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)
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
High School: Booker High
Tax Year: 2025
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)
708 42ND ST, SARASOTA, FL 34234
$649,00080 Days on yellowkey MLS ID: A4688855
REDUCED by $26,000 (3.9%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1210 Built: 1936 Tax: $5,492 (2025)Community: Indian Beach Map OfSingle Family
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. 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)
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)
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
High School: Sarasota High
Middle School: Sarasota Middle
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
Middle School: Booker Middle
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
2374 ARLINGTON ST, SARASOTA, FL 34239
$579,000147 Days on yellowkey MLS ID: A4680088
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1126 Built: 1961 Tax: $6,734 (2025)Community: Arlington ParkSpa: NoSingle Family
Taxes:$6,734
Elementary School: Alta Vista Elementary
Remarks: Virtually Staged. Located in Sarasota’s highly sought-after Arlington Park neighborhood, this thoughtfully updated residence delivers a compelling combination of comfort, functionality, and proximity to the city’s most popular destinations. With a renovated three-bedroom layout, the home is move-in ready and ideally positioned just minutes from downtown Sarasota and the area’s renowned Gulf beaches. The interior features an open-concept design that connects the living, dining, and kitchen areas, creating an easy flow for everyday living and entertaining. Luxury vinyl plank flooring extends throughout the main living spaces, while freshly painted walls in a neutral color palette enhance the light-filled atmosphere. Two updated bathrooms provide modern convenience and a cohesive finish. The kitchen serves as the heart of the home, offering granite countertops, a full-height tile backsplash, ample cabinetry, and a central island that adds workspace and casual seating. Sliding doors open to a spacious, fully fenced backyard—an inviting outdoor setting with room to relax, garden, or create a customized outdoor retreat. Additional exterior storage adds everyday practicality. Residents enjoy immediate access to Arlington Park, known for its playground, fountains, walking paths, picnic areas, basketball courts, and tennis facilities—just moments from the front door. The nearby Southside Village offers popular dining spots, local boutiques, and everyday conveniences, while downtown Sarasota’s arts, dining, and waterfront attractions are only a short drive away. World-famous beaches including Siesta Key Beach and Lido Key are easily accessible, providing endless opportunities for coastal recreation. This Arlington Park home offers an ideal balance of neighborhood charm, city convenience, and access to Sarasota’s best lifestyle amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
6829 CHLOE CT, SARASOTA, FL 34241
$699,99099 Days on yellowkey MLS ID: TB8487039
REDUCED by $30,000 (4.1%) on 04/09/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2908 Built: 2026Monthly Fee: $160 Tax: $6,217 (2026)Community: Lakeview CrossingSingle Family
Taxes:$6,217
Tax Year: 2026
Remarks: Under Construction. Imagine your future with the timeless comforts and top-quality construction you’ll experience in The Messner floor plan by David Weekley Homes brand new, suburban lifestyle community of Lakeview Crossing in Sarasota. There’s a room for everyone in this 5 bedroom, 3.5 bath, 2 car garage luxury home. Expertly placed energy-efficient windows help the family and dining spaces shine with natural light. The streamlined designer kitchen creates an easy culinary layout for the resident chef while granting an open view of the adjacent living spaces. Head up stairs to find the Owner’s retreat, an en suite Owner’s Bath and sizable walk-in closet to contribute to the everyday getaway. You’ll also find a multipurpose loft for a family movie theater or game night HQ as well as 3 additional bedrooms, 1 full bath and your indoor laundry room conveniently located on the second floor. Finishing out the first floor is your guest bedroom with en-suite bath so your visitors have their own getaway, as well as a study and powder room. The generous back yard boasts plenty of room to build your outdoor, pool inspired oasis. How do you imagine your #LivingWeekley experience with this new home in Lakeview Crossing? You are conveniently located close to downtown Sarasota (10 miles), UTC shopping center (9.4 miles), Siesta Key Beach (12 miles) & SQR airport (15 miles) in the fully gated community of Lakeview Crossing.
Listing is courtesy of: WEEKLEY HOMES REALTY COMPANY (866-493-3553)
Listing Agent: Robert St. Pierre
2314 PROSPECT ST, SARASOTA, FL 34239
$2,275,000110 Days on yellowkey MLS ID: A4684572
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3651 Built: 2024 Tax: $18,837 (2025)Community: Loma Linda ParkSpa: YesSingle Family
Taxes:$18,837
Remarks: A statement of modern elegance in the heart of Sarasota, this exceptional Arlington Park residence delivers refined luxury, architectural presence, and elevated design at every turn. Offering 5 bedrooms, 5.5 bathrooms, and 3,651 square feet under air, this custom-built home was thoughtfully designed for those who appreciate both sophisticated entertaining and comfortable everyday living. From the moment you enter, soaring 12-foot ceilings and a dramatic staircase create an unforgettable first impression. The main living spaces are open, expansive, and filled with natural light. A designer kitchen anchors the home, showcasing solid wood cabinetry, quartz countertops, an oversized waterfall island, and premium Thermador appliances which are perfectly suited for culinary enthusiasts and elegant gatherings alike. A custom built-in feature wall enhances the living area with both style and function. Sliders seamlessly connect indoor and outdoor spaces, creating effortless Florida living. A private first-floor office offers a quiet retreat for work or study. Upstairs, 10-foot ceilings and rich hardwood flooring continue the home’s elevated aesthetic. The owner’s suite is a true sanctuary, complete with a private balcony overlooking the backyard, custom vanity, a soaking tub, and an oversized walk-in shower finished with striking designer tile. Each additional bedroom features its own en-suite bath and walk-in closet, ensuring comfort and privacy for family and guests. A spacious second-floor den provides flexible space for a media room, lounge, or game area. The outdoor setting rivals a private resort. The saltwater pool with waterfall and sun shelf is complemented by a spa, outdoor shower, and dedicated pool bath. A modern aluminum pergola adds architectural interest and shaded relaxation, while the lanai invites seamless entertaining year-round. No detail was overlooked: impact-rated windows and doors, epoxy-finished 2.5-car garage, irrigation system, integrated indoor/outdoor speakers, pre-wiring for security cameras, and dual A/C systems for optimal efficiency. Located in highly desirable Arlington Park, this home places you minutes from downtown Sarasota, Sarasota Memorial Hospital, and the area’s renowned dining and cultural destinations. World-class beaches including Siesta Key and Lido Key are just a short distance away. This is more than a home...it is a lifestyle defined by quality, design, and distinction. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Kroshus (941-303-3429)
2660 DICK WILSON DR, SARASOTA, FL 34240
$1,299,00067 Days on yellowkey MLS ID: A4690365
REDUCED by $50,000 (3.7%) on 06/05/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3166 Built: 1997Monthly Fee: $369 Tax: $6,823 (2025)Community: Laurel Oak Estates Sec 10Single Family
Taxes:$6,823
Remarks: Under contract-accepting backup offers. Laurel Oak Estates, beautifully on a private .91-acre lot with mature landscaping, this spacious four-bedroom home with office/den offers 3,166 square feet of comfortable living. Thoughtfully designed with custom window treatments, crown molding, and a deluxe lighting system throughout, the home blends elegance with everyday functionality. Kitchen features a large island, Corian countertops, white cabinetry and opens to the main living areas. Sliding glass doors lead to an expansive outdoor space with a large pool and spa, creating an indoor-outdoor lifestyle. Additional highlights include impact windows, a newer tile roof, and a three-car garage providing ample storage. In the guard-gated community, this private property offers security and serenity in a beautiful setting. Membership in Laurel Oak Country Club is optional. Two championship golf courses, 12 Tru-Har tennis courts, pickleball and an active social calendar. Come live the lifestyle!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Linda Dooley (941-400-7359)
4304 MIDLAND RD, SARASOTA, FL 34231
$340,00055 Days on yellowkey MLS ID: TB8502989
REDUCED by $34,900 (9.3%) on 05/26/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1447 Built: 1952 Tax: $3,143 (2025)Community: Floral Park HomesteadsSpa: YesSingle Family
Taxes:$3,143
Elementary School: Wilkinson Elementary
Remarks: This meticulously maintained 3-bedroom residence offers the ideal blend of vintage Florida character and high-quality contemporary improvements—all in a prime Sarasota location. Metal roof (2011), new HVAC system (2023), and tankless water heater (2020). Original wall planking replaced with new Sheetrock and insulation to improve energy efficiency. New flooring installed in 2020 flows throughout the open-concept living areas. Private fenced backyard with a sparkling pool (2019) and an above-ground heated spa—perfect for year-round enjoyment. Conveniently situated near Sarasota’s most desirable destinations. Approximately 5 miles to the world-renowned Siesta Key Beach; it is also close to Lido Key Beach. Minutes to St. Armands Circle and Downtown Sarasota’s vibrant restaurant and cultural scene. Near major retailers, grocery stores, and the shops along Bee Ridge Road and Southside Village. Just around the corner from Bee Ridge Park with green space, playgrounds, and community activities.
Listing Agent: Brenda Olivas (407-280-0208)
8420 WEBBER RD, SARASOTA, FL 34240
$1,399,00091 Days on yellowkey MLS ID: A4687127
REDUCED by $101,000 (6.7%) on 05/06/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3104 Built: 2010Monthly Fee: $133 Tax: $5,532 (2025)Community: Regent LakeSpa: NoSingle Family
Taxes:$5,532
Remarks: One or more photo(s) has been virtually staged. LUXURY,LAND & 24 ACRE LAKE VIEW THE ULTIMATE FLORIDA LIFESTYLE Exclusive 13-Home Community- A True Hidden Gem Experience the pinnacle of Sarasota luxury living in this exceptional lakefront pool home estate set on over one plus private acre in the exclusive Regent Lake community. Showcasing the highly desirable Osprey floor plan, this expansive residence with 3104 sq ft of living space offers 4-bedrooms, office /library 3-bath offers refined living with an oversized 3-car garage and a thoughtfully designed split floor plan ideal for both entertaining and everyday comfort. From the moment you arrive, you are greeted with breathtaking panoramic views of a 25-acre spring-fed lake, delivering stunning sunsets and a peaceful, no-through-traffic setting that is truly rare to find. Inside, elegance meets functionality with formal living and dining rooms, a spacious family room, and a gourmet kitchen designed to impress. Featuring stainless steel appliances, granite countertops, upgraded wood cabinetry, built in oven microwave combination, cooktop, custom wood vent hood, walk-in pantry, breakfast bar, center island, and a bright morning room — this kitchen is truly the heart of the home. The luxurious primary suite is a private retreat, offering direct access to the pool and lanai along with serene lake views. The spa-style bath includes a garden tub, walk-in shower, dual vanities, and dual closets, including an oversized walk-in. Step outside to your screened lanai and pool area where indoor and outdoor living blend seamlessly. Enjoy tranquil lakefront views, breathtaking sunsets, and a private fenced area perfect for pets. Recent upgrades provide peace of mind and modern efficiency, including: ** Bahama hurricane shutters throughout ** New A/C (2025) ** New water heater (2025) ** Whole-house generator with buried 500-gallon propane tank ** Reinforced garage door (150 mph rated) ** Added attic insulation ** All Bedrooms have brand new Laminate flooring just installed last week Regent Lake is an intimate community of just 13 homes, offering low HOA fees, no CDD, and a lifestyle centered around privacy and nature. The spring-fed lake is navigable by canoe or kayak, adding to the unique charm of this one-of-a-kind property. Conveniently located near shopping and top-rated Tatum Ridge Elementary School, this home offers the perfect blend of luxury, location, and lifestyle. This is more than a home — it’s a rare opportunity to own a private waterfront estate in one of Sarasota’s most exclusive settings.
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
5146 COTE DU RHONE WAY, SARASOTA, FL 34238
$699,90012 Days on yellowkey MLS ID: A4696420
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2578 Built: 2003Monthly Fee: $684 Tax: $5,216 (2025)Community: Silver OakSingle Family
Taxes:$5,216
Remarks: Under contract-accepting backup offers. Beautifully upgraded& expanded Tuscan style maintenance free home located in The Vineyards of Silver Oak on Palmer Ranch. Custom built by Gibralter builders & expanded to nearly 2600 sq. ft. under air. Recent upgrades include: New tile roof in 2019,replumbed in 2023, new stainless appliances in kitchen & new washer & dryer. 3 bedrooms (hidden office closet), 3 baths 2 full & 1 half bath. Upgraded Travertine look tiles, custom wood look floors in the primary & second bedrooms. Very open, light & bright great room floor plan. Kitchen has wood cabinets & granite counters. Large extended screened lanai overlooking very private preserve views ( no road noise). This boutique community of 72 homes providing maintenance for complete landscaping & irrigation maintenance. A private community center available only to The Vineyards offers a pool, fitness & cozy clubhouse with kitchen for special events. The Vineyards is located in this Executive community of Silver Oak on Palmer Ranch close to shopping, restaurants, The Legacy bike trail & just minutes from world famous Siesta Key Beach.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Cynthia Bowers (941-650-4808)
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