Downtown Homes with Two Story Style

Downtown Homes with Two Story Style

Welcome to Downtown Sarasota, Florida – a vibrant gem nestled on the Gulf Coast, where the sun-kissed beaches meet a bustling urban lifestyle. Known for its rich cultural scene, Downtown Sarasota is a captivating blend of art, dining, and outdoor recreation. The area boasts a variety of attractions, including the renowned Ringling Museum of Art, the picturesque Marie Selby Botanical Gardens, and a thriving farmers market every Saturday morning. With its stunning waterfront views and a plethora of parks, residents can enjoy a leisurely stroll along the bay or indulge in a picnic under the swaying palms.

For those seeking a home that embodies both elegance and comfort, Downtown Sarasota offers an impressive selection of two-story houses. These architectural marvels provide ample space for families and individuals alike, with thoughtfully designed layouts that maximize both functionality and style. Picture yourself entertaining guests in a spacious living area or enjoying quiet evenings on a cozy balcony that overlooks the vibrant cityscape.

The two-story homes in Downtown Sarasota often feature modern amenities, high ceilings, and expansive windows that flood the interiors with natural light. Many properties are conveniently located near trendy shops, gourmet restaurants, and cultural hotspots, making it easy to embrace the lively lifestyle this city has to offer.

Whether you’re looking for a chic urban retreat or a family-friendly haven, Downtown Sarasota’s two-story homes promise the perfect blend of sophistication and convenience. Discover your dream home in this enchanting city where every day feels like a vacation!

Newest Downtown Homes with Two Story Style

$1,595,000
5 Beds ⋅ 5 Baths ⋅ A4702560 MLS
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, Downtown
$310,000
2 Beds ⋅ 3 Baths ⋅ A4702360 MLS ⋅ 3 BLDG.
Central Park ll is located close to the downtown area of Sarasota and also just minutes to a large hospital when emergency or hospital care is needed. You could walk or ride a bicycle to the downtown area in minutes. The unit is located in the back of the complex. It is a two bedroom, two and half bath townhouse. The kitchen has been updated with cabinets, counter tops, stove and microwave. The flooring is laminate and carpet. Both bedrooms are upstairs, each having a bathroom. The half bath is downstairs. A stackable washer and dryer are also located in the unit. There is a small storage area under the stairs in the living room. There are two storage rooms located on the side of each patio. This community offers a community pool, fitness center and clubhouse. There is also a kayak launch and storage that residents may use. Buyers to verify all room sizes.

850 S Tamiami Trail Unit 325, Downtown
$529,000
2 Beds ⋅ 2 Baths ⋅ A4701573 MLS ⋅ Cityscape At Courthouse Centre BLDG.
Experience a distinctive downtown lifestyle from this rare two-story penthouse residence at Cityscape at Courthouse Centre. Offering two bedrooms, two baths, 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 ideal 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. Ideally 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 near 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 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 ready for its next chapter, the residence offers timeless potential for personalization while preserving the distinctive architectural appeal of this rarely available floor plan. The air conditioning system was replaced in 2023, providing added peace of mind, while both bedrooms feature convenient motorized window shades for enhanced comfort and privacy. 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 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 4, Downtown
$2,595,000
3 Beds ⋅ 3 Baths ⋅ A4701211 MLS
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, Downtown
$1,749,990
3 Beds ⋅ 3 Baths ⋅ A4700595 MLS
Often desired but rarely found! Perfectly positioned in the heart of Laurel Park - one of Sarasota's most coveted neighborhoods - this exceptional 3-bedroom, 3-bath custom residence spanning 2,335 sqft offers the ultimate downtown Sarasota lifestyle. While Laurel Park is celebrated for its historic charm, opportunities to own a newer custom-built home with today's construction standards, modern design aesthetic, luxury finishes and a private pool are exceptionally rare. From your front door, enjoy a short stroll to award-winning restaurants, boutique shopping, the Bayfront, Marina Jack, Selby Gardens, theaters, art galleries, Payne Park and the weekly farmers market. Designed by acclaimed architect Mark Sultana of DSDG and built in 2019, this meticulously crafted residence offers the quality and peace of mind you'll appreciate - including concrete block construction, hurricane-impact windows and doors, a whole-house generator (2025), EV charger and energy-efficient systems. Inside, modern designed interiors with clean lines create a sophisticated yet welcoming atmosphere. The thoughtfully designed floor plan features light-filled living spaces with luxury vinyl plank flooring throughout, custom cabinetry, quartz countertops, pocketing sliders and spacious guest suites. The gourmet kitchen is equipped with a large split island with seating, premium LG appliances, Bosch dishwasher, walk-in pantry and a wine cooler. Living and dining spaces are open and light filled - perfect for entertaining or enjoying the tropical views and zen-like gardens. Step outside to the gas-heated saltwater pool and spa - the centerpiece of this private backyard retreat. Enjoy an outdoor kitchen with Artisan grill, multiple entertaining spaces, an expansive rooftop deck and professionally-designed landscaping that beautifully showcases the Selby-like botanical grounds. The result is a tranquil, resort-inspired setting that feels worlds away - yet is just blocks from downtown Sarasota. For buyers seeking the rare combination of downtown walkability, newer construction and contemporary architecture - 543 Columbia Court represents one of Laurel Park's finest offerings. A home of this caliber—with a pool, rooftop deck and today's build quality in one of Sarasota's most cherished neighborhoods — is an opportunity that seldom comes to market.

543 Columbia Court, Downtown
$749,000
2 Beds ⋅ 3 Baths ⋅ A4700912 MLS ⋅ 5th & Central BLDG.
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, Downtown
$2,749,000
5 Beds ⋅ 4 Baths ⋅ A4698379 MLS
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, Downtown
$2,799,000
5 Beds ⋅ 5 Baths ⋅ A4697829 MLS
Virtually Staged. Rare brand-new construction in the heart of Laurel Park, 1681 Oak Street offers the ideal blend of modern luxury, thoughtful functionality, and an unbeatable downtown Sarasota lifestyle. Perfectly positioned in one of Sarasota’s most sought-after neighborhoods, this newly built residence places you just moments from downtown dining, shopping, Bayfront Park, Burns Court, Marina Jack, and Sarasota’s world-renowned Gulf beaches, while offering the charm and convenience of coveted downtown living. Spanning 3,128 square feet, the thoughtfully designed two-story floor plan features five bedrooms and four baths, 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 layout that balances everyday comfort with long-term versatility. Designed for both elevated entertaining and daily living, the open-concept interior is centered around a beautifully appointed kitchen with premium Thermador appliances, custom cabinetry, quartzite surfaces, and seamless connection to the main living spaces. Expansive impact-rated PGT windows and doors fill the home with natural light while providing peace of mind and enhancing the home’s clean, modern aesthetic. Outside, a serene private pool creates a true backyard retreat and extends the living experience outdoors for year-round enjoyment. Whether hosting friends after dinner downtown or enjoying a quiet afternoon at home, the outdoor setting offers the perfect balance of privacy and relaxation. Located within the highly sought-after Southside Elementary School district and just minutes from Sarasota’s beaches, cultural amenities, restaurants, parks, and waterfront, 1681 Oak Street presents a rare opportunity to own a newly built home in Laurel Park, where quality construction, location, and lifestyle come together in one exceptional offering.

1681 Oak Street, Downtown
$1,259,000
2 Beds ⋅ 3 Baths ⋅ A4686656 MLS ⋅ Thegallerysarasota BLDG.
Under Construction. Residence 401G at The Gallery Sarasota offers a rare blend of single-level convenience, private rooftop living, and boutique downtown design. This 2-bedroom plus office residence features 2.5 baths, 1,334 square feet of interior living space, and a private rooftop terrace with a partial water view. The main level is designed for effortless everyday living, with 10'4" ceilings, full-height windows, a generous primary suite, powder bath, laundry, and a modern kitchen anchored by a 10-foot statement island. Upstairs, the private rooftop level creates a distinctive retreat with a 156-square-foot terrace, a private office or den, and a second primary suite with its own terrace. The dual-suite layout offers exceptional flexibility for guests, extended stays, or shared ownership. The Gallery Sarasota is an iconic 6-level, 60-residence boutique mid-rise located above the floodplain in a highly walkable downtown setting near the bay, Whole Foods, Main Street, The Bay Park, and the Rosemary District. Residents enjoy direct-to-outdoors entries for a more private, less hotel-like feel, impeccably crafted Italian finishes, deeded private garage parking, storage, a rooftop pool and social lounge, and a two-room fitness center with yoga studio. With just one residence remaining in the Majestic Rooftop Collection, 401G presents a rare opportunity to experience private rooftop living in downtown Sarasota. Schedule a private hardhat tour to experience the residence, amenities, and walkable downtown location firsthand.

1305 4th Street Unit 401G RT, Downtown
$317,500
2 Beds ⋅ 3 Baths ⋅ A4684292 MLS ⋅ Central Park BLDG.
Beautiful townhouse in Central Park II Recently painted with laminant flooring thruout the unit, two bedrooms upstairs each with own bath a half baths located close to downtown. This pet friendly complex has swimming pool , clubhouse and tennis courts. Close to downtown and a short ride to St Armands and the beaches.

850 S Tamiami Trail Unit 630, Downtown
$1,895,000
5 Beds ⋅ 4 Baths ⋅ A4680261 MLS
Own a Sarasota Bay view home today. Introducing 1156 Cocoanut Avenue, a newly built modern residence that delivers bold architecture, refined finishes, and effortless urban living in the heart of Sarasota. Designed for today’s lifestyle, this striking home blends clean lines, open spaces, and elevated craftsmanship into a seamless expression of contemporary luxury. The home features five bedrooms and four bathrooms across 2,882 square feet. You are greeted by large-format, marble-look tile throughout the first floor for a seamless, elegant flow. From the moment you arrive, the home’s sleek exterior and architectural presence make a powerful first impression. Inside, light-filled interiors unfold with expansive open-concept living areas, high ceilings, and thoughtfully selected finishes that feel both high end and inviting. The Gourmet chef’s kitchen is equipped with top-of-the-line Café appliances featuring elegant gold accents, premium cabinetry, and seamless Calcutta quartz countertops throughout the home. The waterfall center island seats 6 comfortably, ideal for family meals, casual gatherings, or hosting large dinner parties. The layout is ideal for modern living—entertaining, everyday comfort, and stylish retreat. Having two spacious living rooms, one on each floor, offers versatile entertaining or relaxed family time. The primary suite is a true retreat with a spa-style bath, soaking tub, walk-in shower, and generous his-and-hers closets. Large-format tile flooring, energy-efficient construction, a two-car garage, and modern architectural details enhance both form and function. Outdoors, a private resort-style backyard awaits with a custom Pebble Tec pool, covered patio with tongue-and-groove ceiling plus stylish full summer kitchen, and a fully fenced lot with rear alley access for added privacy and ease. Additional features include a 2-car garage, energy-efficient design, and modern architectural finishes that emphasize comfort and style. Every element has been intentionally curated to reflect quality and design-forward living, creating a home that feels fresh, refined, and effortlessly functional. Ideally located in Sarasota’s sought-after downtown corridor, near Sarasota’s vibrant downtown, you’re just moments from the Rosemary District, world-class dining, art galleries, theaters, shopping, and the city’s renowned cultural scene. Enjoy quick access to the waterfront, marinas, and Sarasota’s award-winning beaches, all while being tucked into a rapidly growing and highly sought after neighborhood. You are just steps from the Bay and the Van Wezel through the beautiful Pioneer Park path. This is a rare opportunity to own a newly built modern home in one of Sarasota’s most dynamic locations. Schedule your private showing today and experience the lifestyle waiting for you! Would also make an excellent Airbnb. Call today for a showing!

1156 Cocoanut Avenue, Downtown
$975,000
2 Beds ⋅ 3 Baths ⋅ A4676689 MLS ⋅ Library Mews BLDG.
A Hidden Gem in the heart of Downtown Sarasota! Experience vibrant urban living with an old-world European style ambiance at Library Mews. This enclave is a unique intimate gated community of 11 townhome villas. The welcoming private courtyard entrance framed by an arch canopy of bougainvillea leads to the home and sets the stage for the residence’s charm. The private brick-paved courtyard leads you to your shaded indoor-outdoor patio space, an excellent place to dine or simply enjoying Sarasota’s weather. This 1,721 square foot villa features two spacious bedroom suites, two and a half baths plus a separate second-floor garden terrace, and a private garage. Upon entering the front door, the tone is set with creative architecture that provides just the right balance of a pleasing floor plan with functionally-defined living spaces. Warm hardwood floors flow throughout the kitchen, living and dining areas, complimented by soft neutral finishes such as light fixtures, crown molding, tray ceilings with LED lighting, and ceiling fans. The generous living room is highlighted by a stylish gas fireplace, high ceilings, and oversized windows with custom crown molding and a southern exposure for abundant natural light. Hurricane rated sliding glass doors seamlessly connect to the indoor and outdoor spaces. The kitchen overlooks the tranquil courtyard and features a cooking island, stunning Carrera countertops, sleek cabinets, gas cook top, and GE-pro appliances, providing style and functionality. Adjacent to the kitchen is the laundry room with a closet pantry with pull-out drawers, cabinets with countertop space, and a Koolmore washer/dryer combination. Upstairs, the spacious master bedroom boasts a vaulted ceiling and floor-to-ceiling hurricane rated sliding glass doors with cityscape views, along with a large walk-in closet and well-appointed en-suite bathroom. The second bedroom features a custom wall storage with a barndoor and includes a cozy niche area that makes a great reading or office space. For added convenience, a second stackable LG washer/dryer is located on the second level. A few steps up from the two bedrooms is the resurfaced garden terrace offering an idyllic space for relaxing while enjoying views of the city. A single-car garage, accessed from Cocoanut Avenue, is enhanced with custom cabinetry, a butcher block top and a sink. Thoughtfully designed storage is abundant throughout the home, featuring multiple closets, custom cabinetry, built-ins, and a well-equipped garage to keep everything organized and out of sight. Further upgrades include impact sliding doors and bedroom windows, hurricane impact skylight, security system, new roof (2025), new exterior paint, gutters and awnings, hurricane garage door, new tankless water heater and saltwater softener system. This delightful townhouse is situated just steps from the Sarasota Theater District, Sarasota Opera, library, world-class restaurants, Whole Foods grocery store, Marina Jack, and Main Street shopping. Come live and play in the heart of Downtown Sarasota.

200 Cocoanut Avenue Unit 7, Downtown
Start Your Search