Location: Sarasota
Do Not Show Listings
5701 BENTGRASS DR #18-104, SARASOTA, FL 34235
$354,00016 Days on yellowkey MLS ID: A4695155
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1559 Built: 2002 Tax: $3,435 (2025)Community: Las Palmas Of SarasotaSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,435
Elementary School: Emma E. Booker Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to an exceptional opportunity in the heart of Sarasota’s desirable 34235 area. This inviting condominium offers a comfortable and well-designed layout filled with natural light, creating a warm and welcoming atmosphere from the moment you enter. Perfectly positioned within a peaceful and established community, this home combines convenience and lifestyle—just minutes from shopping, dining, golf courses, and everyday essentials, with easy access to Sarasota’s stunning beaches and vibrant cultural scene. Whether you’re looking for a full-time residence, seasonal retreat, or a smart investment, this property offers the ideal blend of comfort, location, and value. A true Sarasota lifestyle opportunity—ready for you to make it your own. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Rosa Mesia (941-962-0041)
1143 LONGFELLOW RD, SARASOTA, FL 34243
$165,500151 Days on yellowkey MLS ID: A4678360
1 Days Off yellowkey (back on 6/1/2026)
REDUCED by $9,495 (5.4%) on 05/08/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1408 Built: 1979 Tax: $1,093 (2024)Community: Shadybrook Village AmdCondo
Taxes:$1,093
Elementary School: Florine J. Abel Elementary
High School: Southeast High
Tax Year: 2024
Middle School: Electa Arcotte Lee Magnet
Remarks: Under contract-accepting backup offers. Welcome to 1143 Longfellow Rd, widely regarded as the most desirable unit in Shadybrook Village. This beautifully maintained 3-bedroom, 3-bathroom home offers a warm, inviting ambiance that instantly feels like home. From the moment you step inside, you’re greeted by neutral tones, tile flooring, and abundant natural light that enhances every space. The kitchen is both stylish and functional, featuring solid maple cabinetry, granite countertops, stainless steel appliances, and a customized walk-in pantry with built-in shelving. Elegant tray ceilings add architectural charm and a custom touch to the main living area. The first level includes a full bathroom for guests and residents alike, complete with thoughtful built-in features that will impress even the most discerning buyer. Durable vinyl flooring flows seamlessly up the staircase and throughout the entire second level. Just off the stairs, the first bedroom offers an incredible water view, while the second bedroom includes additional storage access for added convenience. The owner’s suite is a true retreat, boasting two separate closets, a tastefully shiplapped vanity, and a private shower and toilet area. Step outside to a peaceful, private patio with a paved pathway and ample space to create the garden oasis of your dreams. Tucked away behind a fence, this serene outdoor setting offers your own slice of paradise. Shadybrook Village residents enjoy a host of amenities, including a swimming pool, tennis and basketball courts, clubhouse, and playground area. Ideally located just 8 miles from University Town Center shopping and dining, 10 miles from the beach, and only minutes from Sarasota Airport, this home is perfectly suited as a primary residence or seasonal getaway. Don’t miss your opportunity to own one of Shadybrook’s finest homes.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Molly Higdon, Llc (941-875-1722)
2609 WOODGATE LN #K4, SARASOTA, FL 34231
$159,90062 Days on yellowkey MLS ID: N6143915
REDUCED by $5,000 (3.0%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1982Monthly Fee: $588 Tax: $2,358 (2025)Community: Pinewood Village IxCondo
Taxes:$2,358
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: You're five miles from one of the best beaches in America. You just didn't know you could afford to live this close. Ground floor, pool-facing, fully furnished 2BR/2BA in Pinewood Village. Walk out your lanai and you're at the pool. Walk out the front door and Siesta Key Beach, St. Armands Circle, Marina Jack, and downtown Sarasota are minutes away. The best-priced unit in the community — and better than anything else available right now. Ground floor instead of stairs. Tile throughout instead of carpet. Fully furnished and move-in ready the day you close. The only comparable unit in this section spent 385 days on the market and just went pending. This one won't last that long. Flood Zone X. No flood insurance required — a real financial advantage in today's Sarasota market. Outside your door, Sarasota delivers everything. Sarasota Memorial Hospital three miles away. Phillippi Estate Park around the corner. The Van Wezel, the Asolo, the Ringling, the Opera — ten minutes from your front door. The restaurants, the boutiques of St. Armands, the farmers markets, the sailing — all of it yours. Pinewood Village itself overdelivers at this price. Heated pool, fitness center, sauna, shuffleboard, full clubhouse with kitchen. HOA covers cable, water, sewer, trash, pest control, exterior maintenance and building insurance. Phillippi Shores Elementary, Brookside Middle, Riverview High. Association approval required. Sold As-Is. Seller motivated.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jeffery K. Twigg, Pa (941-412-6505)
7160 FAIRWAY BEND CIR, SARASOTA, FL 34243
$334,00076 Days on yellowkey MLS ID: A4688464
REDUCED by $5,000 (1.5%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1756 Built: 1979 Tax: $4,455 (2025)Community: Fairway BendVilla
Taxes:$4,455
Elementary School: None
High School: None
Middle School: None
Remarks: Don't miss this desirable two bedroom, two bath villa in Palm Aire Country Club's Fairway Bend. New Roof in 2022. Windows and Sliders replaced in 2014 . Kitchen, bathrooms and flooring were updated during ownership. You'll appreciate the spacious rooms including the bonus enclosed lanai. There's plenty of room to entertain friends and family in this spacious floor plan. The Fairway Bend clubhouse and pool are second to none in the Palm Aire community. Membership in Palm Aire Country Club is optional, but you'll find multiples plans available. Palm Aire is located off University Parkway and offers top notch goods and services including the UTC mall, restaurants, grocery stores and shopping. It's a quick drive to Downtown Sarasota, SRQ airport and our multiple top rated beaches are a short drive away.
Listing is courtesy of: PALM AIRE REALTY PARTNERS LLC (941-355-6300)
Listing Agent: Gini Fine (941-587-2141)
3710 EL POINIER CT #511, SARASOTA, FL 34232
$159,00045 Days on yellowkey MLS ID: A4691115
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 899 Built: 1974 Tax: $1,816 (2025)Community: Village Plaza Sec 3Condo
Taxes:$1,816
Elementary School: Wilkinson Elementary
High School: Sarasota High
Remarks: Step into this beautifully updated, turnkey furnished ground floor condo offering convenience, comfort, and an unbeatable location within the community. The updated kitchen features white shaker cabinets, a tile backsplash, recessed lighting, crown molding with uplighting, and a full white appliance package, creating a clean and timeless look. The layout flows seamlessly with tile flooring in the kitchen, laminate in the dining area, and carpet in both the living room and primary bedroom, with ceiling fans installed throughout. Comes with a 1 Home Warranty available to the buyers. One of the standout features of this unit is the enclosed additional living space, converted from the outdoor area, providing valuable extra square footage and flexibility. This space includes towel drying racks, perfect for coming back from the pool, and is filled with natural light thanks to the unit’s southern rear exposure. A slider from the primary bedroom leads directly into this space, enhancing the overall flow and usability. The bathroom has been updated with a glass shower door and grab bar for added functionality. The unit is truly move-in ready, being offered turnkey furnished with everything included from furniture to pots, pans, linens, and more. Location within the community is exceptional. This unit sits directly across from the heated pool and clubhouse, making it one of the most conveniently positioned units available. You are just steps to the on-site laundry facility, with machines costing only $1.00 per load, and the mailbox is located right next to the unit for added ease. A private storage closet is also included, located just around the corner. Living on the ground floor offers added value with easy access, no stairs, and everyday convenience. The community amenities are extensive, featuring a clubhouse with billiards, an active event room with regular social gatherings, a large library, fitness center, and sauna. Outdoors, residents enjoy a heated pool, community bbq grilling area, shuffleboard court, and pickleball. Major systems include a 2008 HVAC and 2015 water heater. Close to Bus Line & Shopping. One mile from the 18.5 mile long Legacy Trail for walking and biking. This is a rare opportunity to own a well-updated, fully furnished, and ideally located unit that offers both comfort and lifestyle.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
1126 GRANTHAM DR, SARASOTA, FL 34234
$255,00045 Days on yellowkey MLS ID: A4691797
0 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1252 Built: 2010Monthly Fee: $266 Tax: $2,834 (2025)Community: Bradford Manor Twnhms RepSpa: NoTownhouse
Taxes:$2,834
Remarks: $5K FLEX CASH! USE YOUR WAY! 2-bedroom, 2.5-bathroom END UNIT townhome located in Sarasota, offering added privacy, extra natural light, and fewer shared walls compared to interior units. Ideally situated just 10 minutes to Downtown Sarasota, 15 minutes to UTC, and approximately 20 minutes to the area’s beaches, this property combines convenience with comfortable living. The home features a functional two-story layout with an open main living area, a half bath downstairs for guests, and two spacious bedrooms upstairs, each with access to its own bathroom. Recent upgrades include a new roof (2025) with a transferable warranty, a new AC system (2025) with warranty, and brand new carpet (2026), providing peace of mind for the next owner. Enjoy a pet-friendly community and a low-maintenance lifestyle in a well-located Sarasota setting. $5,000 flex cash available to buyer, which can be applied toward closing costs, interest rate buydown, or purchase price. Cameras on premises. Some images have been edited for clarity.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Joseph Hoolihan, Pll (727-271-9980)
6100 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$6,499,000183 Days on yellowkey MLS ID: A4672432
2 Days Off yellowkey (back on 3/13/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3882 Built: 2019 Tax: $55,984 (2024)Community: Halcyon Siesta KeySpa: NoCondo
Taxes:$55,984
Remarks: Under contract-accepting backup offers. Welcome to Residence #201 at Halcyon Siesta Key—a rare opportunity within one of the island’s most exclusive boutique communities. With only six Gulf-front residences, Halcyon offers the ultimate in privacy, luxury, and architectural sophistication. This exquisite coastal retreat blends modern design with relaxed seaside living. Engineered hardwood floors, soft coastal hues, and floor-to-ceiling hurricane-impact windows frame sweeping views of the turquoise Gulf waters. Step off your private elevator into a bright, open floor plan designed for effortless entertaining. The gourmet kitchen features Wolf appliances, a wine fridge, and an oversized island flowing seamlessly into the dining and living spaces. The Gulf-front primary suite is a serene escape with a spa-inspired bath boasting dual vanities, a soaking tub, and a glass-enclosed shower. Two additional guest suites—each with private en-suite baths—offer exceptional comfort, while a versatile den/office provides flexibility for work or an additional bedroom. Unwind on your private Gulf-front terrace, where sunsets and sea breezes set the tone for everyday tranquility. Enjoy direct private beach access and the exclusive front amenity cabin, complete with a fitness center, bathrooms, comfortable lounge area, and an expansive deck ideal for entertaining or relaxing after a day by the water. A private two-car garage and resort-style amenities—including a beachfront pool and fire pit—complete this one-of-a-kind coastal lifestyle!
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
70 AVENIDA VENECCIA #204, SARASOTA, FL 34242
$5,400,000505 Days on yellowkey MLS ID: A4637710
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4154 Built: 2025 Tax: $7,518 (2023)Community: Sunset BeachSpa: YesCondo
Taxes:$7,518
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Under Construction. One or more photos have been virtually staged. Currently under construction with an estimated completion in the first half of 2026, Sunset Beach embodies the pinnacle of luxurious beachfront living on Siesta Key. Nestled within a neighborhood-inspired enclave surrounded by newly built homes, it offers a prime location just steps from the vibrant shops and restaurants of Siesta Key Village. This exclusive collection of 11 exquisitely designed residences redefines coastal luxury, offering unparalleled Gulf views and seamless integration with the natural beauty of its surroundings. At Sunset Beach, every detail of the residences has been thoughtfully crafted to elevate your living experience while embracing the beauty of Siesta Key’s Gulf-front serenity. Each home begins with direct private elevator entry, ensuring privacy and exclusivity from the moment you arrive. Once inside, you’ll be greeted by 10-foot ceilings, floor-to-ceiling windows, and oversized terraces that frame spectacular Gulf views, offering seamless indoor-outdoor living. The spacious layouts are perfect for living, dining, and entertaining, featuring custom kitchens and bars equipped with Sub-Zero and Wolf appliances, ensuring a culinary experience as refined as the setting. The solid-core 8-foot-high entry and interior doors, floor-to-ceiling hurricane-resistant balcony sliders with laminated solar-tint glass, and glass balcony railings harmonize style with durability, ensuring your home is both beautiful and secure. To enhance your comfort and convenience, the residences are pre-wired for state-of-the-art Smart Home technology, allowing you to tailor your living environment with ease. Outdoors, the terraces feature elegant stained tongue-and-groove ceilings, providing a warm, timeless aesthetic to complement the panoramic Gulf views. Whether you’re relaxing in solitude or entertaining guests, these terraces are the perfect space to savor the beauty of the coastline. At Sunset Beach, the thoughtful design and high-end finishes ensure every moment feels luxurious, from your private retreat to the breathtaking surroundings of Siesta Key. Every feature has been carefully curated to provide the ideal balance of comfort, style, and functionality in a beachfront sanctuary that truly redefines coastal living. Don’t miss your opportunity to own one of these exclusive residences. Spend your day relaxing by the poolside or take a few steps to a beachside lounge chair, where you can relax under an umbrella and enjoy the stunning views of crystal-clear water and white sand. Amenities include a beachfront swimming pool, spa, cabanas, and fire pit, lounge chairs, umbrellas, kayaks, paddle boards, and bikes, a state-of-the-art fitness center, beachfront grilling area, and private on-site storage units.Contact us today to schedule your private tour of Sunset Beach and take the first step toward living your coastal dream. Your new chapter of beachfront luxury begins here.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-867-9866)
70 AVENIDA VENECCIA #202, SARASOTA, FL 34242
$6,900,000505 Days on yellowkey MLS ID: A4637462
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3550 Built: 2025 Tax: $7,518 (2023)Community: Sunset BeachSpa: YesCondo
1702 WALDEMERE ST, SARASOTA, FL 34239
$1,375,00057 Days on yellowkey MLS ID: A4690683
2 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1950 Tax: $1,597 (2025)Community: Hudson BayouSingle Family
Taxes:$1,597
Remarks: Wonderful opportunity to build your dream home in the heart of Sarasota. Found in the desired West of Trail area, this quarter acre lot is 75' wide and offers endless possibilities. Located only one block from Sarasota Memorial Hospital, three blocks to Southside Village with tons of wonderful restaurants and shops, along with Morton's Market, and less than 1.5 miles to Main St in Downtown Sarasota. Also, conveniently right between our two beautiful white sand beaches - Lido and Siesta Key. Come build your perfect piece of paradise in Sarasota, Florida!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Victoria Beckham (941-544-6734)
727 N JEFFERSON AVE #727, SARASOTA, FL 34237
$219,000524 Days on yellowkey MLS ID: A4634891
REDUCED by $26,000 (10.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 936 Built: 1983Monthly Fee: $557 Tax: $2,761 (2024)Community: Jefferson PinesVilla
Taxes:$2,761
Remarks: Welcome to your newly renovated two bedroom two bath villa/condo in the community of Jefferson Pines. Close proximity to downtown Sarasota to experience all the restaurants, shopping and waterfront the city has. This unit has been completely remodeled from top to bottom to include vinyl flooring and 6 inch baseboard throughout, recessed lighting throughout, new air conditioning unit in 2024, new hot water heater in 2024, new bathrooms, vanities, showers, and tub, as well as a completely remodeled kitchen with solid wood cabinets, and all new stainless appliances and of course fresh paint throughout the unit. Also, a completely new lanai enclosure as well as new concrete slab. The community itself has matured landscaping, a community pool and is a very quiet, peaceful neighborhood. The unit also includes two numbered/assigned parking spots directly in front of the unit for your convenience. If you’re looking for all the conveniences of Sarasota and a move-in ready Villa come take a look. Motivated Seller, Let's talk today!
Listing is courtesy of: ESLINGER REALTY INC (941-915-9961)
Listing Agent: Andy Mcdonald (941-724-6207)
12314 MYRTLE BAY CT, SARASOTA, FL 34238
$460,00075 Days on yellowkey MLS ID: A4688267
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 2019Monthly Fee: $417 Tax: $3,096 (2025)Community: Hammock Preserve On Palmer RanchSingle Family
Taxes:$3,096
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Sarasota Middle
Remarks: Perfectly positioned within the gated community of Hammock Preserve on Palmer Ranch, this well-priced 2-bedroom, 2-bath villa with a den/office offers a refined yet effortless approach to Florida living. Built in 2019 and thoughtfully maintained, the home features quartz countertops, stainless steel appliances, and tile flooring throughout the main living areas, complemented by plush carpeting in the bedrooms for added comfort. The open living space extends to a screened lanai overlooking a tranquil lake, creating a peaceful setting for both quiet mornings and relaxed evenings. Designed with “right-sizing” in mind, this residence delivers the ideal balance of space, style, and low-maintenance living. Residents of Hammock Preserve enjoy a true lifestyle community with resort-style amenities including tennis, a fully equipped fitness center, social spaces for gatherings and events, a pool and spa, and dedicated dog parks for both large and small pets—all offered with notably low HOA fees that enhance the overall value. Ideally located near shopping, dining, and area parks, and just a short drive to the world-renowned beaches of Siesta Key, this is an exceptional opportunity to enjoy a sophisticated, amenity-rich lifestyle in one of Sarasota’s most desirable communities.
Listing Agent: Ryndie Brusco (941-809-6913)
3127 BAY SHORE RD, SARASOTA, FL 34234
$2,750,00087 Days on yellowkey MLS ID: A4687057
REDUCED by $200,000 (6.8%) on 06/01/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3219 Built: 1953 Tax: $26,788 (2025)Community: Indian Beach Map OfSingle Family
Taxes:$26,788
Remarks: 60% OWNER FINANCING AVAILABLE - Open the gate and arrive at your private waterfront retreat on Bay Shore Road, where every day revolves around the water. Step into your backyard and onto your dock, complete with a dedicated jet ski and kayak lift platform (can be converted easily to boat lift), designed for effortless access and enjoyment. Spend your days by the pool and your evenings taking in sunset views over the bay from the pool deck or the large master bedroom balcony. This is waterfront living that feels both private and effortless. The home has been thoughtfully upgraded to enhance both comfort and resilience, featuring impact glass windows and doors for added protection during storms. Notably, the house DID NOT EXPERIENCE FLOODING during recent major hurricanes. Recent improvements include brand new sand finish stucco, new seawall, new dock with jet ski and kayak lift platform, new pool heater, Tesla charger, and two new gate motors. An impact-rated garage door is currently being installed. Set behind a private gate and located just minutes from downtown Sarasota, dining, and shopping, this property offers a rare combination of lifestyle, upgrades, and location.
Listing is courtesy of: LUXIO REAL ESTATE LLC (941-266-0300)
Listing Agent: Hugo Gagliardi (941-266-0300)
160 GARDEN LN, SARASOTA, FL 34242
$4,250,000293 Days on yellowkey MLS ID: A4663247
1 Days Off yellowkey (back on 4/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4086 Built: 2025 Tax: $10,687 (2024)Community: Siesta Rev Plat OfSpa: YesSingle Family
Taxes:$10,687
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef’s kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota’s sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key’s world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Chad Fonder (941-961-3865)
1405 INGRAM AVE, SARASOTA, FL 34232
$339,000188 Days on yellowkey MLS ID: A4674354
REDUCED by $10,900 (3.1%) on 06/01/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 874 Built: 1958 Tax: $860 (2024)Community: Bahia Vista HeightsSingle Family
Taxes:$860
Remarks: PRICE IMPROVEMENT!!!LOCATION! LOCATION! LOCATION! Backs up to the NEW LEGACY TRAIL!!! 3 Bedroom Home with a Carport!!Solid home with terrazzo floors throughout. New Roof, Hurricane Impact Windows and Doors in 2014. Good bones, just needs some TLC and updating. NO deed restrictions or HOA! Plenty of space for RV or boat parking! Centrally located in the heart of Sarasota, Just a short walk to Der Dutchman Amish restaurant and the Village of Pinecraft, minutes from everything including I-75 and downtown. See it today!
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Philip Graber (941-320-5451)
3331 OLD OAK DR, SARASOTA, FL 34239
$1,895,000169 Days on yellowkey MLS ID: A4675449
REDUCED by $55,000 (2.8%) on 06/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2483 Built: 1950 Tax: $18,715 (2025)Community: Shoreland Woods SubSpa: YesSingle Family
Taxes:$18,715
Remarks: A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks, setting an unforgettable first impression of timeless elegance and privacy. Wrapped in a freshly painted pecky cypress façade and crowned by a newer standing-seam metal roof, the residence honors classic Florida design while embracing today’s luxury standards. Inside, a welcoming foyer unfolds into an airy, open-concept living space anchored by rich natural wood floors and impeccable finishes throughout. A dramatic dual-sided stone fireplace creates a striking focal point between the living and dining areas, while a sophisticated dry bar sets the stage for effortless entertaining. A private office—thoughtfully positioned away from the main living areas—offers flexibility as a refined workspace or guest retreat, complete with an adjacent half bath. At the heart of the home, the chef’s kitchen is nothing short of spectacular, featuring premium stainless steel appliances, a natural gas range, custom cabinetry, designer backsplash, and an oversized marble island that commands attention. A built-in coffee bar adds a touch of indulgence, while French doors invite the outdoors in. Step into a resort-inspired sanctuary where a heated saltwater pool and spa shimmer beneath a newly installed panoramic screen enclosure. Entertain with ease in the fully equipped summer kitchen, complete with stainless gas grill, vent hood, and prep station, or gather around the gas fire pit for evenings under the palms. A newly updated outdoor shower with hot and cold water enhances the spa-like ambiance, while the expansive, lushly landscaped yard offers exceptional privacy and room to relax, play, or unwind. The primary suite is a true retreat, featuring three generous closets, a cozy fireplace, and French doors opening directly to the lanai for seamless indoor-outdoor living. The spa-inspired en-suite bath showcases luxurious finishes, custom vanities, and a walk-in shower designed for pure relaxation. Additional highlights include a spacious laundry room, oversized two-car garage, and curated architectural lighting that bathes the estate in a warm, elegant glow at dusk. Perfectly located just minutes from the Siesta Key North Bridge and the boutiques and dining of Southside Village, this property offers the rare balance of serene seclusion and coastal convenience. Situated outside of a flood zone—with flood insurance optional—this estate represents both luxury and peace of mind.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
1249 S BASIN LN, SARASOTA, FL 34242
$8,950,00055 Days on yellowkey MLS ID: A4690355
Bed: 6 Bath: 7.0 Gar: 8 Liv Area Sq Ft: 10642 Built: 1951Monthly Fee: $933 Tax: $40,641 (2025)Community: Siesta Properties IncSpa: YesSingle Family
Taxes:$40,641
Remarks: Rarely does a property of this caliber become available on Siesta Key. Spanning approximately 1.6 acres, this exceptional waterfront estate is framed by majestic oak trees and lush, mature landscaping, creating a private, quiet, and timeless retreat. This legacy property showcases expansive bayfront views that wrap gracefully around to a protected canal, offering both breathtaking vistas and sheltered water access. At its heart stands a classic and formal Southern-style residence, remodeled in 2008, rich in character and designed for an elegant lifestyle. Grand, beautifully proportioned rooms are designed for effortless entertainment, highlighted by a stately formal dining room worthy of the most important occasions. The expansive country kitchen is both functional and refined, featuring a professional-grade Wolf range with custom copper hood, an oversized Sub-Zero refrigerator, vintage tile flooring, and a striking chandelier that brings a touch of timeless elegance to space. A classic wood-burning fireplace adds warmth and character to the cozy wood paneled den with charming French doors opening to bayfront views. With six spacious bedrooms, six full bathrooms, and two additional half baths, this home offers exceptional comfort and ample space to accommodate family and guests with ease. Car enthusiasts will appreciate the 8 garages. Boaters will appreciate the ample opportunities to enhance this property with custom docks or lifts. For those envisioning a custom estate, the property also offers a rare opportunity to build your dream home while comfortably residing on-site in the charming guest cottage, complete with bedroom suite and kitchen—allowing you to plan, design, and construct at your own pace without ever leaving this exceptional setting. Additionally, the property can be split into 3 separate waterfront parcels with the smallest water frontage being 99 ft. This is a true legacy offering, where expansive space and stunning waterfront beauty come together seamlessly, enhanced by breathtaking views that elevate every moment in this extraordinary setting. The Sanderling Club, the only guard-gated, single-family neighborhood on Siesta Key, offering residents tennis and pickleball courts, playground, and deeded access to a pristine stretch of Siesta Beach. Located minutes from Siesta Village, this property provides the perfect balance of serene seclusion and proximity to Sarasota’s vibrant cultural and culinary attractions.
Listing Agent: Kim Ogilvie (941-951-6660)
707 S GULFSTREAM AVE #802, SARASOTA, FL 34236
$899,00091 Days on yellowkey MLS ID: A4686314
REDUCED by $51,000 (5.4%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1419 Built: 1974 Tax: $4,500 (2025)Community: Essex HouseSpa: NoCondo
Taxes:$4,500
Elementary School: Southside Elementary
Remarks: Experience the best of downtown Sarasota living from this beautifully renovated corner-unit condominium at 707 S. Gulfstream Avenue, ideally positioned near the bayfront, Marina Jack, Bayfront Park, Main Street, Palm Avenue, restaurants, shopping, arts, and everything downtown Sarasota has to offer. Designed for buyers seeking bayfront proximity, and easy lock-and-leave living, this move-in-ready 2-bedroom, 2-bath residence combines modern updates, everyday convenience, and peace of mind. Extensively remodeled with a fresh, sophisticated aesthetic, the condo features hurricane impact windows and doors, an open-concept layout, abundant natural light, and stylish designer finishes throughout. The oversized gourmet kitchen offers quartz countertops, premium appliances, custom cabinetry, and generous space for entertaining. The spacious primary suite includes a beautifully updated spa-inspired en-suite bath, creating a comfortable private retreat. Additional upgrades include brand-new plumbing and electrical systems. The building has also recently upgraded its generator following the 2024 storms, further adding to the value and confidence of ownership. Residents enjoy secure entry, covered parking, a resort-style pool, fitness center, and club room, all in a highly desirable downtown Sarasota location. Whether used as a full-time residence, seasonal retreat, or low-maintenance second home, this renovated Sarasota condo offers an exceptional combination of location, updates, storm protection, amenities, and lock-and-leave convenience just moments from the waterfront.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
4650 10TH ST, SARASOTA, FL 34232
$1,875,00063 Days on yellowkey MLS ID: A4689601
3 Days Off yellowkey (back on 6/1/2026)
Bed: 5 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 2915 Built: 2017 Tax: $11,533 (2025)Community: Acreage & UnrecSpa: NoSingle Family
Taxes:$11,533
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Welcome to your dream oasis in the heart of Sarasota, close to I-75 just North of Fruitville. This stunning, newer build boasts a prime location that perfectly couples lifestyle with tranquility. Situated on just under 1 acre, this coastal contemporary offers the perfect blend of modern luxury and serene natural beauty. As you drive onto the property, you'll be greeted by a private setting that instantly puts you at ease; providing a retreat-like atmosphere that's hard to find West of I-75.The main residence showcases simplistic yet thoughtful design, with every detail carefully curated to create an atmosphere of elegance and comfort. The open layout with polished concrete floors allow for seamless flow between living spaces, making it ideal for both entertaining and everyday living. At the heart of the home is the beautifully appointed kitchen, featuring top-of-the-line Thermador appliances that cater to the needs of any chef or baker. The fine craftsman styling with transom windows and custom millwork are a real treat. As you step out to your lanai, you'll discover a private outdoor haven that invites relaxation and leisure. Lounge on your spacious patio, complete with outdoor kitchen perfect for al fresco dining or simply enjoying the Florida sunshine in the gorgeous pool. With a nod to versatility, this property also includes a secondary building that offers endless opportunity. Compete with a rare and highly desirable upstairs guest apartment boasting 266 sqft of space. This brand new, never lived in studio, comes complete with a full bath and washer/dryer. Whether you envision a home office, a personal gym, or an art studio this space can adapt to your desires with ease. The 28’ x 48’ garage is large enough to house your offshore boat, RV, car collection or equipment. Don't miss the chance to own this exceptional property, where newer construction, prime location, and coastal contemporary design come together in perfect harmony. Experience the best of Sarasota living in your own private sanctuary. Schedule your private showing!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Jeff Hinrichs (941-456-1251)
4140 OAKHURST CIR W #3166, SARASOTA, FL 34233
$254,00097 Days on yellowkey MLS ID: A4685181
REDUCED by $4,000 (1.6%) on 05/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1374 Built: 1981 Tax: $1,534 (2025)Community: Oakhurst Ph IiVilla
Taxes:$1,534
Remarks: Under contract-accepting backup offers. TURN-KEY VILLA IN DESIRABLE OAKHURST! Welcome to easy Florida living in a friendly 55+ community. This 2 BDRM, 2 BTHRM paired villa with a 2 CAR-GARAGE is filled with natural light and designed for comfortable, open-concept living. The eat-in kitchen opens directly to the Florida room, creating a bright and inviting space. Sliding doors bring in more sunshine and provide a seamless indoor-outdoor feel. The kitchen has been replumbed, offering added peace of mind. The primary bedroom features a remodelled ensuite bathroom. IMPACT WINDOWS throughout the home provide storm protection and energy efficiency. Additional updates include a brand-new roof installed in December 2025, and beautiful flooring. This home is being sold turn-key furnished, making it easy to move right in. Residents of Oakhurst enjoy wonderful amenities including a heated community pool and an active clubhouse. Whether this is your new full-time residence or your winter getaway in the sun, you are sure to enjoy all that Oakhurst offers. Cable TV, INTERNET, the roof, pest control, exterior maintenance, and landscaping are ALL INCLUDED in the monthly condo fee ($662). Don't miss this one!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)
Listing Agent: Susan Honsberger (941-549-9749)
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