4 Bedroom Homes For Sale In Sarasota - Sarasota FL Real Estate

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

EXCEPTIONAL VALUE IN PINE BAY. A rare opportunity in the coveted West of Trail enclave of Pine Bay, this beautifully renovated 4-bedroom, 3.5-bath residence offers sophisticated design, exceptional privacy, and effortless Florida living. Tucked away on a quiet dead-end street near the historic Field Club, the light-filled home features soaring vaulted ceilings, clerestory windows, dramatic walls of glass, and twelve sets of sliding doors that seamlessly connect the interiors to a spectacular screened courtyard. A heated pool and spa create a private, resort-like setting rarely found at this price point. Beautifully staged to showcase its exceptional scale and design, the interior features quartz countertops, custom cabinetry, induction cooking, rich engineered hardwood flooring, custom built-ins, designer finishes, and integrated smart home technology. The thoughtfully designed spaces flow effortlessly for both everyday living and elegant entertaining. Mature tropical landscaping surrounds the renovated pool and spa retreat, complete with new tile and resurfacing, 2026 pump, expanded deck areas, upgraded drainage, landscape lighting, irrigation, and a remote-controlled privacy screen. Extensive improvements include a 2020 renovated kitchen and baths, 2020 tile roof on the main residence, Miami/Dade hurricane-rated windows 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, 1428 Pine Bay Drive offers the rare combination of a private West of Trail retreat and exceptional convenience. With its fresh presentation this exceptional Sarasota residence is ready to be discovered.

1428 Pine Bay Drive, Sarasota

$1,899,500

4 Beds ⋅ 6 Baths ⋅ 1350 Main Residential SubDv. ⋅ 34241 Zip Code

Experience the perfect blend of luxury, comfort, and modern design in this 2023 built estate in Cassia at Skye Ranch. This unique, turn key opportunity presents 4,562 square feet of thoughtfully designed living space. This remarkable residence features 4 bedrooms, 6 bathrooms and multiple gathering areas with an impressive array of custom upgrades that elevate everyday living. The gourmet kitchen includes a custom built pantry, GE Café appliances, a seamless double oven and a oversized quartz island with motion-sense faucet. The main living space demands upward attention with its soaring tray ceilings with crown molding. This beautiful upgrade stretches to each and every room in the house. Indulge in music anytime with built-in speakers in the main living space, as well as outside. Enjoy an abundance of space in this master suite with his and hers walk in closets and an extremely oversized shower with both dual rain and detachable shower heads. Each one of the guest bedrooms showcase walk in closets, private ensuites with the continuation of the quartz vanities. One of the home's most impressive features is the custom upstairs addition, creating a private guest or multigenerational living space complete with a spacious great room, kitchenette with sink, dishwasher and beverage refrigerator, private bedroom with en-suite bath, and additional half bath. The 1,400 square foot covered lanai allows for effortless entertaining. Outside you'll find a beautiful resort-style saltwater pool with a sun self, stunning waterfall features and oversized spa. With the upraded gas heater, you can enjoy year-round relaxation in just minutes. The outdoor kitchen includes a beverage center, granite countertops, large sink and hooded ventilation. With a much sought after extended yard, this house uniquely sits on 0.301 acres with a wooded conservation backdrop, enhanced by extensive landscaping, expanded irrigation, and fenced pool equipment areas. Other outdoor features include built-in garage storage, car charge station, an extended driveway, landscape lights, gutters, and easy to install hurricane shutters. Skye Ranch residents enjoy resort style amenities such as walking/biking trails, both indoor and outdoor basketball/pickleball courts, parks, rock climbing, fitness center, spa facilities, and a water playground. This opportunity to own in one of Florida's most dynamic master-planned communities is truly unique. Just 12 miles from Siesta beach, and minutes from our brand new Skye Ranch school, your new journey starts here!

9479 Tequila Sunrise Drive, Sarasota

$1,899,000

4 Beds ⋅ 6 Baths ⋅ Skye Ranch Neighborhood Four North SubDv. ⋅ 34241 Zip Code

A showcase of craftsmanship, design, and lifestyle, this former builder model in Cassia at Skye Ranch represents one of the community’s most distinguished opportunities. Positioned on a private preserve homesite, this 4 bedroom, 4.5 bath residence offers 4,541 square feet of thoughtfully designed living space with soaring ceilings, crown molding, professionally designed custom wall treatments, and exceptional designer finishes throughout. The great room is anchored by custom built-ins and a fireplace, while the chef’s kitchen features an oversized island, built-in ovens, illuminated cabinetry, premium appliances, and a spacious walk-in pantry. The main level includes a private study, formal dining area, two en suite guest bedrooms, and a luxurious owner’s retreat with lanai access, dual custom closets, and a spa inspired bath with an oversized dual entry shower. Upstairs, a spacious game room with wet bar and full bath offers flexible space for guests, recreation, or multi generational living. Pocketing sliders open to a resort style outdoor retreat featuring a covered lanai, summer kitchen, pool, spa, and tranquil preserve views. Premium upgrades include impact windows and doors, motorized shades, integrated smart home technology, whole home audio, three zone HVAC, whole home surge protection, an on demand tankless water heater, tile roof, paver driveway, designer lighting, custom closet systems, and an oversized three car garage. Residents enjoy access to Skye Ranch’s resort style amenities, parks, trails, and recreational facilities, all just minutes from top rated schools, Waterside Place, downtown Sarasota, and world renowned Siesta Key Beach. One of the finest homes offered within Cassia at Skye Ranch, this exceptional residence delivers a level of design, privacy, and lifestyle rarely found in today’s market.

8232 Summer Night Road, Sarasota

$1,895,000

4 Beds ⋅ 4 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code

A rare blend of modern luxury, income potential + lifestyle flexibility awaits in this striking custom 2023 duplex in the heart of Gillespie Park, moments from downtown Sarasota. Designed for those wanting more than just a home, this architectural standout offers 4,400+ sq ft of elevated living with two fully independent residences, each approx 2,200 sq ft featuring 2 bedrooms, 2 bathrooms, private laundry, soaring ceilings + a light-filled expansive design. Whether downsizing, creating a multi-gen retreat, or offsetting your lifestyle with income, this property delivers exceptional versatility, live in one + generate revenue from the other (currently $3,600/month). The main level showcases a chef-inspired kitchen with premium Thermador appliances, gas cooking, dual dishwashers, walk-in pantry + built-in coffee/wine bar, while the upper level offers a refined private living experience with sleek Bosch appliances+ ensuite bedrooms. Outdoor living feels like a private resort with a secluded courtyard featuring an outdoor kitchen and hot tub, plus an expansive second-level balcony ideal for relaxing. Built for efficiency + longevity with solar power, natural gas tankless water heaters, elevator access + rare 3-car alley-access garage, features seldom found this close to downtown. Zoned for short-term rentals and crafted as a high-end multigenerational retreat with full custom handicap-accessible design, delivering an exclusive lifestyle in a prime location.

1755 7th Street, Sarasota

$1,870,000

4 Beds ⋅ 4 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code

This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel was built in 1956 and was originally a 2/2. The original bathrooms are still in their original state and are in good condition providing a cool retro vibe. The original hardwood floors and fireplace exude warmth and sophisticated charm. The current owner purchased the home in 1989 and remodeled the kitchen and added a new wing on the house with 2 additional large bedrooms ensuite with baths. Copious amounts of storage in all 4 bedrooms and a huge laundry room with lots of closet space as well. The garage is oversize and there is a picturesque circular driveway for ample parking. There is plenty of room to put in a pool of your own design. The house was re-roofed in 2018. Some of the most beautiful homes in Sarasota are your neighbors in Harbor Acres. And Flower Drive is a special address with the highly sought after Southside Elementary School just 1-mile away, you can’t beat this property. In real estate it is all about Location, Location, Location. This home has plenty of room for the family, so, come on home!

1541 Flower Drive, Sarasota

$1,850,000

4 Beds ⋅ 6 Baths ⋅ Skye Ranch Neighborhood Four North SubDv. ⋅ 34241 Zip Code

Experience the perfect blend of luxury, comfort, and modern design in this nearly new estate home in Cassia at Skye Ranch. Offering approximately 4,898 square feet of thoughtfully designed living space, this exceptional residence features four bedrooms, multiple gathering areas, and an impressive array of custom upgrades that elevate everyday living. At the heart of the home is a spectacular gourmet kitchen designed to impress. Outfitted with an upgraded GE Monogram Luxury Pro appliance package, Bosch counter-depth refrigerator, upgraded Kohler porcelain sink, motion-sense faucet, custom pantry storage, pass-through bar with wine refrigerator, and premium finishes throughout, this space effortlessly combines style and functionality. The kitchen opens seamlessly to the expansive living and dining areas, enhanced by soaring ceilings, crown molding, tray ceilings, built-in ceiling speakers, and abundant natural light. The primary suite serves as a private retreat, featuring a spa-inspired bath with a freestanding soaking tub, custom walk-in closets, and luxurious finishes. Additional bedrooms offer generous accommodations for family and guests, while custom closets throughout the home provide exceptional organization. One of the home's most impressive features is the custom upstairs addition, creating a private guest or multigenerational living space complete with a spacious great room, kitchenette with sink, dishwasher and beverage refrigerator, private bedroom with en-suite bath, and additional half bath. Florida living reaches its finest outdoors. The resort-style saltwater pool showcases an oversized spa, sun shelf, heater, and chiller, creating year-round enjoyment. An outdoor kitchen with beverage refrigerator, expansive covered lanai, and bonus room overlooking the pool provide the ideal setting for entertaining. The private backyard enjoys the serenity of a wooded conservation backdrop, enhanced by extensive landscaping, expanded irrigation, and fenced pool equipment areas. Additional upgrades include whole-house surge protection, generator transfer switch, built-in garage storage and Monkey Bar organization system, extended driveway, upgraded gutters, custom storage solutions, and built-in speaker systems in the main living areas, lanai, and upstairs great room. Residents of Cassia at Skye Ranch enjoy an extraordinary lifestyle with world-class amenities including tennis and pickleball courts, bocce ball, a year-round heated Olympic-style pool, indoor basketball court, fitness center, spa facilities, and a water playground. Conveniently located near Sarasota's renowned beaches, dining, shopping, cultural attractions, and top-rated schools, this exceptional home offers the luxury lifestyle you've been waiting for. Your legacy begins here.

9463 Tequila Sunrise Drive, Sarasota

$1,849,000

4 Beds ⋅ 5 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code

The Gillespie Park Casa del Sol Is Finally on the Market! Nestled beneath a canopy of majestic oaks in Sarasota's beloved and historic Gillespie Park, Casa del Sol is an extraordinary Mediterranean-inspired estate where timeless architecture, modern luxury, and resort-style living come together just moments from the heart of downtown. Built in 2007 with solid masonry construction, this remarkable property offers 3,338 total square feet, including a 2,854-square-foot main residence, a beautifully appointed 484-square-foot detached studio casita resting above the spacious detached 2 car garage w/covered carport. This 4 bedrooms, 4.5 bathrooms, is offered for well under $2 million. Designed to capture the romance of an authentic Mediterranean villa, the home showcases imported Colombian roof tiles, handcrafted Colombian brick pavers, rich hardwood flooring, elegant French doors, a chef's kitchen with stainless steel appliances, a gas range and fireplace, dual-zone HVAC, a tankless water heater, and a convenient second-floor laundry room. Every detail reflects exceptional craftsmanship while blending seamlessly with today's modern lifestyle. Step outside to your own private tropical retreat, where lush landscaping, a sparkling heated pool (with fountain water feature), and a newly installed privacy fence create an atmosphere of serenity and effortless entertaining. The detached studio casita offers outstanding flexibility as a luxurious guest suite, executive office, fitness studio, creative space, or income-producing accommodation. It is separately metered for convenience. Just a 2 min walk from the 10-acre John Hamilton Gillespie Park and a 2 minute drive (or short walk or bike ride) from Downtown Main Street and Sarasota's award-winning restaurants, boutiques, theaters, galleries, waterfront, and renowned Farmers Market, Casa del Sol places the very best of Sarasota at your doorstep. Located within the desirable Downtown Neighborhood (DTN) zoning district allowing one-week minimum short-term rentals, the property presents a rare opportunity as a primary residence, seasonal escape, or exceptional investment. Rarely does a home provide this level of architectural distinction, walkable downtown convenience, investment flexibility, and resort-inspired living. Casa del Sol is finally on the market, offering an extraordinary opportunity to experience one of Sarasota's most coveted lifestyles.

1719 7th Street, Sarasota

$1,795,000

4 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Just bring your wardrobe! Welcome to this beautifully updated and fully furnished and equipped 4-bedroom, 3-bath cottage-style home in one of Siesta Key’s most sought-after neighborhoods - just a short stroll to public beach access at top-rated Siesta Key Beach. Meticulously renovated in 2025, this true turnkey entertainer's paradise offers a vacation-every-day lifestyle complete with thoughtful upgrades and everything you need to move right in. Inside you’ll find all-new tile flooring, fresh paint throughout, storm-rated windows, a new 310 Lennox air-conditioning system with a 10-year warranty, updated plumbing and electrical, a reverse-osmosis water system, a whole-house generator (gas or propane), and a newer roof (2021). The backyard oasis features a 50-foot saltwater pool, spa, and sundeck surrounded by elegant Italian marble, plus pool floats, basketball hoops, and a volleyball net for endless fun. Enjoy the outdoor shower, raised gardens, a Napoleon Prestige gas grill, fire table, electric vehicle charger, and a louvered pergola that opens or closes for perfect sun or shade, a 75-inch TV, and a Sonos outdoor surround sound system - ideal for outdoor movie nights. Ultimate privacy is provided by an 8-foot vinyl fence. The artificial turf in the front and backyard creates a clean and maintenance free living with a coastal feel. The gourmet kitchen is fully stocked and ready for entertaining, featuring 2025 Thermador appliances (refrigerator, stove top, dishwasher, and oven) plus a new LG washer and dryer. Practical extras include a Shark vacuum, clothes steamer, iron and board, and even towels, and washcloths already stocked in every bathroom. The home comes completely furnished with all shown décor, lamps, linens, and towels. Two of the bathrooms include bidets and large walk-in showers. Beach days are effortless thanks to the included beach chairs, towels, beach cart, and umbrella shade. A Ring camera system conveys with the home sale, offering peace of mind. Bonus: This home includes an assumable flood insurance policy for just under $4,700 annually. This is the fully equipped Siesta Key lifestyle you’ve been dreaming of. Call today to schedule your private showing!

5143 Sandy Beach Avenue, Sarasota

$1,775,000

4 Beds ⋅ 3 Baths ⋅ Hampton Lakes SubDv. ⋅ 34240 Zip Code

Experience the perfect blend of luxury, privacy, and acreage living in the gated estate community of Hampton Lakes. Set on an exceptional 4.66-acre homesite, this custom residence offers the space and flexibility that are increasingly rare in Sarasota, providing endless possibilities for collectors, outdoor enthusiasts, and hobbyists alike, with room for vehicles (4-car garage 30'x50' with two 9'x18' doors and 12' ceiling), recreational equipment, equestrian pursuits, and more. Designed to embrace its tranquil surroundings, this Grand Santa Maria home features 4 bedrooms, a bonus room, and 3 full bathrooms, complemented by soaring ceilings, 8’ doors, expansive living spaces, and picturesque views of mature trees and the tranquil countryside landscape beyond. Large impact-rated windows and sliding glass doors fill the home with natural light while creating a seamless connection to the outdoors. Built with today's lifestyle in mind, the residence offers the qualities modern buyers seek, including newer construction, an open-concept floor plan, higher ceilings, energy-efficient features, hurricane-resistant standards, and stylish contemporary finishes that blend comfort, functionality, and peace of mind. At the heart of the home, the kitchen is tastefully appointed with quartz countertops and farmhouse sink, plus a prep island and sink, built-in double ovens, induction cooktop, wine cooler, walk-in pantry, and a dinette with aquarium window. The spacious lanai is designed for year-round enjoyment, featuring a heated pool, abundant covered outdoor living space, and plumbing stubbed for a future outdoor kitchen. Whether entertaining guests or enjoying a quiet evening, the peaceful setting provides a remarkable sense of space and privacy. Exceptional attention to detail continues throughout the home with premium porcelain and ceramic tile flooring, rounded wall corners, upgraded lighting and ceiling fans, a whole-house water softener and iron filtration system, and a central vacuum system with concealed retractable hoses. Additional amenities include a secure 6' x 12' storage room with a safe, RV hookups, and a security system pre-wired for cameras. Thoughtful site improvements include buried gutter drains feeding French drain systems along both sides of the residence, as well as a fenced backyard enclosure. The expansive homesite also offers the opportunity to construct an additional outbuilding, or two if attached. Car enthusiasts, hobbyists, and collectors will appreciate the impressive four-car garage with insulated block construction and insulated doors. The garage is fully equipped with a mini-split air-conditioning system, three ceiling fans, air compressor with 5 ports, utility sink, shelving, and 12-foot ceiling—providing ample clearance for a hydraulic vehicle lift. The floor is reinforced with rebar in designated parking bay. Two tractors, as well as the hydraulic lift and jack, are available for purchase under a separate contract. Complemented by its private estate setting, Hampton Lakes offers convenient access to everything that makes Sarasota and Lakewood Ranch so desirable, including UTC shopping and dining, downtown Sarasota's vibrant arts and cultural venues, Gulf Coast beaches and boating, championship golf clubs, the Sarasota Polo Club, and the natural beauty of Myakka River State Park. This is a rare opportunity to enjoy rural-estate living with acreage, privacy, and endless possibilities.

3503 Recurve Circle, Sarasota

$1,775,000

4 Beds ⋅ 3 Baths ⋅ Mcclellan Park SubDv. ⋅ 34239 Zip Code

This Spanish Mediterranean style home built in 1925 is nestled in the coveted "West of Trail" subdivision of DeSota Park in the South Poinsettia park Neighborhood just two blocks from the fine dining and boutique shopping offered in Southside Village. This home is ideally located outside of any flood zones and weathered the 2024 hurricane season without any damage. This listed historic home with detached casita is rich with character. The beautifully designed residence offers 2,330 square feet of living space. The home boasts a total of 12 rooms featuring a spacious entry, open plan living area including a formal dining room, living space and chef's kitchen and a versatile family room located directly off the pool area. The 3 bedroom main house has 2 bedrooms with their own en-suite bathrooms plus an additional 3rd bedroom/office/flex space, updated hurricane rated windows and whole home tankless hot water heater. The casita offers the 4th bedroom with en suite bath and kitchenette. Upon entering the tiled courtyard you are invited to step inside and discover an abundance of architectural details like the hurricane rated pecky cypress entry door, arched doorways, pecky cypress beams and fireplace mantel, custom built-ins and original architectural details that all add up to the unique touches of sophistication. The northern exposure fills the home with natural light, highlighting the garden views through casement dual pane hurricane rated windows adorned with tasteful and functional window treatments. Inside the spacious foyer your attention is drawn to the custom window treatments and new flooring and opens to an expansive open plan living room featuring a working fireplace with a pecky cypress mantel that adds warmth and ambiance and pecky cypress beams. The living space is flanked by a light filled dining room that opens to a second private courtyard and the recently renovated gourmet chef's kitchen that includes custom cabinetry, Taj Mahal quartzite countertops, zellige tile backsplash and top of the line appliances - SubZero refrigerator, Thermador warming drawer and Italian Fulgor Milano gas range. Down the hall the main floor primary suite includes a large ensuite bathroom with a separate shower, four closets for ample storage and a convenient laundry space. The second bedroom suite is tucked away with dual closets, dressing area, its own courtyard and private access to the pool. At the back of the home the 3rd bedroom/office/flexroom is located off a large and comfortable family room with pecky cypress beams and tile flooring that opens up through a wall of hurricane rated stack glass back doors to the pool area. The pool area is a tropical paradise featuring a heated pool and hot tub with a new remote controlled electronic system. The pool cage encompasses plenty of space for lounging and dining and includes the entry to the casita and full bath with mini split unit, tile flooring and wooden beams, includes built-in murphy bed and a dedicated generator. Outside the casita is a large paver courtyard with a custom outdoor cooking area that includes a plumbed 36" natural gas grill with rotisserie and pizza oven accessories and an outdoor refrigerator. This "West of Trail" home is ideally located in the Southside Elementary School district, convenient to Sarasota Memorial Hospital and located just steps away from Morton's Gourmet Grocery and some of Sarasota's best restaurants, shopping and art galleries.

1864 Clematis St Street, Sarasota

$1,750,000

4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Discover a rare opportunity on Palm Island, one of Siesta Key’s most distinctive residential enclaves, where quiet island living meets exceptional access to the very best of Sarasota’s Gulf Coast lifestyle. Ideally located at 5334 Calle Florida, this custom-built residence offers privacy and character while remaining just moments from the white sands of Siesta Key Beach, the Village, boating, dining, and everything that makes this part of the island so desirable. Set on a generously sized lot and elevated approximately 10 feet above sea level, the home was thoughtfully constructed with island living in mind. The elevated Key West-inspired design provides an added sense of security, with the main residence having never experienced flooding during any storm. Inside, the home immediately makes an impression. Soaring 20-foot ceilings rise above the dramatic great room, while the open-concept design allows the kitchen, dining, and living spaces to flow naturally together. Abundant natural light and the impressive ceiling height create a bright, airy atmosphere that feels both sophisticated and relaxed. With 2,838 square feet of living space, four bedrooms, and three bathrooms, the home offers the scale and flexibility for full-time living, entertaining, or an exceptional Siesta Key retreat. The oversized primary suite provides a private escape with a custom-built window seat, two walk-in closets, and a spacious primary bath. Built-in speakers extend throughout the residence and onto the back porch, creating a seamless atmosphere for everyday living and entertaining. Outdoor living is equally impressive. The elevated heated pool and hot tub create a private resort-like setting complemented by an outdoor shower and generous areas for relaxing or gathering with friends and family. Thoughtful exterior details include landscape lighting and electrical power in the soffits for seasonal or year-round accent lighting. The home is also well equipped for coastal living with three-zone air conditioning, hurricane-rated Kevlar screens, a hurricane-rated front door and garage door, and a spacious two-car garage with ample storage. Recent improvements include a new roof in 2021, pool resurfacing in 2024, pool cage repainting and rescreening in 2025, and a new water heater in 2025. What truly sets 5334 Calle Florida apart is the combination of location and architecture: a custom, elevated residence with dramatic ceiling heights and open living spaces, tucked away on Palm Island yet remarkably close to the beach and Siesta Key lifestyle. It is a distinctive opportunity to enjoy privacy, elevation, and luxury in one of Sarasota’s most sought-after island settings.

5334 Calle Florida, Sarasota

$1,750,000

4 Beds ⋅ 4 Baths ⋅ Alta Vista Heights SubDv. ⋅ 34237 Zip Code

This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for a strong six figure range income annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.

2231 Wood Street, Sarasota

$1,749,000

4 Beds ⋅ 3 Baths ⋅ Terrace Gardens SubDv. ⋅ 34237 Zip Code

Introducing THE RETREAT, a stunning two-story residence. FOUR (4) bedroom, THREE (3) bath. Paver driveway, 3 CAR GARAGE, LVP flooring. Home has been professionally staged. Pool size is 12 x 26 , leaving plenty of green space for pets in the backyard! Back yard fence will fully enclose the back yard with gates on both sides of the home. This exceptional new build boasts superior block construction, a durable metal roof, impact-resistant windows, doors, and sliders. Inside is a thoughtfully designed open floor plan, featuring soaring 10-foot ceilings and elegant 8-foot solid core doors that enhance the home’s impressiveness. The gourmet kitchen is complete with a 6-foot island, luxurious quartz countertops, custom shaker cabinetry, and a top-of-the-line appliance package, perfect for both daily meals and entertaining. The primary bedroom, located on the main level, is a serene retreat with stunning tray ceilings, large his/her walk-in closets, double vanity, and a spacious walk-in shower. Bedroom #2, also on the first floor, is versatile and can serve as an additional bedroom or a home office. Upstairs, you'll find two more generously sized bedrooms that share a beautifully appointed full bathroom. The home’s detailed interior is complemented by luxury vinyl plank flooring throughout both levels, providing durability and style. Outdoors, a gas-heated saltwater pool and paver deck creates the ideal setting for relaxation and entertainment. Conveniently located with easy access to downtown Sarasota, the Legacy Trail, Payne Park, Sarasota Memorial Hospital, and the world-renowned beaches of Longboat and Siesta Keys, this home offers the perfect blend of luxury, comfort, and convenience for modern family living. Experience elevated living at its finest in "your RETREAT"!

217 S Shade Avenue, Sarasota

$1,700,000

4 Beds ⋅ 3 Baths ⋅ Palmer Farms SubDv. ⋅ 34240 Zip Code

RARE 5-ACRE SARASOTA ESTATE - COUNTRY LIVING WITH CITY CONVENIENCE! Welcome to your own private piece of paradise! This charming and meticulously maintained 4-bedroom, 3-bath, 2-Car Garage, Pool home offers approximately 2,580 square feet (3,422 gross sq ft) of living space. Tucked away on a quiet dead-end road, this unique property offers exceptional privacy, abundant wildlife and an increasingly rare opportunity to enjoy acreage living while remaining just minutes to everything in Sarasota! Lovingly maintained by the original owners, this concrete block and stucco home features an updated kitchen with island seating, a wood-burning fireplace, a spacious 18' x 22' family/game room, formal living/dining rooms and a newer A/C replaced in 2024. A generator provides additional peace of mind. Step outside and discover what truly makes this property amazing. The 15' x 30' inground pool features a screened enclosure and an expansive covered lanai perfect for relaxing, entertaining and enjoying Florida living year-round. The grounds are simply beautiful, with approximately 145 majestic oak trees, a gorgeous magnolia tree, gazebo, storage shed with workshop and a freshwater canal along the rear of the property. This estate is also Perfect for Horse Lovers! This property features an existing horse stall/building with a fenced paddock and you'll have plenty of acreage for grazing and roaming. Wire and wood fencing surround the property and there are no deed restrictions, no HOA and no vehicle restrictions. The home is high and dry and had no wind or water damage from recent hurricanes. The property's flexible OUE zoning creates exciting possibilities for those seeking additional living space, a family compound, accessory structures or the ability to operate certain businesses from home, subject to applicable county requirements. With five acres, there is plenty of room to explore future possibilities while enjoying the existing home today! The location is absolutely hard to beat! Enjoy the peace and privacy of country living while being only minutes to world famous Siesta Key Beaches, Cultural Downtown Sarasota, I-75, University Mall, Mote Marine, Polo Fields, Waterside, fine restaurants and many nearby golf courses. You may go days without seeing a neighbor, yet everything in Sarasota is within easy reach! Ride your four-wheelers, bring your horses and farm animals, park your RV or boat and experience the freedom to call this 5 acre estate YOURS! Properties offering this combination of acreage, privacy, flexibility and location are increasingly difficult to find. This is the one you've been dreaming about, so HURRY!

6455 Mckown Road, Sarasota

$1,695,000

4 Beds ⋅ 4 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code

Don’t miss this unique opportunity to own an "outstanding" 4-bedroom, 3.5-bath residence located within the gates of Laurel Oak. This home is ideally positioned on a ½ acre plus premium lake lot with exceptional "natural" privacy, serene water and preserve views from your picture framed lanai. Every home has a story, and this one began in 2020 when it was taken down to the studs and thoughtfully reimagined through a custom renovation—blending timeless design with modern functionality, and delivering a move-in ready experience with lasting peace of mind. The architectural details include crown molding, tray and volume ceilings that highlight the sense of openness and elegance throughout the living spaces. The kitchen has been meticulously designed with expansive counter space and custom cabinetry, creating a natural balance between everyday comfort and functionality. It’s a space that supports daily living with ease while also accommodating those moments that call for gathering and celebration, it is open, practical, and tailored to the flow of everyday life. The transition from the interior living spaces to the exterior spaces creates a true indoor-outdoor lifestyle: inviting, open, and designed for everyday living. Multiple access points from room to room including the Primary & Secondary en-suites extend the living space outward, connecting naturally to the expansive under-cover lanai and pool area showcasing postcard-worthy views with peaceful sightlines. It’s a layout that offers flexibility. Schedule your private showing today to experience this rare Laurel Oak Estates property. Residents have the option to join Laurel Oak Country Club, offering two 18-hole championship golf courses, 12 Har-Tru tennis courts, six pickleball courts, and an active social calendar. Ownership includes moving to the top of the waitlist and (next spot) priority placement on the country club waiting list. Beyond the gates, the location places you near shopping, dining, entertainment, medical facilities, major roadways, and Sarasota’s renowned beaches.

7732 Donald Ross Road W, Sarasota

$1,675,000

4 Beds ⋅ 4 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code

Welcome to 7767 Alister Mackenzie Drive, a gracious 4 bedroom residence with an office/home gym, 3.5 bathrooms, and a heated saltwater pool, ideally positioned on over 2/3 of an acre, along the golf course in Laurel Oak Estates. Set within Sarasota’s established, guard-gated, golf cart-friendly neighborhood, this 3,903-square-foot residence pairs golf course views with a light-filled, thoughtfully designed open floorplan. * High ceilings and abundant natural light create an immediate sense of scale, while the home’s open central living spaces flow naturally into more defined areas for work, entertaining, and quiet retreat. The split floorplan also features a ground floor Primary bedroom, which features automated blackout shades and plantation shutters, 2 walk-in closets, and a soaking tub. From the wet bar that offers tons of storage for whatever you're pouring, to the kitchen with bar seating and a breakfast nook, to the enormous storage closet, to the ample shaded space on the screened patio, your entertaining needs will be covered. To top it off, there is a cocktail tree growing outside, which provides lemons, limes, and oranges during the citrus season. * The kitchen and gathering spaces connect easily to the outdoor living area, where the heated saltwater pool and spa, a covered area with a retractable awning, and the Florida kitchen are the final touches to live the Laurel Oak Lifestyle. And finally, we can't forget furry friends: there is a fenced dog run with a doggy door and invisible fencing around the house, so your canine companions can live their best life! * Hardwood flooring adds warmth throughout the main living areas, and impact windows, slider shutters, and new impact garage doors give peace of mind. The solar panels are connected to a Tesla Powerwall, which allows the owners to determine when they want to be on or off the grid. The insulated three car garage has ample space for 3 cars, hobbies like a golf simulator, or additional storage needs. * Enjoy the privacy and natural beauty of Laurel Oak Estates, a distinguished Sarasota community known for its mature landscaping and preserved green space. The 813-acre community was planned around balancing the hammocks and preserves with the Laurel Oak Country Club, a private, member-owned club offering golf, tennis, pickleball, swimming, dining, and social activities. The neighborhood is gated with a guard and there is no CDD. This is one of THE most desirable neighborhoods in Sarasota, is in a great school district, is just minutes to The Classical Academy, and is wonderful for all ages.

7767 Alister Mackenzie Drive, Sarasota

$1,650,000

4 Beds ⋅ 4 Baths ⋅ The Landings SubDv. ⋅ 34231 Zip Code

Virtually Staged. Welcome to 5166 Kestrel Park Terrace, an exceptional opportunity in the highly sought-after gated community of The Landings. Privately positioned on an oversized, fully fenced homesite, this expansive 3,993-square-foot residence offers impressive scale, an abundance of natural light and a thoughtfully designed single-level floor plan with tremendous potential to create a truly exceptional home. The residence features four bedrooms, three full baths and one half bath, arranged in a desirable split plan that provides privacy for each bedroom. Soaring 12-foot ceilings throughout enhance the home’s open, airy feel, while generous windows fill the interiors with natural light. The gracious formal living room with wet bar and separate formal dining room are ideal for entertaining. A spacious family room with a wood-burning fireplace provides a comfortable gathering space, while a private office and separate den offer flexibility for work, relaxation or additional living space. The generously proportioned kitchen features a large center island and abundant workspace, offering an excellent foundation for a beautifully redesigned chef’s kitchen. An adjoining breakfast area provides a casual dining space and opens to a private deck with convenient access for grilling. The home’s living spaces flow seamlessly to the expansive brick-paver lanai and private swimming pool, creating an inviting setting for outdoor living and entertaining. Surrounded by the privacy of the oversized, fenced property, the outdoor areas offer ample room to relax and enjoy the Florida lifestyle. Additional features include a three-car garage, a 2018 tile roof and whole home hurricane protection. With nearly 4,000 square feet of living space all on one level, this residence presents a wonderful opportunity to reimagine and renovate an exceptionally well-proportioned home to reflect today’s style and finishes. The spacious rooms, high ceilings, abundant natural light, private bedroom configuration and oversized homesite provide the ideal canvas for creating a beautifully customized residence with the feel of a new home. Located within The Landings, one of Sarasota’s most established and desirable communities, this home offers a rare combination of space, privacy, flexibility and potential in an exceptional setting. Residents enjoy exclusive access to the private Landings Racquet Club, featuring eight Har-Tru tennis courts, pickleball facilities, a heated swimming pool, fitness center, meeting rooms and a well-stocked library. The community also offers 24-hour security and a beautiful natural setting with access to Sarasota Bay, providing a distinctive lifestyle in the heart of Sarasota.

5166 Kestral Park Terrace, Sarasota

$1,597,000

4 Beds ⋅ 4 Baths ⋅ Phillippi Gardens SubDv. ⋅ 34231 Zip Code

Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.

5500 Merrimac Drive, Sarasota

$1,595,000

4 Beds ⋅ 4 Baths ⋅ Premier On Main SubDv. ⋅ 34237 Zip Code

Nearly new, turnkey furnished, four-bedroom luxury townhome in Sarasota’s uptown district. Located on upper Main Street with easy access to the city’s galleries, cafes, restaurants and boutiques. This exceptional location places you minutes from pristine beaches, championship golf, the hospital, airport and top cultural venues. The property sits adjacent to the northern end of the Bay Runner trolley, providing complimentary rides to downtown, St. Armands Circle and Lido Beach. The smart, 2,763-square-foot, four-level floor plan maximizes both privacy and entertaining space, featuring a private elevator, double-concrete construction, high ceilings, eight-foot interior doors, energy-efficient systems, hurricane-rated impact windows, multiple balconies, a finished rooftop and parking for four vehicles in the two-car garage plus attached carport. The ground level offers a private guest suite perfect for visitors or additional income. The main second level presents an open floor plan connecting the kitchen, dining and living areas. The gourmet kitchen delights with sophisticated European cabinetry, quartz countertops, under-cabinet lighting, a center island with a waterfall feature and high-end Samsung and Bosch stainless steel appliances. The third level houses three bedrooms and two baths, including the primary suite, which boasts an outdoor balcony, walk-in closet and luxurious ensuite bath. The crown jewel is the finished rooftop level designed for outdoor living, featuring multiple gathering spaces, an outdoor kitchen, a jetted spa and glass railing with captivating city views. Weekly rentals are permitted and this residence has a strong, established record of successful rental performance. This home combines a prime location, exceptional design, turnkey convenience and proven rental history for the ultimate Sarasota lifestyle.

62 Audubon Place, Sarasota

$1,575,000

4 Beds ⋅ 4 Baths ⋅ Prestancia SubDv. ⋅ 34238 Zip Code

Nestled behind the gates of one of Sarasota’s most established neighborhoods, this Prestancia home offers quiet luxury and golf course views, where expansive indoor and outdoor living spaces epitomize Florida-living. The thoughtfully designed layout boasts a private master wing on one side, and casual living areas and additional bedrooms on the opposite. Joining the two wings are a formal dining and living room, distinguished by high ceilings, transom windows, and sliding doors which lead to an inviting outdoor retreat. The grand, master suite includes a dressing area, large walk-in closets, and a convenient, wall-enclosed dog yard for pets to safely enjoy. The adjoining master bath hosts separate custom vanities, a Roman walk-in shower, and a water-closet equipped with a hands-free electronic toilet/bidet. Just beyond the spa tub, double French doors open onto a secluded outdoor gathering space complete with a fireplace, perfect for unwinding on cozy evenings. The spacious kitchen is well suited for preparing both gourmet meals and quick refreshments served through the pass-through sliding windows that open to the outdoor eating area. Adjacent the kitchen is a large family room with soaring ceilings, a stone fireplace, and full wet bar. The outdoor oasis is bordered by the home on three sides and the 3rd hole of TPC Prestancia on the fourth, and includes a sparkling pool and spa, integrated grill, shaded area for dining and plenty of space to enjoy Florida sunshine. Residents of this Audubon Cooperative Sanctuary community enjoy watching families of sandhill cranes while bald eagles soar overhead. Just minutes from Siesta Key Beach and downtown Sarasota, the home’s new roof, pull down storm shutters, and a whole home generator provide worry-free living. Optional membership is available at TPC Prestancia Golf Club featuring two 18-hole courses, dining, and social activities.

3988 Losillias Drive, Sarasota

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