Location: Sarasota
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
5103 GREENCROFT RD, SARASOTA, FL 34235
$295,000649 Days on yellowkey MLS ID: N6134516
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1979Monthly Fee: $567 Tax: $3,642 (2023)Community: Vivienda At The MeadowsVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,642
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2023
Middle School: Booker Middle
Remarks: Resort-Style Living Maintenance-Free includes Tile Roof. One of Sarasota’s most desirable communities. This spacious 2 bedroom, 2 bath, car garage home offers multiple living areas, including a living room, open-concept kitchen/family/dining area, and tranquil greenbelt view from the lanai. Ideally positioned not direct-facing neighbors, this home boasts a generous front yard and privacy. Enjoy true ease of living—landscaping and TILE roof maintenance are covered by the HOA, with reserves in place for future care. Recent upgrades include HVAC (2021), Water Heater (2023), Washing Machine (2024), Refrigerator (2022), as well as a new kitchen faucet, range hood fan, and light (2024). The Meadows Country Club offers membership access to 54 holes of golf, 17 Har-Tru tennis courts, pickleball, a junior Olympic-size pool, fitness center, two restaurants, and over 200 annual events. Explore 14 miles of scenic walking, biking, and nature trails, all just minutes from downtown Sarasota, UTC Mall, and I75. Come home to comfort, community, and the carefree lifestyle you’ve been looking for. Resort-Style Living in The Meadows Golf & Country Club Welcome to The Vivienda, a maintenance-free enclave within The Meadows, one of Sarasota’s most desirable communities.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY (941-207-5055)
Listing Agent: Janet Linaburg (941-225-5289)
5551 BENTGRASS DR #11-117, SARASOTA, FL 34235
$299,00016 Days on yellowkey MLS ID: A4696165
REDUCED by $6,000 (2.0%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1395 Built: 2002Monthly Fee: $656 Tax: $3,109 (2025)Community: Las Palmas Of SarasotaSpa: NoCondo
Taxes:$3,109
Elementary School: Emma E. Booker Elementary
Tax Year: 2025
Remarks: Virtually Staged. Welcome to Las Palmas, a gated community where convenience meets resort-style living in one of Sarasota’s most desirable locations. Ideally situated just moments from Benderson Park, UTC Mall, I-75, and dining, with a short drive to world-famous Gulf beaches, downtown Sarasota, hospitals, and the airport. This beautifully updated second-floor end unit offers 3 bedrooms, 2 bathrooms, and an attached one-car garage. Additional windows fill the home with natural light, creating a bright and airy atmosphere. A private entrance and staircase lead to an inviting open-concept layout featuring a desirable split-bedroom floor plan, newly installed flooring, fresh interior paint, updated lighting, upgraded kitchen cabinetry, and elegant quartz countertops in both the kitchen and bathrooms. The screened lanai overlooks a tranquil nature preserve, providing exceptional privacy and peaceful views. A full-size laundry room and generous closet space add everyday convenience. Major updates include a new roof (2024), A/C (2020), and water heater (2022). Residents enjoy an impressive array of resort-style amenities, including two swimming pools, a hot tub, a fitness center, a clubhouse, tennis courts, a playground, a dog park, an outdoor grilling area, a car wash station, and more. Affordable on-site RV and boat storage is also available. Whether you're a first-time homebuyer, investor, or seasonal resident, this exceptional property offers the perfect blend of comfort, style, and location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Keiko Donnelly (941-544-4664)
3602 QUIET DR, SARASOTA, FL 34240
$599,90011 Days on yellowkey MLS ID: A4695639
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2168 Built: 2021Monthly Fee: $150 Tax: $5,963 (2025)Community: Hidden Crk Ph 2Spa: NoSingle Family
Taxes:$5,963
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Discover The Ultimate Florida Retreat In This Meticulously Maintained 2021 MI Homes Masterpiece. Perfectly Positioned Directly Across From A Scenic Park And Playground, The Incredible Curb Appeal Is Just The Beginning. Step Inside To A Bright And Open Layout Designed For The Way You Truly Want To Live. Right Off The Entry, A Highly Desirable SPACIOUS FLEX ROOM Offers The Perfect Setup For A Home Office, Media Room, Or Formal Gathering Area. At The Heart Of The Home Is A Stunning CHEFS KITCHEN Featuring A Massive Center Island, 42-Inch Cabinetry, Upgraded Stainless Steel Appliances, And Generous Storage That Flows Seamlessly Into The Dining And Great Room. Tucked Away For Ultimate Privacy Is A Dedicated Bedroom Wing Boasting Three Generously Sized Bedrooms And A Full Bath To Easily Accommodate Family Or Guests, Perfectly Complementing The Spacious Primary Suite. Every Inch Feels Premium With Upgraded Baseboards, Modern Finishes, And Epoxy-Coated Garage Floors. Step Through The Sliders To Your Own Private Tropical Oasis Complete With A Screened Lanai And A BRAND NEW SALTWATER POOL. Entertain, Relax, And Soak Up The Sun In Your FULLY FENCED BACKYARD Kept Lush And Green Year-Round By Eco-Friendly Pond-Fed Irrigation. Location Is Absolutely Everything! Nestled Right Next To The Windward Community, This Property Features Direct GOLF CART ACCESS To The Incredible Dining, Entertainment, And Farmers Market At WATERSIDE PLACE. Zoned For The Highly Sought-After TATUM RIDGE SCHOOL DISTRICT And Incredibly Convenient To I-75 And Fruitville Road. You Are Just Minutes Away From Downtown Sarasota And World-Class Gulf Coast Beaches. Why Deal With Builder Delays When This Pristine Move-In Ready Pool Home Is Available Right Now?
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Anita Shanahan (630-212-1436)
2455 MIDNIGHT PEARL DR, SARASOTA, FL 34240
$385,00019 Days on yellowkey MLS ID: A4695883
REDUCED by $14,000 (3.5%) on 06/15/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1725 Built: 2021 Tax: $4,084 (2025)Community: Bay LandingTownhouse
Taxes:$4,084
Remarks: Stunning 3-Bedroom, 2 1/2 Bath Home in Bay Landing, Sarasota! Welcome to this beautifully maintained residence in the sought-after Bay Landing community. Boasting elegant curb appeal with lush landscaping and a grand entrance, this 1,725 sq ft home offers three spacious bedrooms and modern comforts throughout. Inside, you'll find crown molding on the first floor, granite countertops in the gourmet kitchen, and ceiling fans in every room. The open-concept living areas are bright and inviting, with new carpet upstairs and a smart-feature-ready setup for modern living. The primary suite is a true retreat, while the epoxy-coated lanai provides the perfect spot to relax and enjoy sweeping views of the nature preserve right behind the home.Residents enjoy access to the community’s large heated pool and resort-style amenities. Ideally located near UTC, Mote Marine Laboratory, and major roadways, this move-in ready gem delivers the ultimate Florida lifestyle. Don’t miss your opportunity to call this beauty home!
Listing is courtesy of: MITCHELL REAL ESTATE (941-400-2662)
Listing Agent: Michael Mitchell, Llc (941-400-2662)
3720 ALLENWOOD ST, SARASOTA, FL 34232
$499,90074 Days on yellowkey MLS ID: A4689606
REDUCED by $20,000 (3.8%) on 05/18/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1683 Built: 1971 Tax: $2,836 (2025)Community: Glen Oaks Cntry Club EstatesSpa: YesSingle Family
Taxes:$2,836
Elementary School: Tuttle Elementary
Remarks: Welcome to this beautifully maintained Zen-inspired pool home in the sought after Glen Oaks Country Club Estates community of Sarasota. Situated on a spacious.22-acre lot, this move-in ready residence offers 2,115 square feet of thoughtfully designed living space, featuring two bedrooms, two bathrooms, a Florida room and a two-car garage. Step inside to discover new luxury vinyl flooring throughout, designer finishes, crown molding, and a stunning shiplap accent wall. The flexible floor plan provides comfortable everyday living while offering additional space for a home office, study, or hobby space. A separate dining room creates the perfect setting for entertainment family and friends. The kitchen features granite countertops and flows seamlessly into the main living areas, making it both functional and inviting. The spacious primary suite includes a walk-in closet, a large window overlooking the pool, beautifully updated finishes and a walk and shower. Thoughtfully positioned away from the guest bedroom, the suite provides added privacy and a peaceful retreat. Outside your private retreat awaits. The sparkling south-facing pool and expansive screened lanai creates a peaceful setting for year-round enjoyment. The fully fenced back yard includes a secure dog run and xeriscape landscaping for low maintenance living. Major updates provide peace of mind including a new roof, HVAC system, water heater in 2023, new plumbing lines completed in 2026, and a newly installed hurricane-rated front entry door. The property is not located in a flood zone and includes hurricane shutters including clear plan panels that allow natural light to filter into the home while providing added storm protection. Best of all, the HOA is voluntary. The location is hard to beat just a golf cart drive away from Bobby Jones Golf Course, approximately 3 miles from vibrant downtown Sarasota and a short drive to the area's renowned Gulf beaches, dining, shopping, and cultural attractions. University Town Center (UTC) with its exceptional shopping, restaurants, and entertainment is only 6 miles away. Lovingly maintained and thoughtfully updated this special home combines timeless character and modern conveniences in one of Sarasota's most desirable locations. Move in ready and full of warmth it offers a wonderful opportunity to relax, entertain, and enjoy the Florida lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lori Carey, Llc (941-780-3427)
2054 RACIMO DR, SARASOTA, FL 34240
$719,999205 Days on yellowkey MLS ID: A4670940
REDUCED by $29,001 (3.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1739 Built: 1982 Tax: $4,715 (2024)Community: Racimo RanchesSpa: NoSingle Family
Taxes:$4,715
Tax Year: 2024
Remarks: One acre, corner lot! Welcome to the highly sought-after location of Racimo Ranches community, where you’ll enjoy the perfect blend of country charm and modern convenience with NO HOA and NO DEED RESTRICTIONS. Situated on an open one-acre corner lot with multiple access points, this beautifully remodeled 3-bedroom, 2-bath home features a FRESHLY PAINTED exterior, mature landscaping, and excellent curb appeal. Inside, the bright and spacious living room features luxury vinyl plank flooring throughout. At the same time, the UPDATED KITCHEN boasts shaker-style cabinetry, quartz countertops, a subway tile backsplash, LED lighting, stainless steel appliances, and a cozy dining area. Just off the dining space is a versatile bonus flex room ideal for a home office, den, or playroom that overlooks the backyard. Step outside to enjoy Florida living on the back deck with plenty of room for seating and grilling, perfect for entertaining. The desirable split-bedroom floor plan provides a spacious primary suite with an en suite bath featuring a walk-in shower and a large closet, while two additional bedrooms share a bright second bathroom with a relaxing jacuzzi tub. Additional highlights include a two-car garage, a detached shed, and plenty of room to BUILD IN-LAW SUITE, park your boat or motorhome, and enjoy the FREEDOM of acreage living. Conveniently located, you can ride your golf cart to restaurants and Publix, and you’re less than 3 miles from I-75 and only 6 miles from University Town Center. This move-in-ready home offers exceptional UPGRADES and peace of mind, including a BRAND NEW ROOF (2025), A/C replacement (2022), water softener system (2022), iron and sulfur blocker (2022), well pump (2024), lift station replacement (2022), drain field replacement (2022), a FULL INTERIOR RENOVATION in 2022 with added flex room, stainless steel appliances (2022), water heater (2022), and washer and dryer (2024). If you're interested in living in freedom, give us a call today to chat further!
Listing Agent: Janette Schafer (954-298-7791)
1218 GRANTHAM DR, SARASOTA, FL 34234
$339,000216 Days on yellowkey MLS ID: A4672728
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2143 Built: 2019Monthly Fee: $299 Tax: $3,038 (2024)Community: Bradford Manor TwnhmsTownhouse
Taxes:$3,038
Remarks: This beautifully maintained townhome sits within a secure gated community and offers 3 bedrooms, 2.5 baths, over 2,143 sq. ft., and a spacious screened patio. A covered entry leads into an open-concept layout with a welcoming foyer and ceramic tile flowing through the main living areas. The kitchen features granite countertops, espresso cabinetry, stainless steel appliances, a glass cooktop, pantry, and a large snack bar perfect for casual dining. The dining area accommodates larger gatherings and opens directly to the screened patio, while the living room offers soft carpet, recessed lighting, and plenty of natural light. The covered patio is ideal for morning coffee or evening relaxation, complete with lighting, ceiling fan, and ample seating space. A convenient half bath completes the main floor. Upstairs, the primary suite offers plenty of room for larger furniture, a walk-in closet, and an ensuite bath with dual sinks and a glass-enclosed shower. The second level also includes a full-size laundry area, a guest bedroom with private ensuite and double-sink vanity, a third bedroom, and a versatile bonus room perfect for an office, media space, or playroom. Enjoy resort-style amenities including a community pool, spa, and clubhouse. Located in a quiet neighborhood just minutes from St. Armand's Circle, Sarasota’s world-famous beaches, and less than 10 minutes to Sarasota/Bradenton International Airport—this home blends comfort, convenience, and Florida living at its best.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lee Brewer (941-724-3448)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$285,00029 Days on yellowkey MLS ID: TB8511154
REDUCED by $14,000 (4.7%) on 06/15/2026
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)
1005 GREYSTONE LN, SARASOTA, FL 34232
$548,0007 Days on yellowkey MLS ID: A4697312
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1834 Built: 1988Monthly Fee: $75 Tax: $2,361 (2025)Community: GreystoneSingle Family
Taxes:$2,361
Remarks: 1005 Greystone Lane in Sarasota, A completely remodeled pool home that perfectly combines modern updates with timeless architectural character. Featuring a new roof installed in 2025 and newer A/C with warranty, this move-in-ready residence offers both style and peace of mind. As you enter the home, you're greeted by soaring 13-foot ceilings in the main living area, creating an impressive sense of space and openness. The thoughtfully designed open-concept floor plan is ideal for entertaining, seamlessly connecting the living, dining, and kitchen areas. One of the home's most distinctive features is the abundance of natural light streaming through the beautiful half-dome transom windows above, adding warmth, charm, and character that many newer homes simply don't offer. These architectural details create a bright and inviting atmosphere throughout the home. The spacious primary suite serves as a private retreat, featuring French doors that open directly to the pool patio, allowing for seamless indoor-outdoor living. The home's convenient pool bath provides easy access from the outdoor entertaining area, making pool days and gatherings effortless for family and guests alike. Step outside to your own backyard oasis with a sparkling swimming pool and covered patio space, perfect for relaxing, entertaining, and enjoying Sarasota's year-round sunshine. Located within a quaint and well-maintained community of just 21 homes, residents enjoy the benefits of a small neighborhood atmosphere along with low HOA fees. Ideally situated near I-75, University Town Center (UTC), Nathan Benderson Park, Mote SEA Aquarium, premier shopping and dining, playgrounds, golf courses, baseball fields, soccer fields, and numerous recreational amenities. Sarasota's renowned Gulf Coast beaches, including Siesta Key Beach, are only a short drive away. This beautifully remodeled home offers the rare combination of modern upgrades, architectural character, resort-style outdoor living, and an exceptional Sarasota location.
Listing is courtesy of: THE SHORELINE FL REALTY LLC (941-544-1133)
Listing Agent: Eleanor Pojer (941-441-8210)
2387 MIDNIGHT PEARL DR, SARASOTA, FL 34240
$374,50019 Days on yellowkey MLS ID: A4695912
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1725 Built: 2019Monthly Fee: $180 Tax: $4,058 (2025)Community: Bay LandingTownhouse
Taxes:$4,058
Remarks: Welcome to Bay Landing, a beautifully maintained community in Sarasota, where comfort, convenience, and carefree living come together. Built in 2019, this spacious 3 bedroom, 2.5 bath townhome offers modern finishes and a peaceful setting overlooking a serene preserve. Step inside to discover an inviting floor plan featuring ceramic tile flooring throughout the foyer, kitchen, and bathrooms. The well appointed kitchen showcases granite countertops, crown molding cabinetry, stainless steel appliances, an electric range, over the range microwave, built in dishwasher, side-by-side refrigerator, and garbage disposal. The open living and dining areas flow seamlessly to the screened lanai, where you can relax and enjoy tranquil preserve views and Florida’s beautiful weather year round. The spacious primary suite serves as a private retreat, complete with a large walk in closet, an extra storage closet, and an en-suite bathroom. Two additional bedrooms provide comfortable accommodations for family, guests, or a home office. All bathrooms are thoughtfully appointed with granite countertops and raised vanities. Additional highlights include storm-rated windows and sliding glass doors, hurricane shutters with dedicated storage space in the garage, and an in home washer and dryer. The one car garage features durable epoxy flooring, while the extended two car driveway provides ample parking convenience. Enjoy maintenance-free living with lawn care included, allowing you more time to take advantage of community’s exceptional amenities, including a clubhouse, fitness center, resort style pool, dog park, and tot lot. Ideally located just minutes away from fine dining, entertainment, shopping, and the stunning Gulf Coast beaches. This move in ready home offers the perfect blend of modern living and an unbeatable Sarasota lifestyle. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jenn Augustin (941-473-6286)
128 GOLDEN GATE PT #202A, SARASOTA, FL 34236
$1,995,00055 Days on yellowkey MLS ID: A4691688
REDUCED by $180,000 (8.3%) on 06/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3317 Built: 2004 Tax: $22,705 (2025)Community: Vista Bay PointSpa: YesCondo
Taxes:$22,705
Elementary School: Southside Elementary
Remarks: Experience elevated coastal luxury at Vista Bay Point, ideally on prestigious Golden Gate Point in the heart of downtown Sarasota. This exceptional, one-of-a-kind second-floor residence delivers a rare combination of privacy, sophistication and effortless access, with a private elevator opening directly into your own foyer and an oversized two-car garage with additional storage on the level below, along with a private staircase that connects directly to the residence. In addition to all this, there is direct access to a private wraparound terrace, the only residence in the building with an outdoor area of this size, and up to two dogs are welcome, allowing them plenty of room to roam. From the moment you enter, the home is bathed in natural light, with expansive impact glass windows throughout framing serene bay views, shimmering city lights and Sarasota’s iconic sunsets. The open, flowing design is elegant and inviting, enhanced by refined finishes and custom details that create a sense of arrival, while a Sonos sound system and Crestron lighting system add to the thoughtful touches that make this home exceptional. Taking center stage, the gourmet kitchen is designed to impress, featuring custom cabinetry, rich stone surfaces, a generous island with seating for up to six, and premium appliances including Sub-Zero refrigeration and a professional Thermador 48-inch gas range with grill, griddle and dual ovens, all seamlessly connected to the dining and living spaces to create an effortless indoor outdoor lifestyle. The terrace provides a setting for morning coffee, evening cocktails or dining, offering multiple seating areas along with beautiful bay views. The owner’s suite offers a peaceful retreat with a spacious walk-in closet and a beautifully appointed bath designed for relaxation, while two separate guest suites with full baths ensure comfort and privacy for visiting family and friends. Vista Bay Point is an exclusive, gated boutique community offering a full suite of luxury amenities, including a heated pool and spa, sundeck with grilling area, fitness center with premium equipment, theater room, elegant owners lounge with pool table and bar, and a private guest suite for extended stays. This residence places you just moments from Sarasota’s vibrant downtown, the marina, world-class dining, Ringling Bridge, cultural attractions, St. Armands Circle and the region’s award-winning beaches, making this more than a residence, it is a lifestyle defined by privacy, prestige and the best of Sarasota waterfront living. Ask for the complete property catalog with all the information about this residence.
Listing Agent: Thomas Netzel (941-539-0633)
5515 DOWNHAM MDWS, SARASOTA, FL 34235
$675,000119 Days on yellowkey MLS ID: A4681324
REDUCED by $24,000 (3.4%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2640 Built: 1992Monthly Fee: $193 Tax: $4,691 (2025)Community: Devonshire PlaceSpa: YesSingle Family
Taxes:$4,691
Remarks: Curb appeal begins at the street with beautifully selected driveway pavers that create an inviting approach and set the stage for what awaits inside. Step through the double-door entry and you are immediately drawn to sweeping views—across the expansive lanai and solar-heated pool and spa, over the tranquil lake that winds through The Meadows, and onward to the lush fairways of the golf course. * * * Offering 3 bedrooms, 2.5 baths, and 2,640 square feet under air, this thoughtfully designed residence provides a comfortable and highly functional layout ideal for both everyday living and entertaining. The primary suite is privately situated apart from the secondary bedrooms, creating a peaceful retreat, while the guest bedrooms at the opposite end of the home offer flexibility and privacy for family or visitors. * * * Multiple living spaces enhance the home’s versatility, including formal living and dining rooms, as well as a spacious great-room style family room that includes a casual dining area just off the kitchen. A striking coral stone fireplace serves as a beautiful focal point in the family room, adding warmth, character, and architectural interest to the space. * * * The kitchen is light and bright, featuring white cabinetry and light gray countertops that create a fresh, timeless feel. Abundant, well-designed cabinetry surrounds the cook, offering exceptional storage and an efficient layout that makes meal preparation both comfortable and convenient. * * * Outdoor living is equally impressive. The large screened lanai, solar-heated pool, and spa provide the perfect backdrop for relaxing afternoons, evening swims, or entertaining friends while taking in picturesque water and golf course views. The seamless indoor-outdoor flow embodies the very best of the Florida lifestyle. * * * Residents of The Meadows enjoy one of Sarasota’s most established and amenity-rich communities, known for its scenic lakes, miles of walking and biking trails, golf and social opportunities, and convenient proximity to University Town Center, I-75, downtown Sarasota, and renowned Gulf Coast beaches. * * * A home that combines generous living spaces, exceptional views, and an outstanding location—an opportunity not to be missed.
Listing Agent: Marilyn Kneafsey (941-373-0999)
7740 CASTLEISLAND DR, SARASOTA, FL 34240
$570,00053 Days on yellowkey MLS ID: A4691962
REDUCED by $15,000 (2.6%) on 06/01/2026
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)
462 OAK HILL CIR #5, SARASOTA, FL 34232
$234,900286 Days on yellowkey MLS ID: A4664046
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1254 Built: 1985Monthly Fee: $520 Tax: $1,196 (2024)Community: Village Oaks Sec DVilla
Taxes:$1,196
Remarks: Welcome to 462 Oak Hill Cir! This 2-bedroom, 2-bath home with a spacious two-car garage offers comfort, function, and the chance to put your personal touch on a well-located property in Sarasota. The home features an open layout, abundant natural light, and a split-bedroom design that balances privacy and convenience. Step outside and enjoy the community’s tranquil setting, while being just minutes from University Town Center shopping, Benderson Park, golf courses, and the cultural attractions of downtown Sarasota. World-famous Siesta Key and Lido beaches are also a short drive away, making this an ideal home base for enjoying all the area has available. Curious? Don’t wait to see this home in person—it’s a property that needs to be experienced, not just viewed online. No sight-unseen offers will be entertained. Schedule your private showing today and explore the possibilities!
Listing is courtesy of: KONA REALTY (941-718-8293)
Listing Agent: Dan Ivanov (941-544-0475)
1350 5TH ST #402, SARASOTA, FL 34236
$695,00035 Days on yellowkey MLS ID: A4691938
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 784 Built: 2019Monthly Fee: $724 Tax: $5,936 (2025)Community: Risdon On 5ThSpa: NoCondo
Taxes:$5,936
Elementary School: Alta Vista Elementary
Remarks: Stunning one bedroom penthouse in the heart of the Rosemary District, one of downtown Sarasota’s most vibrant and sought after neighborhoods, featuring an exclusive private garage, an exceptionally rare offering in luxury condo living. Positioned on a private penthouse level with only four residences, this sophisticated urban retreat combines privacy, security, contemporary design, and unmatched walkability. Filled with natural light, the residence features soaring ceilings, impact rated windows and doors, electric blinds, and refined modern finishes throughout. The open concept layout is complemented by a beautifully appointed kitchen with a premium appliance package, sleek cabinetry, and an oversized single cell sink designed for both style and functionality. Designed by Halflants + Pichette Studio for Modern Architecture, Risdon on 5th showcases striking contemporary architecture and an elevated downtown Sarasota lifestyle. Step outside your door to enjoy the rooftop pool and observation lounges, offering resort style amenities and an elevated atmosphere perfect for relaxing or entertaining. The gated community provides peace of mind while placing you in the center of downtown Sarasota’s thriving arts and entertainment scene. Residents enjoy unbeatable walkability to the Sarasota Opera House, theaters, acclaimed dining, rooftop bars, art galleries, boutique shopping, coffee shops, nightlife, and waterfront attractions. The private one car garage is a true rarity for downtown Sarasota penthouse living, adding convenience and long term value rarely found in the Rosemary District. Ideal as a full time residence, seasonal retreat, or investment opportunity, this exceptional penthouse offers the perfect lock and leave lifestyle in one of Sarasota’s most desirable urban locations.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Joseph Mcdonald, Llc (941-375-9646)
1216 34TH ST, SARASOTA, FL 34234
$375,00018 Days on yellowkey MLS ID: A4695350
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 2004 Tax: $3,840 (2026)Community: North Riverside ParkSingle Family
Taxes:$3,840
Elementary School: Bay Haven Sch of Basics Plus Elementary
Tax Year: 2026
Remarks: Looking for a fantastic investment opportunity, or your new family home, look no further. This stunning three bedroom, two bath ranch-style home nestled in the Bayou Oaks community offers an open floor plan with high ceilings, and updated flooring. The ranch-style front porch could be great for outdoor entertaining and relaxation. The large beautiful fenced back yard is an open canvas allowing space to add a grill, outdoor furniture, patio deck, and or a pool. This Sarasota property is in a prime location, making it the perfect choice for savvy investors, or future first time home owners. If you're looking to add a valuable asset to your portfolio this home is sure to attract top-notch tenants and generate impressive rental income. Conveniently located around the corner from a community park, and a community garden. Also located minutes from several parks, shopping, dining, boat ramp and Longboat Key Beach. Don't miss out on this incredible opportunity to own a piece of prime Sarasota real estate. Contact me today if you have any questions, or would like to schedule a tour today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Crystyn Cramer (941-284-4961)
1065 LEWIS AVE, SARASOTA, FL 34237
$389,90024 Days on yellowkey MLS ID: A4695338
0 Days Off yellowkey (back on 6/20/2026)
REDUCED by $10,000 (2.5%) on 06/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1295 Built: 1996 Tax: $2,544 (2025)Community: FairwaySpa: NoSingle Family
Taxes:$2,544
Remarks: Under contract-accepting backup offers. NO HOA • NO FLOOD ZONE • BLOCK CONSTRUCTION • NEW ROOF 2022 • OVERSIZED 2-CAR GARAGE Welcome to this beautifully maintained 3-bedroom, 2-bath home ideally located in the heart of Sarasota. Built with durable block construction and featuring a new roof installed in 2022, this property offers peace of mind, flexibility, and exceptional value. Inside, you'll find a bright open floor plan filled with natural light, updated finishes, and a spacious kitchen featuring granite countertops, stainless steel appliances, and modern cabinetry—perfect for both everyday living and entertaining. Step outside to enjoy the large screened lanai overlooking a fully fenced backyard complete with a storage shed, offering plenty of space for pets, gardening, outdoor gatherings, or simply relaxing in your own private retreat. One of this home's biggest advantages is its unbeatable location. Just minutes from Downtown Sarasota, Payne Park, Sarasota Memorial Hospital, Ed Smith Stadium, shopping, dining, and Sarasota's world-famous beaches, you'll enjoy easy access to everything that makes Sarasota one of Florida's most desirable places to live.Whether you're a first-time homebuyer, looking to downsize, or searching for a solid investment opportunity, this home offers the perfect combination of location, comfort, and everyday convenience. Schedule your private showing today.
Listing is courtesy of: PARADISUS REALTY GROUP CO (941-281-4973)
Listing Agent: Andres Salgado (941-875-2949)
4870 TIVOLI CT, SARASOTA, FL 34235
$424,900118 Days on yellowkey MLS ID: A4675116
REDUCED by $25,000 (5.6%) on 04/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2147 Built: 1988Monthly Fee: $919 Tax: $3,866 (2025)Community: Longwood Villas Unit 3Villa
Taxes:$3,866
Remarks: NEW ROOF (2026), Awesome lake views! You will not find a better lake view out there, and it is a real lake! Well-maintained 3-bedroom, 2-bath home offering 2,147 square feet under air with a 2-car garage. Major updates include a new tile roof (2026), new A/C (2024), new electric panel (2020), and includes an auxiliary generator (2020) with included propane tanks. Most windows have been upgraded to impact glass (excluding sliders and kitchen window) (2018). The kitchen features granite counters, custom cabinets and stainless-steel appliances. Both bathroom showers have ceramic tile all the way up to the ceiling. As already stated, the home offers one of the best lake views, visible from the owner's suite, main living areas and large screened lanai. A spacious, private side courtyard provides additional outdoor living space, ideal for entertaining and relaxing. Basically, you have outside living along the back and entire side of the home. No CDD"s. HOA handles roof replacement and repairs; outside painting; pressure washing; irrigation and pump; driveway and walkway repairs; and mowing, trimming and edging. Also, because the HOA handles the roof and exterior, the homeowner's insurance is lower than it would be on a single family home. Even though this home is called a villa, it is like a single family home because there are no shared living walls. Kayaking and canoeing are allowed on the lake, for leisure, fishing or wildlife watching. Conveniently located near UTC Mall, Downtown Sarasota, Mote Marine, Whole Foods, Fresh Market, tons of restaurants, shopping and a short drive to the best beaches around.
Listing is courtesy of: HOOVER REALTY LLC (941-266-5623)
Listing Agent: Garin Hoover (941-266-5623)
5526 CHANTECLAIRE #31, SARASOTA, FL 34235
$449,90047 Days on yellowkey MLS ID: A4689277
REDUCED by $10,100 (2.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985Monthly Fee: $617 Tax: $2,477 (2025)Community: ChanteclaireVilla
Taxes:$2,477
Remarks: Virtually Staged. Welcome to this beautifully reimagined villa in the highly sought-after Meadows community, where timeless design meets modern sophistication. This fully renovated residence offers 2 bedrooms with a flexible third space that can serve as a private den, office, or easily function as a third bedroom tailored to fit your lifestyle. Every detail has been thoughtfully curated, showcasing a light, bright interior with an elegant, airy aesthetic. As reflected in the virtual staging, the open-concept design is complemented by clean lines, upscale finishes, and a seamless flow between living spaces perfect for both relaxed everyday living and effortless entertaining. Natural light fills the home, enhancing the soft, neutral palette and creating a warm yet refined ambiance throughout. Ideally located in The Meadows, known for its lush landscapes, walking trails, and proximity to dining, shopping, and Sarasota’s finest amenities, this residence offers the perfect balance of tranquility and convenience. Unlock exceptional living in one of Sarasota’s most desirable communities.
Listing is courtesy of: LUXEKEY REAL ESTATE LLC (941-404-3173)
Listing Agent: Robin Eekhof (941-504-1941)
5737 FORESTER LAKE DR, SARASOTA, FL 34243
$525,00022 Days on yellowkey MLS ID: A4695165
1 Days Off yellowkey (back on 6/20/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1990 Built: 1988Monthly Fee: $67 Tax: $4,933 (2025)Community: Cedar CreekSpa: NoSingle Family
Taxes:$4,933
Remarks: Under contract-accepting backup offers. Welcome to Cedar Creek, one of Sarasota's most sought-after communities, where tree-lined streets, mature landscaping, and an unbeatable location create the perfect place to call home. This beautifully maintained 4-bedroom, 2-bath pool home combines modern updates with comfortable Florida living. Step inside to discover an open-concept floor plan filled with natural light, soaring ceilings, fresh interior paint, and stylish plank tile flooring throughout the home. At the heart of the home, the fully renovated kitchen shines with elegant quartz countertops, crisp white cabinetry, and an inviting layout that seamlessly connects to the living and dining spaces—ideal for everyday living and entertaining alike. Designed with privacy in mind, the split-bedroom floor plan offers a peaceful retreat for owners and guests. The spacious primary suite features direct access to the lanai, a generous walk-in closet, and an ensuite bath with a large walk-in shower. Multiple sliding glass doors from the family room, dining room, and primary suite open to the expansive screened lanai, creating a true indoor-outdoor lifestyle. Relax under the covered seating area, take a refreshing swim in the sparkling pool, or enjoy the privacy provided by lush tropical landscaping that surrounds the outdoor living space. This home has been lovingly maintained and thoughtfully updated, including a newer roof (2021), A/C (2018), newer pool pump (2026), and recently replaced lanai screens, offering peace of mind for years to come. Residents of Cedar Creek enjoy low HOA fees, no CDD fees, and a prime location just minutes from UTC shopping and dining, Nathan Benderson Park, Lakewood Ranch, Sarasota-Bradenton International Airport, world-class golf courses, downtown Sarasota, vibrant arts and entertainment venues, and the area's renowned Gulf Coast beaches. Move-in ready and perfectly positioned in the heart of Sarasota, this exceptional pool home offers the lifestyle you've been searching for. Schedule your private showing today!
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Daria Chmyl (941-900-4344)
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