't last. Tucked inside the intimate Carriage House II community, this 2-bedroom, 2-bath plus spacious den residence delivers the feel of a single-family home wrapped in the ease of maintenance-free living — and it's move-in ready. Inside, tile flooring flows throughout, anchoring a bright, open layout that feels larger than its footprint suggests. The updated kitchen impresses with a modern aesthetic, solid surface counters, and finishes that feel fresh and intentional, not dated. Both bathrooms have been thoughtfully remodeled, featuring solid surface counters and elegant tile enclosures. A wood-burning fireplace adds warmth and character, making this home as livable as it is lovely. The very spacious den offers the flexibility to serve as a home office, guest room, or hobby space — whatever your lifestyle calls for. An additional den space provides even more room to spread out, work, or create. Your private one-car garage sits just beyond a charming paver driveway shared with only one neighbor — a quiet, neighborly setup that feels nothing like a typical condo. When it comes to outdoor living, this home truly delivers: an expansive screened-in patio sets the stage for year-round enjoyment, while a separate open-air patio offers a sun-drenched spot to relax, garden, or simply soak in the Florida lifestyle. Peace of mind comes standard: a brand-new 2026 roof means this home is as solid as it is stylish. Offered unfurnished and ready for immediate occupancy. Residents of Carriage House II enjoy access to a beautiful pool and clubhouse, all set amid lush, manicured grounds surrounding a tranquil lake with fountains, turtles, and ducks. Membership to The Landings Racquet Club is available but not included or required — a wonderful option for those who want the full lifestyle package. The Landings' coveted location west of the Trail puts everything within easy reach.

4820 Kestral Park Circle Unit 18, Sarasota
$529,800
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Attention Buyers — This is the one! A rare FIRST-FLOOR condo in Pelican Cove with direct Bay Views and unbeatable indoor/outdoor living. Step into your new 2-bedroom, 2-bath home featuring an open floor plan that flows seamlessly from the kitchen through the dining and living areas straight out to your private waterfront deck. Both bathrooms offer walk-in showers, and the condo is being sold fully furnished, making your move effortless. This residence is vacant and easy to show, and the moment you walk in, the water views will grab your attention. Sit outside and enjoy boats passing by throughout the day and spectacular sunsets in the evening. It’s the perfect blend of comfort, convenience, and coastal beauty. Pelican Cove located in South Sarasota west of the trail. This community is over 80 acres in a lush gated tropical setting! Your new condominium is on the FIRST floor. Lots of natural light pours into your home. The setting at the back of the condo is a tropical paradise and it’s also private. Open floor with many upgrades throughout your home! Condo will be sold furnished and very easy to show! Pelican Cove is a 75-acre, gated, vibrant-waterfront community nestled among manicured tropical foliage. Truly offering something for everyone. Abundant amenities include the 86-slip boat harbor with excellent rates & a launch dock for kayaks and canoes, 6 heated swimming pools, hot-tub, 3 clubhouses, lighted tennis/pickleball courts, basketball, dog walk area, walking trails and boardwalks, as well as fishing gazebos, water exercise classes, exercise facility, 2 art studios and a pottery classroom. Take classes at Pelican Cove University or join one of the more than 37 clubs for photography, fiber art, bike riding, culinary arts and card clubs. Woodworking, sculpting, and evening jazz & classical music concerts round out the active lifestyle. Come and see what you have been waiting for.

1515 Pelican Point Drive Unit BA185, Sarasota
$349,800
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Pelican Cove – Turnkey Furnished First-Floor End Unit. Welcome to Pelican Cove, one of Sarasota’s most sought-after gated waterfront communities. This first-floor END unit offers the perfect blend of comfort, privacy, and Florida living at its best. Inside, the main bathroom features a walk-in shower, while the guest bath includes a convenient tub/shower combination. This residence is being sold turnkey furnished, allowing you to move right in and start enjoying the Pelican Cove lifestyle from day one. Recent upgrades include new water tank, air/heating, heavy duty garbage disposal, ceramic floor in living room and kitchen, full handicap entrance wheel chair/scooter accessible, new up to code electrical box, outside outlet, combination door lock. Step outside and explore miles of scenic walking trails that wind through a bird sanctuary and lush botanical gardens. Residents enjoy an impressive array of amenities, including: Six heated pools, well-equipped fitness center, lighted tennis/pickleball courts, three clubhouses with a full calendar of activities, 87-slip safe-harbor marina with kayak and paddleboard launch. Boaters will appreciate direct access to the Intracoastal Waterway, Little Sarasota Bay, and the sparkling Gulf Coast. This charming 2-bed/2-bath condo offers an affordable opportunity to enjoy the Pelican Cove lifestyle. Start your mornings with coffee on the private patio off the kitchen, surrounded by nature. The main living area overlooks a peaceful preserve, creating a serene indoor/outdoor experience that feels uniquely Floridian. Residents also receive a monthly community newsletter filled with special events, classes, and social gatherings—there’s always something happening in Pelican Cove.

1707 Pelican Cove Road Unit GL351, Sarasota
$349,000
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Located in Pelican Cove, this TRUE 3-bedroom condo has exceptional light/bright views with complete privacy all around. The living areas enjoy natural light and are surrounded by lush, mature foliage. The master suite includes a sitting/reading area, walk-in closet/storage. Two additional split bedrooms and a laundry room with additional storage, complete this condo. As you drive past the gate, the lush tropical setting, fruit trees, bird watching and manatee sightings in the harbor will offer instant serenity and relaxation. Amenities include: art studio, woodworking shop, sculpting garden, 6 pools, yoga, tennis, pickle-ball, water aerobics, biking, new exercise room and kayak launches to name a few activities. Enjoy an impressive offering of performing arts, annual art show, cinema & culinary club, bridge and fiber arts club.

1636 Brookhouse Drive Unit 230, Sarasota
$277,500
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Welcome to one of the best locations in Crooked Creek! This beautifully updated first-floor 2 bedroom, 2 bath split-plan condominium is ideally situated in the building directly next to the heated pool and just steps from the private community gate leading into the stunning Red Bug Slough Preserve. Light, bright, and open, the residence features expansive floor-to-ceiling windows that bring the outdoors in, showcasing peaceful views of Crooked Creek, a charming footbridge, and lush Florida landscaping filled with native foliage and wildlife. Enjoy your morning coffee or evening beverage from one of two serene lanais surrounded by nature. The Interior has been COMPLETELY UPDATED IN 2021, and now has a BRAND NEW A/C UNIT just installed May 2026. This stunning home offers a MODERN UPDATED KITCHEN with solid surface counters, stylish cabinetry, updated appliances, recessed and under-cabinet lighting, along with new laminate and tile flooring throughout. Both BATHROOMS were BEAUTIFULLY RENOVATED, and the home also features fresh interior paint, plantation shutters, and recessed lighting in the kitchen, dining area, and guest bedroom. The versatile guest room includes a Murphy bed with built-in desk, making it perfect for visitors or a convenient home office. Crooked Creek residents enjoy numerous community improvements including NEW ROOFS (2019-2021), CARPORTS, EXTERIOR PAINT (2025), RESURFACED HEATED POOL (2025), and an updated poolside COMMUNITY KITCHEN (2025). Each unit includes covered parking and a private storage locker in a large community shed. Outdoor amenities include a heated pool, large pool deck with covered pergolas. A gazebo area with gas grills for BBQ gatherings, and a tennis/ pickleball court. Designed by RENOWNED ARCHITECT TIM SEIBERT of Sarasota School of Architecture, the Crooked Creek community is thoughtfully nestled within nature, with winding paths and tranquil surroundings that make it a true hidden gem. A must-see for nature lovers seeking peaceful Florida living just moments from everything Sarasota has to offer.

3361 Cross Creek Drive Unit 3361, Sarasota
$484,700
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Get to this condo before it’s gone! Stunning views from the main bedroom, lanai and an outside deck. It’s like your sitting out on the water! Just fabulous views. Plus you get to see pelicans fishing * fish jumping * dolphins swimming. Your new 2 bedroom/2bath condo is on the first floor. New vinyl flooring, freshly painted and comes furnished! Pelican Cove is a 75-acre, gated, vibrant-waterfront community nestled among manicured tropical foliage. Truly offering something for everyone. Abundant amenities include the 86-slip boat harbor with excellent rates & a launch dock for kayaks and canoes, 6 heated swimming pools, hot-tub, 3 clubhouses, lighted tennis/pickleball courts, basketball, dog walk area, walking trails and boardwalks, as well as fishing gazebos, water exercise classes, exercise facility, 2 art studios and a pottery classroom. Take classes at Pelican Cove University or join one of the more than 37 clubs for photography, fiber art, bike riding, culinary arts and card clubs. Woodworking, sculpting, and evening jazz & classical music concerts round out the active lifestyle. Come and see what you have been waiting for.

1511 Pelican Point Drive Unit BA180, Sarasota
$259,000
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Welcome to Crooked Creek, a hidden gem in Sarasota with its own private gated access to the Red Bug Slough Preserve. This beautifully maintained 2-bedroom, 2-bath 2nd floor residence was completely updated in 2021 and offers serene views of Crooked Creek, a charming wooden bridge, and lush park-like surroundings. The open and airy floor plan features hardwood floors and tile throughout, plantation shutters, a skylight at entry, and modern finishes. The updated kitchen includes white cabinetry, solid surface countertops with a large peninsula, tile backsplash, smart stainless steel appliances ( fridge and dishwasher 2025, oven and microwave 2021), a spacious pantry, and a garden window. Additional updates are water heater 2018, and reverse osmosis for kitchen sink 2025. The primary suite enjoys peaceful water, a walk-in closet, linen closet and sliding doors to a covered screened lanai. The updated bath has a washer/ dryer (2021)in separate laundry closet, as well as tile floors, a modern vanity, and tile shower . The guest bedroom offers flexible use with a built-in workstation and queen-size Murphy bed. Additional features include two screened covered lanais, reverse osmosis water system for kitchen sink, covered carport, and ample guest parking. Crooked Creek is a 78-unit community offering a heated resurfaced pool, updated poolside kitchen, gazebo with seating, gas and charcoal grills, tennis/pickleball court, community storage with individual lockers, newer roofs (2021), new carports, and recently painted buildings. HOA fees have been reduced by $69 per month from 2025, reflecting strong reserves and excellent financial management. Conveniently located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, and dining. A true nature lover’s paradise.

3363 Cross Creek Drive Unit 3363, Sarasota
$685,000
3 Beds ⋅ 3 Baths ⋅ Landings Treehouse SubDv. ⋅ 34231 Zip Code
Nestled among lush tropical foliage in the highly sought-after Landings community, this one-of-a-kind treehouse retreat offers the perfect blend of nature, light, and waterfront living. Ideally positioned along the scenic boardwalk near Sarasota Bay, this spacious residence is filled with sunshine and tranquil views from nearly every room. The first floor is wrapped in walls of glass, creating an airy indoor-outdoor feel and showcasing peaceful water and garden vistas. A versatile flex space offers endless possibilities as a large home office, family room, fitness studio, or creative retreat. The open kitchen features a generous dining area surrounded by windows, making every meal feel connected to the beauty of nature. Generously sized rooms throughout the home, including all bedrooms, provide comfort and flexibility for everyday living and entertaining. Just steps away, enjoy the community pool or stroll along the winding nature path through mature tropical landscaping to the bayfront gazebo — the perfect setting for spectacular sunsets and watching dolphins play in the water. Residents enjoy easy access to downtown Sarasota, world-famous beaches, exceptional dining, and shopping. Optional membership to the Landings Racquet Club offers resort-style amenities including a super sized pool, tennis and pickleball courts, fitness center, library, and welcoming social spaces to connect with neighbors and friends.

1347 Landings Drive Unit 6, Sarasota
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