Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
1711 KENILWORTH ST, SARASOTA, FL 34231
$1,699,0006 Days on yellowkey MLS ID: A4700129
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3734 Built: 2013 Tax: $13,105 (2025)Community: Kenilworth EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,105
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to 1711 Kenilworth Street, an exceptional opportunity to own a move-in-ready home in one of Sarasota’s most desirable West of the Trail neighborhoods. Located within the highly coveted corridor between Field Road and Mound Street, this home offers more than 3,700 square feet, four bedrooms, three full bathrooms, a first-floor office, and a rare three-car garage. At the time of listing, this is the lowest-priced move-in-ready home per square foot in this sought-after West of the Trail area, making it an outstanding value for buyers who want generous living space without sacrificing location, condition, or lifestyle. What truly sets this home apart is its peaceful lakefront setting. From the moment you enter, the open great room draws your attention through large sliding glass doors to the expansive water views beyond. The lake creates a beautiful backdrop throughout the home and offers a sense of privacy and tranquility that is incredibly difficult to find this close to downtown Sarasota. Over the past year, move-in-ready West of the Trail homes offering comparable water views have sold or been listed near the $4 million range, highlighting just how rare and valuable this setting is. Here, you can enjoy the same peaceful waterfront lifestyle at a substantially more approachable price. A welcoming front porch leads into the foyer and spacious great room, where beautiful oak flooring adds warmth and character. The fully screened lanai and travertine deck provide an ideal place to relax, entertain, dine outdoors, or simply enjoy the view. A private dock offers the perfect spot to fish, watch the turtles, and take in the abundant birdlife surrounding the lake. The expansive kitchen features a gas cooktop, abundant workspace, and a large gathering area designed for hosting family and friends. The primary suite feels like a true private retreat, with an oversized bedroom, two walk-in closets, a spacious bathroom with excellent storage, and a private owner’s office overlooking the water. The three additional bedrooms are also generously sized, giving family members and guests the space and privacy they need. A separate first-floor office adds even more flexibility for working from home, managing a busy household, or creating a quiet study. Upstairs, a large loft and oversized media, fitness, or recreation room provide additional space for entertaining and everyday living. This is a home that truly has everything you need from a space and functionality standpoint. There is room to spread out, work, host, relax, and move in comfortably without immediately needing to reconfigure the home or take on a major project. Outside, the clean, attractive landscaping complements the home without creating unnecessary upkeep. The property offers beautiful curb appeal while remaining relatively low maintenance, making it ideal for buyers who want to enjoy the Sarasota lifestyle without spending every weekend working on the house. Located just minutes from Sarasota Memorial Hospital, Southside Village, downtown Sarasota, Siesta Key, and some of the area’s best dining, shopping, and beaches, 1711 Kenilworth Street offers an increasingly rare combination of space, water views, a three-car garage, low-maintenance living, and an exceptional West of the Trail location. For buyers searching for a move-in-ready home in one of Sarasota’s most luxurious and established neighborhoods, this is a value that is difficult to duplicate.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Cole Collins (941-350-8360)
2225 FLORINDA ST, SARASOTA, FL 34231
$1,500,00060 Days on yellowkey MLS ID: A4690756
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2607 Built: 2026 Tax: $1,570 (2025)Community: Tamiami TerraceSpa: YesSingle Family
Taxes:$1,570
Remarks: Virtually Staged. 2225 Florinda Street — arrival as destination. Pull into the driveway, pass the two car garage and follow a landscaped walkway to arrive at a gracious covered entry; decorative metal screening catches the Florida light accenting the french pattern travertine entry and frames an oversize full glass door. Step inside and the experience unfolds: Large format porcelain tile, 10' ceilings and abundant windows bathing the open plan in natural light. Gulfside Homes, a Sarasota Custom Home builder for over 25 years, crafted this over 2,600 sq ft Calista model showcase with thoughtful and custom upgrades you’ll notice throughout—builtin conveniences, premium appliances and finish selections that read like an owner’s wish list already checked. The main level is made for living and entertaining: an elegant dining area flows to a true gourmet kitchen with gas range, pot filler, LG stainless appliances, microwave drawer and an oversized quartz waterfall island. The family room sits beyond, flooded by light from large windows and glass doors that frame the ivory travertine pool deck and spa. Opposite the island and tucked under the stairs is a purposeful coffee bar and prep station with a deep sink (cuttingboard/dryingrack/colander), coordinated floating shelving, abundant storage and a twozone undercabinet beverage refrigerator—one of the many touches that make daily rituals effortless. Also on the first floor is a flexible, large en-suite guest room whose bath doubles as a powder room and provides direct access to the outdoors and access to the pool—perfect for visitors and carefree pool days. Upstairs the home is arranged for privacy and function: a split bedroom plan placing the primary suite apart from two large secondary bedrooms. The primary is a serene retreat with a spa caliber bath—soaking vessel tub, floor to ceiling Calacatta porcelain shower with double rain heads, dual vanities—and generous closet space. A dedicated laundry on the bedroom level adds convenience. A roomy office/den/media room opens to a covered deck for quiet moments or flexible workspace. Outside is your private Sarasota oasis: 12×24 pool with six person spa, travertine decking and glass waterline tile, pre-plumbed for heating and framed by an 8' fenced yard. Premium systems and Gulfside upgrades that other builders don’t automatically provide—impact windows, underground 500gal propane tank, Rinnai tankless water heater with recirculating system, large format porcelain tile on the main level, waterproof luxury vinyl plank upstairs, timber stairs with stainless cable railing, upgraded lighting and hardware, Ring cameras and low maintenance tropical landscaping—deliver comfort, security and low upkeep. Only blocks to The Landings shopping center with several restaurants, gym, and Publix. Minutes from the John and Mable Ringling Museum of Art, Sarasota Art Museum, Van Wezel Performing Arts Hall, Marina Jack, downtown dining, farmers’ markets, marinas and Siesta Key and gulf beaches, 2225 Florinda is a refined, turnkey Sarasota lifestyle crafted by an experienced custom builder. Schedule your private showing to experience the details in person.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Karen Sweat (941-323-6707)
5830 MIDNIGHT PASS RD #29, SARASOTA, FL 34242
$525,00068 Days on yellowkey MLS ID: A4694023
REDUCED by $20,000 (3.7%) on 07/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1962Monthly Fee: $1,226 Tax: $3,460 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,460
High School: Sarasota High
Remarks: SIESTA KEY INVESTMENT! Live the ultimate beachfront lifestyle in this beautifully renovated condo located on world-famous Siesta Key, home to the #1 beach in the United States. Completely updated with stylish modern finishes, this coastal retreat offers the perfect blend of comfort, luxury, and location. Enjoy direct access to the powdery quartz sand beaches and stunning Gulf sunsets just yards away. Whether you are looking for a vacation getaway, investment opportunity, or full-time residence, this property offers excellent rental potential in one of Florida’s most sought-after beach destinations. A rare opportunity to own a fully renovated slice of paradise on iconic Midnight Pass Road.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Cristina Campbell, Pa (561-239-1498)
3411 SEA VIEW ST, SARASOTA, FL 34239
$275,00018 Days on yellowkey MLS ID: A4699337
0 Days Off yellowkey (back on 7/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1897 Built: 1972Monthly Fee: $8 Tax: $2,508 (2025)Community: Frst Lakes Country Club EstatesSingle Family
Taxes:$2,508
Elementary School: Alta Vista Elementary
Remarks: Incredible opportunity in Forest Lakes Country Club Estates . The value is in the land. This 3 bedroom , 2 bath , 2 car garage home has STRUCTURAL ISSUES . Build your new dream home here . Close to downtown Sarasota , UTC Mall and the beautiful crystal sandy beaches on Siesta Key . Shop , then have lunch downtown at ST Armands Circle and then go to Lido public beach or South Lido Beach . Close to; Sarasota Opera House, the Van Wezel Performing Arts Center , Sarasota Boat Ramps and great restaurants in downtown Sarasota Property being Sold " AS IS " Please provide "Proof of funds" with all offers . CASH OFFERS ONLY . THERE ARE STRUCTURAL ISSUES . Please DO NOT PICK OR CHISEL OFF THE STUCCO WHILE SHOWING THIS HOME. PLEASE leave the house as you found iThe AC isn't working don't turn it on. Please lock all doors and shut off all the lights .
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Colette Jay (941-713-7711)
3337 SPRING MILL CIR, SARASOTA, FL 34239
$489,000355 Days on yellowkey MLS ID: A4660789
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1989 Built: 1971Monthly Fee: $8 Tax: $3,196 (2024)Community: Village Green Club EstatesSingle Family
Taxes:$3,196
Elementary School: Wilkinson Elementary
Tax Year: 2024
Remarks: Price Reduced! Beautifully Updated GOLF COURSE Frontage Home with the ABSOLUTE BEST LOT and BEST Panoramic PRIVATE NATURE GOLF COURSE VIEWS in all of Village Green Club Estates! This Lovely HOME FEATURES: 3 Bedrooms, 2 Baths, 3rd Bedroom makes a perfect Den/Flex Room, Master Suite w/Updated Private Bath w/Granite Counters, Walk-in Closet w/Built-ins plus Slider to Covered Lanai, Open Living Room w/Gorgeous Private Panoramic Golf Course Views, Formal Dining Area, Family Room Area, Updated Kitchen w/Granite Counters and Eating Bar, Stainless Appliances, Pantry Closet; Breakfast Nook w/Slider to Screened Lanai, Updated Hall Bath w/Tub and Granite Counters, HUGE Laundry Room Large Enough to be Used as an Office, House Re-Plumb, Updated w/Windows w/Hurricane Shutters, (2007) Roof, (2022-2023) AC and Hot-Water Heater, Porcelain Tile in all areas except the Master Suite and One Guest Bedroom, Oversized 2 Car Garage, Private Paver Patio Shaded by a Majestic Oak Tree and Designer Landscaping w/Irrigation. COMMUNITY FEATURES: Golf Clubhouse is Close-by. NO CDD Fees plus SUPER Low $100 Annual HOA Fees! This is a Fabulous Location close to Everything - Publix Grocery Store, Walmart, Walgreens, Starbucks, Legacy Bike Trail, Downtown Sarasota Restaurants, I-75, UTC Mall and the Siesta Key Beaches!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
1759 WALDEMERE ST, SARASOTA, FL 34239
$4,299,999292 Days on yellowkey MLS ID: A4666725
REDUCED by $150,000 (3.4%) on 07/08/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4513 Built: 2025 Tax: $13,348 (2024)Community: Midwood ManorSpa: YesSingle Family
Taxes:$13,348
Elementary School: Southside Elementary
Remarks: Virtually Staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary craftsmanship, and intentional indoor–outdoor living. Set on a .33-acre lot just steps from Southside Village and Sarasota Memorial, the home delivers sophistication, convenience, and exceptional attention to detail in one of Sarasota’s most sought-after neighborhoods — a rare opportunity in the coveted West of Trail community. Spanning 4,513 square feet, the two-story floor plan features four bedrooms, five baths, an office with private entry, and a media room that opens to a 480-square-foot balcony overlooking the property. Designed for both everyday living and elegant entertaining, the home showcases expansive sliding glass doors that blur the line between indoors and out, opening to a heated saltwater pool, spa, and lush landscaped backyard for year-round enjoyment. The designer kitchen serves as the heart of the home, featuring Sub-Zero and Wolf appliances, custom cabinetry, imported stone, and a hidden butler’s pantry. The first-floor primary suite epitomizes luxury with zero-corner sliders that open directly to the pool and outdoor living area. Inside, a spa-inspired bath includes a freestanding tub, walk-in shower, and a custom built-in walk-in closet. Upstairs, two en suite bedrooms and a second-floor primary suite give privacy for family or guests. A versatile media room and expansive outdoor terrace complete the level, overlooking the serene backyard oasis. Every detail has been thoughtfully curated — from the bespoke, locally handcrafted Sapele wood entry door to hurricane-impact windows and doors, a three-car garage with epoxy flooring, and professional landscaping surrounding the fenced backyard. Ideally located in the highly regarded Southside Elementary School district, near Sarasota Memorial Hospital and the shops and dining of Southside Village, with downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle just minutes away. This is more than a home — it’s a statement of Sarasota luxury living.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rachel Hamrick (941-529-1773)
5950 MIDNIGHT PASS RD #101, SARASOTA, FL 34242
$485,99965 Days on yellowkey MLS ID: A4694128
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 513 Built: 1957 Tax: $3,441 (2025)Community: Siesta Beach HouseCondo
Taxes:$3,441
Remarks: An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Located within Siesta Beach House Condominiums, this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.
Listing Agent: Rachel Tritschler (941-993-5892)
5938 MURDOCK AVE, SARASOTA, FL 34231
$297,70011 Days on yellowkey MLS ID: A4697066
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1381 Built: 1961 Tax: $1,431 (2025)Community: Golden Acres 1St AddSingle Family
Taxes:$1,431
Elementary School: Gulf Gate Elementary
Remarks: Under contract-accepting backup offers. Opportunity knocks at 5938 Murdock Ave, a 2-bedroom, 1-bathroom home offering 1,381 square feet of potential in the heart of Gulf Gate Estates. Priced to invite your imagination, this residence is a rare canvas for buyers eager to build sweat equity in one of South Sarasota's most established and convenient neighborhoods. Set on one of the area's largest lots, the property enjoys a coveted position beside a tranquil pond — meaning no neighbors on one side and daily visits from Florida's wildlife. A screened front porch greets you, while a back screened lanai overlooks a sprawling backyard perfect for gardening, gathering, or simply unwinding. Inside, an eat-in kitchen flows into a comfortable living room and a flexible bonus room ready to adapt to your needs. The laundry room off the garage presents a smart opportunity to add a second full bathroom, boosting both function and value. A one-car extended garage and separate storage shed round out the practical features, and recent upgrades — including a new roof/2024 and new water heater — give you a solid foundation to renovate with confidence. The location is unbeatable. You're moments from Gulf Gate Elementary, Riverview High School, Publix at Sarasota Pavilion, and easy I-75 access. The world-famous white sands of Siesta Key sit just minutes away, adding genuine VRBO income appeal. Ready for a new generation to make it shine, this is your chance to transform potential into a personalized Sarasota retreat.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Michael Ballantyne (941-404-7374)
1630 ASSISI DR #18, SARASOTA, FL 34231
$1,997,00055 Days on yellowkey MLS ID: A4695360
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3602 Built: 2008Monthly Fee: $388 Tax: $12,299 (2025)Community: Portofino On The BaySingle Family
Taxes:$12,299
Remarks: Under contract-accepting backup offers. Welcome to a beautiful custom residence in Portofino on the Bay, a boutique waterfront community nestled along Little Sarasota Bay. Privately positioned on a quiet cul-de-sac and just a short walk from the water and its private deeded boat slip, this stunning Mediterranean-inspired home offers an elevated lifestyle defined by elegance, comfort, and exceptional design. A dramatic yet inviting entry introduces soaring 23-foot ceilings, abundant natural light, and expansive living spaces thoughtfully designed for entertaining and effortless everyday living. The grand living room, anchored by a fireplace and walls of glass sliders, seamlessly opens to the screened saltwater pool and spa, creating a true indoor-outdoor retreat. The state-of-the-art chef’s kitchen is both beautiful and functional, featuring granite countertops, custom cabinetry, an oversized island, premium appliances, a Viking range, and a warming drawer designed to impress culinary enthusiasts and guests alike. The luxurious first-floor primary suite is a private sanctuary, offering spacious custom his-and-her closets and a spa-inspired ensuite bath complete with dual vanities, a large soaking tub, and a steam shower featuring three shower heads. Also conveniently located on the first floor are a spacious den/office with two built-in desks and a Murphy bed, as well as one of the guest bedrooms. Upstairs, a dramatic balcony overlooks the main living spaces below, while three additional guest bedrooms offer beautifully appointed accommodations with custom built-in closets. One bedroom features an ensuite bath, while the other two share an elegant Jack-and-Jill bathroom. Designed with comfort and wellness in mind, the home also features a whole-house water filtration system and reverse osmosis water systems with remineralization in both the kitchen and upstairs living area. With no flood insurance required, enjoy the benefits of living near waterfront, including peaceful walks to watch spectacular sunsets, fishing from the dock, and effortless boating from your private deeded boat slip with a 10,000-pound lift and direct access to the Intracoastal Waterway and Gulf waters beyond. Additional community amenities include kayak launch access, dedicated kayak storage, and a guest boat slip for visiting boaters. Ideally located just minutes from the nationally recognized Pine View School, world-class dining, shopping, downtown Sarasota's cultural attractions, and the white sands of Siesta Key Beach, as well as Nokomis Beach and charming downtown Venice. Opportunities like this in Portofino on the Bay are rare—don't miss your chance to make this stunning home your own!
Listing Agent: Tatyana Mullin (850-294-9225)
5880 MIDNIGHT PASS RD #804, SARASOTA, FL 34242
$1,350,000177 Days on yellowkey MLS ID: A4680425
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $11,821 (2025)Community: CasarinaSpa: YesCondo
Taxes:$11,821
Remarks: An unusual price for an unusual seaside residence. Completely renovated with stunning views from every window. Enjoy your morning coffee on the lanai and relish the downtown skyline as well as the Gulf of Mexico and Siesta Beach. Renovations include completely repainted, impact resistance windows, new interior doors, closet organizers and new front door. Casarina amenities include heated pool/spa, pickle ball/tennis courts, exercise room, gas grills, etc. This is worth a visit to see everything you can bring into your life.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000184 Days on yellowkey MLS ID: A4678951
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Bev Murray (941-724-4995)
2452 ASHTON RD, SARASOTA, FL 34231
$400,00019 Days on yellowkey MLS ID: A4698811
1 Days Off yellowkey (back on 7/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1298 Built: 2009 Tax: $3,088 (2025)Community: Wades SubSingle Family
Taxes:$3,088
Remarks: Buyers seeking to put in sweat equity, and investors, take notice! This 3 bedroom, 2 bath home is packed with potential! Situated on a large .45 acre lot, this home gives you the option of creating the type of home environment you choose, from sprawling gardens to storage for recreational vehicles, there is plenty of space for whatever you envision. In addition to 3 good-sized bedrooms and 2 full bathrooms, the well maintained interior features a kitchen with dinette and pantry and a large laundry room with a utility sink and cabinets. Wades Sub is a historic residential subdivision located south of Clark Road and west of Swift Road. Centrally located, homes in this neighborhood are within close proximity to a wide variety of shopping and dining venues and the area’s world renowned beaches. A short drive North takes you to vibrant downtown Sarasota and all its cultural and recreational offerings. A rare opportunity in this neighborhood, don’t let this gem get away!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
800 HUDSON AVE #106, SARASOTA, FL 34236
$515,000230 Days on yellowkey MLS ID: A4673881
REDUCED by $35,000 (6.4%) on 07/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1562 Built: 1984 Tax: $3,822 (2025)Community: Hudson HarbourCondo
Taxes:$3,822
Remarks: Unbeatable value and location in downtown Sarasota. This 3-bedroom, 3 full bath residence lives more like a townhome than a condo. No elevators, park right in front of your front door and walk out to the pool. Ideally located across from Selby Gardens and only one block from Sarasota Bay. Hudson Harbour is not in the AE flood zone, has covered parking and is pet-friendly, allowing one small dog and multiple cats. The three versatile bedrooms in this residence provide exceptional flexibility. The first-floor bedroom & bath can serve as a convenient primary suite, while the second-floor option offers additional privacy—ideal for guests, family, hobbies, or a home office. Enjoy two private balcony lanais overlooking a lush tropical garden and tranquil fountain, creating the perfect setting for morning coffee or relaxing evenings. Inside, the home features light soft neutral tones complemented by neutral tile flooring and elegant crown molding throughout. The thoughtfully designed kitchen includes a spacious eat-in dining area and breakfast bar that opens seamlessly to the living and dining spaces—perfect for everyday living and entertaining. Numerous updates have been completed over the years, including: Brand-new AC (2024), New windows and sliding glass doors, renovated bathrooms, updated kitchen appliances, New washer and dryer, Water heater replacement and fresh interior paint. Hudson Harbour offers a private downtown, intimate tropical setting with only 18 units centered around a heated community pool. Living here places you within walking distance to the Sarasota Bayfront Park for nightly sunsets, a boat cruise or waterfront dining and of course all of Sarasota’s downtown restaurant and theater options. Outdoor lovers will appreciate easy access to Legacy Trail, Payne Park and Lido Beach. Take the free downtown trolley to St. Armands Circle and Lido Beach. Schedule a showing and don’t miss this best priced Downtown Sarasota residence on the market today !
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Maureen Doherty (941-993-3159)
5780 MIDNIGHT PASS RD #B105, SARASOTA, FL 34242
$1,100,00060 Days on yellowkey MLS ID: A4693221
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $8,709 (2025)Community: Gulf & Bay ClubCondo
Taxes:$8,709
Remarks: Experience the best of beachfront living at Gulf & Bay Club, one of Siesta Key's premier Gulf-front communities on the world-famous white quartz sands of Siesta Key Beach. This beautiful ground-floor residence offers 2 bedrooms/2 baths, office area, dining & living rooms, and in unit laundry - all surrounded by lush tropical landscaping that creates a peaceful, private setting. The open-concept floor plan features warm coastal finishes, crown molding, and an updated kitchen with newer appliances, abundant cabinetry, a convenient beverage cooler, and an in-unit LG washer/dryer. Expansive sliding glass doors fill the home with natural light while showcasing views of two lagoon fountains, tropical landscaping, and partial Gulf views that provide spectacular sunset backdrops. Recent updates include an A/C (Nov. 2021), hot water heater (Mar. 2026), and GE microwave (2025). Ideally located just steps from one of the community's grilling areas, this residence offers the perfect blend of comfort and convenience. Gulf & Bay Club is a gated 32-acre beachfront community with 800 feet of private Gulf frontage and exceptional resort-style amenities, including three heated pools, two clubhouses, a fitness center, hot tub, dry saunas, eight tennis courts, racquetball and basketball courts, a scenic lagoon with a charming island, electric vehicle charging stations, and an active social calendar with organized events and activities. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this exceptional condominium offers the ultimate Siesta Key lifestyle.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
1160 WAGON WHEEL DR, SARASOTA, FL 34240
$1,500,000233 Days on yellowkey MLS ID: A4673997
REDUCED by $25,000 (1.6%) on 06/06/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2467 Built: 1976 Tax: $5,221 (2024)Community: Fox Creek AcresSingle Family
Taxes:$5,221
Remarks: Welcome to a private 5 acre luxury estate, a rare multi residence retreat in the heart of Sarasota. Tucked behind a picturesque canopy of mature oaks and white ranch fencing, this exceptional property offers unmatched space, serenity, and versatility, featuring a beautifully maintained main residence, a fully equipped two story barn home with both upstairs and downstairs living accommodations, a sparkling saltwater pool, and acres of cleared usable land. The main home offers 3 bedrooms plus a large game room with a full closet that can serve as a fourth bedroom, office, or flex space depending on the buyer’s needs, along with multiple living areas and wide open spaces filled with natural light and peaceful views of the pool and surrounding acreage. Meaningful updates include appliances replaced in 2024, a whole house water softener system in 2024 including the apartment, septic pumped in 2024 with a new leech bed installed for both the home and apartment, a saltwater pool pump replaced in 2024, AC replaced in 2020, water heater replaced in 2019, and a durable metal roof from 2008. The expansive kitchen opens to the pool and living areas, complemented by a beautiful stone fireplace and a large bonus room perfect for a billiards room, playroom, gym, or hobby space. Outdoor living shines with a fenced saltwater pool and paver deck, ideal for sunny afternoons and relaxed evenings under the mature oak trees. The two story barn home is divided into two separate units, offering incredible flexibility for multigenerational living or rental income. The upstairs unit features 2 bedrooms and 1 and a half bathrooms, along with 2015 appliances and a private screened balcony overlooking the property. The downstairs unit includes 1 bedroom and 1 bathroom, updated flooring, granite counters, a 2020 stove and dishwasher, and a 2022 refrigerator. The barn also features a metal roof from 2006 and benefits from the recent septic upgrades. The full 5 acres are fully fenced and usable, perfect for horses, gardens, recreational vehicles, or future expansion, all accessed by a beautiful winding paved driveway and an oversized three car garage. This property offers peaceful privacy while still being close to shopping, dining, medical facilities, parks, I 75, and just a short drive to Siesta Key, Lido Key, and the world renowned Gulf Coast beaches.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Katie Cobb (913-744-0248)
1915 CLEMATIS ST, SARASOTA, FL 34239
$3,200,00045 Days on yellowkey MLS ID: A4694616
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3161 Built: 2009 Tax: $32,815 (2025)Community: Desota ParkSpa: YesSingle Family
Taxes:$32,815
Remarks: A timeless statement of modern luxury, this impeccably reimagined West of Trail residence exudes sophistication, serenity and refined coastal elegance. Completely remodeled, professionally designed and expertly curated, this extraordinary Sarasota home showcases one-of-a-kind craftsmanship, elevated design and exceptional finishes throughout, creating an unparalleled luxury living experience in one of Sarasota’s sought-after neighborhoods. Distinguished appointments include custom cabinetry by Das Holz Haus, reclaimed wood architectural elements, engineered luxury hardwood flooring, designer lighting with Lutron controls, rich designer paint finishes and bespoke décor. Encompassing 3,161 square feet heated and 4,194 total, this floor plan is designed for everyday living, entertaining and relaxing. At the heart of the home, the chef’s kitchen, anchored by two oversized islands, including a breakfast bar, and surrounded by artisan-crafted solid wood cabinetry. Brushed honey bronze fixtures and hardware complement Calcutta quartz countertops, while a farmhouse sink with a designer faucet enhances beauty and functionality. Culinary enthusiasts will appreciate the professional-grade appliance package highlighted by a 2021 La Cornue five-burner gas range with double convection ovens, custom chimney hood and premium ventilation system. Complimented by 2021 Sub-Zero refrigerator, 2021 Sub-Zero refrigerator drawers, 2021 Sharp microwave, 2021 Miele built-in coffee maker, 2025 Sub-Zero wine cooler, 2021 Scotsman ice maker, 2025 Galley sink tap, Shaw fireclay main sink, Shaw fireclay bar sink and Zip water system for bar (hot, cold, sparkling). The kitchen flows seamlessly into the dining area and living room, where a sleek linear color-changing electric fireplace framed by reclaimed wood creates a warm contemporary ambiance. Designed for effortless indoor-outdoor living, the residence offers inviting spaces to relax and entertain. The serene primary suite serves as a private retreat with direct access to the covered lanai. A spa-inspired primary bath features a custom natural wood double vanity, Duravit wash basins, Robern mirrored medicine cabinets with integrated lighting, heated towel warmer, freestanding concrete soaking tub, and a luxurious walk-in shower with multiple showerheads and body sprays. A well-appointed laundry room offers custom cabinetry, 2023 LG stack washer/dryer and ample folding space. A private guest suite with its bath is conveniently on the main level, and a 2025 remodeled bath. Upstairs, a spacious 300-square-foot loft with an 11-foot tray ceiling serves as a gathering space between secondary bedrooms and baths, one being en suite. Complementing the home is an epoxy-coated three-car garage with storage, workspace and room for recreational equipment. Resort-inspired outdoor living environment features travertine tile flooring, a heated pool and spa, and covered entertaining areas, including a 2026 built-in outdoor kitchen, covered dining space and lounging areas. Residence exterior freshly painted 2025, lush landscaping installed 2024, two house HVACs 2025, garage HVAC 2023, whole-house generator 32kVA and pool filter 2025. Ideally in Sarasota’s desired West of Trail neighborhood, offering convenient access to Southside Village, Sarasota Memorial Hospital, Southside Elementary School, Marina Jack, world-class dining, boutique shopping and Gulf beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Moriah Taliaferro (941-504-9910)
3224 WOODBERRY LN, SARASOTA, FL 34231
$449,90027 Days on yellowkey MLS ID: N6144779
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1550 Built: 1998Monthly Fee: $296 Tax: $4,441 (2025)Community: Ashley OaksSingle Family
Taxes:$4,441
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated three-bedroom, two-bath home offering maintenance-free living in an intimate community of just 27 homes. From the moment you go inside, you'll appreciate the light, bright open floor plan featuring new luxury vinyl plank flooring throughout, fresh interior paint and a stunning remodeled kitchen. The kitchen is sure to impress with new shaker cabinetry, gorgeous quartz countertops, and new refrigerator and range. A sunny breakfast nook provides the ideal spot to enjoy your morning coffee, while the breakfast bar overlooks the dining and living areas, making entertaining effortless. A spacious pantry offers additional storage. The living room opens through sliding glass doors to the screened lanai, where you'll enjoy peaceful pond views, abundant birdlife and exceptional privacy. The spacious primary suite also features private lanai access, a walk-in closet, and an updated ensuite bath with a double quartz vanity and walk-in shower. Two additional bedrooms provide comfortable accommodations for family or guests, and the guest bath has been refreshed with a new vanity, new luxury vinyl floors and fresh paint. Additional features include an interior laundry room with extra storage space and a two-car garage. New roof in 2017 and new air conditioner in 2020. Residents enjoy a community pool and the ease of maintenance-free living. Ideally just minutes from Siesta Beach, as well as exceptional shopping, dining, parks and everyday conveniences, this move-in-ready home offers a combination of style, comfort and location. A beautifully updated home in a peaceful setting is ready for you to move in and enjoy!
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Martha Pike (941-716-4392)
2411 VALENCIA DR, SARASOTA, FL 34239
$795,000153 Days on yellowkey MLS ID: A4683111
REDUCED by $24,000 (2.9%) on 07/14/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1927 Built: 1958 Tax: $6,459 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,459
Remarks: Looking for an oversized garage and storage? At 781 sf, this one may have room for everything! Welcome to this beautiful redux in the desirable South Gate community of Sarasota. Originally constructed more than 60 years ago by exceptional craftsmen, this mid-century home has been meticulously updated with a modern interpretation of the classic South Gate style. Updated electric, completely re-piped, new HVAC, and new hurricane-rated impact windows and doors are the most important updates offered here. Three new baths and a completely reimagined kitchen and dining area bring everything and everyone together. Even the landscaping has been optimized for resilience and maintenance simplicity. With a generous two-bay garage, extra parking for entertaining, privacy fencing, and an oversized lot, this home will satisfy the needs and vision of many discerning buyers, and certainly its next fortunate owner. Positioned on an elevated lot well above any flood zone, owners will rest easily, no matter what the weather brings. This extraordinary home provides all this, quality, style, modernity and safety, while being only a few minutes from everything people desire in this area. Siesta Key and downtown Sarasota, wonderful beaches and vibrant lifestyle will be the daily experience for the next owner of this fine home. Find out what life could be like for you in this special place!
Listing Agent: Christopher Bush (941-404-9504)
4444 SWIFT RD #4, SARASOTA, FL 34231
$122,900308 Days on yellowkey MLS ID: A4665781
REDUCED by $5,000 (3.9%) on 07/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 598 Built: 1969 Tax: $1,804 (2024)Community: Lucaya Country Club VillageCondo
Taxes:$1,804
Remarks: WELCOME to this beautifully UPGRADED 1 bedroom, 1 bath condo in Lucaya Country Club Villas!!! From the moment you arrive, you'll appreciate the attention to detail, starting with the painted and SCREENED front porch, perfect for year-round enjoyment. Step inside to an inviting open floor plan featuring spacious living room and dining room combo. The kitchen has been tastefully upgraded with MODERN cabinets, countertops, and an eat-in area with stools. The spacious bedroom offers ample closet space, while the bathroom includes a tub and shower combo for convenience. Throughout the condo, you'll find LUXURY VINYL FLOORING, adding to both style and durability. As part of Lucaya Country Club Villas, you'll enjoy access to a community pool, along with a prime location just a short drive to amazing restaurants, shopping, Sarasota's downtown vibrant scene, Sarasota Airport, Siesta Key and the WORLD FAMOUS GULF beaches. Whether you're searching for an investment property or a primary residence, this condo is exactly what you're looking for. This home is truly MOVE-IN ready, offering comfort, charm, and a maintenance-free lifestyle in a desirable community and it's waiting for you to enjoy! Don't wait to make this YOUR home and begin your FLORIDA Lifestyle!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Christy Peterson (774-287-5322)
850 S TAMIAMI TRL #630, SARASOTA, FL 34236
$317,500145 Days on yellowkey MLS ID: A4684292
REDUCED by $11,500 (3.5%) on 05/17/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1224 Built: 1998 Tax: $1,963 (2025)Community: Central Park Sec 2 Ph 1Condo
Taxes:$1,963
Remarks: 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.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Tom Ward (941-350-2463)
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