Sarasota County Homes with Custom Architectural style

Sarasota County Homes with Custom Architectural style

Welcome to Sarasota County, Florida, a captivating coastal gem known for its stunning beaches, vibrant arts scene, and rich cultural heritage. Nestled on the southwestern coast of the Sunshine State, Sarasota boasts a unique blend of natural beauty and urban sophistication. With its pristine shores along the Gulf of Mexico, residents and visitors alike can indulge in sun-soaked days, whether lounging on the famous Siesta Key Beach or exploring the scenic parks and nature preserves that dot the landscape.

One of the most alluring aspects of Sarasota is its diverse architectural styles, particularly in the realm of custom homes. Here, you’ll find a treasure trove of residences that showcase innovative designs and personalized touches. From Mediterranean-inspired villas to modern masterpieces, Sarasota’s custom homes reflect the individuality of their owners while harmonizing with the stunning surroundings. Imagine waking up in a home that boasts expansive windows framing breathtaking views of the Gulf or a cozy retreat with lush landscaping and outdoor living spaces perfect for entertaining.

The real estate market in Sarasota is thriving, offering an array of options for those seeking their dream home. Whether you’re looking for a luxurious waterfront estate, a charming bungalow in a historic neighborhood, or a contemporary condo with resort-style amenities, Sarasota has it all. With its warm climate, thriving community, and a plethora of recreational activities, it’s no wonder that Sarasota County is a sought-after destination for those looking to plant roots in a picturesque setting. Come explore the possibilities and discover your perfect Sarasota home today!

Newest Sarasota County Homes with Custom Architectural style

156 Bishopscourt Road, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ Bishops Court At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home features a Sonos surround sound throughout. The backyard, overlooking the preserve, is a quiet sanctuary, where you can enjoy the open air, freeform pool with spa in complete privacy. The whole-house stereo system goes out to the enclosed back patio, making a lovely place to sit and enjoy a peaceful, rare rainy afternoon with a good book and a cuppa. There is an additional 732 square feet of outdoor deck space off the second floor and rooftop. Recent renovations in 2023 include two main bathrooms with high-end decorator tile, premium glass enclosures, and premium plumbing fixtures, including an elegant standalone bathtub. The powder room has also been completely renovated. The kitchen boasts new ceramic tile floors, backsplashes, an induction cooktop, an LG smart refrigerator, a farmhouse sink, and a garburetor. The laundry room features new ceramic tile floors, a washer and dryer, extensive shiplap walls, and a sliding hanging barn door to the pantry. The second-floor bathroom has new tub fixtures, shiplap walls, and a decorator granite sink area. Additional updates include crown moldings throughout the ground floor, new ceiling fans in all bedrooms and the den/office, with a decorator oversized 52-inch windmill fan in the main bedroom. The home also has new LED ceiling can lights, new plantation shutters in the front hall/foyer, and new Levolor blinds in the kitchen and laundry room. The pool area has been upgraded with a new heat pump pool heater, a new filtration system, and a new pool pump and motor. The lanai has new aluminum framing and screening with a screen door, installed in 2025. The second floor has a new flat roof by Curry Roofing with a warranty. The landscape has been renewed with new trees, bushes, sod, and flower plantings worth $20,000, completed in 2022. Premium decorator light fixtures have been added to the dining room, kitchen, and foyer. The entire house exterior was painted in August 2025, and a new second-floor deck was also completed in August 2025. The pristine condition of the lovely home, combined with the quiet, private setting on double lot at the end of a cul-de-sac, makes it the perfect Florida retreat for you and your loved ones. Situated in the enclave of Bishopscourt, a maintenance-free neighborhood behind the gates of The Oaks Preserve, lawn and landscape maintenance, as well as irrigation, are included in the homeowner’s association fees. You will delight in this graceful, inviting home. Membership in The Oaks, Sarasota’s finest golf and country club, is required with homeownership. With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of social events, The Oaks is truly Sarasota’s premier golf and country club. There is currently no waiting list for either Golf or Sports/Social membership.

156 Bishopscourt Road, Osprey

3787 Eagle Hammock Drive, Sarasota
$950,000
4 Beds ⋅ 3 Baths ⋅ Hammocks SubDv. ⋅ 34240 Zip Code
Set behind lush, mature landscaping on a premium preserve-view lot, this custom-built pool residence by Coachman Homes offers refined Florida living in the desirable gated community of The Hammocks in Sarasota. Featuring 4 bedrooms, 3 full bathrooms, a dedicated office, and a 3-car garage with epoxy floors, this beautifully maintained home combines elegant architectural details, exceptional entertaining spaces, and a private natural backdrop. Fresh new interior and exterior paint enhance its beautifully maintained appeal. Soaring 14-20 foot ceilings with elegant tray and double tray ceilings, ceramic tile flooring, tray ceilings, crown molding, and a double-sided gas fireplace create an inviting atmosphere throughout the open living spaces. The chef’s kitchen features quartz countertops, wood cabinetry, a five-burner gas cooktop with updated vent, double ovens, updated backsplash, a spacious center island, and convenient slide-out cabinet storage. Expansive pocketing sliders open to a generous lanai featuring a resort-style gas heated pool and spa all framed by tranquil preserve views. One of the home’s standout features is the fully enclosed, climate-controlled second/outdoor kitchen and entertaining space, complete with a separate brand new mini-split A/C system, gas grill, side burner, commercial vent hood, beverage refrigerator, dishwasher, wine cooler, and beverage cooler. With direct access to the pool and lanai, this impressive addition creates an exceptional setting for hosting guests and enjoying the Florida lifestyle. The spacious primary suite offers private lanai access, picturesque views, dual walk-in closets with upgraded storage systems, and a well-appointed bath featuring dual vanities, a Jacuzzi soaking tub, and a separate walk-in shower. A dedicated office with custom built-in cabinetry and wood flooring provides a comfortable, functional workspace. Additional highlights include security system, comprehensive hurricane protection with impact glass and a whole-house gas generator installed in 2019. Recent improvements include A/C systems (2021 and 2016), a pool pump (2020), pool heater (2023), washer and dryer (2021), wine and beverage coolers (2021), refrigerator and dishwasher (2025), and a new water heater. The irrigation system, sourced from a private well, supports vibrant landscaping, and landscape lighting elevates the property’s curb appeal. Enjoy the privacy of a preserve setting with convenient access to shopping, dining, golf, entertainment, and major roadways. Publix is less than a mile away, and Siesta Key is within reach for a day at the beach. Combining impressive architectural details, exceptional indoor-outdoor living, a distinctive second kitchen, and inviting pool and spa, this remarkable residence with no CDD fees offers a sophisticated Sarasota lifestyle. Schedule your private showing today!

3787 Eagle Hammock Drive, Sarasota

2555 Ruffing Court, Sarasota
$690,000
3 Beds ⋅ 4 Baths ⋅ Payne Park Sub SubDv. ⋅ 34237 Zip Code
Virtually Staged. Enjoy modern style and low-maintenance living in this three-story, end-unit townhome with only one shared wall at 2555 Ruffing Court in Payne Park Village. Built by David Weekley Homes, this home presents inviting indoor spaces and the charm of a coastal neighborhood, just across from Payne Park and The Legacy Trail. A fenced courtyard with tropical landscaping and a covered entry creates a welcoming first impression. Inside this 3-bedroom, 3.5-bath residence, luxury vinyl plank flooring flows through the main living areas, while MSI Quartz countertops provide a consistent upscale finish throughout the kitchen and baths. Carpeting adds comfort to all three bedrooms, while tile flooring provides a practical finish in each bathroom. With a bedroom and full bath on each of the three levels, along with flexible living spaces, this thoughtfully designed layout offers versatility for multi-generational living, so you can choose your preferred primary suite on any floor. The first floor includes a private bedroom with direct access to a bath. A flex nook, foyer, and attached two-car garage with storage add functionality. Upstairs, the second level is the heart of the home, where an open great room, dining area, and kitchen create space for living and effortless entertaining. The kitchen is appointed with white cabinetry, MSI Quartz counters, stainless steel appliances, a tiled backsplash, recessed lighting, and a center island with sink and breakfast bar seating. Luxury vinyl plank floors and abundant natural light enhance the space. This level also includes a powder room, laundry closet, and pantry. The primary suite includes a walk-in closet and en suite bath with dual vanities, MSI Quartz surfaces, private water closet, and a walk-in shower with a rainfall showerhead. The third floor adds a bedroom with a walk-in closet, a full bath, and an inviting loft overlooking the great room below. The loft can serve as a home office, media lounge, creative studio, or additional gathering space. Payne Park Village provides an appealing combination of coastal architecture, landscaped courtyards, green spaces, and private community amenities, including a swimming pool and spa. Payne Park, just across the street, features tennis courts, multi-use paths, disc golf, a skate park, a playground, an amphitheater, a café, and open green areas. The Legacy Trail has additional pedestrian and biking options. Located near downtown Sarasota, this home is close to restaurants, boutiques, galleries, theaters, cultural attractions, and the bayfront. Golfers will appreciate the nearby Bobby Jones Golf Club. Marina Jack, St. Armands Circle, and the beautiful Gulf Coast beaches are also within easy reach. From Payne Park's green space to downtown Sarasota's restaurants, culture, and waterfront, this location puts so much of what makes Sarasota special within easy reach.

2555 Ruffing Court, Sarasota

1241 Gulf Of Mexico Drive Unit 803, Longboat Key
$3,195,000
3 Beds ⋅ 4 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code
The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include TWO under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.

1241 Gulf Of Mexico Drive Unit 803, Longboat Key

1591 Gulf Of Mexico Drive Unit 515, Longboat Key
$2,670,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to be a resident at The St. Regis Longboat Key for under $3,000,000. Enter your private elevator into a dramatic living area with high ceilings and expansive glass featuring spectacular views of Sarasota Bay. The living area opens to a large outdoor terrace with a Wolf gas grill for easy entertainment. The chef’s kitchen is equipped Poggenpohl cabinetry, top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, large refrigerator and beverage center. If you don’t feel like cooking, just order room service from one of The St. Regis’s esteemed dining venues. The Earth finishes were curated by Marc Michaels Interior Design and were selected to remain timeless. The owner’s suite is luxurious and opens to the outdoor terrace for your morning coffee. Relax after a day at the beach or saltwater lagoon in the spa like bathroom boasting double vanities, water closet with Toto bidet toilet, soaking tub and oversize shower with seamless glass enclosure. The floor plan was altered to include two full bathrooms and is large enough to graciously accommodate overnight guests. A custom built owner’s suite closet and motorized blinds complete this beautiful residence. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!

1591 Gulf Of Mexico Drive Unit 515, Longboat Key

1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key
$5,995,000
3 Beds ⋅ 5 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code
Experience an exceptional expression of Gulf-front living in this impeccably maintained penthouse at The Water Club on Longboat Key. Occupying the coveted northwest penthouse position on the 11th floor of Building One, this pristine residence encompasses approximately 3,400 square feet with three bedrooms and four-and-a-half baths. Three separate balconies capture sweeping views of the Gulf of America, providing inviting settings for morning coffee, alfresco relaxation, and spectacular sunsets. An under-building parking space and an additional semi-private garage complement this distinguished waterfront offering. Set within 16 acres of magnificent beachfront grounds, The Water Club offers an extraordinary collection of amenities that extends the comforts of home well beyond your residence. The beautifully renovated, 18,000-square-foot clubhouse provides elegant spaces for relaxation, recreation, and entertaining, including a club room with billiards, a library with fireplace, and a ballroom with catering kitchen. Four lighted Har-Tru tennis courts, a heated junior Olympic pool, hot tub, spa, and fitness center create a resort experience, while a firepit, grills, and direct access to a beautiful stretch of beach invite you to embrace the coastal lifestyle. Gated security, concierge services, on-site management, and climate-controlled storage add everyday comfort and convenience. Ideally situated at the southern end of Longboat Key, this residence places you minutes from the boutiques and dining of St. Armands Circle, downtown Sarasota’s vibrant waterfront and cultural attractions, and an array of exceptional restaurants. Nearby conveniences include Publix and CVS, with the Longboat Key Club’s golf, tennis, and dining offerings close at hand. The neighboring St. Regis further enhances this desirable coastal setting, and Sarasota Bradenton International Airport is approximately 20 minutes away. Welcoming up to two pets, The Water Club is equally appealing as a full-time residence or a refined seasonal retreat. Discover the rare combination of penthouse privacy, generous living spaces, captivating Gulf views, and an exceptional beachfront lifestyle. Schedule your private showing today.

1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key

871 Macewen Drive, Osprey
$3,190,000
5 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
A gracious columned front porch, classic dormers and a grand entry staircase introduce this distinctive residence in The Oaks. Set along the 13th hole, the home and separate guesthouse occupy more than half an acre framed by mature trees, with southern exposure, expansive greenspace to the east and no golf cart path bordering the property's side of the course. The setting feels remarkably private and spacious, with beautiful views from virtually every room. Timeless Southern character meets thoughtful updates, including a new tile roof, new hurricane-rated windows and skylights, freshly painted interiors and exterior, refinished wood floors, new upstairs flooring and updated lighting inside and out. Designer wallpaper and a new powder room vanity add fresh style, while the generous covered front porch offers an inviting place for morning coffee and relaxed gatherings. The kitchen features white cabinetry, quartz countertops, a waterfall-edge peninsula and a walk-in pantry. An oversized Viking six-burner gas range with a griddle, a Thermador refrigerator, a EuroCave wine cooler, a built-in Miele coffee maker and reverse osmosis system complement the space. Formal dining, a living room with a fireplace and a light-filled family room create inviting settings for entertaining and everyday living. The main-level primary suite overlooks the pool and grounds, spacious custom-organized closet, dual vanities, soaking tub and separate shower. A study and an exceptionally large laundry room with abundant storage complete the first floor. Upstairs, three bedrooms each feature an en suite bath and walk-in closet. A hidden playroom with skylights offers a magical retreat for imagination and creativity, with its area additional to the stated living square footage. With a full kitchen and bath, the separate guesthouse provides flexible accommodations for visitors, extended family or an au pair. Together, the main home and guesthouse frame an inviting outdoor retreat with an open-air pool and spa, palms and expansive golf course views. Generous entertaining areas, a fenced yard and a screened patio with a fireplace offer spaces to gather or unwind throughout the seasons. The home also includes a recently installed whole-house Generac generator with a 200-gallon buried propane tank. The Oaks lifestyle includes golf, tennis, pickleball, fitness and multiple dining venues, complemented by social gatherings and holiday traditions. Enjoy a casual meal at the Overlook or an evening celebration at the club, with the Legacy Trail, Pine View School and the beaches of Siesta Key and Casey Key nearby. Located in Flood Zone X with no reported history of flooding, this residence brings together architectural charm, substantial recent improvements and an exceptional golf course setting.

871 Macewen Drive, Osprey

1875 Oleander Street, Sarasota
$2,395,000
3 Beds ⋅ 3 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Impeccably maintained and thoughtfully designed, this custom-built John Cannon home offers an inviting blend of timeless elegance, spacious interiors, and relaxed Florida living in Sarasota’s desirable West of Trail neighborhood. Set along beautiful, tree-lined Oleander Street adjacent to Cherokee Park, this residence welcomes you with an open floor plan and soaring 14-foot ceilings that create an immediate sense of space and light. The well-appointed kitchen features solid wood cabinetry, Bosch stainless steel appliances, and a breakfast bar with seating for four—ideal for casual dining and entertaining. The inviting family room, complete with a fireplace, overlooks the pool and patio, while pocketing sliding glass doors seamlessly connect indoor and outdoor living. A professionally painted mural gives the formal dining room a rich botanical backdrop infused with tropical elegance. There is a private office with built-in cabinetry providing a comfortable, dedicated workspace The expansive primary suite is a peaceful retreat, featuring dual walk-in closets, separate vanities, dual sinks, a jetted soaking tub, and a separate shower. Two additional bedrooms provide generous closet space, with one featuring an ensuite bath. Plantation shutters throughout enhance the home’s understated elegance and tropical ambiance. Outdoors, a gorgeous, screened pool and spa are surrounded by an expansive tiled patio and outdoor kitchen have abundant space for lounging, dining, and entertaining in the Florida sunshine. Practical amenities include a spacious laundry room with a sink and built-in cabinetry, plus an oversized two-car garage with workshop cabinetry and access to a large attic for additional storage. The location is equally appealing. Enjoy a short walk to Southside Elementary School and stroll a few blocks north to the boutiques, restaurants, and Morton's Gourmet Market in Southside Village. Sarasota Memorial Hospital, Downtown Sarasota, the Bayfront, and the area’s beautiful beaches are all conveniently accessible. Experience the elegance, comfort, and exceptional location of this West of Trail residence. Schedule your private showing today.

1875 Oleander Street, Sarasota

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