Location: Sarasota
Do Not Show Listings
5645 CHURCHILL DOWNS RD, SARASOTA, FL 34241
$1,295,000532 Days on yellowkey MLS ID: A4634600
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $355,000 (21.5%) on 05/27/2026
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2541 Built: 1973 Tax: $5,153 (2023)Community: Sarasota PlantationsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,153
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Under contract-accepting backup offers. Private compound ~ House & Guest House on almost 5 acres tucked at the end of a quiet country lane. Not in flood zone ! This serene oasis includes beautiful pond and 5000 SF outbuilding with successful Pet Resort business, perfect for home-based businesses. The charming, established neighborhood is conveniently located to beautiful beaches and vibrant downtown city life. It is also very HORSE FRIENDLY! The main house (3 Bed/2.1 Bath) & guest house (2 Bed/1.1 Bath) are updated. All buildings have new/newer roofs & windows! Feels far away, yet so close to Siesta Key beaches, downtown Sarasota and SRQ airport. Tons of updates throughout the property. The main house features a modern kitchen and bath updates with a new roof in 2023. The open floor plan and soaring ceilings perfectly frame the lovely views of the L-shaped pond. Thoughtfully designed, this home offers ample storage with a large pantry and separate laundry room with half bath. The large decks provide expansive views of the pond and garden area. The guesthouse, situated well away from the main home, was nicely renovated in 2020. The two-bedroom, one-and-a-half-bath cottage with vaulted ceiling and open floor plan feels and lives much larger than its 1,500 square feet. The living room sliders opening to a walled patio/garden space create a private, serene retreat. The freestanding kennel building, measuring about 5,000 square feet, includes reception and grooming areas, plus a half bath. The kennel includes 30 dog runs, nine cat rooms and three isolation areas for flexible accommodations. The proximity to population centers and easy highway access offers so much potential for pet boarding, doggie daycare, professional dog trainers or show handlers. This well-maintained property is truly an unexpected find and a rare opportunity that blends privacy and convenience. If you've been searching for a family compound, home-based business, dog property or horse property, schedule your private tour today. Check out the tour links, and don't miss the drone tour in link 2! More photos available upon request.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Bill Blume (941-525-6257)
4015 ASBURY PL, SARASOTA, FL 34233
$355,000391 Days on yellowkey MLS ID: A4654008
REDUCED by $4,900 (1.4%) on 06/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1957 Tax: $945 (2024)Community: Spring Lake Sub Add 1Single Family
Taxes:$945
Tax Year: 2024
Remarks: This charming and versatile home is located in a quiet neighborhood and offers features for both living and investment. The main home includes a den, a utility room with washer & dryer and solar power for energy efficiency. The private in law suite is complete with a separate entrance and kitchenette, ideal for multigenerational living or rental income. Recent upgrades includes a new roof (2020) and a new well pump (2024) ensuring peace of mind for years to come. Outside you'll find a detached storage shed for additional space and convenience. This is the perfect home with flexible living options and great investment potential. Schedule your viewing today!
Listing is courtesy of: ALIGN RIGHT REALTY SRQ OPULENCE (941-362-3300)
Listing Agent: James Frederick (941-812-1982)
4142 CENTRAL SARASOTA PKWY #1423, SARASOTA, FL 34238
$164,900397 Days on yellowkey MLS ID: A4652838
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 759 Built: 1998 Tax: $1,970 (2024)Community: Bella Villino IvCondo
Taxes:$1,970
Remarks: Virtually Staged. Welcome to this beautifully updated second-floor condo in the highly sought-after gated community of Bella Villino, located in the heart of Palmer Ranch, Sarasota. This 1-bedroom, 1-bathroom unit offers 759 sq. ft. of thoughtfully designed living space, perfect for year-round residents or seasonal getaways. Step inside to discover a host of recent upgrades, including impact-resistant thermal windows throughout, new laminate flooring, and a modern kitchen featuring solid wood cabinetry, granite countertops, and all-new stainless steel appliances. The spacious bedroom boasts an en-suite bathroom and his-and-hers closets, providing ample storage. For added convenience, the unit includes an in-unit laundry closet equipped with a washer and dryer. Enjoy the peace of mind that comes with an assigned covered parking space, and take advantage of the community's resort-style amenities. Bella Villino offers residents access to a clubhouse, heated swimming pool and spa, fitness center, indoor racquetball and basketball courts, billiards room, business center, lighted tennis courts, BBQ picnic areas, and a car care center. Situated just minutes from Siesta Key Beach, Legacy Trail, and a variety of shopping and dining options, this condo combines comfort, style, and an unbeatable location.
Listing is courtesy of: M&M PROPERTY MANAGEMENT GROUP (941-320-4287)
Listing Agent: Joe Meszaros (941-320-4287)
33 S PALM AVE #902, SARASOTA, FL 34236
$949,000158 Days on yellowkey MLS ID: A4678251
REDUCED by $21,000 (2.2%) on 06/19/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1397 Built: 2024 Tax: $8,181 (2025)Community: The DemarcaySpa: NoCondo
Taxes:$8,181
Tax Year: 2025
Remarks: One or more photo(s) has been virtually staged. Live in the heart of Downtown Sarasota at a sought-after Palm Avenue address. A refined expression of form and function, this impeccably maintained New Construction 2 bedroom, 2 full bathroom residence offers timeless design and enduring value. Designed for both elegance and livability, the open floor plan is complemented by soaring 11-foot ceilings and exceptional storage throughout, including two built-out primary suite closets, a large pantry, and an oversized laundry room with a sink. The kitchen anchors the home with a premium Miele appliance package featuring a gas cooktop, upgraded Italian cabinetry, a custom Japanese ceramic tile backsplash, and a striking waterfall-edge island—ideal for everyday living and entertaining alike. Thoughtful upgrades continue with electric window treatments and a curated smart-home lighting system with ceiling fans, seamlessly blending modern convenience with classic appeal. Equally well suited as a sophisticated pied-à-terre, a full-time residence, or a long-term investment, the home is set within an intimate boutique building offering rooftop amenities including a temperature-controlled saltwater pool, a fitness center, and an elegant club room with a catering kitchen, along with 24/7 valet parking and security. A rare opportunity to own a luxury downtown condominium that combines lasting design, prime location, and lifestyle-driven value.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lisa Allen (312-848-1636)
50 CENTRAL AVE #17PHD, SARASOTA, FL 34236
$2,890,000421 Days on yellowkey MLS ID: A4650526
4 Days Off yellowkey (back on 6/19/2026)
REDUCED by $310,000 (9.7%) on 04/20/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4095 Built: 2005 Tax: $34,554 (2024)Community: Plaza At 05 Points ResidencesSpa: YesCondo
Taxes:$34,554
Elementary School: Alta Vista Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Penthouse Perfection in the Heart of Downtown Sarasota — The Plaza at Five Points Poised high above the vibrant cultural epicenter of Sarasota, this exceptionally renovated 17th-floor penthouse at The Plaza at Five Points epitomizes modern elegance and urban sophistication. Perfectly situated across from Five Points Park, The Selby Library, and the Sarasota Opera House, this distinguished residence places you steps from world-class dining, galleries, theaters, and boutique shopping. With floor-to-ceiling windows and an expansive open-plan layout, this luxurious home in the sky offers breathtaking, panoramic vistas that sweep across the city skyline, Sarasota Bay, the marina, and onward to the shimmering horizon of the Gulf of Mexico. The terrace invites tranquil mornings and unforgettable sunsets, framing the coastal beauty of Florida at its finest. Designed for both effortless entertaining and serene living, the interior boasts soaring volume ceilings and exquisite contemporary finishes throughout. The main living space is a masterclass in modern design, featuring refined stone flooring, custom built-ins, a striking marble-clad gas fireplace, and a fully integrated wet bar with stone counter and led illumination. The gourmet kitchen is a chef’s dream—adorned with new sleek cabinetry, stone countertops, cabinet paneled refrigerator and high-end stainless-steel appliances, a spacious island, large eat in area, and designer tile backsplash - all blending style with functionality. The primary suite is a private sanctuary, complete with a secluded terrace, dual luxurious bathrooms, and generous his-and-her walk-in closets. A sumptuous Jacuzzi tub, separate walk-in shower, and elegant stone finishes elevate the spa-like ambiance. Two additional en-suite bedrooms—one of which serves as a sophisticated study with built-in storage and a hidden Murphy bed—offer privacy, versatility, and guest accommodations of the highest standard. Life at The Plaza at Five Points is defined by its world-class amenities and unwavering attention to detail. Residents enjoy a private, secured lobby entrance, full-time concierge, and valet services. Socialize or entertain in the elegant club room with a fireplace and catering kitchen, hold meetings in the professional conference room, or unwind in the rooftop heated pool and spa, surrounded by expansive sun decks and covered lounging areas. Additional amenities include a fully equipped state-of-the-art fitness center, a furnished guest suite, gazebo and grill area, and a Grand Motor Court. This penthouse residence also includes two secure garage parking spaces and an oversized, climate-controlled storage unit ideally located just steps from the unit’s hallway. The pet-friendly building offers the ultimate convenience for those seeking refined urban living in one of Florida’s most sought-after coastal cities. Don't wait to build, this new apartment is ready for you. Where Sophistication Meets the Sky — Experience the Pinnacle of Sarasota Living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Ann Martin (941-356-7717)
1045 FOX CREEK DR, SARASOTA, FL 34240
$3,400,00027 Days on yellowkey MLS ID: A4694380
Bed: 4 Bath: 5.0 Gar: 5 Liv Area Sq Ft: 6721 Built: 2007Monthly Fee: $25 Tax: $12,620 (2025)Community: Fox Creek AcresSingle Family
Taxes:$12,620
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Exclusively situated on 5.1 expansive acres, this custom-built Sarasota estate is masterfully designed as a fully self-contained private family enclave. Completely insulated from the outside world, the property is introduced by a long, palm-lined approach and a sweeping circular paver driveway, where total privacy and the Florida lifestyle are immediately evident. The primary residence spans 6,721 square feet of luxurious living space, making a grand architectural statement the moment you enter a foyer flanked by towering 24-foot ceilings. The estate showcases abundant natural light, French doors and rich maple built-ins throughout. At the heart of the home, the epicurean kitchen features elite millwork by Campbell Cabinetry, a spacious L-shaped island, a butler's pantry, and professional-grade Wolf and Sub-Zero appliances—including dual ovens and a specialized warming drawer. The fluid floor plan offers unmatched versatility, hosting a formal dining room with custom tray ceilings, a magnificent Great Room with fireplace under a 22-foot ceiling, two separate private offices, one of which has a wood-beamed cedar ceiling, and a spectacular, approximately 1,000-square-foot recreation wing outfitted with its own full kitchen and bath. Retreat to the first-floor owner’s suite, an elegant sanctuary featuring a private sitting area, a spa-inspired bath, and peaceful views overlooking the estate and pool. Outdoor living captures the estate-style relaxation, with a vast screened lanai and a sparkling saltwater pool overlooking open lawns and mature perimeter landscaping that naturally buffers the property. Recreational amenities are premier, featuring an integrated basketball court and a dedicated section of the driveway already marked for pickleball. The sprawling grounds serve as a grand retreat, anchored by an exceptional detached multi-car garage pavilion. Perfect for collectors or specialized hobbyists, this secondary structure features oversized 11-foot doors, a dedicated RV and boat storage area, carport, and a versatile, fully plumbed auxiliary suite with a full shower, ideal as a detached executive workspace or private retreat. Unequaled in structural integrity, the home functions as a fortified private fortress engineered with poured-concrete construction, comprehensive rebar reinforcement, elevated foundation, standby generator, salt-and-carbon water filtration system, separate sprinkler well, and advanced 13-camera security system. Providing space perfectly zoned to accommodate equestrian pursuits, miniature horses, alpacas, or exotic hobby collections, the OUE1 acreage offers absolute lifestyle freedom, all while being securely situated in Flood Zone X, with an exceptionally low annual HOA fee and no CDD. Positioned at the absolute center of convenience, the estate sits just 3.5 miles from Waterside Place, 4 miles from the University Town Center district, and 4.5 miles from Main Street Lakewood Ranch—placing championship golf courses, premier dining, luxury shopping, and active community calendars right at your fingertips. Surrounded by the tranquility of your private sanctuary, allure of downtown Sarasota and world-renowned Gulf Coast beaches await just moments beyond your gates.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Judi Taulbee (941-544-6227)
5365 BARTOLOMEO ST, SARASOTA, FL 34238
$725,00012 Days on yellowkey MLS ID: A4696542
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1918 Built: 2019Monthly Fee: $520 Tax: $3,651 (2025)Community: Esplanade On Palmer RanchSingle Family
Taxes:$3,651
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: Virtually Staged. One or more photo(s) has been virtually staged. Built in 2019, this meticulously maintained 3-bedroom, 2-bath residence offers 1,918 sq.ft. of thoughtfully upgraded living space designed for both comfort and functionality. The home features a spacious extended lanai complete with a Hot Springs hot tub, creating the perfect setting for outdoor relaxation and entertaining. Interior upgrades include custom California Closets in the primary suite, custom cabinetry in the laundry room, and elegant plantation shutters throughout. Additional enhancements include a 240-volt hookup for a home generator, whole-house surge protector, Culligan whole-home water filtration system, lanai hurricane shade, plantation shutters, and an extended driveway for added convenience and parking flexibility. This property combines modern construction with quality upgrades and attention to detail throughout. Esplanade on Palmer Ranch delivers a true resort lifestyle with the on-site Bahama Bar restaurant, resort pools and spa, fitness center with studio classes, 8 pickle ball courts, 2 tennis courts, 3 dog parks, scenic nature trails, and direct Legacy Trail access. Oscar Scherer State Park is just one mile away. More than a home, this is a private luxury retreat offering the ultimate blend of elegance, recreation, wellness, and Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Quire (941-993-5706)
5290 HYLAND HILLS AVE #1916, SARASOTA, FL 34241
$315,00062 Days on yellowkey MLS ID: A4691026
REDUCED by $34,000 (9.7%) on 06/18/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1684 Built: 2002Monthly Fee: $383 Tax: $3,963 (2025)Community: Heritage Oaks Veranda 8Condo
Taxes:$3,963
Remarks: Welcome to your private coastal retreat in the highly sought after Heritage Oaks Golf & Country Club. This beautifully renovated Abby floorplan offers the perfect blend of elegance, comfort and Florida lifestyle. This first floor corner unit shows off all of the natural light and lush landscaping throughout the entire day. The open floorplan features an open kitchen with breakfast nook seating, two bedrooms, two bathrooms, a versatile den/office and private garage. Every detail has been carefully curated with a light, elegant coastal design-creating a serene and inviting atmosphere with serene views of the golf course, nature, and water from the private screen lanai. The den provides flexibility for a home office guest space or additional lounge area. Heritage Oaks is a bundled Golf community, where residents can enjoy championship golf, tennis, fitness center clubhouse dining pool and active social lifestyle all within a beautifully maintained gated setting.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kelli Eggen (941-376-9844)
708 42ND ST, SARASOTA, FL 34234
$649,00077 Days on yellowkey MLS ID: A4688859
REDUCED by $26,000 (3.9%) on 06/19/2026
Bed: 3 Bath: 0.0 Gar: 1 Liv Area Sq Ft: 1210 Built: 1936 Tax: $5,492 (2025)Community: Indian Beach Map OfApartment
Taxes:$5,492
Remarks: Come see this charming and peaceful Old Florida gem with detached cottage ideally situated in the desirable Indian Beach/Sapphire Shores neighborhood located west of the trail. Here is a rare opportunity to own two meticulously maintained homes within the city limits in Indian Beach/Sapphire Shores, a community rich with art, culture, and history. This property has been a high-yielding asset for the seller. The seller gets a high volume of applicants, and it has required minimal effort to lease. Picture tree-lined streets, character-filled homes, and being just moments from the shimmering Sarasota Bay. You are in for a treat as you enter the main home through a central air-conditioned enclosed front porch into a home with all of its original, timeless character including glass doorknobs, lovely baseboards and trim, vintage light fixtures, painted heart of pine floors, and functional double-hung windows. This original 1930s home (732 sf) features two bedrooms (freestanding wardrobes), one bath, and a spacious combination dining/living area. An additional wonderful highlight is the central air conditioned detached guest cottage (478 sf) with kitchen, living area, one bathroom and bedroom alcove along with a screened porch and patio, and attached one-car garage. This cottage is ideal for multi-generational living or Airbnb or full-time lease opportunities. All furnishings and fixtures convey: the front unit is partially furnished; the back unit is turn-key furnished. The property includes a very nice new 12x16 Tuff Shed ideal for an artist’s studio, workshop, or just additional storage. Set on a lush 12,000+ square foot lot, the property is spacious with plenty of room for parking, entertainment and other possibilities. You are sure to enjoy the established vegetable and flower gardens. Adding to the charm, you may catch sight of the neighborhood's colorful wild peacocks who love to display their feathers. Excellent location just minutes from the Ringling Museum, SRQ Airport, and downtown Sarasota as well as close proximity to Lido Key Beach, St. Armands Circle, and Siesta Key. Two high-end homes are currently under construction on the block. This sweet property is waiting to fit your needs whether as live-in residences, a rental investment, multi-generational living, or any combination thereof. This peaceful neighborhood in "Turks Cap" (sometimes referred to as the Museum District) has a rural feel with narrow, tree-lined streets and roaming peacocks. This is a no through street with no traffic. If you want quiet and relaxed, you have found the neighborhood.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Helen Magill (941-320-7166)
$649,00080 Days on yellowkey MLS ID: A4688855
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1210 Built: 1936 Tax: $5,492 (2025)Community: Indian Beach Map OfSingle Family
Remarks: Come see this charming and peaceful Old Florida gem with detached cottage ideally situated in the desirable Indian Beach/Sapphire Shores neighborhood located west of the trail. Here is a rare opportunity to own two meticulously maintained homes within the city limits in Indian Beach/Sapphire Shores, a community rich with art, culture, and history. Picture tree-lined streets, character-filled homes, and being just moments from the shimmering Sarasota Bay. You are in for a treat as you enter the main home through a central air-conditioned enclosed front porch into a home with all of its original, timeless character including glass doorknobs, lovely baseboards and trim, vintage light fixtures, painted heart of pine floors, and functional double-hung windows. This original 1930s home (732 sf) features two bedrooms (freestanding wardrobes), one bath, and a spacious combination dining/living area. An additional wonderful highlight is the central air conditioned detached guest cottage (478 sf) with kitchen, living area, one bathroom and bedroom alcove along with a screened porch and patio, and attached one-car garage. This cottage is ideal for multi-generational living or Airbnb or full-time lease opportunities. All furnishings and fixtures convey: the front unit is partially furnished; the back unit is turn-key furnished. The property includes a very nice new 12x16 Tuff Shed ideal for an artist’s studio, workshop, or just additional storage. Set on a lush 12,000+ square foot lot, the property is spacious with plenty of room for parking, entertainment and other possibilities. You are sure to enjoy the established vegetable and flower gardens. Adding to the charm, you may catch sight of the neighborhood's colorful wild peacocks who love to display their feathers. Excellent location just minutes from the Ringling Museum, SRQ Airport, and downtown Sarasota as well as close proximity to Lido Key Beach, St. Armands Circle, and Siesta Key. Two high-end homes are currently under construction on the block. This sweet property is waiting to fit your needs whether as live-in residences, a rental investment, multi-generational living, or any combination thereof. This peaceful neighborhood in "Turks Cap" (sometimes referred to as the Museum District) has a rural feel with narrow, tree-lined streets and roaming peacocks. This is a no through street with no traffic. If you want quiet and relaxed, you have found the neighborhood.
5361 SAN JUAN DR, SARASOTA, FL 34235
$385,00080 Days on yellowkey MLS ID: N6143756
REDUCED by $14,000 (3.5%) on 06/19/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1913 Built: 1972 Tax: $1,722 (2025)Community: De Soto LakesSingle Family
Taxes:$1,722
Remarks: One or more photo(s) has been virtually staged. MOTIVATED SELLER – BRING YOUR OFFERS! Imagine waking up each morning to peaceful lake views and ending your day with breathtaking sunsets over Crown Lake. Nestled on an oversized lot in the desirable Desoto Lakes community, this beautifully renovated 2-bedroom, 2-bath home offers nearly 2,000 square feet of stylish, move-in-ready living space in one of Sarasota’s most convenient locations. From the moment you step inside, you’ll appreciate the bright, open-concept design that fills the home with natural light and creates an inviting atmosphere perfect for both everyday living and entertaining. The stunning renovated kitchen serves as the heart of the home, featuring brand-new appliances, sleek countertops, modern cabinetry, and a seamless flow into the spacious living and dining areas. Thoughtfully updated throughout, this home blends modern finishes with comfortable living. The previously screened lanai has been professionally converted into additional interior living space, providing endless possibilities for a family room, home office, hobby space, or entertaining area while maximizing the home’s functionality and square footage. One of the most valuable upgrades is already complete—brand-new hurricane impact windows installed throughout the home in 2025, providing enhanced storm protection, energy efficiency, and peace of mind for years to come. For hobbyists, car enthusiasts, or anyone needing extra workspace, the oversized garage and workshop is a rare find. Complete with epoxy flooring and an air compressor, it offers the perfect setup for projects, storage, or pursuing your favorite hobbies. Step outside and enjoy the beauty of your private backyard oasis overlooking picturesque Crown Lake. The manicured grounds and tranquil water views create a peaceful, resort-style setting that feels like a vacation every day. Best of all, with NO HOA and NO deed restrictions, you’ll enjoy the freedom and flexibility to truly make this property your own. Adding even more value, this property is NOT located in a flood zone, meaning NO flood insurance is required. Location is everything, and this home delivers. Conveniently situated just minutes from downtown Sarasota, world-famous Gulf Coast beaches, University Town Center, Lakewood Ranch, exceptional dining, shopping, entertainment, and Sarasota-Bradenton International Airport, you’ll enjoy easy access to everything that makes the Sarasota lifestyle so desirable. Homes offering this combination of lake views, extensive updates, oversized lot, workshop space, hurricane impact windows, and an unbeatable Sarasota location are hard to find. Don’t miss this incredible opportunity—schedule your private showing today and discover why this could be your perfect Florida home.
Listing is courtesy of: CORNERSTONE R.E OF SW FL (941-404-4620)
Listing Agent: Ashley Leroy (941-724-1621)
1864 CLEMATIS ST ST, SARASOTA, FL 34239
$1,799,50015 Days on yellowkey MLS ID: A4696114
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2330 Built: 1925 Tax: $14,946 (2025)Community: Lot 13 & W 25 Ft Of Lot 15 Blk C Desota ParkSpa: YesSingle Family
Taxes:$14,946
Elementary School: Southside Elementary
Remarks: This Spanish Mediterranean style home built in 1925 is nestled in the coveted "West of Trail" subdivision of DeSota Park in the South Poinsettia park Neighborhood just two blocks from the fine dining and boutique shopping offered in Southside Village. This home is ideally located outside of any flood zones and weathered the 2024 hurricane season without any damage. This listed historic home with detached casita is rich with character. The beautifully designed residence offers 2,330 square feet of living space. The home boasts a total of 12 rooms featuring a spacious entry, open plan living area including a formal dining room, living space and chef's kitchen and a versatile family room located directly off the pool area. The 3 bedroom main house has 2 bedrooms with their own en-suite bathrooms plus an additional 3rd bedroom/office/flex space, updated hurricane rated windows and whole home tankless hot water heater. The casita offers the 4th bedroom with en suite bath and kitchenette. Upon entering the tiled courtyard you are invited to step inside and discover an abundance of architectural details like the hurricane rated pecky cypress entry door, arched doorways, pecky cypress beams and fireplace mantel, custom built-ins and original architectural details that all add up to the unique touches of sophistication. The northern exposure fills the home with natural light, highlighting the garden views through casement dual pane hurricane rated windows adorned with tasteful and functional window treatments. Inside the spacious foyer your attention is drawn to the custom window treatments and new flooring and opens to an expansive open plan living room featuring a working fireplace with a pecky cypress mantel that adds warmth and ambiance and pecky cypress beams. The living space is flanked by a light filled dining room that opens to a second private courtyard and the recently renovated gourmet chef's kitchen that includes custom cabinetry, Taj Mahal quartzite countertops, zellige tile backsplash and top of the line appliances - SubZero refrigerator, Thermador warming drawer and Italian Fulgor Milano gas range. Down the hall the main floor primary suite includes a large ensuite bathroom with a separate shower, four closets for ample storage and a convenient laundry space. The second bedroom suite is tucked away with dual closets, dressing area, its own courtyard and private access to the pool. At the back of the home the 3rd bedroom/office/flexroom is located off a large and comfortable family room with pecky cypress beams and tile flooring that opens up through a wall of hurricane rated stack glass back doors to the pool area. The pool area is a tropical paradise featuring a heated pool and hot tub with a new remote controlled electronic system. The pool cage encompasses plenty of space for lounging and dining and includes the entry to the casita and full bath with mini split unit, tile flooring and wooden beams, includes built-in murphy bed and a dedicated generator. Outside the casita is a large paver courtyard with a custom outdoor cooking area that includes a plumbed 36" natural gas grill with rotisserie and pizza oven accessories and an outdoor refrigerator. This "West of Trail" home is ideally located in the Southside Elementary School district, convenient to Sarasota Memorial Hospital and located just steps away from Morton's Gourmet Grocery and some of Sarasota's best restaurants, shopping and art galleries.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Tra Raines, Iii (941-415-2508)
7461 W COUNTRY CLUB DR N #203, SARASOTA, FL 34243
$250,00041 Days on yellowkey MLS ID: A4693369
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1090 Built: 1973 Tax: $3,228 (2025)Community: No 1 Palm-Aire Desoto Lakes Cc Apt CondoCondo
Taxes:$3,228
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Turnkey furnished and income-producing! This beautifully maintained 2-bedroom, 2-bathroom condo in the highly sought-after Palm-Aire DeSoto Lakes community offers the perfect blend of comfort and convenience. Featuring updated impact windows for peace of mind and energy efficiency, this light and bright residence is ideal for full-time living, seasonal enjoyment, or as an investment property. The open-concept living and dining area flows seamlessly to a private lanai, perfect for morning coffee or evening relaxation. The primary suite includes an en-suite bathroom and generous closet space. This condo also comes with a storage unit with ample space. Enjoy access to resort-style amenities, including pools, walking paths, and nearby golf courses. Conveniently located close to University Town Center, restaurants, shopping, and I-75. A rare opportunity to own a move-in-ready condo in a desirable location with strong rental potential.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Dawnelle Lanners (727-804-9228)
5721 CASA DEL SOL BLVD #3223, SARASOTA, FL 34233
$267,50097 Days on yellowkey MLS ID: A4686344
REDUCED by $7,500 (2.7%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1313 Built: 1989 Tax: $1,774 (2025)Community: Casa Del Sol Sec IiVilla
Taxes:$1,774
Elementary School: Ashton Elementary
High School: Sarasota High
Middle School: Sarasota Middle
Remarks: RARELY AVAILABLE END-UNIT VILLA WITH PRESERVE VIEWS, OVERSIZED COURTYARD, AND TRUE 2-CAR GARAGE IN HIGHLY DESIRABLE CASA DEL SOL! Positioned in one of the MOST PRIVATE AND SOUGHT-AFTER locations within Casa Del Sol, this exceptional end-unit villa immediately stands apart with tranquil PRESERVE VIEWS, additional green space, and a setting that offers both privacy and serenity. Unlike many homes in the community that overlook neighboring properties, this residence enjoys a peaceful natural backdrop that creates a far more desirable living experience. Inside, the bright and open floor plan offers multiple living spaces designed for both comfort and flexibility. An additional sitting room with WOOD FLOORING and a SKYLIGHT fills the home with natural light and opens directly to the patio, seamlessly blending indoor and outdoor living. The layout features an open living and dining area, kitchen with breakfast bar, and a MAIN-LEVEL PRIMARY SUITE complete with walk-in closet and en-suite bath. This villa also benefits from EXTRA OUTDOOR SPACE rarely found in neighboring units, enhancing both privacy and functionality. The OVERSIZED PRIVATE COURTYARD is ideal for entertaining, relaxing, or enjoying the Florida lifestyle—with no A/C equipment taking up valuable outdoor space. Additional highlights include a TRUE 2-CAR GARAGE, minimal traffic due to its location at the far end of the community, only ONE SHARED WALL, and the added natural light and openness that come with end-unit living. From a long-term ownership perspective, this property delivers exceptional value. Casa Del Sol has actually LOWERED HOA DUES for certain sections in 2026, including this one—an uncommon advantage that reflects strong financial and community management. The A/C is a Rheem and under warranty until 11/15/2028 and the ROOFS were proactively replaced by the HOA approximately 10 years ago for added peace of mind .Hot water heater: Rheem, installed 5/2023>Dishwasher: Frigidaire installed 2023>Hurricane shutters: Mostly metal, some plastic to allow for light into the home. All Screws have been drilled in exterior walls. Upgraded whole-house plumbing system to flow guard gold pipe and fittings. Sunroom was remodeled 2005 with Wood flooring. Residents enjoy access to a community featuring a CLUBHOUSE, FITNESS CENTER, POOL, and TENNIS COURTS, all within a beautifully maintained setting. LOCATION IS EVERYTHING—and this home places you minutes from Sarasota’s most desirable destinations. Conveniently located off Cattlemen Road between US-41 and I-75, you are close to Downtown Sarasota, Siesta Key Beach, Lido Beach, Legacy Trail, Payne Park, Sarasota Art Museum, Colonial Oaks Park, YMCA, Yoder’s Fresh Market, Big Olaf Ice Cream, and more. OPPORTUNITIES LIKE THIS RARELY COME AVAILABLE IN CASA DEL SOL. Plus a 1 year home warranty offered by Seller! Schedule your private showing today and experience the privacy, views and lifestyle this exceptional villa has to offer before it’s gone!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
3165 REGATTA CIR, SARASOTA, FL 34231
$459,000116 Days on yellowkey MLS ID: A4683961
REDUCED by $5,900 (1.3%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Turnkey furnishing option is also available which could make for an easy second home. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
7505 WEEPING WILLOW BLVD, SARASOTA, FL 34241
$860,000272 Days on yellowkey MLS ID: O6346384
REDUCED by $15,000 (1.7%) on 06/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3141 Built: 1987Monthly Fee: $119 Tax: $8,342 (2024)Community: Bent Tree VillageSingle Family
Taxes:$8,342
Elementary School: Lakeview Elementary
Remarks: Virtually Staged. Luxurious Lakefront Living in The Woodlands of Bent Tree! This beautiful home offers a private setting on over half an acre, backing onto a spring-fed lake in the gated Woodlands of Bent Tree. Nestled in an A-rated school district and surrounded by lush landscaping, this property combines elegance, comfort, and convenience in one perfect package. Featuring 4 bedrooms, 3 baths, a 2-car side-entry garage, and a brand new roof, the split plan design showcases both functionality and style. Enjoy formal living and dining rooms, a spacious family room with soaring ceilings, a fireplace, and a stylish wet bar. The chef’s eat-in kitchen is a showstopper with quartz countertops, stainless steel appliances, and direct access to the family room—ideal for gatherings and entertaining. Your expansive primary suite includes a spa-inspired bath with dual sinks, a jetted garden tub, large walk-in shower, and generous walk-in closet. Secondary bedrooms are equally spacious, offering flexibility for guests, family, or office space. Step outside to your private oasis: a screened pool and spa overlooking breathtaking lake views, with plenty of room to relax or entertain. The expansive backyard provides additional space to enjoy the outdoors. Just a short golf cart ride to Bent Tree Country Club or Laurel Oak Country Club, and minutes from Siesta Key Beach, UTC Mall, downtown Sarasota, shopping, and dining—this home has it all. Don’t miss this rare opportunity to own in The Woodlands of Bent Tree—schedule your private showing today and fall in love with the perfect blend of luxury, privacy, and natural beauty!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Christine Landrau (407-949-1421)
1595 PINYON PINE DR, SARASOTA, FL 34240
$649,90011 Days on yellowkey MLS ID: A4696972
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2359 Built: 2004Monthly Fee: $80 Tax: $3,631 (2025)Community: Villages At Pinetree Spruce PiSpa: NoSingle Family
Taxes:$3,631
Remarks: WELCOME TO YOUR DREAM HOME! Situated in a highly sought-after community with low HOA fees and no CDD fees, this beautifully maintained 3 bedroom, 3 bathroom single-family home delivers the perfect blend of comfort, functionality, and modern Florida living. Prepare to fall in love with this stunning, turnkey residence that perfectly blends modern luxury with everyday comfort. Every major detail has been meticulously updated, offering your total peace of mind and a true “move-in-ready” experience. THE HEART Of the HOME - Step in to a bright, expansive open-concept layout featuring a very large living room, a spacious dining room and seperate cozy den - perfect for a family movie nights or a quiet reading nook. The entire home boasts brand- new luxury vinyl plank flooring (2024), freshly painted walls in a crisp, modern palette, and beautiful designer light fixtures that add a tough of elegance to every room. MODERN CHEF’S KITCHEN - The show stoping new kitchen (2024)features contemporary cabinets, sleek countertops, ample space for meal prep and entertaining. WORK FROM HOME - The private home office is a standout feature, complete with stylish functional barn doors that adds the perfect balance of privacy and architectural charm. OUTDOOR OASIS - Step outside into your personal paradise. The sparkling swimming pool is surrounded by brand new pavers (2024), creating a pristine, resort-style setting for summer BBQs, sunbathing or evening cocktails under the stars. KEY UPGRADES - HVAC System 2024, Flooring durable luxury vinyl 2024, Paint 2024, Pool Pavers 2024, Kitchen 2024 Schedule your tour Today! This Immaculate home combines top- tier2024 renovations and won’t stay long on the market!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Basia Lenczowski (941-779-5571)
4779 TIVOLI PL, SARASOTA, FL 34235
$299,00035 Days on yellowkey MLS ID: A4693816
1 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1428 Built: 1996Monthly Fee: $919 Tax: $2,321 (2025)Community: Longwood VillasSingle Family
Taxes:$2,321
Elementary School: Emma E. Booker Elementary
Remarks: Under contract-accepting backup offers. Welcome to this single family home that has been recently painted inside and out. New carpets have been installed in the 3 rooms and a deep clean has been done recently. A spacious private lanai outback is welcomed by a lovely preserve and this home is located on a cul-de-sac for maximum privacy. There are no CDD's in here and the HOA handles the roof replacement and repairs,outside painting,pressure washing,irrigation,driveway and walk repairs along with mowing, trimming and edging.There are lakes that residents can use for kayaking,fishing or just for viewing wildlife. Longwood Run public park is just down the street for enjoying tennis,pickleball,basketball or the playground.Coveniently located to UTC mall, restaurants,markets and much more.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: David Short (941-961-3995)
4060 WEBBER ST, SARASOTA, FL 34232
$329,50062 Days on yellowkey MLS ID: A4691042
REDUCED by $19,500 (5.6%) on 06/04/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1546 Built: 1960 Tax: $3,916 (2025)Community: Southern ViewSpa: NoSingle Family
Taxes:$3,916
Elementary School: Brentwood Elementary
Remarks: Virtually Staged. Welcome to 4060 Webber Street—an ideally located Sarasota home offering convenience, flexibility, and access to some of the area’s most sought-after outdoor amenities. Just moments from the Legacy Trail, the Sarasota Springs Trailhead, Downtown Sarasota, UTC, and world renowned beaches. This property is perfect for those looking to enjoy all that the Florida lifestyle has to offer. The home features a comfortable layout with inviting living spaces and plenty of natural light, enhanced by luxury vinyl plank flooring throughout the main living areas and primary bedroom for a clean, modern feel. The living room is anchored by a cozy wood-burning fireplace, creating a warm focal point for relaxing or entertaining. The spacious, open kitchen offers ample room for cooking, gathering, and hosting, making it the true heart of the home. The property features a fully fenced yard with a double gate on the side, providing direct access to a concrete pad—ideal for storing a boat, trailer, or additional vehicles. With no HOA restrictions, you’ll enjoy the freedom to make the most of your property without added limitations—whether for personal use or investment purposes. Located just a short drive to Siesta Key, downtown Sarasota, shopping, dining, and major roadways, this home combines accessibility with lifestyle appeal. Don’t miss this opportunity to own a versatile property in a prime central Sarasota location
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Derek Robbins (941-356-4906)
2927 WEBBER ST, SARASOTA, FL 34239
$575,000161 Days on yellowkey MLS ID: A4678196
1 Days Off yellowkey (back on 5/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1961Monthly Fee: $17 Tax: $6,193 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,193
Remarks: Under contract-accepting backup offers. Wonderful mid-century ranch in Southgate offering 3 spacious bedrooms, 2 bathrooms, a 2-car garage, and a heated saltwater pool. The dining room and living room both feature walls of pocket sliding doors that open to a large covered patio and screened pool area—perfect for enjoying the indoor-outdoor Florida lifestyle. Inside, restored terrazzo floors keep the home cool and timeless. The updated kitchen features stainless steel appliances, granite countertops, and a farmhouse sink. The primary suite includes a walk-in closet, and both bathrooms have been updated with marble tile and granite countertops. A convenient pool bath opens directly to the outdoor area. The heated saltwater pool was converted and upgraded in 2021 with a new pump, heater (2025), LED lighting, fountain feature, and solar cover. A fully fenced backyard and fire pit create a private outdoor setting ideal for entertaining or relaxing. Hurricane-impact windows were installed in 2021, along with extensive upgrades inside and out. The home features a newer roof (2022), A/C (2018), and new ductwork installed in 2022. There is ample space in the front of the property to add a circular driveway if desired. Optional membership is available to the South Gate Community Association, offering access to a community pool, park, and recreation facilities. Ideally located close to world-renowned beaches, downtown Sarasota, cultural attractions, outdoor trails, and highly rated schools.
Listing Agent: Fred Sassen (404-408-5956)
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