South Sarasota Homes with Trees/Woods View

6 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 34231 Zip Code

Location, location location best in all words close to Siesta Key beaches downtown and I 75 shopping is restaurant the hose inside need updating. Bring your ideas and taste , make $1 million Dollar home house very spacious six bedroom, three bathrooms and family room dining room, living room room big glass Team, Florida room and two car garage no deed restriction bring your RV

2705 Wilkinson Road, Sarasota

$250,000

2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code

Enjoy all the benefits of Siesta Key living—without the traffic! Ideally situated at the south entrance to Siesta Key in the sought-after waterfront community of Castel del Mare, this light-filled first-floor, 2-bedroom, 2-bath residence offers the perfect combination of comfort, convenience, and coastal lifestyle. Just moments from world-renowned Siesta Key Beach, you'll appreciate easy island access while remaining close to mainland shopping, dining, entertainment, and everyday conveniences. The thoughtfully designed 2 bedroom 2-bathroom floor plan features an inviting open-concept living and dining area enhanced by abundant natural light. The spacious living room flows seamlessly into the enclosed garden-view lanai, creating a peaceful space to enjoy your morning coffee, read a book, or unwind while overlooking the lush tropical landscaping. The kitchen offers warm wood cabinetry, generous storage, ample counter space, and a functional layout with pass through to the dining room that makes meal preparation effortless. The primary suite provides a tranquil retreat with a walk-in closet, en-suite bath featuring an updated vanity and walk-in shower, while the guest bedroom is generously sized and conveniently located near the second full bath—perfect for visiting family and friends, can easily be used as flex space accommodating a home office, reading nook, or hobby area. Beyond the residence, Castel Del Mare offers an exceptional collection of resort-style amenities, including two heated swimming pools, tennis and pickleball courts, shuffleboard, a clubhouse, kayak launch and storage, fishing, and a scenic waterfront boardwalk that winds throughout the beautifully landscaped community. Spend your days relaxing beside the bayfront pool, launching a kayak on the Intracoastal Waterway, watching dolphins and boats drift by, or taking in breathtaking Sarasota sunsets. With Siesta Key Beach just moments away and everything Sarasota has to offer within easy reach, this waterfront retreat delivers an exceptional combination of location, lifestyle, and value. Schedule your private showing today and experience the best of Florida waterfront living. Long-term tenant in place.

1638 Stickney Point Road Unit 38-102, Sarasota

$434,900

2 Beds ⋅ 2 Baths ⋅ Gulf Gate SubDv. ⋅ 34231 Zip Code

Unlock the potential at 2711 Gulf Gate Drive! Situated on a desirable corner lot at the entrance to a quiet cul-de-sac, this spacious single-family home is the perfect opportunity for first-time homebuyers, investors, or anyone searching for their next renovation project. The exterior has been exceptionally well maintained, with several major improvements already completed, including a new roof (2021), A/C replaced in 2019, new flush-mount lighting throughout, updated electrical fixtures, a retiled guest bathroom, and an upgraded lanai. With many of the costly exterior and mechanical updates already taken care of, you can focus on bringing the interior to life. Inside, the home is ready for a complete cosmetic transformation, offering a blank canvas to create a modern living space tailored to your style. Whether you're looking to renovate your first home, complete a profitable flip, or create a strong long-term rental, this property offers the ideal foundation to add value and build equity. Conveniently located just minutes from Siesta Key Beach, Gulf Gate's popular restaurants and shopping, downtown Sarasota, and everyday conveniences, this home combines an outstanding location with incredible upside. If you've been searching for a property with great bones, solid updates, and endless possibilities, 2711 Gulf Gate Drive is ready for its next chapter.

2711 Gulf Gate Drive, Sarasota

$200,000

2 Beds ⋅ 2 Baths ⋅ Summerside SubDv. ⋅ 34231 Zip Code

Virtually Staged. Welcome to Summerside, a quiet, tree-canopied community tucked just minutes from the sugar-sand beaches of Siesta Key and the easy rhythm of Sarasota's Gulf Coast. This ground-level end unit is ready for some TLC, offered as-is as a blank canvas for the right buyer to renovate to their own taste. Being an end unit means no upstairs neighbor and no shared ceiling overhead, just a private, all-on-one-floor layout wrapped in mature tropical landscaping and swaying palms. For an investor looking to flip, craft a seasonal getaway, or add an income-producing rental to the portfolio, the bones, the layout, and above all the location make this one worth a close look. Inside, soaring cathedral ceilings and a skylight pull natural light across an open living and dining space that flows toward a screened lanai out back. Tile runs through the main living areas, both bedrooms are laid in wood-look plank flooring, and the home lives larger than its two-bedroom, two-bath plan suggests. The kitchen sits at the heart of it all with generous cabinetry, a pass-through breakfast bar open to the gathering space, and a sliding door to one of two private, fenced outdoor retreats. The primary suite is its own corner of calm, complete with a walk-in closet, a private bath, and sliding-glass access to the screened lanai. The second bedroom shares that indoor-outdoor connection with a slider to its own fenced patio and a full bath close by. A dedicated interior laundry room and a covered front entry with a gated courtyard round out the everyday practicality. Beyond your doorstep, Summerside offers a sparkling community pool framed by a wide paver sun deck, plenty of lounge chairs, and a shaded pavilion tucked beneath grand oak trees, the kind of low-key gathering spot that makes a neighborhood feel like home. Assigned carport parking and a friendly, established setting round out the appeal. With a little vision and some finishing work, this retreat can become exactly what you imagine, all moments from Siesta Key's world-famous shoreline and within quick reach of Sarasota's dining, shopping, and signature Gulf Coast lifestyle. Bring your vision and make it your own. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

5683 Summerside Lane Unit 25A, Sarasota

$125,000

1 Beds ⋅ 1 Baths ⋅ Gulf Gate Gardens SubDv. ⋅ 34231 Zip Code

Virtually Staged. Welcome to effortless Florida living in this beautifully updated 1-bedroom, 1-bathroom end-unit condominium, perfectly nestled within a peaceful, tree-lined community in the heart of Sarasota. Offering the added privacy of having no neighboring unit on one side, this light-filled residence blends modern style, low-maintenance living, and an unbeatable central location. Inside, you'll find a bright, open-concept floor plan designed for both comfortable everyday living and effortless entertaining. Luxury vinyl plank flooring, fresh neutral paint, and an abundance of natural light create a warm and inviting atmosphere throughout. The beautifully renovated kitchen is both stylish and functional, featuring timeless white shaker cabinetry, elegant marble-look countertops, stainless steel appliances, and generous cabinet storage. The spacious primary bedroom serves as a relaxing retreat, complete with sliding glass doors that open directly to the private screened lanai. Surrounded by lush tropical landscaping, this peaceful outdoor space is ideal for enjoying your morning coffee, unwinding after a long day, or embracing Florida's year-round indoor-outdoor lifestyle. The updated bathroom complements the home with a modern vanity, tasteful finishes, and a tub/shower combination. Adding even more value, the HOA fee includes water, sewer, trash, cable, and high-speed internet, allowing for truly worry-free living. This pet-friendly community welcomes two pets, and with no minimum ownership period required before leasing, the property presents an outstanding opportunity for full-time residents, seasonal homeowners, and investors alike. Ideally located just 7.8 miles from the world-famous Siesta Key Beach, approximately 15 minutes from vibrant Downtown Sarasota, and only 10 minutes to I-75, you'll enjoy convenient access to premier shopping, dining, golf courses, parks, medical facilities, Sarasota-Bradenton International Airport, and Florida's spectacular Gulf Coast beaches.

7217 Cloister Drive Unit 203, Sarasota

$434,900

3 Beds ⋅ 2 Baths ⋅ Golden Acres SubDv. ⋅ 34231 Zip Code

Experience the blend of classic character and modern updates in this beautifully updated Gulf Gate home, ideally located in one of Sarasota's most desirable neighborhoods. Nestled on a large oversized lot with a peaceful creek backdrop, this move-in-ready property offers exceptional privacy, flexibility, and convenience just 4 miles from the world-famous Siesta Key Beach. Enjoy the freedom of no HOA or deed restrictions, an 8-foot private wood fence surrounding the property, a large parking area, and plenty of space for RV and boat parking, making this home as functional as it is inviting. Inside, you'll find a thoughtfully updated interior featuring luxury vinyl plank flooring, 3 bedrooms plus a dedicated office/flex room, providing plenty of space for working from home, guests, or hobbies. The remodeled kitchen showcases modern finishes, dark stainless steel appliances, updated lighting, and opens seamlessly to the living and dining areas, highlighted by a stylish sliding barn door. Fresh interior paint, including the ceilings, creates a bright and welcoming atmosphere throughout the home. Extensive improvements provide peace of mind and exceptional value, including a metal roof (2010), main HVAC system (2022), rear AC system (2023), washer and dryer (2023), and a brand-new septic system and drain field with lift station (2025). Additional upgrades include a sealed paver driveway, replaced front and side entry doors, commercial-grade solar window tinting, updated dining room and kitchen island lighting, built-in cabinetry, a custom coffee bar, and hurricane-ready, cut and numbered plywood panels for all windows and doors. The expansive backyard offers endless possibilities for entertaining, gardening, pets, or future additions. Two 10-foot access gates and abundant outdoor space make it easy to accommodate recreational vehicles, trailers, or extra parking while still enjoying the privacy of the beautifully fenced yard. Located in one of Sarasota's most convenient neighborhoods, you'll enjoy quick access to Siesta Key Beach, Gulf Gate's popular restaurants and shops, Gulf Gate Library, parks, golf courses, Downtown Sarasota, St. Armands Circle, Sarasota Memorial Hospital, grocery stores, retail shopping, and top-rated schools. Whether you're looking for a primary residence, seasonal getaway, or investment property, this beautifully updated home offers a rare combination of privacy, flexibility, and an unbeatable Sarasota location.

3138 Williamsburg Street, Sarasota

$655,000

3 Beds ⋅ 3 Baths ⋅ The Landings SubDv. ⋅ 34231 Zip Code

Escape to your own private retreat nestled amongst the trees in the desirable Landings Treehouse community! This stunning residence offers the perfect blend of modern elegance and comfort, just moments from Sarasota Bay and the area's beautiful beaches. Relax on the expansive screened deck overlooking lush greenery, or step inside to discover a spacious 3-bedroom, 2.5-bath layout featuring vaulted ceilings, skylights, a custom arched window, and an updated wood-burning fireplace. The beautifully renovated kitchen boasts premium appliances, sleek countertops, and a cozy breakfast area with tranquil views from both sides of the home. Neutral tones and elegant tile flooring create a warm and inviting atmosphere throughout. Upstairs, the spacious primary suite features high ceilings, a private balcony, and a fully renovated en-suite bath. Two additional guest bedrooms, each with its own balcony, share an updated bathroom. Enjoy the community's scenic tree-lined streets and nature trails leading to the Intracoastal Waterway, with optional membership available at The Landings Racquet Club, offering tennis, fitness, pool, spa, and social events. Conveniently located near shopping, dining, parks, and major highways.

1479 Landings Circle Unit 41, Sarasota

$234,788

2 Beds ⋅ 2 Baths ⋅ Woodside Village East SubDv. ⋅ 34231 Zip Code

This 2-bedroom, 2-bath villa nestled beneath tropical oak canopy in Woodside Village East, Sarasota, offers a blend of tranquil living and convenient access to local attractions. This villa features an updated interior with an open floor plan and cathedral ceilings. The clerestory windows flood the interior with natural light. A Florida room provides an additional 117 sq ft of living space. Recent updates include quartz countertops, new cabinets, brand new stainless steel appliances, luxury vinyl flooring throughout, and updated bathrooms. The community of Woodside Village East provides residents with a heated pool and tennis/pickleball courts, set within a tropical landscape. The property is situated just a few miles from Siesta Key Beach, known for its Powdered-Sugar sands. Downtown Sarasota, with its cultural venues, dining, and shopping options, is also easily accessible. Cultural attractions in downtown Sarasota include the Van Wezel Performing Arts Hall, the Sarasota Opera House, and various art galleries along Palm Avenue, also known as "Gallery Row". The shops of Gulf Gate, offering a mix of local businesses and national chains, are nearby for daily needs and entertainment. This villa presents an opportunity for those seeking a getaway near the beach and cultural attractions, or a permanent residence in Southwest Florida. Virtually Staged

6947 Woodwind Drive Unit 77, Sarasota

$1,925,000

3 Beds ⋅ 2 Baths ⋅ Bay View Acres SubDv. ⋅ 34231 Zip Code

ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly opened Midnight Pass where pristine waters flow freely into the Gulf. 10,000 pound boat lift - gorgeous trex decking - 45+ foot dock with fish stand. Walk to Siesta Key. This beautifully updated waterfront residence offers refined Florida coastal living in a truly exceptional setting. Positioned on a picturesque “Y” intersection of two canals, the property provides serene water views, privacy, and effortless access for deep water boating and outdoor enjoyment—just minutes from Siesta Key’s renowned white sand beaches. A stately approach framed by mature oaks and professional landscaping leads to a custom paver drive and striking hurricane-impact glass entry. Inside, the open, light-filled floor plan showcases original terrazzo and travertine flooring, PGT impact windows, and seamless indoor-outdoor flow. Impact French doors open to expansive gardens, tranquil fountains, a private pool, and classic Chicago brick pavers. Designed for entertaining, the home features multiple outdoor living spaces, including an expansive Trex deck overlooking the canal, a pergola, screened patio, boat dock and covered cabana. The kitchen is appointed with quartz countertops, ceiling-height shaker cabinetry, stainless steel appliances, reverse-osmosis water, and generous windows overlooking the backyard. Living and dining spaces flow effortlessly, complemented by a separate family room, opening to a screened lanai. Renovated guest accommodations complete the main level with 2 bedrooms including sun-drenched guest room, office with Murphy bed and full bath. The second level is devoted entirely to the primary suite, a private retreat with resort quality features as: hardwood floors, water views in every direction, French doors with retractable screens, a private balcony, and a spa-inspired bath with dual vanities, a Carrara-tiled walk-in shower, and custom walk-in closets. Ideally located near Siesta Key, downtown Sarasota, and the region’s cultural, dining, and shopping destinations. Evening relaxation - picture this: you’ve had an amazing day on the water and now you’re ready to cook up your catch right in your own backyard. Perfect sunset dinner awaits! This waterfront gem offers everything you need for the ultimate boaters lifestyle – easy access, premium amenities, and the perfect set up for enjoying your evenings. Ready to make waves in your new home? **No hurricane damage. HOME NOT IN A FLOOD ZONE.

1827 Baywood Drive, Sarasota

$2,000,000

3 Beds ⋅ 3 Baths ⋅ Ridgewood SubDv. ⋅ 34231 Zip Code

Modern Waterfront Living on Phillippi Creek with 170 Ft Water Frontage: this stunning residence was completely rebuilt down to the studs in 2023, this move-in ready modern contemporary waterfront residence sits on a rare 0.36-acre lot with 170 feet of water frontage and complete privacy across the creek—offering open water views, and breathtaking westerly Sarasota sunsets. Home has never had water intrusion from any storms due to its elevation. Located on a quiet cul-de-sac just 5 miles to Downtown Sarasota and 3 miles to Siesta Key, the property combines convenience with a peaceful waterfront setting. The home has never flooded and was thoughtfully renovated with long-term durability and quality construction in mind. Boating enthusiasts will appreciate the 5ft +/- water depth at the dock, with additional dredging happening along the creek and an expansive boat dock with new flow-through composite decking, boat lift, and separate double jet ski lift. Enjoy direct access to Sarasota Bay and the Gulf of America just minutes from your backyard. Inside, soaring ceilings and expansive PGT impact windows and sliders fill the home with natural light while framing serene water views. The open-concept living space is centered around a chef’s kitchen featuring a dramatic oversized quartz waterfall island, sleek quartz countertops & backsplash, custom cabinetry, and premium appliances— designed for both daily living and entertaining. The primary bedroom suite offers generous proportions and a fully customized walk-in closet with boutique-level organization the size of its own bedroom. The comprehensive 2023 renovation included full re-plumbing, all new electrical wiring, and fully remodeled bathrooms. Additional upgrades since then include a handcrafted iron front entry door, modern 4 panel garage door with side mounted motor, epoxy flooring and metal standing seam roof. Outdoor living rivals a private resort with a heated saltwater pool and a 2025 custom outdoor kitchen equipped with gas grill, flat-top hibachi grill, built-in TV, refrigerators, and wine cooler. Exterior enhancements include motorized screen, artificial turf for low maintenance, oversized 5 car paver driveway, landscape lighting, leaf guard gutters, and a 12x34 ft shed on an extended concrete pad down to the water's edge. A rare combination of modern construction, deep water access, wide water frontage, and close proximity to Sarasota’s top destinations—this is move in ready waterfront living without settling. It's not just renovated; it's a rare package. All furnishings are negotiable.

2500 Monterey Street, Sarasota

$499,000

3 Beds ⋅ 2 Baths ⋅ Madison Park SubDv. ⋅ 34231 Zip Code

Oasis in the Heart of Sarasota Central Prime Location | 3 Bed + Den | 2 Bath | 13,800 Sq Ft Lot | Privacy | Nature in Your Front Yard If you’ve been looking for a home that feels like a private retreat yet keeps you close to everything Sarasota has to offer, this is the one. Discover a rare blend of privacy, natural beauty, and effortless Sarasota living in this move-in-ready home. Perfectly positioned on a quiet dead-end street, this secluded retreat offers a serene escape with seamless access to the very best of Florida’s Gulf Coast. Inside, hardwood floors lead to a living room with vaulted ceiling, an upgraded kitchen featuring granite countertops, quality custom made cabinetry, stainless steel appliances, and recessed lighting. The spacious primary suite opens to a private patio, creating a peaceful setting for morning coffee or evening relaxation. A new roof installed in December 2025 provides added peace of mind. Set on a generous 13,800 sq ft double lot, the property offers exceptional potential for a future pool, lush garden retreat, or outdoor entertaining space. Steps from Red Bug Slough Preserve, this home delivers a true Old Florida lifestyle with nature right at your doorstep. Red Bug Slough Preserve spans 72 acres and features more than 3 miles of paved and shaded trails through hammocks and pine flatwoods, a tranquil lake, birdwatching along the Florida Birding Trail, a butterfly garden, playground, fishing pier, and picnic shelters. Enjoy a central Sarasota's prime location with peaceful surroundings and convenient access to: Siesta Key Beach: 5 miles. Sarasota Memorial Hospital: 4.5 miles. Downtown Sarasota and the Bayfront: 6.5 miles. Whether you spend your days walking the trails, biking, birdwatching, fishing, or heading to the beach, this move-in-ready sanctuary offers an exceptional Sarasota lifestyle.

4842 Nutmeg Avenue, Sarasota

$1,915,000

4 Beds ⋅ 4 Baths ⋅ Pine Bay SubDv. ⋅ 34231 Zip Code

A rare opportunity within the coveted West of Trail enclave of Pine Bay, this beautifully renovated residence is nestled on a quiet dead-end street near the historic Field Club and offers the perfect blend of privacy, sophistication, and convenience. Designed for effortless Florida living, this 4-bedroom, 3.5-bath home is filled with natural light, soaring vaulted ceilings, clerestory windows, and dramatic walls of glass. Twelve sets of sliding doors blur the line between indoors and out, wrapping around a stunning screened courtyard with a heated pool and spa to create a private resort-like setting rarely found at this price point. The thoughtfully redesigned interior showcases quartz countertops, custom cabinetry, designer finishes, induction cooking, rich engineered hardwood flooring, custom built-ins, and integrated smart home technology. Every space has been curated for both comfortable daily living and elegant entertaining. Outside, mature tropical landscaping surrounds the renovated pool and spa, featuring new tile, resurfacing, 2026 pump, expanded deck areas, upgraded drainage, landscape lighting, irrigation, and a remote-controlled privacy screen, creating an extraordinary outdoor retreat for gatherings, relaxation, or movie nights under the stars. Peace of mind comes with substantial recent improvements including 2020 renovated kitchen and baths, 2020 tile roof on the main residence, Miami/Dade hurricane-rated glass and doors, 2024 Kohler whole house generator, Savant smart home system with electric blinds, whole house Puronics water purification system, seamless gutters with gutter guards, updated electrical panel, and a 3 car garage with an air conditioned bay. Just minutes from Siesta Key Beach, Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and world class dining, shopping, and cultural attractions, this exceptional West of Trail residence delivers the privacy of a hidden enclave with the convenience of Sarasota’s most desirable destinations at your doorstep.

1428 Pine Bay Drive, Sarasota

South Sarasota Homes with Trees/Woods View

Newest South Sarasota Homes with Trees/Woods View