Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
4471 TRAILS DR, SARASOTA, FL 34232
$575,00038 Days on yellowkey MLS ID: A4683777
REDUCED by $20,000 (3.4%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1721 Built: 1987Monthly Fee: $193 Tax: $3,485 (2025)Community: TimberlakesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,485
Elementary School: Brentwood Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Fresh new price, same incredible lifestyle. Welcome to this beautifully maintained 3-bedroom, 2-bath single-family home in The Lakes, a sought-after community in the heart of Sarasota. Offering 1,721 square feet of comfortable living space, this residence features a thoughtfully designed split-bedroom floor plan that balances privacy with everyday functionality. Enjoy added peace of mind with a 2023 roof and hurricane protection, including impact windows and/or shutters, providing both security and energy efficiency. The spacious living and dining areas flow seamlessly to a screened porch — the perfect spot for morning coffee or relaxing evenings overlooking the private, tree-lined backyard. The serene outdoor setting creates a peaceful retreat with plenty of room to entertain, garden, or simply unwind. Residents of The Lakes enjoy an impressive array of amenities, including one clubhouse and two community pools, tennis and basketball courts, a fitness center, and scenic walking trails. Ideally located in central Sarasota, you’re just minutes from world-class beaches, exceptional dining, premier shopping, and the area’s vibrant cultural attractions.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Mary Pat Phillips Radford (941-587-9905)
4637 WILLOW WOOD CIR #44, SARASOTA, FL 34241
$299,000296 Days on yellowkey MLS ID: A4655394
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1679 Built: 1982 Tax: $2,219 (2024)Community: Hammocks Iii,Bent TreeVilla
Taxes:$2,219
Elementary School: Lakeview Elementary
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: UNDER $300,000 Freshly Painted & updated 3BR/2BA Villa in Bent Tree Hammocks III – No Age Restrictions Tucked away on a quiet dead-end street, this spacious 3-bedroom, 2-bath villa offers privacy and a peaceful, park-like setting. The split floor plan includes formal living and dining rooms, an eat-in kitchen with in-unit laundry, and a 2-car attached garage. Enjoy indoor-outdoor living with a screened lanai that opens to an additional open patio—ideal for morning coffee or casual entertaining. Bent Tree Hammocks III is a well-kept, sought-after community just two miles east of I-75, putting shopping, dining, golf courses, and Sarasota’s beaches within easy reach. Priced below market for a quick sale and easy to show. Seller will consider offers. A great opportunity to own in a desirable community with no age restrictions.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Bouck, Pa (941-374-0165)
707 S GULFSTREAM AVE #505, SARASOTA, FL 34236
$799,000111 Days on yellowkey MLS ID: A4675101
REDUCED by $50,000 (5.9%) on 04/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1974 Tax: $6,333 (2024)Community: Essex HouseCondo
Taxes:$6,333
Elementary School: Southside Elementary
Middle School: Booker Middle
Remarks: Be prepared for the breathtaking, unobstructed water views from this exquisite condominium in the Essex House – one of downtowns most coveted addresses and among the few residences untouched by neighboring development. Exquisitely positioned showcases breathtaking vistas of Siesta Key, Sarasota Big Pass, Marina Jack and Downtown Sarasota. From dramatic floor-to-ceiling windows, enjoy a front-row seat to Sarasota's legendary sunsets every evening. This thoughtfully updated 2+ bedroom, 2 bath residence blends sophistication with comfort. Coffered ceilings with recessed lighting and a built-in electric fireplace create an inviting ambiance - perfect for relaxing as the sun dips into the Gulf. The contemporary kitchen is as functional as it is stylish, featuring stainless steel appliances, open shelving, and expansive quartz countertops ideal for entertaining. The redesigned primary suite offers a serene private retreat, complete with a custom closet, built-in desk area, bench seating with additional storage, dual vanities with quartz countertop, and a beautifully appointed walk-in shower. You will appreciate the clean lines of wood imprinted porcelain tile flooring throughout, additional storage, built-in bookcases and washer/dryer. A true showpiece of the home is the fully enclosed glass Florida Room - an airy and seamless extension of the living space accessible from the living area and both bedrooms. Surrounded by glass and equipped with screens, it is the perfect setting for morning coffee or evening cocktails while soaking in the ever-changing, memorizing views. Located in the vibrant heart of downtown, you are just steps from award-winning dining, theatres, galleries, boutique shopping, and Whole Foods. Residents of the Essex House enjoy premier amenities include a fitness center, pool deck, security, covered garage parking with an assigned space, and pet-friendly living. This is a rare opportunity to own unobstructed water views paired with refined downtown luxury - plus the added peace of mind that all assessments have been paid.
Listing Agent: Scott Rickards, Pa (941-356-7040)
436 CANAL RD #A, SARASOTA, FL 34242
$1,795,00064 Days on yellowkey MLS ID: A4678784
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2756 Built: 2002 Tax: $19,424 (2025)Community: Siesta Villas 1Townhouse
Taxes:$19,424
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Superb Location. Big Family Retreat. Excellent Investment. Quiet Beach Days. The search for your ultimate beach retreat ends at 436 Canal Road. This 3-bedroom, 3 ½ bath home has all the extras you’re looking for. Your home is located just steps to world famous Siesta Key Beach. You are an easy walk, bike ride, or golf cart drive to Siesta Key Village where you will experience great food, entertainment and eclectic shopping. Enjoy fishing or dropping your kayak or paddleboard off your private community dock to explore Siesta Key by water. Or relax by the west-facing pool shared by only 4 units. At home, use your interior elevator to take you to all four floors. The oversized garage comes with a new garage door, a mini-split AC unit and plenty of room for your golf cart and beach toys. The first floor of living space has an open-plan kitchen with stainless steel appliances, a dining area and living room. There is also a balcony, laundry and half-bath on this floor. The next floor contains 3 spacious bedrooms and 2 baths. The Primary bedroom has an en-suite with dual sinks, both a garden tub and shower, and two walk-in closets. The top level had a surprise flex space that opens to the large roof top terrace with stunning views of the gulf. The flex space currently has 2 twin beds, a wet bar with under-counter sink, and a full bath with shower. Your home has a 2026 Roof, 2-AC units (2025 and 2022), and new Garage Door (2025). The property is currently being utilized as a WEEKLY rental and sleeps 8. The community is pet-friendly (owners only). Seller is grossing $100k using VRBO. Projections of $167,000+ with property manager. Come visit paradise on Siesta Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
4508 WOODSIDE RD, SARASOTA, FL 34242
$2,450,000117 Days on yellowkey MLS ID: A4674684
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2276 Built: 1969 Tax: $7,045 (2025)Community: Siestas Bayside Waterside WoodSingle Family
Taxes:$7,045
Remarks: Luxury Waterfront Living Now Priced to Move Welcome to 4508 Woodside Rd, a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this property provides quick access to the Intracoastal and Sarasota Bay, with 95 feet of waterfront and a 75-foot dock designed for serious boating. Inside, the home features a fully renovated interior with designer tile flooring, an open-concept layout, and expansive sliding glass doors that seamlessly connect indoor and outdoor living. The chef’s kitchen is equipped with custom cabinetry, a Viking hood system, gas cooktop, and premium appliances, while a temperature-controlled wine cellar adds a true luxury touch. The primary suite is a private retreat with a spacious layout, oversized walk-in closet, and a spa-style bathroom featuring a glass-enclosed shower and outdoor shower access. Every detail has been thoughtfully designed for comfort and functionality. Step outside to your own private resort complete with a saltwater pool and spa, lush landscaping, integrated lighting, and a covered pergola with outdoor lounge space, propane fire pit, and TV viewing area. A retractable awning and outdoor wet bar enhance the space, making it ideal for entertaining year-round. Additional highlights include a 250-gallon propane tank, 14.5 KW generator, updated HVAC, newer water heater with circulating system, epoxy-finished garage, and hurricane protection features. Originally introduced at $2,690,000, the property has undergone multiple strategic price adjustments and is now positioned to sell, presenting one of the best waterfront opportunities on Siesta Key. With nearby properties trading at significant premiums for land value alone, this offering delivers exceptional value for both end-users and investors. Also available: luxury yacht (inquire for details).
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
2068 SUNNYSIDE LN, SARASOTA, FL 34239
$895,0004 Days on yellowkey MLS ID: N6143339
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1722 Built: 1953 Tax: $2,984 (2025)Community: Hibiscus Park 1Single Family
Taxes:$2,984
Remarks: One or more photo(s) has been virtually staged. Get ready to view and call your home in this pristine and immaculate kept move in ready. This stunning Mid-Century Modern residence located in the heart of the highly sought-after Southgate neighborhood! Minutes to Sarasota Hospital and Downtown Sarasota. This beautifully original quality 3-bedroom, 2-bathroom home with one bathroom is a pool bathroom. Original terrazzo flooring, solid wood doors, real wood cabinets and other quality designs with the history craftsmanship still installed of 1953 with updated functionality. As you walk around your home, feel the unique timeless design of a functional kitchen, all appliances included with even a gas stove. Move into your traditional spacious dining area for meals with family and friends. Wonder into the true comfort of an intimate family room, which leads into a spacious filled with natural light Florida room, air condition. Currently as an artist studio with many future possibilities. Open your French doors and seek out to an oversize Pool and lanai and enjoy a beautiful outside sanctuary retreat at the comfort of your home. But it does not end there. Walk out beyond your lanai to your well-kept private landscaping. Total property sits on 0.349-acre lot. Seamlessly blends timeless design with modern luxury and functionality. Step inside again and view your spacious master bedroom with two additional bedrooms. Recent upgrades provide peace of mind and exceptional value, including hurricane-impact windows, new roof installed in 2019. Recently re-plumbed and new water heater. This type of quality home is unmatched. Enjoy the freedom of no HOA fees while being conveniently located all of what Sarasota offers. This home is timeless quality with of style, comfort, and location in one of Sarasota’s most desirable neighborhoods. Schedule your private showing today and experience Southgate living at its finest.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Lenny Lesaltato (941-350-9238)
2529 GOLDEN POINCIANA PL, SARASOTA, FL 34232
$324,900Listed 04/05/2026 10:17PM MLS ID: A4688911
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1302 Built: 1977 Tax: $3,199 (2025)Community: Brentwood EstatesSingle Family
Taxes:$3,199
Remarks: 3D VIRTUAL TOUR AVAILABLE: CLICK ON VIRTUAL TOUR LINK #1. Very nice 3 bedroom, 2 bath home with a spacious yard and room to park an RV on the side of the home (or a trailer, box truck, boat, etc). This home has a roof from June 2022, and a wonderful back yard with plenty of eureka palms, providing a lush garden feel and additional privacy from the neighbors. Welcome to this charming single-story home offering a blend of comfort, functionality, and opportunity. Featuring a durable shingle roof and a spacious driveway with a one-car garage, this property sits on a generously sized lot with mature trees that provide shade and privacy. Inside, you’ll find an open-concept living and dining area with tile flooring throughout, making for easy maintenance and a clean, cohesive look. The kitchen offers ample cabinet space, formica countertops, and a practical layout that flows seamlessly into the main living areas—ideal for everyday living and entertaining. The home includes three bedrooms with ceiling fans, good natural light, and closet storage. The bathrooms have been updated with modern vanities, fixtures, and a walk-in shower design for a fresh, functional feel. Additional highlights include: Spacious laundry/utility area with extra storage, Attached garage with shelving and workspace potential, Large backyard with room for outdoor living, gardening, or future improvements. This property presents a great opportunity for buyers looking to personalize a home or invest in a well-located property with solid fundamentals. Conveniently situated near local amenities, shopping, dining, and major roadways. Don’t miss the chance to make this versatile property your own—schedule your showing today!
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Maciek Zaremba (941-400-7084)
2442 WOOD ST, SARASOTA, FL 34237
$472,00081 Days on yellowkey MLS ID: A4678152
REDUCED by $23,000 (4.6%) on 04/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1279 Built: 1951 Tax: $5,715 (2025)Community: Hudson ParkSingle Family
Taxes:$5,715
Elementary School: Alta Vista Elementary
Remarks: Live in one of the most desirable Sarasota neighborhoods! This home has 2 nice sized bedrooms and a third room that can be a sunroom, office, or interior in-law suite/studio with its own bathroom, kitchen space, closet, and private entrance from the back of the house. This cozy home features a kitchen nook and comfortable sitting area to relax and unwind. Upgrades include remodeled kitchen, newer roof (2018), Granite vanity top and sink with brushed nickel faucets (2020), water heater (2025), upgraded light fixtures (2025) and many other upgrades throughout this beautiful home. Enjoy your morning coffee from the beautiful front patio or relax on the back patio. Backyard has a 2-car carport and storage sheds. The location is ideal as it is close to shopping and restaurants as well as minutes to downtown Sarasota and world-famous Siesta Key Beach & other local beaches. Schedule an appointment to see this beautiful home today! RV parking available as well as zoned for multi-family if desired.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
3427 RIVIERA DR, SARASOTA, FL 34232
$510,00081 Days on yellowkey MLS ID: A4677588
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1503 Built: 1974Monthly Fee: $5 Tax: $4,875 (2025)Community: Forest LakesSingle Family
Taxes:$4,875
Elementary School: Wilkinson Elementary
Remarks: One or more photo(s) has been virtually staged. An immaculate modern home in the highly desirable Forest Lakes neighborhood is now available! This like-new residence offers comfortable one-level living, a convenient location, low HOA fees, and an ideal floor plan designed for today’s lifestyle. The home features a spacious split-bedroom layout with a light-filled open living and dining area. The well-appointed kitchen showcases crisp white cabinetry, quartz countertops, and stainless steel appliances. A large kitchen window provides picturesque views of the landscaped backyard, while a convenient bar-top pass-through makes serving the screened lanai effortless. Adjacent to the kitchen is a versatile flex space that can easily serve as a formal dining room, den, home office, playroom, library, or music room. The private primary suite is tucked away on one side of the home and includes an en-suite bath with a walk-in shower and a generous closet. On the opposite side, two secondary bedrooms share a large, beautifully updated bathroom with a shower/tub combination. Additional highlights include two sets of sliding glass doors leading to the screened porch—perfect for relaxing and enjoying views of stately oak trees and lush landscaping within the fully fenced backyard—along with a dedicated laundry room with washer and dryer and an attached two-car garage. Recent updates include a new roof (2021), HVAC system (2022), and garage door (2022). Conveniently located near restaurants, shopping, and medical facilities, this home offers exceptional value with low HOA fees.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Donna Boynton (404-323-2012)
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00016 Days on yellowkey MLS ID: A4687031
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2217 Built: 1998Monthly Fee: $1,985 Tax: $13,269 (2025)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$13,269
Remarks: One or more photo(s) has been virtually staged. Experience endless panoramic views of downtown Sarasota and Sarasota Bay from the climate-controlled balcony of this newly renovated top-floor residence in the gated community of Dolphin Bay on Siesta Key. This spacious condo offers over 2,200 square feet of beautifully updated living space, featuring 2 bedrooms, 2 bathrooms, and a den, all enhanced by vaulted ceilings that create an open and airy coastal atmosphere. From the front entryway, enjoy stunning nightly sunsets over Siesta Key Beach, adding to the exceptional appeal of this home. Residents of Dolphin Bay enjoy a true waterfront lifestyle with access to a private community dock, clubhouse, tennis courts, fitness center, and a resort-style pool. A private one-car garage is conveniently located just steps from the elevator, offering ease and security. Perfectly situated within minutes to the beach, shops, and restaurants, this residence combines luxury, convenience, and the best of Siesta Key living. Enjoy the waterfront lifestyle at its finest in this exceptional move-in-ready home.
Listing Agent: Maryana Zilinskiy (941-744-6065)
1850 WEBBER ST, SARASOTA, FL 34239
$3,890,00010 Days on yellowkey MLS ID: A4686673
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026 Tax: $18,011 (2025)Community: Poinsettia Park 2Single Family
Taxes:$18,011
Remarks: One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
1671 ARLINGTON ST, SARASOTA, FL 34239
$2,995,00032 Days on yellowkey MLS ID: A4684899
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3564 Built: 2026 Tax: $10,197 (2025)Community: Lewis Combs SubSingle Family
Taxes:$10,197
Remarks: Located West of Trail, this beautiful new construction five-bedroom, five-and-a-half-bathroom residence captures the essence of Sarasota living. Designed with both comfort and entertaining in mind, the home features expansive sliding glass doors that open the main living areas to a private pool and outdoor gathering space, creating a seamless connection between indoor and outdoor living. Inside, generous living spaces, clean architectural lines, and refined finishes create a warm yet modern atmosphere. The open-concept layout centers around a spacious kitchen and living area, ideal for everyday living while also providing an elegant setting for hosting family and friends. Upstairs, well-appointed bedroom suites give privacy and flexibility, while the primary suite provides a peaceful retreat with a spa-like bath and thoughtfully designed closet space. Every detail of the home has been carefully considered to deliver both functionality and timeless style. Thoughtfully designed for comfort and ease, the property offers a low-maintenance lifestyle that appeals to both full-time residents and seasonal owners looking for a lock-and-leave Sarasota home. Ideally located just minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and the Gulf beaches, the home places you close to the best dining, shopping, and coastal experiences the area has to offer while maintaining the quiet charm that has long made West of Trail one of Sarasota’s most desirable neighborhoods.
Listing Agent: Steven Moore (401-767-7180)
656 TROPICAL CIR, SARASOTA, FL 34242
$4,195,000122 Days on yellowkey MLS ID: A4674326
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5238 Built: 2025Monthly Fee: $54 Tax: $8,623 (2024)Community: Siesta BeachSingle Family
Taxes:$8,623
Remarks: Perfectly positioned in Siesta Beach—just moments from the shoreline—this newly completed 2025 coastal residence delivers a rare combination of striking design, thoughtful functionality, and luxurious indoor-outdoor living. Spanning more than 5,200 square feet of air-conditioned space across two levels, this contemporary home has been professionally staged with high-end furnishings included in the sale, making it truly move-in ready. The elevated architectural facade creates a commanding first impression. Step inside to an expansive great room with wood flooring, soaring coffered ceilings, crown molding, and a dramatic wood-paneled accent wall that anchors the living and dining spaces. Walls of pocketing impact-rated sliders dissolve the boundaries between indoors and out, opening to a resort-style entertaining area. A built-in wet bar with wine cooler enhances the home’s hospitality appeal. The gourmet chef’s kitchen sits at the heart of the first floor, designed to showcase the outdoor views. Outfitted with quartz countertops, sleek shaker cabinetry, hidden appliances, a gas Wolf stove with dual ovens, walk-in pantry, and an oversized island, the kitchen is ideal for everyday use and large-scale gatherings. Adjacent formal dining space is framed by oversized windows, creating a sun-lit setting for memorable meals. Outdoor living unfolds on a spacious covered patio featuring a tongue-and-groove ceiling treatment, summer kitchen with built-in gas grill, lounge and dining areas, and a heated pool and spa surrounded by beautifully landscaped grounds. The primary suite—secluded on the main level—offers vaulted ceilings, dual walk-in closets, and a spa-inspired bath finished with quartz surfaces, stone-clad shower, and refined detailing. A dedicated office, first-floor laundry room, and a pre-planned shaft for a future elevator provide convenience and flexibility. Upstairs, three additional bedroom suites each feature walk-in closets and en-suite baths. A study with generous storage, a media room, a bonus room, and a secondary laundry room complete the second level. A 45-foot balcony connects multiple rooms and overlooks the pool and tropical landscaping. The split three-car garage provides ample storage for vehicles, recreation gear, and coastal living essentials. Situated in the coveted Siesta Beach neighborhood, the home offers a quiet residential setting just minutes from award-winning Siesta Key Beach, world-renowned for its quartz-sand shoreline and turquoise water. Explore Siesta Village for dining and boutique shopping, enjoy boating and kayaking along the Intracoastal Waterway, or venture over the bridge to Sarasota’s vibrant cultural scene—The Bay Park, Ringling Museum, Van Wezel Performing Arts Hall, Marina Jack, Selby Gardens, and the city’s acclaimed restaurants and galleries. This newly constructed coastal estate delivers the perfect blend of design excellence, modern comfort, and proximity to everything that defines the Siesta Key lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
2749 ORCHID OAKS DR #302, SARASOTA, FL 34239
$260,00028 Days on yellowkey MLS ID: A4685445
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1365 Built: 1980 Tax: $3,014 (2025)Community: Orchid Oaks ICondo
Taxes:$3,014
Remarks: Ideally located in the centrally positioned community of Orchid Oaks, this beautifully updated 2-bedroom, 2-bath, 1,365-sq-ft third-floor condominium offers comfortable living with convenient access to the best of Sarasota. Inside, the residence features a thoughtfully updated kitchen with granite countertops and stainless-steel appliances, complemented by generous cabinetry and workspace. The open living and dining areas create an inviting atmosphere for everyday living and entertaining, while the screened lanai provides a peaceful place to relax and enjoy the surrounding tropical setting. The condominium presents an excellent opportunity for seasonal enjoyment, full-time living, or income potential. The rental policy allows a 30-day minimum lease, up to three times per year. Orchid Oaks residents enjoy beautifully maintained grounds and a variety of community amenities. The clubhouse and pool overlook scenic Phillippi Creek, and residents may reserve the clubhouse once per month at no cost for private gatherings. The community also features gazebos, walking trails, a dog run, and a peaceful creekside dock, providing multiple spaces to enjoy the property’s natural beauty. Located just minutes from Downtown Sarasota, Siesta Key’s renowned beaches, shopping, dining, golf courses, and Sarasota-Bradenton International Airport, this residence offers both tranquility and convenience. A wonderful opportunity to enjoy relaxed condominium living in a charming Sarasota setting. The residence is currently tenant-occupied through May 31.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Evan Weber (941-287-9700)
1958 MORRIS ST, SARASOTA, FL 34239
$1,195,00089 Days on yellowkey MLS ID: A4677121
REDUCED by $100,000 (7.7%) on 04/03/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2362 Built: 1957 Tax: $7,088 (2025)Community: HartsdaleSingle Family
Taxes:$7,088
Remarks: One or more photo(s) has been virtually staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite bathroom—ideal for multigenerational living, extended guests, or a private home office retreat. Light-filled living spaces flow effortlessly, creating an inviting atmosphere for both everyday living and entertaining. The functional layout offers privacy where you want it and openness where it matters most, making the home equally suited for relaxed coastal living or hosting family and friends. NEW ROOF 2025. NO STORM DAMAGE. Step outside to your private fenced backyard oasis, where an oversized sparkling swimming pool takes center stage—perfect for year-round enjoyment in Florida’s sunshine. Located West of the Trail, this home places you in one of Sarasota’s most desirable areas. Enjoy the convenience of being just minutes from Downtown Sarasota, with its vibrant arts scene, dining, and waterfront attractions. The popular Morton's Market and Hillview shops and restaurants are close by for everyday errands and casual nights out, "A" rated Southside Elementary School just around the corner, Siesta Key Beach and Sarasota Memorial Hospital are only moments away, adding peace of mind and unmatched accessibility. Whether you’re searching for a full-time residence, seasonal getaway, or smart investment, this home stands out with its versatile floor plan, unbeatable location, and outstanding value. Opportunities like this in such a sought-after Sarasota setting—are rare. Schedule your private showing today and experience the lifestyle this property has to offer.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Jon Patella (941-228-1613)
137 AVENIDA MESSINA #1, SARASOTA, FL 34242
$665,000144 Days on yellowkey MLS ID: A4671658
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1966 Tax: $6,247 (2024)Community: Villa NavarraCondo
Taxes:$6,247
Remarks: Centrally located and fully furnished! Located within the boutique condominium community of Villa Navarra on Siesta Key, this fully updated, turnkey-furnished ground-floor residence offers an exceptional blend of quality, comfort, and convenience. The property is ideally situated one block from Siesta Key Village and approximately two blocks from Siesta Beach, providing easy access to the island’s most popular destinations. Ideal for full time, snow birds or people looking to lease this condo out to renter's for the two month minimum. The residence features two bedrooms and two full bathrooms arranged in an open, functional layout. The spacious living and dining areas flow seamlessly into a thoughtfully renovated kitchen appointed with solid-surface countertops, modern cabinetry, and stainless-steel appliances. Finishes and flooring throughout the home have been carefully selected to create a clean, contemporary aesthetic that complements its coastal setting. The primary suite includes an en-suite bath and generous closet space, while the guest bedroom is conveniently located near the second full bath. The ground-floor design allows direct access to the assigned parking space for added ease. With extensive updates and attention to detail, this residence is move-in ready and designed for practical, comfortable living. Villa Navarra is a well-maintained, low maintenance community of just sixteen units surrounded by tropical landscaping and a relaxed island atmosphere. Residents enjoy convenient access to the free Siesta Key trolley and can easily walk to Siesta Key Village, offering a wide variety of local dining, shopping, and entertainment options. The renowned quartz sands and turquoise waters of Siesta Beach are only a short stroll away. This property is well-suited for a full-time residence, seasonal getaway, or long-term rental investment. Its location, quality, and turnkey condition make it a rare opportunity to enjoy the Siesta Key lifestyle within a private and beautifully maintained setting.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jeffrey Bray, Pllc (941-718-1213)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$749,000169 Days on yellowkey MLS ID: A4669008
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1975 Tax: $5,944 (2025)Community: Pointe On Midnight PassCondo
Taxes:$5,944
Remarks: Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Negotiable furnishings available. Schedule your private showing today.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
2345 BAHIA VISTA ST, SARASOTA, FL 34239
$874,98399 Days on yellowkey MLS ID: A4672606
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2141 Built: 2023 Tax: $8,758 (2024)Community: Avon Heights 2Single Family
Taxes:$8,758
Remarks: One or more photo(s) has been virtually staged. New construction and under $1m in the sought after Southside school district this is very rare, but you have found it right here and your opportunity is knocking. Custom Luxury Living Near Downtown Sarasota! Welcome home to this exquisite, 4 bed 2 and a half bath custom-built residence designed by renowned Piper Navy! This two-story traditional model offers unparalleled craftsmanship and exceptional amenities just moments from Sarasota's vibrant core. Step inside to discover a truly thoughtful design, featuring soaring 9'4'' ceilings and elegant crown molding. The gourmet kitchen is a chef's dream, boasting an entertaining island, all-wood cabinetry, and stunning quartz countertops. Beautiful wood flooring flows seamlessly throughout the entire home. Constructed with block on both floors and featuring upgraded underground electric service, this residence is built for lasting quality. Enjoy peace of mind and abundant natural light thanks to custom hurricane PGT Florida Impact Rated windows and doors. The floor plan includes a gorgeous master suite on the ground floor, with a beautiful ensuite bathroom with carrara tile flooring and free standing bath to wallow the night away in after a hard day, there is also a versatile loft, with ample storage space, Upstairs is a further three guest bedrooms with luxurious bathroom and a bonus landing area that can be utlized and made into an open plan office space, should you need to work from home. Relax or entertain guests on the expansive rear concrete lanai with fenced in mature private gardens. There is also room to build a pool,should you wish to in the future The exterior is completed with an irrigation system, St. Augustine grass, and a paver front driveway, providing beautiful curb appeal.This property offers an unbeatable Sarasota lifestyle! With the boutique area of Hillview around the corner ,Siesta key beach and You are less than 5 minutes from downtown Sarasota's beautiful Marina, cultural attractions, and fine dining. Less than 10 minutes to reach the world-renowned St. Armands Circle and the pristine sands of Lido Beach, offering upscale shopping and entertainment, you are in the best central location you could ask for.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rory Mcdonald (941-961-7247)
2355 BAHIA VISTA ST, SARASOTA, FL 34239
$874,983136 Days on yellowkey MLS ID: A4672605
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2086 Built: 2023 Tax: $8,758 (2024)Community: Avon Heights 2Single Family
Remarks: One or more photo(s) has been virtually staged. UNRIVALED LUXURY LIVING IN PRIME SARASOTA LOCATION! Experience the epitome of luxury with this stunning custom 4 bed 2 and a half bath residential masterpiece! This immaculate two-story traditional home boasts unrivaled craftsmanship and top-tier amenities throughout. Every detail exudes sophistication, from the soaring 9’4” ceilings and elegant crown molding to the pristine wood flooring that extends throughout the home. The gourmet kitchen is an entertainer’s dream, featuring a generous island, all-wood cabinetry, and gorgeous quartz countertops. The gorgeous ground-floor master suite offers the ultimate in convenience and privacy. Indulge in the beautiful ensuite bath, featuring elegant Carrara tile flooring and a free-standing soaking tub, perfect for unwinding after a long day. Upstairs, find three generous guest bedrooms, a luxurious full bathroom, and a versatile loft area with ample storage. The bonus landing area is perfectly designed to be utilized as a dedicated open-plan office space for remote work. Constructed for superior durability and peace of mind, this home features solid block construction and an upgraded underground electric service. Enjoy the enhanced protection and natural light provided by custom PGT Florida Impact Rated windows and doors. Step outside to the expansive concrete rear lanai and embrace the true Florida lifestyle. The meticulously maintained landscaping includes lush St. Augustine grass and is effortlessly maintained by a separate irrigation meter and system. There is also room for a pool should you wish to add to the property. LOCATION, LOCATION, LOCATION! Perfectly situated to enjoy all that Sarasota has to offer. You are just minutes from the vibrant energy of Downtown Sarasota, the exclusive shopping and dining of St. Armands Circle, and the iconic shores of Lido Beach. Enjoy a short drive to world-famous Siesta Beach and the charm of Pinecraft. Exceptional proximity to top-tier medical facilities, being only half a mile to Sarasota Memorial Hospital PLUS the interstate all within 3-5 miles or just steps to public transportation. This is the exceptional lifestyle and quality home you have been waiting for!
116 GARDEN LN, SARASOTA, FL 34242
$2,150,000150 Days on yellowkey MLS ID: A4671064
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
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