Location: Sarasota
Do Not Show Listings
4650 WOODBROOK DR, SARASOTA, FL 34243
$485,00075 Days on yellowkey MLS ID: A4689681
REDUCED by $10,000 (2.0%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1744 Built: 2012Monthly Fee: $194Community: Woodbrook Ph ISpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: Robert E Willis Elementary
High School: Braden River High
Tax Year: 2025
Middle School: Braden River Middle
Remarks: Welcome to the sought-after Woodbrook community in this gated development with private access and resort-style amenities. Just a short walk from the community pool sits this charming traditional Florida home built by Neal Communities. Step inside to a bright, open floor plan with high ceilings and a spacious kitchen island perfect for morning coffee and family meals. The generous living room provides an ideal space for entertaining and gatherings. Outside, the backyard has been transformed into a private oasis with vinyl fencing, offering a safe play area for pets. The home backs to a natural preserve that stretches nearly 0.4 miles, delivering peaceful views and added privacy. Conveniently located, University Town Center is just a 10-minute drive, sandy beaches are approximately 25 minutes away, and downtown Sarasota or Bradenton are about 15 minutes. Easy I-75 access is only 7 minutes away. This is a wonderful opportunity in a prime location. Come see this lovely home today!
Listing is courtesy of: KONA REALTY (941-718-8293)
Listing Agent: Vlado Konatar (941-718-8293)
800 HUDSON AVE #106, SARASOTA, FL 34236
$550,000203 Days on yellowkey MLS ID: A4673881
REDUCED by $37,000 (6.3%) on 05/27/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1562 Built: 1984 Tax: $3,605 (2024)Community: Hudson HarbourCondo
Taxes:$3,605
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
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)
3441 BEEKMAN PL #40, SARASOTA, FL 34235
$275,000205 Days on yellowkey MLS ID: A4674297
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1064 Built: 1990 Tax: $1,342 (2024)Community: Forty-Three West IiCondo
Taxes:$1,342
Elementary School: Emma E. Booker Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Recently Reduced! Tucked away in a small, quiet community yet close to all the action near the UTC Mall—where shopping, restaurants, entertainment, and the new Mote Aquarium are right at your doorstep—this 2-bedroom, 2-bath villa offers the perfect blend of convenience and tranquility. Enjoy front and rear courtyards that create a private tropical paradise for outdoor living, complete with your own lemon tree loaded with fruit. Sliding glass doors to the courtyards from the kitchen, primary bedroom, second bedroom, and living room make these spaces feel like natural extensions of the living areas. Features include a NEW ROOF (2023), plantation shutters, and Hunter Douglas Vertiglide shades for carefree living. The primary suite has it's own private en suite bathroom and an oversized walk in closet. A built-in desk with shelving and a queen-sized Murphy bed in the second bedroom give this room the flexibility of an in-home office or guest space. Close the hall pocket door from the living room to convert this area into a private guest suite. The kitchen and bathrooms have been tastefully updated with beautiful countertops and vanities. A convenient laundry area is tucked behind louvered doors in the kitchen. An attached one-car garage with room for storage and a workbench, plus oversized closets throughout the home, provides more storage space than you would expect in a condo or villa. The friendly community offers a clubhouse, tennis and pickleball courts, and a sparkling pool just around the corner. This home checks all the boxes for enjoying the Florida lifestyle: an excellent location, inviting indoor-outdoor living areas, ample storage, great amenities, and bright, airy rooms made for relaxing. Come and see if this is the right place for you!
Listing is courtesy of: REALTY PLACE (941-212-2828)
Listing Agent: Barbara Beasley (941-724-4334)
1020 SUN AND SEA DR #102, SARASOTA, FL 34242
$575,000257 Days on yellowkey MLS ID: A4667291
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 524 Built: 2009Monthly Fee: $822 Tax: $3,572 (2023)Community: Beach Club At Siesta KeyCondo
Taxes:$3,572
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Welcome to Beach Club at Siesta Key, where an unbeatable investment opportunity awaits just steps from the world-renowned Siesta Key Beach. This charming 1-bedroom, 1-bathroom first-floor condo is the ideal blend of personal escape and income-generating property, boasting a successful history in short-term rentals. As you step inside this fully furnished, turnkey unit, you’re greeted by an open living area is perfect for relaxation, featuring a TV for entertainment, while the kitchen comes equipped with stainless steel appliances. An in-unit washer and dryer add to the convenience, making longer stays comfortable and stress-free. The on-site professional management team handles all the details, from bookings to maintenance, giving owners peace of mind and ensuring that guests have a seamless experience. The property offers desirable amenities, including a heated pool, a soothing hot tub, complimentary Wi-Fi, and beach chairs and umbrellas for enjoying sun-soaked days by the ocean. Positioned mid-island and close to the Stickney Point Bridge, this condo provides easy access to all that Siesta Key has to offer. The Beach Club at Siesta Key is a hidden gem that is perfectly located within walking distance of South Siesta Village, Crescent Market, and local favorites for ice cream, coffee, dining, and more.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Cole Collins (941-350-8360)
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,299,000124 Days on yellowkey MLS ID: A4683108
REDUCED by $50,000 (3.7%) on 05/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $10,806 (2025)Community: Gulf & Bay ClubCondo
Taxes:$10,806
Elementary School: Phillippi Shores Elementary
Remarks: Welcome to the effortless rhythm of island living at Gulf & Bay Club, one of Siesta Key’s most prestigious beachfront communities. Behind the 24-hour guard-gated entrance, this beautifully remodeled, rarely available, three-bedroom residence offers the perfect blend of comfort, privacy, and resort-style living in a setting that feels worlds away from the everyday. Positioned on the first floor as a bright end unit, the home is surrounded by windows on three sides, filling the interior with natural light and creating a relaxed coastal atmosphere throughout. The thoughtfully redesigned floor plan opens beautifully for entertaining, with elegant finishes and carefully curated upgrades that make the residence feel both sophisticated and welcoming. The kitchen was designed with gathering in mind, featuring custom cabinetry, quartz countertops, marble backsplash, and premium Bosch appliances including induction cooktop and stainless vent hood. An additional built-in entertaining area with beverage refrigeration and extra storage makes hosting friends and family effortless. Living and dining areas flow naturally to the private lanai overlooking tropical landscaping and a tranquil lagoon, just steps to one of the community’s three pools, where evenings are often spent enjoying the peaceful surroundings and the soft glow of Siesta Key sunsets. The three-bedroom layout provides exceptional flexibility, whether for hosting guests, accommodating family, or creating a quiet home office. The primary suite offers a peaceful retreat with a walk-in closet and a beautifully updated bath featuring custom cabinetry, quartz countertops, and an expanded designer-tiled shower. Extensive renovations throughout the home include raised ceilings, smooth-finish walls, luxury flooring, updated lighting and electrical systems, new ductwork, upgraded panel box, air handler, and quick-recovery water heater. Importantly, the residence did not experience water intrusion during the recent hurricanes, offering additional peace of mind. Life at Gulf & Bay Club is defined by its resort-style amenities across 32 gated beachfront acres and 800 feet of Siesta Key’s famous quartz sand beach. Residents enjoy three heated pools including a lap pool, tennis and pickleball courts, racquetball, a large fitness center, beautifully landscaped walking paths surrounding the freshwater lagoon, clubhouses for gatherings, electric vehicle charging stations, and professional on-site management — all within a secure 24-hour guard-gated community. Just beyond the gates, the vibrant charm of Siesta Key Village awaits with its locally loved restaurants, boutiques, and island nightlife, while downtown Sarasota’s renowned arts and cultural scene is only a short drive away. This is more than a residence — it is an opportunity to experience the best of beachfront living on Siesta Key.
Listing Agent: Natalie Gutwein (941-993-2660)
1475 LANDINGS CIR #43, SARASOTA, FL 34231
$629,00038 Days on yellowkey MLS ID: A4694471
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2040 Built: 1982 Tax: $674 (2025)Community: Landings TreehouseTownhouse
Taxes:$674
High School: Riverview High
Remarks: There's no place quite like it in Sarasota. Tucked into the canopy of a lush, jungle-like landscape at The Landings, this three-story Treehouse townhome delivers the rare combination of absolute privacy and natural beauty that defines one of the Gulf Coast's most beloved communities. Soaring above the native palms and mossy oaks, this 2,040 sq ft, 3-bedroom, 2-bath + powder room residence has been thoughtfully updated while preserving the treetop retreat feeling that makes these homes so coveted. The 2025 renovated kitchen features fresh cabinetry and all-new washer and dryer ? move-in ready with nothing to do but settle in and listen to the breeze. A wood-burning fireplace anchors the living space with warmth and character, while multiple decks off each level bring the outdoors in at every turn. A private garage, generous lanai, and verdant views from nearly every window complete the picture. Exterior maintenance is included, so the only thing on your to-do list is enjoying it. And for those who travel with four-legged family members ? pets are welcome here with no weight restrictions. The Landings is a gated waterfront community offering residents access to Har-Tru tennis courts, a community pool, and the private Landings Yacht, Golf & Tennis Club (optional membership). All just minutes from world-class dining, the arts, and the sugar sands of Siesta Key. This is more than a home ? it's a lifestyle hiding in plain sight.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
1111 N GULFSTREAM AVE #7C, SARASOTA, FL 34236
$1,285,00056 Days on yellowkey MLS ID: A4692338
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1736 Built: 1974 Tax: $6,860 (2025)Community: One WatergateCondo
Taxes:$6,860
Remarks: This One Watergate condominium in Downtown SRQ FL has location and endless views. Looking for the unexpected, this home will not disappoint. A full, to the studs remodel in 2020 brings versatility to your personal style. These sellers live a warm and eclectic life. The open spaces enhance the water, marina, and city views, and then watch the canvas flip to an evening light-scape of the same view. With this remodeled open floor plan all eyes are drawn to the unobstructed views through the floor to ceiling impact windows and doors onto the wrap around covered patio with glass panel railing. The 7th floor view gives the feeling you are right on the water. Their home has been open to many festivities. My favorite celebration has been the 4th of July with fireworks set off on City Park in the Bay right in front. The decor includes Sonoma Valley American wire-brushed & hand scraped hickory wood flooring, and warm color walls. The kitchen features an extended service and storage design including a wine and beverage refrigerator. Highlights include Kraft Made cabinets and Cambria quartz counter tops. Appliances feature GE Cafe series with induction range, French door refrigerator & dishwasher. Double closet pantries with pull out drawers, and stainless-steel farmhouse sink. The spacious primary bedroom has real views of the Ritz and Quay towers in the background. Soft lighting window treatments are perfect for the day and room blackout shades are perfect for the evenings. The en-suite has a double vanity, storage mirrors with digital LED lights, designer tiling and shower with dual showerheads. The over-sized closet has been designer built out to maximize the square footage for two. The guest bedroom doubles as mobile office. Across the hall from the second bath with complimenting style and finishes with the primary bath. Unit 7C is in the coveted C stack which includes an interior laundry room with exterior venting. So many details to see. One Watergate has completed both Milestone and SIRS reports. They are ahead of the state requirements on compliance. The property has completed many updates within the past 5 years. From new elevators, roof, underground plumbing lines, exterior paint, updated pool, landscaping, lighting, grills & pool furniture, and new fitness center. A complete building remodel includes new tile, carpeting, wall paper, lighting, full catering kitchen and community room, and unit doors from 18th floor down. The building electrical room is being moved to the 2nd floor this spring and the lobby, social rooms, and management support facilities will be completed within weeks. Owners will enjoy a walkable Downtown lifestyle of the Sarasota Arts, restaurants, entertainment and the bay parks. The Ritz spa packages are available to the public. Or pick up the Bay Runner free trolley steps away which stops on St Armand's Circle and Lido Key Beach. With all said, at $740 square footage price Unit 7C is competitively priced. Can easily? compare with other properties square footage priced at $1,000 plus. This is an incredible opportunity to own this wonderful home to live, work, and play.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: James Brown (941-408-3332)
5300 MAHOGANY RUN AVE, SARASOTA, FL 34241
$435,00093 Days on yellowkey MLS ID: A4687853
REDUCED by $15,000 (3.3%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1585 Built: 1999Monthly Fee: $348 Tax: $3,048 (2025)Community: Heritage Oaks G&CcVilla
Taxes:$3,048
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Don’t miss out on this rarely available Arlington end unit in Heritage Oaks Golf and Country Club with lake views overlooking the 12th hole. More natural light and added privacy make this home one of the most desirable locations in the community. This two-bedroom plus office or den home offers the flexibility to easily convert into a three-bedroom. It features a rare private exterior entrance, ideal for guests, a home office, or added privacy. This home is move-in ready with thoughtful upgrades throughout that is rare to find including crown molding, plantation shutters, travertine flooring, stainless steel appliances, bar area, and re-piping. The HVAC system was replaced six years ago, and the garage features all new electrical. Updated hardware throughout the home adds a fresh, modern touch. A hurricane screen less than one year old provides added protection and peace of mind. The primary bedroom suite offers walkout access and a private bathroom with a jacuzzi tub, walk-in shower, and updated countertops and sinks. Inquire about the brand-new bedroom flooring that has been ordered and will be installed. Enjoy a coveted two-car garage and true maintenance-free living with landscaping, roof, exterior painting, and driveway care included. The home is also equipped with fire sprinklers that are maintained by the association, adding an extra layer of safety and convenience. Are you ready to create once-in-a-lifetime memories? Heritage Oaks is more than a community, it is a lifestyle. Enjoy championship golf, an award-winning pro shop, clay tennis courts with clinics and programs, five heated pools, a fitness center with classes and personal training, and both casual and fine dining led by a certified executive chef. A full social calendar and stunning sunset terrace create a vibrant and connected experience. Set within a gated community with 24-hour guard service and an Audubon-certified nature preserve, you will experience beautifully landscaped grounds with deer roaming throughout. With strong reserves and a debt-free structure, this community offers both luxury and peace of mind. Located in what many call the center of it all, you are 10.2 miles to Waterside Place, 11.3 miles to University Mall shopping and dining, 6.1 miles to Doctors Hospital, and under 17 miles to Lido Beach and Siesta Key Beach. Opportunities like this do not come often. Schedule your private showing today!
Listing is courtesy of: DREAMIFY REAL ESTATE LLC (941-827-0700)
Listing Agent: Jessica Peterson (970-222-2891)
3361 CROSS CREEK DR #3361, SARASOTA, FL 34231
$277,500107 Days on yellowkey MLS ID: A4685552
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1984Monthly Fee: $632 Tax: $2,667 (2025)Community: Crooked Creek Sec 7Condo
Taxes:$2,667
Elementary School: Wilkinson Elementary
Remarks: Welcome to one of the best locations in Crooked Creek! This beautifully updated first-floor 2 bedroom, 2 bath split-plan condominium is ideally situated in the building directly next to the heated pool and just steps from the private community gate leading into the stunning Red Bug Slough Preserve. Light, bright, and open, the residence features expansive floor-to-ceiling windows that bring the outdoors in, showcasing peaceful views of Crooked Creek, a charming footbridge, and lush Florida landscaping filled with native foliage and wildlife. Enjoy your morning coffee or evening beverage from one of two serene lanais surrounded by nature. The Interior has been COMPLETELY UPDATED IN 2021, and now has a BRAND NEW A/C UNIT just installed May 2026. This stunning home offers a MODERN UPDATED KITCHEN with solid surface counters, stylish cabinetry, updated appliances, recessed and under-cabinet lighting, along with new laminate and tile flooring throughout. Both BATHROOMS were BEAUTIFULLY RENOVATED, and the home also features fresh interior paint, plantation shutters, and recessed lighting in the kitchen, dining area, and guest bedroom. The versatile guest room includes a Murphy bed with built-in desk, making it perfect for visitors or a convenient home office. Crooked Creek residents enjoy numerous community improvements including NEW ROOFS (2019-2021), CARPORTS, EXTERIOR PAINT (2025), RESURFACED HEATED POOL (2025), and an updated poolside COMMUNITY KITCHEN (2025). Each unit includes covered parking and a private storage locker in a large community shed. Outdoor amenities include a heated pool, large pool deck with covered pergolas. A gazebo area with gas grills for BBQ gatherings, and a tennis/ pickleball court. Designed by RENOWNED ARCHITECT TIM SEIBERT of Sarasota School of Architecture, the Crooked Creek community is thoughtfully nestled within nature, with winding paths and tranquil surroundings that make it a true hidden gem. A must-see for nature lovers seeking peaceful Florida living just moments from everything Sarasota has to offer.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
6287 MIDNIGHT PASS RD #103, SARASOTA, FL 34242
$685,000111 Days on yellowkey MLS ID: A4685468
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1550 Built: 1982 Tax: $7,057 (2025)Community: Excelsior Beach To Bay 6Condo
Taxes:$7,057
Remarks: Welcome to your sunny slice of paradise on Siesta Key. This bright and inviting south-facing condominium offers a great opportunity to enjoy island living just near the world-famous white quartz sand of Siesta Beach. This generously sized two-bedroom, two-bath residence has been well maintained by its original owner and occasionally occupied. The desirable southern exposure fills the condominium with natural light throughout the day, creating an open and welcoming atmosphere. The interior has been recently painted, giving the home a fresh, clean look ready for your personal touches. The unit includes several updates, including a newer stack washer and dryer, newer air-conditioning system, plus energy-efficient LED lighting. The spacious layout provides comfortable living and dining areas along with a generously sized main bedroom en suite, making it ideal for year-round living, seasonal use or take advantage of the Excelsior on-site rental program with a two-week rental minimum. Convenience is key with under-building assigned parking as well as a private storage closet for beach chairs, umbrellas and other beach essentials. This bay-to-beach complex offers an easy distance across the street to the powdery sand and turquoise Gulf waters of internationally recognized Siesta Key Beach. Residents and renters enjoy an impressive array of resort-style amenities. The property features tennis and pickleball courts, beautifully maintained grounds, bayside grilling areas, and bayside and Gulf-side swimming pools. Whether you prefer relaxing by the water, enjoying sunset walks along the beach or staying active with outdoor recreation, this community offers something for everyone. With its prime location, bright southern exposure and access to outstanding amenities, this Siesta Key condominium presents a wonderful opportunity to own a piece of Florida’s sought-after coastal lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
6515 BIG BAYOU DR, SARASOTA, FL 34241
$548,000115 Days on yellowkey MLS ID: A4685060
REDUCED by $10,499 (1.9%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1775 Built: 2024Monthly Fee: $312 Tax: $6,281 (2025)Community: Grand Park Ph 2Single Family
Taxes:$6,281
Remarks: Welcome to this beautiful, almost-new home built in 2024, offering 3 bedrooms, 2 bathrooms, a versatile den, and 1,775 square feet of thoughtfully designed living space filled with natural light. The open-concept floor plan creates a seamless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. This home is loaded with upgrades, including elegant crown molding, tray ceilings, custom woodwork, impact windows, and many additional designer touches that elevate the space throughout. Large sliders showcase peaceful lake views, bringing a sense of tranquility into the home. Located in the highly desirable Grand Park community, residents enjoy resort-style amenities including a luxury clubhouse, sparkling pool, pickleball courts, and a vibrant calendar of social events. Grand Park also offers a prime location with convenient access to shopping, dining, I75, and the world-famous Siesta Key beach, making this home the perfect combination of comfort, style, and lifestyle. This is a wonderful opportunity to enjoy modern luxury living in one of the area’s most sought-after communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Enrique Coletti (941-952-8164)
1611 HYDE PARK ST, SARASOTA, FL 34239
$3,750,000126 Days on yellowkey MLS ID: A4683619
REDUCED by $449,000 (10.7%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2545 Built: 1920 Tax: $6,507 (2025)Community: NoneSpa: YesSingle Family
Taxes:$6,507
Remarks: Located in Sarasota’s established West of Trail neighborhood, this gated and fenced 1920 Craftsman residence offers a rare double lot and a guest cottage. Originally constructed in 1920 and comprehensively renovated in 2025 and 2026, the property preserves its architectural character while integrating modern systems, finishes and upgrades including all impact windows and doors. Spanning 3,609 total square feet, the estate is designed for privacy and flexibility. The main residence includes three bedrooms and two and one-half baths. The primary suite is positioned on the main level with direct access to the pool and courtyard, along with a spacious walk-in closet. Large-format porcelain block flooring extends throughout, complemented by updated lighting and professionally curated design elements introduced during the full vintage renovation. The kitchen supports both daily living and entertaining, anchored by a substantial island with quartz countertops, new appliances and a natural gas five-burner range. A dining nook overlooks the pool and courtyard, while adjacent living and lounge areas create seamless gathering spaces. Outdoor living centers around a private courtyard featuring a heated saltwater pool and spa with rock fountain feature, outdoor kitchen, multiple balconies and sitting areas, a sweeping front porch and the landscape lighting is strategically set among the mature Florida landscaping. A custom-built treehouse fort and chicken coop contribute additional character to the grounds. A detached, air-conditioned two-car garage includes a self-contained guest cottage above with one bedroom, office and one bath, with additional covered parking offering flexibility for extended family, guests or potential rental income. Conveniently located near Hillview Street dining and shopping, Morton’s market, the bayfront, Downtown Sarasota and Southside Elementary School, this property combines preserved Craftsman architecture with modern livability in one of Sarasota’s most desirable in-town locations. Can be sold furnished.
Listing Agent: Lori Carey, Llc (941-780-3427)
8605 RAIN SONG RD, SARASOTA, FL 34238
$479,900158 Days on yellowkey MLS ID: A4678947
REDUCED by $20,000 (4.0%) on 05/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 2019Monthly Fee: $521 Tax: $2,283 (2025)Community: Sunrise PreserveVilla
Taxes:$2,283
Elementary School: Ashton Elementary
Remarks: First time on the market! This newer-built, resilient home was constructed in 2019 to the latest hurricane codes and no flood insurance is required. Featuring a highly sought-after 2BR+Office/2BA floor plan with a 2-car garage, this residence is one of only 10 Maritime models built by Mattamy Homes, making it a rare opportunity. A welcoming front porch with retractable screen door provides wonderful airflow and leads to a gorgeous impact-glass front door. Inside, the open-concept layout is ideal for both everyday living and entertaining. The beautifully appointed kitchen showcases wood cabinetry, glass tile backsplash, quartz countertops, stainless steel appliances, and dimmable pendant lighting. The adjacent dining area comfortably accommodates a variety of table sizes and flows seamlessly into the spacious great room—perfect for gatherings. The primary suite offers a tray ceiling and a luxurious en-suite bath featuring an oversized frameless glass shower with bench seating, dual vanities, and a large walk-in closet. The guest suite is privately tucked away with an adjoining bath, providing excellent separation and privacy. The study includes a built-in desk and French doors, making it ideal for a home office or den. Additional highlights include tile flooring throughout the main living areas and study, 2 carpeted bedrooms, a laundry room with extra storage, and a finished garage with epoxy floors, utility sink, and an additional refrigerator. Crown molding and framed windows/sliders add an elegant, refined finish. Enjoy Florida living from the covered front porch or relax on the covered, rear screened lanai with pavers and privacy screen overlooking peaceful water and park-like views. Situated at the end of a cul-de-sac, this home benefits from minimal drive-by traffic. For added peace of mind, there are Accordion Shutters for all windows and sliders making preparing for hurricane a simple task that only takes minutes. The monthly HOA fee covers roof repair and replacement, exterior painting, exterior insurance, grounds maintenance, irrigation, and access to all community amenities and events. Sunrise Preserve at Palmer Ranch is a gated community offering resort-style amenities including a pool, tennis, pickleball and bocce ball courts, grilling areas, fire pit, clubhouse, and fully equipped fitness center. A robust calendar of social events makes it easy to meet neighbors and stay active. Ideally located in the Palmer Ranch area —convenient to shopping, dining, I-75, and world-class beaches.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Stacey Andrews (941-504-1649)
1804 N LAKE SHORE DR, SARASOTA, FL 34231
$4,995,000159 Days on yellowkey MLS ID: A4679067
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 6854 Built: 2004 Tax: $22,275 (2025)Community: Oyster Bay EstatesSingle Family
Taxes:$22,275
Remarks: A residence of sophistication and luxury, this exceptional home was thoughtfully designed to bring family and friends together—sharing good food, meaningful connection, and the enjoyment of elevated everyday living. Ideally located just 8 miles from Sarasota-Bradenton International Airport, 12 minutes to Siesta Key Beach, and 10 minutes to downtown Sarasota, the property is in close proximity to The Ringling, Van Wezel, Selby Gardens, Asolo, premier dining and shopping, The Field Club, and the Sarasota Yacht Club—creating a seamless blend of culture, convenience, and coastal lifestyle. Elegant yet warm and approachable, the home blends refined architecture with tropical elements, including stone columns, metal pergolas, concrete textures, and lush landscaping, creating a relaxed oasis unlike any other. A surrounding stucco wall enhances privacy, allowing you to unwind to the soothing sound of a tranquil fountain within a peaceful, secluded setting. The main living spaces were intentionally designed for gathering, featuring bead-board stained ceilings in the family room, formal living room, and dining area. The cook’s kitchen is both striking and highly functional, highlighted by a glazed pressed-tin ceiling, unpolished concrete floors, and views into the kitchen garden through multiple French doors and expansive windows—perfectly suited for both everyday living and entertaining.
Listing Agent: Bridget Spiess (941-720-6304)
1166 W PEPPERTREE DR #112D, SARASOTA, FL 34242
$725,000165 Days on yellowkey MLS ID: A4678257
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1974 Tax: $5,936 (2025)Community: Peppertree Bay IiiCondo
Taxes:$5,936
Remarks: Located on Siesta Key, this updated first-floor 2-bedroom, 2-bath condo at 1166 W Peppertree Drive offers an excellent combination of coastal living and rental potential. This home is offered TURN KEY! Just steps from the world-famous Siesta Key Beach, residents enjoy easy access to the island’s renowned white-sand shoreline, along with nearby shopping, dining, and local restaurants. The well-maintained open floor plan features an updated kitchen with granite countertops, custom cabinetry, and stainless-steel appliances. An enclosed lanai provides additional living space with a built-in quartz workspace and owner storage. Both bathrooms offer granite countertops and walk-in showers. Additional features include wood plank tile flooring throughout, updated windows, in-unit washer and dryer, and a remodeled kitchen. Peppertree is a Beach-to-Bay community with resort-style amenities, on-site management, optional rental program, and security, making this property ideal as a primary residence, seasonal retreat, or investment opportunity. Conveniently located near marinas, golf, Siesta village, and downtown Sarasota.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Mike Aveni (941-961-8730)
259 ROBIN DR, SARASOTA, FL 34236
$7,900,000189 Days on yellowkey MLS ID: A4675575
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4078 Built: 1996Monthly Fee: $110 Tax: $31,490 (2024)Community: Bird Key SubSpa: YesSingle Family
Taxes:$31,490
Remarks: An exceptional opportunity on coveted Robin Drive in Bird Key, this fully reimagined bayfront home captures Sarasota’s waterfront lifestyle at its finest. Recently transformed through a meticulous, top-tier renovation, the residence showcases impeccable craftsmanship, elevated finishes, and a seamless blend of sophistication and comfort—where every detail and major system has been thoughtfully curated for effortless, modern coastal living. Elevated above the floodplain with a ground level over 10 feet, sweeping panoramic views span Sarasota Bay, the downtown skyline, and the iconic Ringling Bridge—creating a breathtaking backdrop from sunrise to sunset, with city lights shimmering across the water in the evening. Inside, more than 4,000 square feet of light-filled living space unfolds across two thoughtfully designed levels. Soaring ceilings up to 14 feet and expansive walls of glass bathe the interiors with natural light while framing unobstructed bay views throughout. The main living areas flow seamlessly from the inviting sitting room with a statement fireplace to the dining area and custom-designed kitchen, opening to the family room with a built-in bar—a wonderful gathering area to enjoy the gorgeous backdrop of the bay and downtown lights. The kitchen is anchored by a striking waterfall island and features designer-appointed custom cabinetry, premium Sub-Zero, Wolf, Bosch, and Miele appliances, and refined integrated details throughout. A fully equipped back kitchen and pantry, complete with an additional sink, appliances, and generous prep space, enhances functionality while maintaining a clean, polished aesthetic. The primary suite, privately positioned on the main level, offers direct access to the pool, dual walk-in closets, and a spa-inspired bath with a soaking tub, dual vanities, and elegant finishes. A dedicated office and two powder baths complete the main level. Upstairs, two en-suite bedrooms with bay views, a versatile bonus room, and an additional office space provide comfortable accommodations for family and guests. Outdoor living is equally compelling, featuring an expansive paver terrace, heated pool and spa, and unobstructed views of Sarasota Bay, downtown, and the Ringling Bridge—creating a serene waterfront retreat designed for everyday enjoyment. Set on protected waters, the property offers 120 feet of deep-water frontage along Bird Key’s Pompano Pass, with direct access to Sarasota Bay, Big Pass, and the Gulf. A newly constructed seawall and Trex dock feature fish and dock lighting, a 24,000-pound boat lift, and dedicated kayak and jet ski lifts—perfectly suited for an exceptional boating lifestyle. Additional highlights include a circular driveway, three-car garage with Tesla charger, and irrigation well. Bird Key offers an exceptional coastal lifestyle in one of Sarasota’s most coveted neighborhoods, just moments from downtown’s restaurants, shopping, and cultural venues, as well as the boutiques and dining of St. Armands Circle and the shoreline of Lido Beach. The Bird Key Yacht Club is currently undergoing a full redevelopment and is expected to reopen as a premier destination for boating, tennis, dining, and an active social scene.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
2208 BAHIA VISTA ST #F1, SARASOTA, FL 34239
$250,000195 Days on yellowkey MLS ID: A4675125
1 Days Off yellowkey (back on 5/31/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1313 Built: 1980 Tax: $3,563 (2025)Community: Cordova GardensCondo
Taxes:$3,563
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. EXCEPTIONAL VALUE AND LOCATION. This first-floor entry condo lives like a house! It is so spacious and open with a flexible plan. The community is minutes to downtown Sarasota located in Cordova Gardens which is known for its beautifully maintained gardens, community pool and unbeatable location. This unfurnished condominium has three bedrooms and three full baths (two en suite master baths) and three outdoor patios. READY TO MOVE IN! There are numerous closets, storage space including walk-ins, a pantry and office loft space. The condo is exceptionally clean. The community known as Cordova Gardens is minutes to downtown Sarasota as well as Southside Village and known for its beautifully maintained gardens, community pool and PRIME location for the price. The condo also includes an outdoor storage closet, assigned and guest parking, pool, grounds and building maintenance, pest control, fire/smoke detection and Association management covered by the HOA. The complex is 5 minutes from downtown Sarasota and 15 minutes from Lido and Siesta Key beaches.
Listing is courtesy of: SECURE CAPITAL (203-981-4682)
Listing Agent: Frank Dinardo, Jr (203-981-4682)
2042 COUNTRY MEADOWS PL, SARASOTA, FL 34235
$515,000210 Days on yellowkey MLS ID: A4673225
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2052 Built: 1989Monthly Fee: $46 Tax: $2,868 (2024)Community: Country MeadowsSpa: NoSingle Family
Taxes:$2,868
Elementary School: Gocio Elementary
Remarks: LOCATION AND CONDITION ARE A+++ From the moment you arrive, you’ll feel right at home in this impeccably maintained residence. Meticulous care and attention to detail are evident throughout. The welcoming foyer opens seamlessly to the dining and living areas, offering views of the expansive lanai and oversized backyard. The beautifully remodeled kitchen is truly the heart of the home, designed to inspire and impress. Featuring porcelain tile floors, bright granite countertops, new cabinetry, and new appliances, it opens effortlessly to the family room with a cozy fireplace—perfect for both entertaining and everyday living. A smart thermostat and Ring doorbell add modern convenience and peace of mind. Whether seated at the breakfast bar or in the sunny nook beneath cathedral ceilings and skylights, you’ll appreciate the light-filled, open atmosphere. A generously sized pantry will delight any home chef. The split-bedroom floor plan provides privacy for all. Two guest bedrooms offer walk-in closets and share a roomy bath with direct lanai access. The primary suite is a true retreat, featuring a spacious walk-in closet and a stunning, newly renovated bath with updated tile flooring, new cabinetry, linen storage, and a solid-surface dual-sink vanity. Impact-resistant windows and doors are installed throughout, including private lanai access from the primary suite. Additional highlights include an oversized laundry room, ample floored attic storage, and an extended lanai designed for outdoor enjoyment—complete with granite counter space, sink, gas grill, and vented stainless-steel hood. The oversized lot provides abundant outdoor space and room for a future pool, if desired. Ideally located with convenient access to Downtown Sarasota, UTC Mall, Benderson Park, golf courses, dog parks, and recreation for all ages, this home places you just 15–20 minutes from the airport, Ringling Museum, marinas, colleges, and Lakewood Ranch Main Street. Move-in ready and thoughtfully updated, this exceptional property offers the lifestyle you’ve been waiting for. Schedule your private showing today and experience it for yourself.
Listing Agent: Susan Keal (941-320-1689)
156 SIESTA DR, SARASOTA, FL 34242
$1,649,000320 Days on yellowkey MLS ID: A4661717
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2901 Built: 1977 Tax: $19,016 (2024)Community: Siesta Rev ResubSingle Family
Taxes:$19,016
Remarks: Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
5908 BRIAR ROSE WAY, SARASOTA, FL 34232
$435,00041 Days on yellowkey MLS ID: A4693050
REDUCED by $33,900 (7.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 2019Monthly Fee: $81 Tax: $2,999 (2025)Community: Garden Village Ph 1Single Family
Taxes:$2,999
Elementary School: Fruitville Elementary
Middle School: McIntosh Middle
Remarks: Welcome home! This beautifully updated 3-bedroom, 2-bath home with a 2-car garage checks all the boxes. It is located in one of the most affordable gated communities in the area. The main living area flows effortlessly from room to room, perfect for everyday living and entertaining. You will find thoughtful upgrades throughout including crown moulding in the common areas, electrical upgrades and fresh interior paint. The kitchen has been upgraded for you with granite countertops, all appliances and even a new kitchen sink. Step into the master suite with an ensuite bathroom with granite countertops, upgraded toilet and new shower enclosure. The guest bathroom also features the same granite countertops, upgraded toilet and new shower enclosure as well. Comfort is covered with a whole-home water softener, carpet lain over tile, that could easily be removed, for cozy underfoot warmth. Continue through the home and step outside to your private backyard retreat featuring stunning paver and stonework — low maintenance with a drip irrigation system in the backyard keeping things lush without the work yet designed to impress. Located 2 mins away from I75 for easy commuting and 15 min to Siesta Key Beaches and 10 min from downtown, so conveniently located to everything! This home is truly a move-in ready gem. Come see it before it's gone!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Gary Turner (941-914-2500)
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