Downtown Homes with Two Story Property Description

Downtown Homes with Two Story Property Description

Welcome to Downtown Sarasota, Florida—an enchanting blend of coastal charm and urban sophistication. Nestled along the stunning Gulf Coast, this vibrant city is renowned for its rich cultural scene, beautiful beaches, and a warm, welcoming community. Downtown Sarasota boasts a delightful mix of boutique shops, gourmet restaurants, and art galleries, all set against a backdrop of swaying palm trees and picturesque waterfront views. Whether you’re strolling along the bayfront, enjoying a performance at the Van Wezel Performing Arts Hall, or indulging in fresh seafood at a local eatery, you’ll find that Downtown Sarasota offers an unparalleled lifestyle.

For those seeking the perfect home in this idyllic setting, look no further than the exquisite two-story properties that grace the area. These homes are designed for both comfort and elegance, featuring spacious layouts that seamlessly blend indoor and outdoor living. With ample room for entertaining and family gatherings, two-story homes in Downtown Sarasota often boast modern amenities, high ceilings, and stunning architectural details. Many properties come equipped with lush gardens, private balconies, and even breathtaking views of the sparkling Sarasota Bay.

Living in Downtown Sarasota means enjoying not just a home, but a lifestyle filled with endless opportunities for recreation and relaxation. From the beautiful beaches just a short drive away to the vibrant nightlife and cultural events, every day feels like a vacation. Experience the best of both worlds with a two-story home in this thriving community—where urban excitement meets coastal tranquility. Come discover your dream home in Downtown Sarasota today!

Newest Downtown Homes with Two Story Property Description

1990 Main Street Unit 3, Sarasota
$529,000
2 Beds ⋅ 2 Baths ⋅ Cityscape At Courthouse Centre SubDv. ⋅ 34236 Zip Code
Virtually Staged. Experience a distinctive downtown lifestyle from this rare two-story penthouse residence at Cityscape at Courthouse Centre. Offering 2 bedrooms, 2 bathrooms, secure building access, elevator service, assigned under-building parking, and a thoughtfully designed multi-level floor plan, this unique residence combines the character of an urban loft with the comfort and privacy of a traditional home. Exposed ductwork adds an industrial-chic aesthetic, while the private balcony offers city views and the perfect place to enjoy your morning coffee or unwind at the end of the day. The separation between the living areas and private bedroom level creates an ideal balance for everyday living, entertaining, and hosting overnight guests. Perfectly positioned above Main Street, you'll find yourself immersed in the energy of downtown Sarasota, where award-winning restaurants, sidewalk cafés, artisan coffee shops, boutiques, theaters, galleries, fitness studios, and everyday conveniences are all just steps from your front door. Whether enjoying a morning walk along Sarasota Bay, an evening performance at the Sarasota Opera House, cocktails overlooking the marina, or one of the city's many art festivals and cultural events, this location places the very best of Sarasota within easy reach. Bayfront Park, Marina Jack, Marie Selby Botanical Gardens, Lido Beach, and the renowned shopping and dining of St. Armands Circle are all just minutes away. Thoughtfully maintained and freshly updated, the residence has been freshly painted and features new vinyl flooring, creating a clean, move-in-ready feel while preserving the distinctive architectural appeal of this rarely available floor plan. Hunter Douglas blinds are installed throughout, providing a sophisticated finishing touch along with enhanced comfort, privacy, and control of natural light. Whether you're seeking a full-time residence, a seasonal escape, or an elegant lock-and-leave retreat, this penthouse delivers an exceptional combination of location, style, comfort, and value in the heart of one of Florida's most desirable downtown destinations. Opportunities to own a two-story penthouse in Cityscape at Courthouse Centre are few and far between. Discover the possibilities, embrace Sarasota's vibrant urban lifestyle, and make this exceptional residence your own.

1990 Main Street Unit 3, Sarasota

800 N Tamiami Trail Unit 103, Sarasota
$610,000
1 Beds ⋅ 3 Baths ⋅ Alinari SubDv. ⋅ 34236 Zip Code
Welcome to Unit 103 at Alinari at Rosemary Place, a distinguished residence within one of downtown Sarasota’s premier luxury condominium addresses. Positioned in the vibrant Rosemary District, this spacious first-floor garden-style home offers the rare combination of elegant design, generous scale and desirable ground-level access, delivering comfort of a private residence with the ease of maintenance-free condominium living. Encompassing 1,684 square feet of heated living space and 1,936 total square feet including the outdoor patio, this one-bedroom plus loft residence with three full baths lives exceptionally large. High volume ceilings, expansive glass windows, and sliding doors flood the interiors with natural light, creating an airy ambiance and seamless indoor-outdoor flow. The open and flexible floor plan offers well-proportioned living and dining areas ideal for everyday living and effortless entertaining. The thoughtfully designed layout allows versatility to suit your lifestyle, whether designing a refined lounge, home office, guest retreat or creative loft space. The kitchen integrates beautifully with the main living areas, encouraging intimate evenings and casual gatherings. Multiple full baths provide exceptional convenience and privacy for residents and visitors alike. With building no stairs or elevators required to access your residence, this distinctive residence delivers accessibility and discretion. Alinari elevates daily living with an exceptional suite of resort-style amenities, including 24-hour concierge and security, a heated pool and spa, state-of-the-art fitness center, club room, theater, wine room, business center, library, grilling area, and guest suites for visiting family and friends. The 18-story reinforced concrete high-rise features refined plazas, fountains, a private recreational parcel, redesigned lobby and full front-desk services. Recent 2025 enhancements include upgrades to the pool area, planters, theater, game room and catering kitchen. In Flood Zone X and outside the floodplain, Alinari's lobby and guest parking are elevated approximately 17 feet above base sea level, with residential garage parking positioned more than 30 feet above sea level. This residence includes a secured garage parking space and a climate-controlled assigned storage unit. The association maintains strong reserves with no current or upcoming assessments. Moments from Bayfront Park, Sarasota’s waterfront promenade, world-class dining, cultural venues, boutiques and evolving Sarasota Bay Park project, this residence captures the essence of downtown Sarasota luxury living with coastal accessibility. Unit 103 represents a rare opportunity for refined ground-level living in one of Sarasota’s established and architecturally distinguished condominium communities, where comfort, convenience and elevated Florida living converge.

800 N Tamiami Trail Unit 103, Sarasota

800 N Tamiami Trail Unit 321, Sarasota
$699,000
2 Beds ⋅ 2 Baths ⋅ Alinari SubDv. ⋅ 34236 Zip Code
A rare townhouse-style residence in the heart of Downtown Sarasota, Alinari #321 offers something remarkably difficult to find in condominium living: multiple levels, exceptional private outdoor space and a rooftop terrace all its own. One of Alinari’s distinctive Terrazza residences, this two-bedroom, two-bath home combines 1,734 square feet of interior living with an impressive 3,389 total square feet, creating a city retreat that feels decidedly different from the traditional high-rise floor plan. A private entrance introduces a dramatic, light-filled interior where soaring cathedral ceilings, an open layout and oversized impact windows give the main living spaces an airy sense of volume. The contemporary living and dining areas flow easily together, while French doors extend the interiors outdoors and reinforce the residence’s indoor-outdoor character. Recently renovated, the kitchen is sleek and functional with custom cabinetry, stone countertops, a tile backsplash and stainless-steel appliances. Its open design keeps the kitchen connected to the surrounding entertaining spaces while maintaining a clean, modern aesthetic. With its French door access to the larger terrace, the flexible first-floor bedroom/den is accompanied by a full bath, providing separation from the primary suite and creating an ideal arrangement for overnight guests, a home office or additional living space. An inside laundry room adds everyday convenience. Upstairs, the primary suite becomes a secluded retreat of its own. Generously proportioned and removed from the main living level, it includes a walk-in closet and an en-suite bath with dual sinks, a soaking tub, separate shower and private water closet. French doors open to the second private balcony, adding yet another outdoor connection. Crowning the residence is an expansive private rooftop terrace—an exceptional outdoor retreat above the city. With glimpses of Sarasota Bay and abundant room for lounge seating, dining and entertaining, this rare extension of the home’s living space offers a special opportunity to create a resort-inspired escape above the city. Residence 321 also conveniently includes one deeded covered parking space and a private storage locker. Alinari complements this unusual residence with an extensive collection of amenities, including on-site management, a stylish club room, tearoom, business center and conference rooms, library, wine room with optional owner wine lockers, theater, fitness center, sauna, aerobics room and men’s and women’s locker rooms. Outdoors, residents enjoy a resort-style swimming pool with sundeck and cabanas, grilling areas and a heated spa, while guest suites are available to owners on a first-come basis. Set within Sarasota’s vibrant Rosemary District, Alinari puts the best of the city close at hand. The Bay Park and Sarasota’s waterfront are moments away, with Downtown Sarasota’s restaurants, galleries, theaters, boutiques and Farmers Market nearby. The Van Wezel Performing Arts Hall, Marina Jack and the city’s celebrated cultural attractions add to the downtown lifestyle, while St. Armands Circle and the white sands of Lido Beach are just a short drive away.

800 N Tamiami Trail Unit 321, Sarasota

1513 Oak Street Unit 18, Sarasota
$1,395,000
3 Beds ⋅ 3 Baths ⋅ Burns Court Villas SubDv. ⋅ 34236 Zip Code
Located in the heart of Sarasota’s iconic Burns Court, this three-bedroom, two-story residence at Burns Court Villas offers the privacy and comfort of a single-family home with the walkability and energy of downtown just outside your door. Spanning nearly 2,000 square feet, the thoughtfully designed layout is enhanced by multiple outdoor living spaces—including the largest private courtyard in the community and three private bedroom balconies. Beyond the solid mahogany front door, refined interiors showcase travertine flooring, crown molding, high ceilings, impact-rated windows and doors, and an abundance of natural light throughout. The main level is designed for effortless everyday living and entertaining, flowing seamlessly from the formal living room—anchored by a gas fireplace and custom built-ins—to the dining area and sunlit family room overlooking the lush courtyard. The 2023-remodeled gourmet kitchen is appointed with custom wood cabinetry featuring soft-close drawers and pull-out storage, under-cabinet lighting, thick quartz countertops, and an oversized island with seating. Premium appliances include a Sub-Zero refrigerator (2025), Viking gas range and hood (2007), and Miele dishwasher (2022), while upgraded LED lighting enhances both ambiance and functionality. Upstairs, Brazilian cherry engineered hardwood flooring leads to a serene primary suite featuring a private balcony, custom walk-in closet, and a fully renovated en-suite bath completed in 2025 with dual quartz-topped vanities, a tile-and-glass walk-in shower with bench seating, and a dedicated makeup area. Two additional guest bedrooms—each with its own balcony—share a beautifully updated bath with designer finishes. A second-floor laundry room with additional storage cabinetry adds convenience. Burns Court Villas is known for its tranquil, tucked-away atmosphere in the center of downtown Sarasota, offering covered trellised walkways, lush tropical landscaping, peaceful fountains, and charming courtyard spaces that create a uniquely serene residential setting. Residents enjoy a heated pool and spa, lounge area with outdoor fireplace, secure parking, fob-access gates, and enhanced perimeter security. The association also covers many utilities and services, including management, grounds maintenance, pest control, water, sewer, and waste collection. Perfectly positioned moments from downtown Sarasota’s Cultural Coast, this residence places you near Marina Jack, the Bayfront, theaters, galleries, farmers markets, boutique shopping, and acclaimed dining along Main Street. St. Armands Circle, Lido Beach, and Sarasota’s Gulf beaches are just minutes away, creating an exceptional opportunity to enjoy refined downtown living paired with Sarasota’s celebrated coastal lifestyle. A rare opportunity to enjoy refined city living within one of Sarasota’s most distinctive downtown enclaves.

1513 Oak Street Unit 18, Sarasota

1675 5th Street, Sarasota
$2,299,000
4 Beds ⋅ 5 Baths ⋅ Central Park SubDv. ⋅ 34236 Zip Code
Discover modern downtown living in the heart of Gillespie Park, where this brand-new single-family home offers a rare combination of contemporary design, generous living space and exceptional walkability just moments from Downtown Sarasota and the Rosemary District. The property offers 4 bedrooms in total, including 3 bedrooms plus a dedicated office in the main residence and a private 1-bedroom, 1-bathroom attached apartment. Designed for everyday living and entertaining, the main residence features a spacious open floor plan filled with natural light. Engineered hardwood flooring, PGT impact-rated windows and doors, soaring ceilings and thoughtfully selected finishes complement the home’s clean, contemporary design. At the heart of the home, the kitchen features Thermador appliances, generous workspace and a seamless connection to the main living and dining areas. One of the home’s most distinctive features is the approximately 600-square-foot attached apartment complete with its own private entrance, bedroom, bathroom, living room and kitchen. Ideal for guests, multigenerational living, a private home office or potential rental income, this separate living space provides exceptional flexibility while preserving the privacy of the main residence. An attached 2-car garage and additional covered parking provide everyday convenience rarely found this close to downtown. Just outside your door, enjoy easy access to the Rosemary District, Downtown Sarasota’s restaurants, boutiques and arts scene, the Sarasota bayfront and the area’s renowned Gulf beaches. Whether heading out for morning coffee, dinner downtown or a day at the beach, this brand-new home places the best of the Sarasota lifestyle within easy reach.

1675 5th Street, Sarasota

1621 Bay Point Court, Sarasota
$5,395,000
4 Beds ⋅ 5 Baths ⋅ Mooring At Bay Pointe The SubDv. ⋅ 34236 Zip Code
NOW PRICED BELOW RECENT APPRAISAL. Behind a private gate and beneath a canopy of tropical foliage, 1621 Bay Point Court offers a secluded waterfront retreat just moments from downtown Sarasota and the open waters of Sarasota Bay. Set along Hudson Bayou, the home blends timeless coastal architecture and bright interiors with tropical surroundings, covered terraces, a private pool, and a new dock with a 13,000-pound boat lift. Completed in 2025, the residence encompasses 3,647 square feet of air-conditioned living space with 4 bedrooms, 4.5 baths, 2 private offices, a bonus room with sauna and custom details throughout. Upper transoms fill the main living areas with natural light and capture views of the pool, landscape and bayou. Beyond the foyer, the dining room, great room and kitchen flow together for daily living and entertaining. The great room features a floor-to-ceiling quartz fireplace wall and opens to the covered lanai, and heated pool. Travertine and limestone decking, a fountain, fiber-optic pool lighting and several gathering areas complete the outdoor space. A powder bath is positioned nearby. The kitchen features floor-to-ceiling custom cabinetry, quartz countertops, a pearlized herringbone backsplash and a center island with storage on 3 sides. The Thermador appliance suite includes dual convection wall ovens, cooktop, coffee system, microwave, paneled refrigerator, beverage cooler and dishwasher. A concealed walk-in pantry offers custom storage. The main-level primary suite opens to the lanai and overlooks the pool and water. Its Calacatta Gold marble bath includes a freestanding tub, dual vanity, makeup station and oversized glass-enclosed shower. A custom walk-in closet connects to the laundry room, which features built-in cabinetry, a utility sink and Speed Queen appliances. A second en suite bedroom and a custom office with built-in bookcases and cabinetry complete the first floor. Upstairs are 2 additional en suite bedrooms, a private office and a bonus or fitness room with a mirrored wall, closet storage and sauna. Both bedrooms open to an oversized covered terrace overlooking the bayou, treetops and Sarasota skyline. A finished storage area provides additional space. The gated and fully fenced 0.26-acre property encompasses approximately 67 feet of waterfront and includes a new 322-square-foot dock and boardwalk with a 13,000-pound boat lift. The climate-controlled 2-car garage offers custom flooring, extensive storage and provisions for an electric vehicle charger. Additional features include reinforced masonry construction, impact-rated windows, doors and sliders, spray-foam insulation, whole-house water filtration and softening, instant hot water, commercial-grade Wi-Fi, structured media wiring, surround sound, security cameras, smart lighting and a generator panel. The finished-floor elevation is approximately 12 feet, 4 inches NAVD, and there are no association dues. Offering the privacy of a tropical waterfront retreat in the heart of Sarasota, the property is convenient to downtown dining, shopping and cultural venues, Southside Village, Sarasota Memorial Hospital and St. Armand's Circle. Lido Key and Siesta Key beaches are easily accessible, while Sarasota-Bradenton International Airport is nearby, placing Sarasota’s boating, beaches and other destinations within easy reach.

1621 Bay Point Court, Sarasota

1685 6th Street, Sarasota
$1,595,000
5 Beds ⋅ 5 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
LOCATION, LOCATION, LOCATION! If you are seeking a premier home which is steps from the dining, culture, boutiques, and waterfront recreation of Downtown Sarasota/Main St, The Bay Park, the Rosemary District, Five Points Park, and Gillespie Park, this is the one! This beautifully renovated, Key West–inspired 5-bedroom, 2938 sf pool home welcomes you with a magnificent oak tree and gorgeous tropical landscaping. Inside, the chef-owner’s kitchen is a culinary dream complete with a professional Forno gas range, custom soft-close cabinetry, and sleek quartz countertops. High-end finishes elevate the open living areas, including rich hardwood floors, an electric fireplace, and a custom temperature-controlled wine room. A flexible downstairs bonus area with a half bath and closet can easily convert to a luxurious primary suite/5th bedroom. A 600 sf guest apartment, The Pineapple Loft, is consistently ranked 5 stars on Airbnb and features a vaulted ceiling, full kitchen, induction cooking, laundry, and a private balcony— fully qualifying for high-demand weekly rentals! The exterior features a screened courtyard lanai and a heated pool with a waterfall, while the local 10-acre park provides tennis, pickleball, walking trails, and a lively neighborhood scene. Don't miss this perfect blend of historic character, modern luxury, and ultimate flexibility in an incredible location.

1685 6th Street, Sarasota

1798 Lincoln Park Circle, Sarasota
$2,425,000
3 Beds ⋅ 3 Baths ⋅ Lincoln Park On Hudson Bayou SubDv. ⋅ 34236 Zip Code
Discover exceptional West of Trail living in Lincoln Park, an intimate waterfront enclave located along Hudson Bayou in Sarasota, Florida. This beautifully appointed residence offers the rare combination of privacy, boating access, and proximity to Downtown Sarasota, complete with a private deeded boat slip and 10,000 lb lift providing direct access to Sarasota Bay and the Gulf of Mexico. Situated on a quiet, tree-lined cul-de-sac shared by only eight residences, this distinctive 3-bedroom, 2.5-bath home offers 4,234 square feet of thoughtfully designed living space. Built in 2001, the residence blends timeless architectural details, refined craftsmanship, and comfortable everyday living in one of Sarasota’s most desirable West of Trail locations. The spacious floor plan features a private first-floor primary suite, soaring ceilings, crown molding, French doors, custom built-ins, hardwood and marble flooring, and a gas fireplace. Formal and casual living areas flow seamlessly throughout the home, creating an inviting setting for both entertaining and relaxation. At the heart of the residence, the chef’s kitchen features quality finishes, generous workspace, an eat-in dining area, and convenient access to the home’s main gathering spaces. Upstairs, two additional bedrooms share a Jack-and-Jill bathroom, with one bedroom offering a spacious adjoining sitting room and private terrace. A separate office provides a quiet and flexible space for working from home, reading, or managing daily tasks. The outdoor living spaces are equally impressive. Professionally landscaped gardens, bluestone terraces, ambient landscape lighting, and multiple seating and entertaining areas create a peaceful private sanctuary. An outdoor kitchen provides the perfect setting for alfresco dining, while the deeded dock and boat lift make it easy to enjoy boating, fishing, kayaking, and waterfront adventures throughout Sarasota Bay and the Gulf Coast. Tasteful updates completed over the years enhance the home’s comfort and enduring appeal while preserving its classic character. Whether enjoying quiet mornings in the garden, entertaining beneath the stars, or departing from your private boat slip for a day on the water, this Sarasota waterfront home offers an exceptional coastal lifestyle. Ideally located near Downtown Sarasota, Southside Village, Marie Selby Botanical Gardens, Sarasota Memorial Hospital, the Sarasota Bayfront, St. Armands Circle, and the renowned beaches of Siesta Key and Lido Key, this residence delivers an outstanding balance of privacy, convenience, and boating access.

1798 Lincoln Park Circle, Sarasota

433 Central Avenue, Sarasota
$650,000
2 Beds ⋅ 3 Baths ⋅ Rosemary Park SubDv. ⋅ 34236 Zip Code
Experience the best of downtown Sarasota living in this exceptional luxury condominium, where sophisticated design, walkable convenience, and the vibrant energy of the Rosemary District come together in one remarkable residence. This beautifully appointed TURNKEY two-bedroom, two-and-a-half-bath home is located in an exclusive boutique building with only six private residences, offering a level of privacy rarely found in the heart of downtown. Designed with timeless elegance, the open-concept floor plan showcases soaring ceilings, real hardwood flooring throughout, designer Italian cabinetry, granite countertops, stainless steel appliances, a new refrigerator, and a built-in wine bar with beverage refrigerator. Both bedrooms feature luxurious ensuite bathrooms, while the spacious primary suite opens to a private balcony overlooking the Rosemary District and downtown skyline. Thoughtfully upgraded throughout, this residence includes custom California Closets, remote-controlled blinds, new HVAC systems installed in 2024 and 2025, and a new water heater installed in 2025, all backed by transferable warranties for added peace of mind. Residents enjoy assigned covered parking, elevator access, gated entry, and additional storage, all just moments from Sarasota's most celebrated destinations. Stroll to The Bay Park, Bayfront Marina, Whole Foods, Main Street, the Saturday Farmers Market, art galleries, award-winning restaurants, live entertainment, and the flourishing Rosemary Arts District, or spend the afternoon at Lido Key Beach, just minutes away. Offering an unmatched combination of luxury finishes, boutique living, recent high-value upgrades, and one of Sarasota's most desirable walkable locations, this exceptional residence delivers the very best of downtown Sarasota living.

433 Central Avenue, Sarasota

1680 Cherry Lane, Sarasota
$2,649,000
5 Beds ⋅ 4 Baths ⋅ Laurel Park SubDv. ⋅ 34236 Zip Code
A rare opportunity to own a one of a kind custom built residence in the heart of downtown Sarasota, 1680 Cherry Lane is tucked into one of Laurel Park's most charming streets while being just moments from everything that makes downtown so special. Blending timeless architecture with modern luxury, this brand new residence offers an exceptional lifestyle defined by thoughtful design, refined finishes, and one of Sarasota's most coveted locations. Spanning 3,128 square feet, this thoughtfully designed two story home features five bedrooms and four bathrooms, including a first floor primary suite and an additional main level bedroom that can easily function as a private office, guest suite, or den. Upstairs, three additional bedrooms provide flexibility for family, guests, or multigenerational living, creating a floor plan that is equally suited for everyday living and entertaining. At the heart of the home, the open concept living spaces are centered around a beautifully appointed chef's kitchen featuring premium Thermador appliances, custom cabinetry, quartzite countertops, and an oversized island that seamlessly connects the kitchen, dining, and living areas. Expansive PGT impact rated windows and doors flood the home with natural light while creating a seamless connection to the outdoor living spaces, while the private pool provide the perfect backdrop for year round entertaining and relaxation. Located within the highly sought after Southside Elementary School district, this exceptional residence is just minutes from downtown Sarasota's acclaimed restaurants, boutique shopping, Burns Court, Bayfront Park, Marina Jack, the city's vibrant arts and cultural scene, and Sarasota's world renowned Gulf beaches. Combining custom craftsmanship, luxury finishes, and an unbeatable location, 1680 Cherry Lane presents a rare opportunity to own a brand new custom home in one of Sarasota's most desirable neighborhoods.

1680 Cherry Lane, Sarasota

Start Your Search

How much is your home worth?

Get instant property value now!