Location: Sarasota
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
3416 W CHELMSFORD CT #2, SARASOTA, FL 34235
$420,000508 Days on yellowkey MLS ID: A4634668
3 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1513 Built: 1990 Tax: $4,165 (2023)Community: The MeadowsVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,165
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2023
Middle School: Booker Middle
Remarks: This beautiful villa sits at the end of a dead-end street, a few steps from the community pool and has stunning lake and golf course views. As you enter the walkway you are greeted by a gated entry gaining access to the front loggia that is accented with pavers and leads to your private entrance. The grand foyer is large and is the perfect space to display your art or family heirlooms. The kitchen has been professionally updated with stunning finishes and features high-end appliances. There is an office or den off the kitchen through dual pocket tiffany doors. The guest bedroom is spacious and provides a view to the front lanai. The living room and dining room provide for gracious living and entertaining allowing expansive views of the golf course and lake. Golf views are also from the primary suite with its large bathroom and walk-in closet. This home features high ceilings throughout, extensive levels of crown moldings, elegant features and finishes and is perfect for year-round living or as a wonderful getaway home for seasonal or frequent visitors.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
800 N TAMIAMI TRL #815, SARASOTA, FL 34236
$975,000139 Days on yellowkey MLS ID: A4676300
REDUCED by $50,000 (4.9%) on 05/15/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1323 Built: 2007Monthly Fee: $1,328 Tax: $10,115 (2025)Community: AlinariSpa: YesCondo
Taxes:$10,115
Elementary School: Alta Vista Elementary
Tax Year: 2025
Remarks: Immerse yourself in the vibrant energy of Sarasota’s coveted Rosemary District, where an inspired coastal lifestyle unfolds just beyond your doorstep. Perfectly positioned, moments from The Bay Sarasota and The Quay Sarasota, this residence offers effortless access to the city’s most exciting transformation – lush bayfront greenspaces, scenic walking paths, a new pier, and curated waterfront experiences including free concerts, yoga, and even a kayak launch. Right at your doorstep you will discover a dynamic collection of Rosemary District café’s, acclaimed restaurants, artisan bakeries, and boutique shops, all contributing to a walkable, cultured, and endlessly engaging lifestyle. From morning rituals to sunset dinners along the bay, this residence, set within Alinari at Rosemary Place, invites you to experience Sarasota at its finest. Framed by breathtaking true full water frontage views that stretch across Sarasota Bay and beyond, this beautifully redesigned two-bedroom, two-bath residence captures unobstructed westerly vistas from its highly desirable eighth-floor position in the south tower, where natural light pours in and sunset gazing becomes a daily ritual. The interiors have been thoughtfully re-imagined with a clean, modern aesthetic, featuring wide plank luxury flooring, quartz surfaces, new modern fixtures, and a cohesive move-in ready design. The open layout enhances the connection to the water, while a rare walk-in laundry room and additional flex storage space add everyday convenience. The primary suite offers a serene retreat with a walk-in closet and a well-appointed, fully customized en-suite bath, while the second bedroom is equally versatile for guests or a home office – each space sharing in the residence’s captivating views. Alinari presents a refined residential experience with amenities beyond expectation. Enjoy the privacy of a 3rd floor Olympic length pool and deck where recreation and relaxation can easily be found. The state-of-the art fitness center, modern and fully upgraded theater, business center, guest suites, game room, gated entry garage, 24-hour concierge and on-site security, are just a small sample of Alinari features and lifestyle. Unique to the property you will enjoy a beautifully landscaped 35,000 sq ft gated recreational space that is for the exclusive enjoyment of Alinari owners and their pets. With strong reserves, no current assessments, and elevated construction in Flood Zone X, the building offers peace of mind and enduring value. Complete with two garage parking spaces and climate-controlled storage, this residence is a rare opportunity to enjoy downtown Sarasota living at the intersection of culture, convenience, and sweeping waterfront beauty.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Moriah Taliaferro (941-504-9910)
5021 BARRINGTON CIR #302, SARASOTA, FL 34234
$160,000229 Days on yellowkey MLS ID: A4663516
REDUCED by $15,000 (8.6%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982Monthly Fee: $599 Tax: $2,471 (2024)Community: Barrington WoodsVilla
Taxes:$2,471
Elementary School: Emma E. Booker Elementary
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Embrace the ultimate Sarasota lifestyle in this beautifully maintained 2-bedroom, 2-bathroom villa, perfectly situated in a secure fenced community and featuring elegant, vaulted ceilings and two private screened lanais for enjoying the beautiful Florida weather. This property offers a low-maintenance, resort-style experience with a fantastic community pool and a dedicated carport for convenient parking. The villa's outstanding location provides quick access to both necessities and leisure: it's just minutes from Sarasota-Bradenton International Airport (SRQ), a short drive to the famous Gulf beaches, and centrally located near esteemed institutions like New College and the Ringling School of Art and Design. It's an ideal retreat for anyone seeking the perfect blend of security, comfort, and immediate proximity to Downtown Sarasota's rich scene of arts and culture.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kelly Oatsvall (941-447-7256)
1173 MYRTLE ST, SARASOTA, FL 34234
$375,000235 Days on yellowkey MLS ID: TB8436061
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $14,900 (3.8%) on 05/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1950 Tax: $4,523 (2024)Community: Ford SubSingle Family
Taxes:$4,523
Remarks: Under contract-accepting backup offers. **SHORT TERM RENTALS PERMITTED** This beautiful property is conveniently located within the city limits of Sarasota, allowing for short-term rentals with a minimum of 7 days—offering a lucrative opportunity for investors. This updated home highlights a 3-bedroom, 2-bath layout featuring a separate primary suite complete with a luxurious new bathroom and kitchenette, providing the perfect setup if this space is used as a separate 1-bedroom, 1-bath studio—ideal for high-demand rentals in the area. Option #2 offers an incredible family retreat with plenty of privacy and a resort getaway feel right at home. With its own separate entrance, this flexible space also doubles as a fantastic in-law suite. Together, the spaces provide 1,361 square feet of refreshed living area. Step inside to discover new flooring throughout, a modern kitchen and updated bath, and stylish new lighting that enhances the home’s bright, open feel—all beautifully upgraded with new appliances, AC, water heater, and roof for lasting comfort and value. This property also boasts a generous yard—perfect for those who crave extra outdoor space. Whether you envision a private garden, play area, or space for family pets, this oversized side yard offers endless possibilities. Mature landscaping provides both beauty and privacy, creating a peaceful setting for outdoor relaxation. The outdoor area is made for Florida living—featuring an expansive, oversized pool perfect for lap swimming, entertaining, and making lasting memories. A huge screened lanai invites relaxation and provides plenty of space to host poolside gatherings and parties. A mini golf green adds a playful touch for family and friends. Whether you’re looking for a home with extra income potential or a flexible multi-use property, this one checks all the boxes. Conveniently located near downtown Sarasota, St. Armands Circle, Siesta Key Beach, the Sarasota-Bradenton Airport, and the UTC shopping district, you’ll be right in the heart of everything the Gulf Coast has to offer. A rare opportunity to enjoy a move-in-ready home and an income-producing asset—all in one desirable Sarasota location! **Free 1/0 Interest Rate Buy Down available when using our preferred lender.**
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Andrew Duncan (813-359-8990)
7920 MAINSAIL LN, SARASOTA, FL 34240
$2,150,0009 Days on yellowkey MLS ID: A4694620
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3216 Built: 2021Monthly Fee: $444 Tax: $18,596 (2025)Community: Lakehouse Cove/Waterside Ph 3Spa: YesSingle Family
Taxes:$18,596
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Exclusive custom-designed Talise by Arthur Rutenberg Homes, ideally situated within the highly sought-after Lakehouse Cove at Waterside community. Elegant iron front double doors welcome you into a stunning great room featuring engineered hardwood floors, soaring vaulted ceilings accented with decorative beams, and an expansive open-concept layout filled with abundant natural light. The gourmet kitchen is beautifully appointed with a gas cooktop, built-in double ovens, refrigerator, microwave, wine refrigerator, quartz countertops throughout, custom cabinetry, and a spacious walk-in pantry designed for both style and functionality. Floor-to-ceiling impact sliding glass doors create seamless indoor-outdoor living, opening to a spectacular private retreat complete with a saltwater pool and spa, upgraded ClearView screen enclosure, expansive entertaining area, and fully equipped outdoor kitchen — perfect for enjoying the Florida lifestyle year-round.This thoughtfully designed residence features 3 spacious bedrooms, 3 bathrooms, a private den, powder room, and a versatile bonus room. The luxurious primary suite offers dual walk-in closets, while the multipurpose laundry area includes additional space ideal for a small office, hobby area, or extra storage. Additional upgrades include a tankless hot water heater, integrated Sonos sound system, and refined designer finishes throughout. A 3-car side-loading garage enhances curb appeal while providing generous storage and functionality. Perfectly positioned on a beautiful private preserve homesite, this exceptional residence offers privacy, sophistication, and resort-style living just moments from Waterside Place dining, shopping, entertainment, parks, and the popular farmers market. Residents of Lakehouse Cove at Waterside enjoy premier resort-style amenities including an upscale clubhouse, lakeside pool and spa, fitness center, playground, dog park, walking trails, tennis and pickleball courts, dock house with lake access, and kayak storage. Ideally located near Sarasota’s world-class beaches, cultural attractions, and vibrant lifestyle destinations, this exceptional home offers the very best of luxury Florida living.Schedule your private showing today to experience this exclusive custom residence firsthand.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Susan Alliano (941-735-6571)
7740 CASTLEISLAND DR, SARASOTA, FL 34240
$585,00030 Days on yellowkey MLS ID: A4691962
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2348 Built: 2001Monthly Fee: $295 Tax: $5,092 (2025)Community: Tatum RidgeSingle Family
Taxes:$5,092
Remarks: Welcome to 7740 Castleisland Drive, nestled in the prestigious gated enclave of Legends at Tatum Ridge. This three-bedroom plus flex room residence offers a rare combination of elegance and functionality. The flexible room easily serves as a fourth bedroom, while each of the three true bedrooms is en-suite—providing privacy and a sense of distinct “wings” for each occupant. The primary suite is a sanctuary with tray ceilings and direct access to the screened lap pool, letting you step out for a refreshing swim. With a new roof (2022), new AC (2023), and repiped PEX plumbing (2020), the home is fully updated. The expansive freshly screened pool cage (2022) overlooks the Tatum Ridge Golf Course driving range, offering sweeping views and peaceful privacy. In addition, you will find a 3 car attached garage, a very rare find in this price point! As you step through the front door, your eyes are drawn straight through the open living area to the sparkling lap pool and the wide open views beyond and from your front porch bask in the gorgeous unobstructed water views directly across the street. The soaring 12-foot ceilings, luxurious pillars, and walls of glass fill the space with natural light, creating a seamless indoor-outdoor flow. The open concept effortlessly connects a formal dining room and a sunny breakfast nook, perfect for gatherings. Sliding glass doors open right out to the expansive screened pool area, where a convenient pool bath makes outdoor entertaining even more functional. This central hub is the home’s bright, inviting core! Location is unbeatable—just under 4 miles to Waterside Place’s vibrant shops and dining, and you’re mere seconds from Fruitville Road, making downtown Sarasota just a 15-minute drive. Quick access to the I-75/Fruitville interchange ensures effortless travel. The HOA is a standout feature—no CDD, and all yard maintenance is covered, from lawn care to irrigation, for a truly low-maintenance lifestyle. This home is your key to luxurious, worry-free living in the heart of Sarasota’s best and won't last long. Schedule your showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Johnny Hopper, Pa (941-524-1706)
5450 LONGWOOD RUN BLVD #202, SARASOTA, FL 34243
$185,00081 Days on yellowkey MLS ID: A4685859
INCREASED by $5,000 (2.8%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 954 Built: 1994Monthly Fee: $434 Tax: $2,087 (2025)Community: Magnolia PlaceCondo
Taxes:$2,087
Remarks: Locatin, location, location! Come see this spacious condo located in the heart of Sarasota. You are just 2.5 miles from University Town Center, I-75, shopping and dining. Sarasota Bradenton International Airport, downtown Sarasota, and beautiful Sarasota Bay are within 15 minutes. Longwood Park is only 0.4 miles away and here where you can enjoy dog-friendly areas, tennis and pickleball courts, basketball courts, baseball fields, a playground, gymnasium, a recreational building and more. This well-maintained condo offers two bedrooms and two bathrooms. An inviting open floor plan features a spacious great room, kitchen and dining area. Beautiful, engineered wood floors cover the entire condo. No carpet in this property! New water heater was installed in February 2026. You can enjoy scenic view from the covered and screened lanai. The community only has 16 condos. HOA fees cover your water/sewer, cable TV, interior/exterior pest control, exterior power washing/maintenance, irrigation/landscaping maintenance, as well as common area taxes and insurance.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Delia Valente (571-236-7245)
3597 FOUNDERS CLUB DR, SARASOTA, FL 34240
$1,950,000177 Days on yellowkey MLS ID: A4673915
1 Days Off yellowkey (back on 5/7/2026)
Bed: 4 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3957 Built: 2006Monthly Fee: $467 Tax: $17,901 (2024)Community: Founders ClubSpa: YesSingle Family
Taxes:$17,901
Remarks: A True Gem in The Founders Club Elegance, Comfort, and An Outstanding Location Welcome to 3597 Founders Club Drive, an exquisite residence nestled within Sarasota’s premier gated golf community, The Founders Club. Built in 2006, this residence combines quality construction with modern amenities and is walking distance to the club house. The property sits on a 0.47 acre lot, offering both space and intimacy within a prestigious community known for its Robert Trent Jones jr. golf course, clubhouse, and social activities. Spanning 3,957 square feet of living space, this home features four spacious bedrooms, three full baths, and one half bath, thoughtfully designed with a split floor plan to maximize privacy and comfort. The grand foyer opens into formal living and dining areas, while the family room has pocket sliders which open onto the lanai. High ceilings, crown molding, and expansive windows create a light filled ambiance throughout the house. The gourmet kitchen is a chef’s delight, boasting a large center island, breakfast bar, walk in pantry, and custom cabinetry. Stainless steel appliances and ample counter space make entertaining effortless. Adjacent to the kitchen, the family room offers casual elegance with views of the pool and lanai. A separate breakfast nook provides the perfect spot for morning coffee in the sheltered lanai overlooking the 18th fairway. The primary suite is a private retreat, complete with dual vanities, a walk in shower and separate tub. Generous his and her closet space and direct access to the lanai enhance the sense of luxury. Additional bedrooms are well appointed, ideal for family or guests, while a bonus room and dedicated office/den provide flexibility for work or leisure. Outdoor living is at the heart of this home. The expansive screened lanai showcases a sparkling pool and spa, surrounded by ample deck space for lounging or dining al fresco. Mature landscaping ensures privacy, while the backdrop of The Founders Club’s natural beauty creates a tranquil oasis. With his and her two car garages, there is abundant space for vehicles, golf carts, and storage. Living at The Founders Club means enjoying an exclusive lifestyle. Residents benefit from a limited membership golf club, (for which a membership is available for transfer), little traffic, and a vibrant social calendar. Located east of I 75, the community provides convenient access to downtown Sarasota, world class beaches, cultural venues, and fine dining. This home is more than a residence—it is a statement of elegance and comfort. Whether hosting gatherings, enjoying quiet evenings by the pool, or taking advantage of the community’s amenities, 3597 Founders Club Drive offers the perfect blend of sophistication and Florida living. Don’t miss the opportunity to make this exceptional property your own. Schedule a private tour today and experience the unmatched charm of The Founders Club.
Listing Agent: Richard Hearn (941-313-1591)
801 SEASCAPE PL, SARASOTA, FL 34240
$1,545,00079 Days on yellowkey MLS ID: TB8486565
REDUCED by $30,000 (1.9%) on 04/22/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3982 Built: 2021Monthly Fee: $500 Tax: $14,765 (2025)Community: Shoreview/Lakewood Ranch WaterSpa: YesSingle Family
Taxes:$14,765
Remarks: Under contract-accepting backup offers. Luxury living awaits in Shoreview at Waterside, one of Lakewood Ranch’s most sought-after communities. This Stonewater model by Pulte offers nearly 4,000 square feet of refined living space w/ 4 bedrooms, 4 baths, a private den/office, & an expansive 35’ x 20’ upstairs bonus room. Perfectly positioned on an oversized corner lot, this home features more than $250,000 in high-end upgrades post-closing, which elevate both style and functionality. Inside, soaring 14-foot ceilings, custom designer lighting, plantation shutters, & an open-concept layout create an elegant yet welcoming atmosphere. Abundant natural light and southwest-facing rear exposure further elevate this exceptional home. The chef’s kitchen features upgraded KitchenAid appliances, a natural gas cooktop, oversized island, granite countertops, a large walk-in pantry w/ custom shelving, & a breakfast nook, flowing seamlessly into the great room and formal dining area- perfect for entertaining. The primary bedroom is a serene retreat with the en-suite featuring spa-like finishes, dual vanities, a walk-in shower, a soaking tub, & a large walk-in closet w/ custom shelving. Two additional bedrooms and baths, plus a private den/office, complete the main level, while the upstairs bedroom, full bath, & bonus room provide an ideal space for media room, home gym, or guest retreat. Head outside to your very own resort-style, private backyard escape. The expansive screened lanai features a heated saltwater pool & spa w/ integrated fire features, a fully equipped outdoor kitchen, & lush, layered privacy landscaping- a rare offering that includes enough space for grilling, dining, lounging, & an outdoor living area with TV- an entertainer’s dream! Additional home highlights include hurricane impact windows upstairs, motorized hurricane screens covering the lanai, whole-home water filtration, custom shelving in pantry and closets, EV charging in the 3-car (epoxy coated floor) garage, custom garage ceiling storage racks and 4 wall mounted bike racks, brand-new LG washer & dryer, and a paver driveway. Designer Arhaus furnishings are negotiable for a truly move-in-ready experience. Ideally situated on a low-traffic street just off the main road, this home offers exceptional privacy with no neighbors on one side or directly across the street. Only four other residences share the block, and no homes line the opposite side. A community green space sits directly across from the property, while a scenic walking trail winds between two neighborhood lakes just steps away. The amenity center is an easy five-minute walk, & a well-maintained dog park is located just four houses down. Shoreview residents enjoy a maintenance free community w/ resort style amenities. The nearby amenity center offers a heated community pool & spa, fire pits, fitness center, lighted tennis & pickleball courts, kayak launch, beach area, & events lawn. Located just minutes from Waterside Place, enjoy walking, biking, or taking the free water taxi service to lakeside dining, live music, community events, a weekly farmer’s market, splash pad, & more. This area is desirable due to proximity to all Sarasota has to offer, including world-class beaches. Shoreview Waterside offers the sought-after combination of being in Lakewood Ranch within Sarasota County.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
4345 CALLISTA LN, SARASOTA, FL 34243
$425,00052 Days on yellowkey MLS ID: A4688590
0 Days Off yellowkey (back on 5/1/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1930 Built: 2005Monthly Fee: $243 Tax: $4,396 (2025)Community: Callista VillageSingle Family
Taxes:$4,396
Remarks: Under contract-accepting backup offers. This light and bright home offers an inviting open-concept design with a spacious kitchen that flows seamlessly into the great room, creating the perfect setting for both everyday living and entertaining. Featuring 2 bedrooms, 2 bathrooms, a dedicated office/den, and a 2-car attached garage with a new epoxy finish, this home combines comfort, functionality, and style. The kitchen is equipped with newer stainless steel appliances, while the spacious owner’s suite provides a relaxing retreat with an oversized walk-in closet. Step outside and enjoy your own private saltwater swimming pool, offering a luxurious touch and silky-smooth water for year-round enjoyment. Additional updates include a new air conditioning system installed in 2021, annual servicing, UV lights, and a surge protector for added peace of mind. Pool pump replaced in 2023 and new salt cell and motherboard in 2025. Low community fees add to the appeal and cover yard and shrub maintenance, sprinklers and soakers, and front entrance maintenance. Located just beyond Longwood Park, residents also enjoy easy access to an impressive variety of nearby recreational amenities including baseball, basketball, pickleball, tennis, a playground, picnic pavilion, recreation building, gymnasium, and dog-friendly areas. All within walking distance! Welcome to Callista Village, an intimate community of just 32 homes ideally located west of UTC Mall, where exceptional shopping, dining, and everyday conveniences are all close at hand. A local bus stop just outside the community offers easy access to shopping, the airport, and downtown, adding even more convenience to this desirable location.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Brenda Wilson (941-321-8686)
5378 SARAPOINTE CT, SARASOTA, FL 34232
$550,00012 Days on yellowkey MLS ID: A4694119
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 1986Monthly Fee: $62 Tax: $3,186 (2025)Community: Eastpointe Ph 01Spa: NoSingle Family
Taxes:$3,186
Remarks: Under contract-accepting backup offers. Waterfront Pool Home. Tucked away on a quiet cul-de-sac in the sought-after Eastpointe community, this beautifully maintained 4-bedroom, 2-bath residence offers the perfect blend of comfort, privacy, and Florida lifestyle. Set on a scenic lakefront lot with tranquil water views, this home features a versatile floor plan with two primary suites, including a private second-floor retreat with its own mini-split system. Step inside to soaring vaulted ceilings in the living room, a cozy wood-burning fireplace, and a wet bar—ideal for entertaining. The eat-in kitchen is thoughtfully designed with convenient pull-out shelving in the cabinets, while many major appliances are less than one year old, adding peace of mind for the next owner. The outdoor living space is a true retreat, featuring a heated pool, expansive pavered pool deck, and an outdoor shower, all overlooking the peaceful lake setting. The spacious yard includes multiple fruit trees, creating your own tropical oasis. Additional upgrades include: Impact windows (2025) / Impact-rated garage door /Hardie fiber cement plank siding /Engineered acacia hardwood flooring in bedrooms/Solid core interior doors /Roof replaced in 2016 /A/C replaced in 2017 Located just minutes from downtown Sarasota, this home offers exceptional convenience—only 7.3 miles to Siesta Key Beach, close to Nathan Benderson Park, and near The Mall at University Town Center for premier shopping, dining, and entertainment. Easy access to I-75 makes commuting a breeze. With low HOA fees and no CDD, this exceptional waterfront home offers the ideal combination of location, upgrades, and lifestyle.
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Timothy Trojanowski (941-320-1399)
941 VIRGINIA DR, SARASOTA, FL 34234
$1,500,00089 Days on yellowkey MLS ID: A4684540
Bed: 6 Bath: 4.5 Liv Area Sq Ft: 3492 Built: 1945 Tax: $9,217 (2025)Community: Bay HavenSpa: YesSingle Family
Taxes:$9,217
Remarks: A Rare Piece of Sarasota History. Four turn-key furnished residences. Three City Lots. One Extraordinary Piece of Sarasota History. Welcome to 941 Virginia Drive, a truly unique historic property originally built by John Ringling Jr., offering vintage Sarasota charm paired with modern flexibility and lucrative income. Set on three city lots, this 125-foot-long masonry residence creates an extraordinary private compound with four distinct living spaces. The main residence features two bedrooms, one and a half bathrooms, and an office or den, highlighted by timeless architectural details including stone porches, arched doorways, pecky cypress paneling, tall vaulted beamed ceilings and a wood-burning fireplace. Modern updates complement the historic character with stainless steel appliances, granite countertops, and updated fixtures. The property is designed for lifestyle, opportunity and flexibility for extended family, guests or continued successful short-term rental business. In addition to the main home, the estate includes three separate guest residences providing privacy and versatility. There are two in-law suites that feature full kitchens, a private pool, hot tub, outdoor shower, patio access and a private bathroom; one offers one bedroom and the other two bedrooms. There is an additional one-bedroom dwelling with a convenient kitchenette, private bathroom and laundry. Located just two miles north of downtown Sarasota, the property offers easy access to Lido Key, Longboat Key, St. Armands Circle, and the vibrant dining, arts, and cultural scene of downtown Sarasota. Whether you envision a private historic estate, a multi-generational compound or a unique established vacation rental business, this rare property offers exceptional character, privacy and opportunity in one of Sarasota’s most desirable locations. Don’t miss this opportunity to Own a Piece of Ringling History — A Private Sarasota Compound with Vintage Charm and Resort-Style Living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Angela Adams (941-809-9760)
5354 MYRTLE WOOD #50, SARASOTA, FL 34235
$247,000138 Days on yellowkey MLS ID: A4677059
REDUCED by $8,900 (3.5%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1064 Built: 1981Monthly Fee: $592 Tax: $2,906 (2024)Community: SomersetSpa: NoVilla
Taxes:$2,906
Remarks: NEW PRICE- Welcome to a move-in-ready villa offering effortless Florida living in one of the most sought-after enclaves within The Meadows—where tree-lined streets, mature landscaping, and an active outdoor lifestyle define the experience. Perfectly positioned on a quiet street just moments from community pools and miles of scenic trails, this residence delivers both privacy and immediate access to everything that makes The Meadows so desirable. Inside, vaulted ceilings and an open, light-filled layout create an inviting sense of space, while recent updates—including fresh interior paint and new flooring—provide a clean, modern feel with minimal effort required. The great room seamlessly opens through a full wall of sliding glass doors to a screened lanai surrounded by lush greenery—an ideal setting for morning coffee or a relaxed evening. The kitchen offers a functional and stylish workspace with stone countertops, stainless steel appliances, ample storage, and its own access to a private front lanai. The split-bedroom floor plan enhances comfort and flexibility, with a private primary suite tucked at the rear of the home featuring dual closets and a walk-in shower. A second bedroom with an ensuite bath at the front provides an ideal space for guests or a home office. A dedicated laundry area adds to the home’s practical design. Living in The Meadows means enjoying a 1,650-acre park-like community with over 14 miles of trails, 85 lakes, and optional memberships to golf, tennis, pickleball, a junior Olympic pool, and a fitness center. Just minutes from Nathan Benderson Park, the vibrant shopping and dining at University Town Center, downtown Sarasota, and the renowned beaches of Siesta Key and Lido Key, this villa offers the ideal balance of convenience, lifestyle, and value—whether as a full-time residence or seasonal retreat. Make an appointment to see this villa today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Andy Scherer (315-264-0944)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$299,0006 Days on yellowkey MLS ID: TB8511154
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 721 Built: 1985Monthly Fee: $45 Tax: $1,776 (2025)Community: Deer HollowVilla
Taxes:$1,776
Remarks: Location, location, location! Welcome to this 2 bedroom, 1 bathroom villa ideally situated in the heart of Sarasota with quick access to I-75, making commuting and exploring the area incredibly convenient. This move in ready home has already had the major updates completed for peace of mind, including a new roof in 2022 with a 10 year warranty, hurricane grade windows, slider, and front door installed in 2023, new AC in 2024, and replaced exterior siding. Enjoy low HOA fees of just $335 annually while taking advantage of community amenities including a playground and peaceful preserve walking paths. Whether you’re looking for a primary residence or a seasonal getaway this villa offers comfort, convenience, and value all in one. Perfectly positioned near the vibrant UTC area, this home is just minutes from Nathan Benderson Park, The Mall at University Town Center, top rated dining, shopping, Sarasota-Bradenton International Airport, Downtown Sarasota, and the world famous beaches of Siesta Key and Lido Key. Schedule your showing today!
Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)
Listing Agent: Ali Kochno (813-766-7143)
630 CORWOOD DR, SARASOTA, FL 34234
$824,50042 Days on yellowkey MLS ID: A4690643
REDUCED by $50,500 (5.8%) on 05/25/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1897 Built: 1963 Tax: $7,711 (2025)Community: Corwood ParkSpa: NoSingle Family
Taxes:$7,711
Remarks: Discover the perfect blend of location, lifestyle, and future potential in this beautifully updated residence in the desirable Corwood Park neighborhood. Situated on an expansive ~0.22-acre lot, this property offers a rare opportunity to enjoy move-in-ready comfort today while preserving room for tomorrow’s vision. Thoughtfully renovated, the home showcases a modern kitchen with shaker cabinetry, new countertops, new High Efficiency washer and dryer and stainless-steel appliances, complemented by updated bathrooms, new tile flooring throughout, and impact patio doors. The outdoor space is equally impressive, featuring a refreshed pool area ideal for entertaining or relaxing under the Florida sun. What truly sets this property apart is the generous lot size, flexibility and expanded living spaces, demonstrating the strong upside potential for expansion or redevelopment. Surrounded by lush tropical vegetation and mature trees, the property offers privacy and a serene setting, with ample space to add square footage, a guest house, or enhanced outdoor living features—subject to local zoning. Ideally located west of the Trail, this home is just moments from Sarasota Bay, where you can enjoy evening sunsets, and only minutes to cultural landmarks like the Ringling Museum, Sarasota Jungle Gardens, downtown Sarasota, SRQ Airport, and world-class beaches. Whether you’re seeking a primary residence, seasonal retreat, or investment with upside potential, this property delivers location, land value, and lifestyle—all in one of Sarasota’s most promising growth corridors.
Listing is courtesy of: CCI REALTY (954-667-6692)
Listing Agent: Oscar Betancourt (954-854-3959)
3332 TALLYWOOD CT #7086, SARASOTA, FL 34237
$150,00024 Days on yellowkey MLS ID: A4692649
1 Days Off yellowkey (back on 5/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1109 Built: 1983 Tax: $975 (2025)Community: Tallywood Ph 1 & 2Condo
Taxes:$975
Elementary School: Tuttle Elementary
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in the desirable 55+ Tallywood community of Sarasota! This charming 2-bedroom, 2-bath condo offers a spacious and comfortable layout designed for relaxed living and entertaining. The home is clean, well maintained, and offers a great opportunity to personalize and update to your own taste and style. Enjoy a bright open living and dining area, a functional kitchen with ample cabinet space, and a private primary suite with en-suite bath and generous closet storage. The second bedroom and bath provide flexibility for guests, hobbies, or a home office. The second bedroom has a built in Murphy bed and built in desk, which both convey. Step outside to enjoy your private outdoor space and experience the lifestyle that makes Tallywood so special. This pet-friendly community offers wonderful amenities including a heated screened-in pool, shuffleboard courts, a dog park, and a welcoming community center where neighbors gather for social activities and events. Beautifully maintained grounds and a peaceful atmosphere create the perfect setting for active living. Conveniently located near shopping, dining, golf courses, medical facilities, and Sarasota’s world-famous Gulf Coast beaches, this villa is ideal as a seasonal retreat or full-time residence. Enjoy low-maintenance living in one of Sarasota’s most established and friendly 55+ communities.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Jenifer Funk (941-330-3373)
1937 GOLD AVE, SARASOTA, FL 34235
$374,900104 Days on yellowkey MLS ID: N6142964
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1723 Built: 1958 Tax: $3,079 (2025)Community: Kensington ParkSingle Family
Taxes:$3,079
Remarks: Under contract-accepting backup offers. ****BACK on MARKET. Buyer financing fell through**** Welcome to this charming 3-bedroom, 2-bath single-family home nestled in the established Kensington Park neighborhood of Sarasota. Offering over 1,700 square feet of living space, this home features a flexible and inviting layout with spacious living areas and a versatile bonus room—perfect for a home office, family room, or playroom. Situated on a generous lot, the property provides ample outdoor space and additional parking, including room for a boat, RV, or work trailer. The open floor plan is ideal for entertaining, while the split-bedroom design offers privacy and comfort. Newer roof, vaulted ceilings, solid wood cabinets, new stainless-steel appliances, and hurricane shutters add peace of mind, making the home truly move-in ready while still allowing room to personalize. This spacious home features a large fenced-in backyard made for relaxing or entertaining and an enclosed lanai perfect for your morning coffee or evening unwind, rain or shine. Conveniently located near shopping, dining, golf, parks, and world-renowned beaches, this home offers easy access to everything Sarasota has to offer. A perfect match for anyone seeking comfortable, flexible Florida living. Schedule your tour today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Vicky Imbriaco (941-586-7448)
2700 COCONUT BAY LN #419, SARASOTA, FL 34237
$174,950359 Days on yellowkey MLS ID: S5127342
INCREASED by $20,000 (12.9%) on 05/25/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1974Monthly Fee: $299 Tax: $1,696 (2024)Community: Sarasota PalmsCondo
Taxes:$1,696
Remarks: Welcome to the luxurious gated community of Sarasota Palms! This beautifully updated first-floor condo is a perfect blend of comfort, convenience and elegance. As you enter the home, you will be greeted by the beautiful tray ceilings and the warmth of the solid wood cabinetry and granite countertops in the kitchen, with the same tasteful upgrades carrying on into the bathroom. This home also features updated laminate flooring in the bedroom, recently installed double paned hurricane windows and sliding doors, and a screened in porch for you to sit outside and enjoy your morning coffee. The clubhouse is a fantastic amenity for residents, featuring a fully equipped fitness center, sauna, upgraded theatre room, billiards room, and business center, complete with WiFi throughout the community. You'll also have access to the largest pool and fitness center of any association in Sarasota County. Bring your furry friend to the large fenced dog park or enjoy the playground and tennis courts. Host a barbecue in the grilling and picnic area or take a relaxing walk around the lake. This condo is conveniently located near the Ed Smith Stadium, the spring training home for the Baltimore Orioles. You'll also be just minutes away from downtown Sarasota and the nearby marina. For beach lovers, St. Armand's Circle and Lido Key are only 5 miles away, offering some of the most beautiful powder sand beaches in the world. Plus, the Sarasota/Bradenton International Airport is just a short 5-mile drive away. This condo is perfect for those who value comfort, convenience, and luxury living. Whether it’s a primary residence, second home, or an investment, don't miss out on the opportunity to make this yours! Seller financing and rent-to-own options are available. Seller financing available with 40% down payment, at a 6.9% interest rate with a 1 year balloon period on a 10 year amortization schedule. Other terms can be offered with 20% down.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Amber Koepke (512-630-8394)
3521 49TH ST, SARASOTA, FL 34235
$325,00068 Days on yellowkey MLS ID: A4687177
2 Days Off yellowkey (back on 5/25/2026)
REDUCED by $15,000 (4.4%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 945 Built: 1983 Tax: $1,501 (2025)Community: Not ApplicableSingle Family
Taxes:$1,501
Remarks: Under contract-accepting backup offers. Welcome to this charming Florida retreat, where comfort, efficiency, and effortless outdoor living come together beautifully. This well-maintained home features a bright, open-concept layout filled with natural light, creating a warm and inviting atmosphere from the moment you step inside. The spacious living area seamlessly connects to the kitchen, offering ample cabinetry and generous counter space perfect for both everyday living and entertaining. The home includes two comfortable bedrooms, highlighted by a private primary suite with an en-suite bath for added convenience and relaxation. Step outside to your own private oasis, complete with a screened-in lanai and sparkling pool ideal for unwinding or hosting guests year-round. The fenced backyard provides plenty of space for pets, play, or gardening, along with a convenient storage shed. Recent upgrades add even more value and peace of mind, including a new roof (2023) and impact-resistant storm windows (2018). Additional features include solar panels for enhanced energy efficiency, a one-car garage, and a quiet residential setting surrounded by mature trees while still being just minutes from shopping, dining, and Florida’s stunning Gulf Coast beaches.
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Abigail Lange (941-218-8543)
4316 CALLISTA LN, SARASOTA, FL 34243
$495,000177 Days on yellowkey MLS ID: A4674352
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1930 Built: 2005Monthly Fee: $243 Tax: $4,677 (2023)Community: Callista VillageVilla
Taxes:$4,677
Remarks: Experience modern living in this beautifully remodeled two-bedroom plus den home, perfectly situated in a prime location now available! The versatile den offers the perfect solution for a home office, guest room, or movie room. Nestled on a peaceful dead-end street for ultimate privacy and tranquility. Discover the ease of maintenance-free living allowing you to enjoy a relaxed lifestyle without the hassle of upkeep. Enjoy modern updates throughout, designed for comfort and style with natural light all throughout. Located in a highly desirable area near University Town Center that offers shopping, dining, and entertainment. Whether you're downsizing, retiring, or seeking a hassle-free lifestyle, this home is must-see. Don't miss this exceptional opportunity!
Listing Agent: Samantha Jennen (941-321-6095)
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