Location: Sarasota
Do Not Show Listings
5766 FORESTER PINE CT, SARASOTA, FL 34243
$399,900143 Days on yellowkey MLS ID: A4673990
REDUCED by $75,000 (15.8%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1866 Built: 1990Monthly Fee: $12 Tax: $4,072 (2024)Community: Cedar CreekSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,072
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Short Sale. PRICE ADJUSTMENT! Don’t miss out on this MOVE IN READY home in the highly desirable Cedar Creek subdivision—where comfort, style, and convenience meet. Every detail has been lovingly attended to, creating a move-in-ready sanctuary with modern upgrades throughout. As you enter, you’ll immediately notice the beautifully refreshed furnishings most of which are negotiable for a seamless move-in experience. Major system upgrades offer peace of mind, including newer electrical outlets (2016), fully cleaned and serviced ductwork, air handler, and exterior AC unit (2017), AC motor replacement and full service (2018), capacitor replacement during 2023 maintenance, a new water heater (2021), and a 30-year roof installed in 2010. All upstairs carpets were replaced in 2024. The spacious living room features laminate flooring and updated curtains and rods, creating a warm and inviting atmosphere. The kitchen and dining areas have been tastefully remodeled with shiplap accents, open shelving, an island, a custom oven hood, and updated lighting. Built-in window seats provide both dining space and convenient extra storage. The downstairs bathroom was refreshed in August 2023 with new paint, updated lighting, and a new faucet. The AIR CONDITIONED garage was treated to textured walls and fresh paint in August 2023, and the garage door was also serviced in 2023. Upstairs, the primary suite offers a peaceful retreat with fresh paint and a new ceiling fan. The primary bathroom was fully gutted and completely remodeled in August 2023, featuring new tile, flooring, fixtures, and a fully updated shower. The guest bathroom received the same level of attention with a new tub, tile, fixtures, toilet, flooring, and paint. Its one-of-a-kind vanity—sourced from a boathouse near the Ringling Museum and beautifully refurbished—adds a unique nautical charm. The third bedroom, features fresh paint and a newer ceiling fan. The additional guest room offers comfort for visitors. The stairs, hallway, and all doors have been freshly painted, tying the entire upstairs together with a polished finish. The home’s exterior is just as impressive, featuring a welcoming fountain, updated front door hardware, Ring security cameras, full pressure washing, fresh landscaping, trimmed trees, updated lighting, and soffit and trim repairs—creating exceptional curb appeal. Living in Cedar Creek means enjoying one of Sarasota’s most convenient and centrally located communities. You’re just minutes from University Town Center that includes world-class dining, shopping, and the vibrant arts scene of downtown Sarasota, while the tranquil Gulf beaches are only a short drive away—perfect for weekend relaxation and waterfront adventures. Don’t miss this opportunity to own a beautifully updated, truly turn-key home in Cedar Creek. Schedule your private showing today and experience for yourself the comfort, beauty, and care this exceptional property offers.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Jenna Genovese (860-575-0088)
132 TALL TREES CT, SARASOTA, FL 34232
$530,00016 Days on yellowkey MLS ID: A4689367
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1865 Built: 2001Monthly Fee: $199 Tax: $3,522 (2025)Community: Oak Court Ph 2-A & 2-BSpa: YesSingle Family
Taxes:$3,522
Elementary School: Fruitville Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Located in Oak Court, a gated community of approximately 60+ homes just off Fruitville Road, this updated, west-facing, single-story residence offers convenient access to downtown Sarasota, University Town Center (UTC), Gulf beaches, golf courses, parks, and I-75. Set on a private dead-end street with mature canopy trees and landscaped surroundings. Extensive upgrades include roof (2021), AC (2025), and water heater (2026). Interior features professionally curated paint selections and 24-inch tile flooring (2025) in select areas including two bedrooms and foyer. The layout offers a flexible front room off the entry, ideal for dining, sitting, or office use. The home then opens into the main living area with vaulted ceilings and an open connection to the kitchen. A separate dining area is positioned just off the kitchen, creating a natural flow for everyday living and entertaining. The living space provides direct access to the screened lanai and hot tub, which conveys with the sale. Kitchen features a Samsung appliance suite (2025), soft-close cabinetry, pull-out drawers, island workspace, and adjacent dining area. Bathrooms updated with Calcutta wall tile and energy-efficient commodes (2025). Primary suite includes dual sinks, walk-in shower, and walk-in closet. Secondary bedrooms offer built-in storage and custom paint finishes. Smart home features include Eufy video doorbell and upgraded digital AC thermostat. Additional interior improvements include plantation shutters, vertical blinds, updated lighting fixtures, and ceiling fans. Garage includes epoxy-coated floor (Galaxy Blue, 2025), custom overhead storage, and fresh interior paint. Exterior upgrades include backyard privacy landscaping with Areca palms (2025) and redesigned irrigation system. Community amenities include pool, cabana, lake with fountain, and irrigation.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Antonio Lopez (626-664-5124)
8008 MIDNIGHT PASS RD, SARASOTA, FL 34242
$3,750,000156 Days on yellowkey MLS ID: A4672889
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4190 Built: 2015 Tax: $25,117 (2024)Community: Mira Mar SubSpa: YesSingle Family
Taxes:$25,117
Remarks: Welcome to the side of Siesta Key most visitors never discover — and many locals refuse to leave. Located on the peaceful southern stretch of Midnight Pass Road, 8008 Midnight Pass sits far enough from the congestion of the Village and Beach Road traffic, yet only minutes from Crescent Beach and waterfront dining. Here, mornings start with bike rides under a canopy of palms, neighbors walk dogs along quiet streets, and evenings end with sunsets reflecting across Heron Lagoon. This is the residential, laid-back Siesta Key lifestyle buyers search for but rarely find available. Behind a newly installed private gate, fresh coastal landscaping and a new perimeter wall create a true sense of arrival and privacy. The 2015-built waterfront home has been extensively improved, offering the feel of a newer construction property without the wait, cost, or uncertainty of building on the island. Inside, the home has been refreshed with new flooring throughout, fresh interior paint, updated stair railings, and designer lighting. A full Sonos surround sound system, Brilliant smart switches, Philips Hue lighting, and an upgraded security system provide modern convenience, while spray-foam attic insulation improves comfort and efficiency year-round. The completely reimagined kitchen serves as the centerpiece of the home, featuring Viking appliances, quartzite countertops and backsplash, custom cabinetry with under-cabinet lighting, a custom hood, dedicated bar area, and Viking ice maker. The open living space flows directly to expansive sliders overlooking the calm waters of Heron Lagoon — a view that immediately explains why owners love this side of the island. A flexible den with a custom Murphy bed provides additional guest accommodations, and upstairs guest bedrooms have been enhanced with wainscoting and designer wallpaper. One guest bathroom has been fully remodeled and all bathrooms have been updated with new fixtures and lighting. Outdoor living is where the property truly shines. The lagoon-front setting offers a kayak and paddleboard launch from your backyard, an IPE dock for fishing or sunset watching, and a revitalized pool area with new equipment and LED lighting. A newly screened upper balcony lanai creates a peaceful retreat above the water, while the private basketball court adds a rare amenity not commonly found on Siesta Key. This is a home designed for those who want Siesta Key without the crowds — boating, biking, paddleboarding, and quiet evenings just minutes from the beach. 8008 Midnight Pass is not just a waterfront property; it’s an opportunity to experience the calmer, residential side of island living while still being close to everything that makes Siesta Key world-famous. Schedule your private showing and experience the difference in person.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeff Lauer (941-441-6555)
6564 SILVERSTAR DR, SARASOTA, FL 34240
$405,000103 Days on yellowkey MLS ID: A4677768
0 Days Off yellowkey (back on 4/13/2026)
REDUCED by $20,000 (4.7%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1256 Built: 2024Monthly Fee: $199 Tax: $5,150 (2025)Community: Avanti/WatersideSingle Family
Taxes:$5,150
Remarks: One or more photo(s) has been virtually staged. Experience stylish lakeside living in this 2024 built, 3-bedroom, 2-bath lakefront cottage located in the highly desirable Avanti at Waterside, Lakewood Ranch. This light and airy home combines the best of contemporary design, energy efficiency and relaxed Florida Living. Enjoy lakeside living with an open-concept layout, with the living area flowing seamlessly to the 20' x 30' portrait view screened caged lanai overlooking the lake perfect for indoor-outdoor entertaining and taking in serene waterfront sunsets. This move-in-ready home combines the security of new construction with the high-end finishes and charm of thoughtful ownership. Additional seller upgrades include laminate flooring replacing all carpet, designer light fixtures with dimmers, plantation shutters, rain gutters, and a barn door in the primary ensuite. Constructed to high velocity hurricane zone standards, the home features Low-E impact-resistant widows, insulated doors and transferable builder warranties for true peace of mind. Ideally located within walking or biking distance to Waterside Place, residents enjoy convenient access to shopping, dining, and a highly regarded weekly Farmer’s Market. Waterside also offers a play area and interactive water park, along with community favorites such as Ranch Nites on Wednesdays, featuring food trucks, live music, lawn games, and cornhole tournaments. This well-proportioned home delivers the perfect balance of waterfront serenity and an active, social lifestyle in the heart of Lakewood Ranch. Conveniently located to I-75, premier dining and shopping, top-rated schools, and cultural amenities. Award-winning beaches and international airports are a short drive away, making travel and leisure a breeze.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (941-706-2142)
Listing Agent: Georgia Sotiriou (301-346-6227)
476 MEADOW LARK DR, SARASOTA, FL 34236
$4,495,00014 Days on yellowkey MLS ID: A4689563
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3336 Built: 1985Monthly Fee: $110 Tax: $41,567 (2025)Community: Bird Key SubSpa: NoSingle Family
Taxes:$41,567
Remarks: A Key West-inspired waterfront retreat in prestigious Bird Key, this residence blends timeless coastal design with extensive updates and exceptional indoor-outdoor living. Set along 101 feet of canal frontage with direct access to Sarasota Bay, the property offers a rare opportunity to enjoy a boating lifestyle in one of the area’s most sought-after neighborhoods. Manicured landscaping and inviting front porches introduce the home’s architectural charm, while inside, nearly 3,400 square feet of living space unfolds across two levels (furnishings may be purchased separately). Beautiful hardwood flooring connects the open layout, where vaulted ceilings, skylights, and impact-rated PGT windows and doors fill the interiors with natural light. The double glass and solid wood entry opens to a bright, contemporary living space that flows effortlessly into the formal dining area. At the heart of the home, the eat-in chef’s kitchen is thoughtfully designed with shaker-style cabinetry, quartz countertops, stainless steel appliances, a center island, and a breakfast bar peninsula. A dedicated cafe-style dining area is complemented by a wet bar featuring dual wine cooler/beverage refrigerator, and floating shelving. Impact sliding glass doors open to the covered outdoor entertaining area and pool deck beyond. This inviting space overlooks the family room. Upstairs, the oversized primary suite offers a private retreat with terrace access, a spacious en-suite bathroom, and a walk-in closet. A second en-suite bedroom also enjoys its own terrace, while two additional guest bedrooms share a third bath, providing flexibility for family and visitors. Outdoor living is designed for both relaxation and entertaining. The heated swimming pool is surrounded by a brick paver deck, with an additional open deck ideal for lounging. Just beyond, the extended dock and newly reinforced seawall (2025) create a seamless connection to the water, offering direct access to the waterway that flows out to Sarasota Bay, for boating and waterfront enjoyment. A long list of improvements enhances the home’s value and peace of mind, including a 2023 metal roof, impact PGT windows and doors, updated mechanical systems, and recent exterior upgrades such as new soffit, fascia, and gutters (2026). Bird Key is known for its central location between downtown Sarasota and St. Armands Circle, offering residents convenient access to waterfront dining, boutique shopping, and cultural venues. Just minutes away, Lido Beach and Longboat Key provide some of the region’s most celebrated Gulf-front shorelines, while nearby marinas and yacht clubs complement the boating lifestyle that defines this exceptional community.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
8684 WOODBRIAR DR, SARASOTA, FL 34238
$664,00054 Days on yellowkey MLS ID: A4684548
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2329 Built: 1992Monthly Fee: $205 Tax: $4,830 (2025)Community: Deer CreekSpa: NoSingle Family
Taxes:$4,830
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Nestled within a gated community, this Lee Wetherington custom-built home offers a rare blend of privacy and comfort with all hurricane impact windows, refinished pool and private backyard. From the moment you enter the community, you'll appreciate the sense of tranquility and security that defines this neighborhood. The home features three bedrooms, one of them currently set up as an office, two full bathrooms, and one-half bath, thoughtfully arranged to provide both functionality and comfort. Natural light fills the living spaces, enhancing the warm and inviting layout that is ideal for everyday living as well as entertaining guests. The well-designed floor plan allows for seamless flow between living, dining, and gathering areas, creating a space that feels open yet cozy. Step outside to your own private backyard retreat, where a sparkling private pool is surrounded by mature greenery, offering exceptional privacy. Located within a gated community, residents enjoy an added level of security and exclusivity, along with a well-maintained environment that reflects pride of ownership. Roof was replaced in 2016, HVAC and water heater 2019, pool heater 2025, windows 2018-2020 and pool was resurfaced in 2022. In addition, Costco, YMCA, Legacy Trail and Siesta Key are only short drive away.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Andrea Williams (941-225-1520)
8057 TIDAL POINTE WAY, SARASOTA, FL 34240
$799,00081 Days on yellowkey MLS ID: A4681077
4 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2427 Built: 2021Monthly Fee: $373 Tax: $10,422 (2025)Community: Lakehouse Cove/Waterside Ph 2Single Family
Taxes:$10,422
Elementary School: Tatum Ridge Elementary
High School: Booker High
Remarks: Welcome to Lakehouse Cove at Waterside where maintenance- free living meets vibrant resort style amenities in the heart of Lakewood Ranch. Move right in to this cozy, coastal craftsman fully furnished Halyard model from Homes by Towne with 2 bedrooms, a den, and a light drenched bonus room on a conservation lot. This spacious and well-designed home has a sense of openness from the moment you walk into the warm and dramatic foyer. The heart of the home features a gourmet kitchen with Cambria quartz countertops, beautiful cabinetry, under-cabinet lighting, a large walk-in pantry, and eat-in dining area. The kitchen blends seamlessly with the expansive Great Room that boasts striking volume tray ceilings, built-ins, and shiplap detailing. A thoughtful split floor plan offers privacy for guests or family members and the modified 330 square foot bonus room provides an additional spot to relax and unwind separate from the Great Room. Newer construction provides peace of mind as the home is equipped with impact windows, sliders, and doors. Additional features include a 20,000 watt Kohler generator and an Aquasana 5 stage water filtration system. Life at Lakehouse Cove means more than just a beautiful home- it’s a lifestyle. Enjoy 6 pickleball courts, a resort-style pool and spa overlooking Lake Kingfisher, a state-of-the-art fitness center, boathouse with kayak launch, 2 dog parks, community club house and fire pits where neighbors gather for breathtaking sunsets. Just a short stroll brings you to Waterside Place where you can enjoy shopping, dining, a weekly farmers market and other year round events. Don’t miss the opportunity to make your dream Florida lifestyle a reality.
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Sasha Rosin (941-323-0261)
1363 23RD ST, SARASOTA, FL 34234
$284,90026 Days on yellowkey MLS ID: A4687997
REDUCED by $15,000 (5.0%) on 04/13/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1100 Built: 1956 Tax: $2,253 (2025)Community: Central HeightsSingle Family
Taxes:$2,253
Elementary School: Gocio Elementary
Middle School: Booker Middle
Remarks: Located in Central Heights within Sarasota city limits, this 1,100 sq ft single-family home sits on a spacious .19 acre lot and offers a great central location. You’re just minutes to downtown Sarasota, Sarasota Airport, shopping, restaurants, and about 10 minutes to Lido Beach. Inside features tile flooring throughout for easy maintenance, along with fresh interior and exterior paint. The kitchen offers shaker-style cabinets and stainless steel appliances with plenty of space to work with. The home includes 3 bedrooms all split, one full bathroom with a shower/tub combo and ceiling fans in the bedrooms and main living areas. Major updates include a 2021 A/C system and a new hot water heater, with a 2013 roof already in place. The large yard provides room to expand, entertain, or store toys—lots of potential depending on your needs. Solid option for a primary residence, rental, or a simple Florida getaway in a convenient location. Property is vacant and easy to show!
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Dane Peterson (239-357-5692)
3310 MINEOLA DR, SARASOTA, FL 34239
$675,000110 Days on yellowkey MLS ID: A4676490
REDUCED by $50,000 (6.9%) on 03/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1818 Built: 1958Monthly Fee: $17 Tax: $3,383 (2025)Community: South GateSpa: YesSingle Family
Taxes:$3,383
Elementary School: Southside Elementary
Middle School: Brookside Middle
Remarks: Nature lovers will enjoy overlooking the Jaffa Canal connecting to Phillippi Creek, then Access out to Little Sarasota Bay, the Intercoastal Waterway & Gulf Waters! County dredging project underway of creek and canal behind this home! Discover Paradise in this Beautifully detailed Pool home built on 1/3 acre on an island & private cul-de-sac. It is ideal for a full-time homestead or seasonal residence, located in the highly desirable South Gate neighborhood & Southside Elementary school district! Relax in your own outdoor oasis with one of the largest pools in the neighborhood, 8’ deep with aerating fountains and a 7’x7’ built in heated Spa! The open floor plan of this home makes it flexible for your needs with 2 larger bedrooms and 3rd used as a den with built-ins in closet. Master suite has custom walk-in closet and updated bath with Travertine, glass-enclosed shower, vanity & cabinet w/pull-outs. The French doors open to beautiful palm trees giving privacy to the outdoor spa area! the flex/family room also opens up to the 59’x24’ screened pool area, covered lanai and pool deck above Jaffa Canal (will be dredged four feet at 10 ft. from seawall when complete) and is excellent for observing FLorida wildlife, manatees and birds!! Use the flex room as a den, art studio/craft room, informal dining & family room. Entry hall closet also has built-in shelving/drawers. French doors can be open or closed to afford privacy to the great room and adjacent updated kitchen with granite counters, warm wood cabinets & stainless steel appliances *New Refrigerator 2025 *New Air Conditioner 2025 *Shingle Roof 2019 *Sewer Connect 2015 **Pool added in 1999 ~ Re-marcited in 2013, Pool/Spa Heat pump 2015, Pool Motor 2019 *Two Water heaters (on each end of home age 3 & 5) *Many additional updates since original build include electrical switches/outlets, 5" baseboards, wood casing detail, doors, hardware, windows & underground utilities *Well for irrigation of lush tropical, low-maintenance Florida friendly landscaped yard on this 13,000 sq. ft. lot. with seawall. The 460 sq. ft. 2 car garage has built in work bench & laundry room w/storage closet. Located just minutes to Sarasota Memorial Hospital, Downtown Sarasota, Shopping, Southside Village, St. Armand's Circle, World-famous Siesta Key and Lido Beaches! *HOA is optional only $200/year ~ Schedule your visit today!
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Solveiga Spalvins (941-320-6860)
1621 DR MARTIN LUTHER KING WAY, SARASOTA, FL 34234
$525,00023 Days on yellowkey MLS ID: O6395721
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2075 Built: 2009 Tax: $1,424 (2026)Community: Newtown Heights First Add ToSingle Family
Taxes:$1,424
Tax Year: 2026
Remarks: This multi-tribe property at 1621 Dr Martin Luther King Way is a fantastic investment opportunity. Open concept layout with an elegant fireplace in the living room and a kitchen design for entertaining with stainless steel appliances and granite countertops. Conveniently located near shopping, dining, and public transportation. This home is 10 minutes from Sarasota's nearest award winning sugar sand beach, the library, Van Wenzel performing Art Hall, restaurants, walking distance to downtown Sarasota, hospital, major shopping Mall, Ringling Museum and Ringling Art school, five minutes from Sarasota - Bradenton airport. The property provides easy access to everything the area has to accord. The exterior boasts well-maintained landscaping, providing a welcoming first impression. Don't miss the chance to own this versatile income-producing property. The home has two bedrooms with attached bathrooms, one on the first floor, and the other on the second floor.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
3136 GULF GATE DR, SARASOTA, FL 34231
$425,00023 Days on yellowkey MLS ID: N6143660
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1187 Built: 1966 Tax: $2,055 (2025)Community: Gulf GateSingle Family
Taxes:$2,055
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained pool home in the heart of Gulf Gate—one of Sarasota’s most established and sought-after neighborhoods known for its charm, walkability, and unbeatable convenience. This 2-bedroom, 2-bath residence features a bright, open-concept layout with an easy, natural flow between the living, dining, and kitchen areas, creating an ideal setting for both everyday living and entertaining. The kitchen is appointed with classic white cabinetry, offering a clean, timeless look that enhances the home’s light and inviting atmosphere. Large sliding glass doors fill the interior with natural light and open to a spacious screened lanai, where a recently resurfaced pool provides your own private outdoor retreat. The primary suite is thoughtfully designed with a walk-in closet, en suite bathroom, and direct access to the pool area—perfect for enjoying Florida living at its finest. The second bedroom is generously sized and versatile, well-suited for guests, a home office, or additional living space. Notable upgrades include a 2020 Roof, an attractive paver driveway, and a spacious two-car garage with epoxy flooring, offering both function and durability. Gulf Gate is highly regarded for its mature landscaping, friendly atmosphere, and close proximity to everyday conveniences. Just minutes away, Gulf Gate Village offers a vibrant mix of locally owned restaurants, cafés, and shops. Publix, Trader Joe’s, and Costco are all within easy reach, along with top-rated Sarasota schools. Best of all, Siesta Key Beach—world-renowned for its powdery white sand and stunning Gulf waters—is only a short drive away. Whether you’re seeking a full-time residence, seasonal escape, or investment opportunity, this move-in-ready home delivers the perfect combination of comfort, location, and the quintessential Florida lifestyle.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rick Tritschler, Jr. (941-928-1292)
1504 S LODGE DR, SARASOTA, FL 34239
$6,990,00047 Days on yellowkey MLS ID: A4683855
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5450 Built: 1965Monthly Fee: $25 Tax: $15,432 (2025)Community: Cherokee LodgeSpa: YesSingle Family
Taxes:$15,432
Remarks: First time available in 40 years! "Tween Bridges" is a rare bayfront property located in highly sought-after Cherokee Park, West of Trail. This 4-bedroom,3.5 bath residence offers unobstructed panoramic views of Sarasota Bay. The breathtaking sunsets and stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations. "Tween Bridges" is named for its location between The Ringling Bridge and The Siesta Key north bridge.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Melody Davis (908-202-4085)
7885 MAINSAIL LN, SARASOTA, FL 34240
$1,795,00071 Days on yellowkey MLS ID: A4682351
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2487 Built: 2022Monthly Fee: $500 Tax: $17,017 (2024)Community: Shoreview At Lakewood Ranch WatersideSpa: YesSingle Family
Taxes:$17,017
Remarks: Under contract-accepting backup offers. This beautifully appointed three-bedroom, three-bath plus den custom Pulte Pinnacle model showcases refined design, thoughtful upgrades, designer touches, and serene waterfront living in the highly desirable Shoreview community of Waterside. From the moment you arrive, the striking stone front façade, manicured landscaping and elegant glass entry door create a sophisticated first impression. Inside, tile flooring flows seamlessly throughout the home, complemented by modern designer lighting, stylish ceiling fans, tray ceilings, crown molding and curated architectural accents that elevate every space. The open-concept floor plan is designed for effortless entertaining and comfortable everyday living. The spacious great room features tray ceilings and pocketing sliding glass doors that fully open to the oversized lanai, blending indoor and outdoor living while framing stunning lake views. The adjacent dining area is positioned to enjoy natural light and water vistas, while the chef’s kitchen serves as the heart of the home with KitchenAid and Whirlpool appliances, sleek cabinetry, and a large eat-at bar ideal for gatherings and casual dining. Go outside to your private Florida retreat where an expansive screened lanai overlooks tranquil water views. The heated saltwater pool and spa are set against a panoramic screen enclosure, creating a breathtaking backdrop of shimmering lake views. An outdoor kitchen enhances the space, making it ideal for alfresco dining and entertaining year-round. The primary suite is a peaceful sanctuary featuring a tray ceiling, large picture window overlooking the pool and lake, and a beautifully appointed spa-inspired bath with a spacious walk-in shower and refined finishes. One guest bedroom with stunning window-filled bump-out offers its en-suite bath, while the second guest bedroom is serviced by a dedicated full bath, providing privacy and comfort for family or visitors. The private den, accessed through double doors, features a tray ceiling and built-in designer cabinetry, ideal for a home office, library or creative space. Additional highlights include hurricane-rated windows for peace of mind, a spacious three-car garage with ample storage and meticulous landscaping that enhances the home’s curb appeal. In Shoreview at Waterside, residents enjoy a resort-inspired lifestyle with access to a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, dog parks, playground and scenic walking trails along Kingfisher Lake. Waterside offers charming waterfront dining, boutique shopping, vibrant community events and picturesque views throughout the area, creating a dynamic yet peaceful setting. This exceptional residence offers a blend of luxury, comfort and community in one of Lakewood Ranch’s sought-after neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Laura Stavola Pllc (941-447-4875)
2280 MIDNIGHT PEARL DR, SARASOTA, FL 34240
$475,00026 Days on yellowkey MLS ID: N6143658
REDUCED by $10,000 (2.1%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2019Monthly Fee: $124 Tax: $3,509 (2025)Community: Bay LandingSingle Family
Taxes:$3,509
Remarks: Welcome to 2280 Midnight Pearl Dr, a beautifully designed and maintained one-story home offering comfort, functionality and modern style. Built with durable all-concrete block construction, this residence features a truly open-concept layout perfect for both everyday living and entertaining. At the heart of the home, a spacious kitchen with a large island overlooks the dining area, great room and cozy breakfast nook, creating a seamless flow of living space. From here, step out onto the covered lanai and enjoy the screened back porch—ideal for relaxing or hosting guests year-round. A sun tunnel skylight fills the home with natural light, helping reduce the need for artificial lighting during the day and contributing to lower power bills. The owner’s suite is thoughtfully positioned at the rear of the home, providing optimal privacy along with an ensuite bath. Two additional bedrooms are located at the front and share a full bathroom, making this layout ideal for families or guests. Convenience meets practicality with a laundry room just off the garage, functioning perfectly as a mudroom entry into the kitchen. The home also comes equipped with stainless steel appliances, including a dishwasher, range, refrigerator and microwave. Residents enjoy a low HOA fee of just $124 per month, which includes access to a beautiful heated community pool and fitness room. Additional updates include a newly replaced roof in September 2025, offering peace of mind for years to come. Ideally located with easy access to I-75, this home is just a short drive from Sarasota’s world-famous beaches, shopping, dining and top-rated schools. This well-maintained home combines modern features with a smart layout in a spectacular and convenient location—ready for you to move in and enjoy.
Listing is courtesy of: PELICAN REALTY CORP (941-270-2650)
Listing Agent: Anna Bridinger, Pa (941-544-8195)
4662 BEACON DR, SARASOTA, FL 34232
$390,00031 Days on yellowkey MLS ID: A4686944
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1609 Built: 1977 Tax: $1,991 (2025)Community: Sarasota SpgsSingle Family
Taxes:$1,991
Elementary School: Brentwood Elementary
Remarks: Under contract-accepting backup offers. Check out this 3-bedroom, 2-bath home with a 2-car garage in a centrally located neighborhood. This home features a split floor plan with a spacious formal living room, a separate family room at the rear of the home, and a formal dining room with built-in buffet-style cabinets. The galley kitchen is conveniently located in the center of the home, and there is an abundance of closet space throughout. This property does need some TLC, but the major updates include a roof replaced in 2019, A/C in 2013, and water heater in 2016. The partially fenced backyard offers a large 16x30 wood deck built around a beautiful oak tree, plus a spacious 14x11 shed with two loft areas, ideal for extra storage, a workshop, a man cave, or a she shed, with a paver brick patio off it. Located within walking distance to the elementary school and a neighborhood park with grills and picnic tables, and just a short drive to shopping, restaurants, and the beautiful beaches. Don’t miss this great opportunity to make this home your own
Listing Agent: Lisa Bouck, Pa (941-374-0165)
941 VIRGINIA DR, SARASOTA, FL 34234
$1,500,00053 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
Elementary School: Emma E. Booker Elementary
Remarks: A Rare Piece of Sarasota History with current income of over 167,000 / yr. 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)
1775 STAPLETON ST, SARASOTA, FL 34239
$1,545,000177 Days on yellowkey MLS ID: A4670359
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2853 Built: 2007Monthly Fee: $568 Tax: $8,620 (2024)Community: Granada ParkSingle Family
Taxes:$8,620
Remarks: Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid concrete block construction for lasting durability, recent improvements include new UV purification in air-conditioning units, a new roof and fresh exterior paint. The well-designed floor plan offers four bedrooms and three baths, with a flowing open layout that connects the great room, dining area and kitchen beneath high ceilings filled with natural light. A private guest suite above the garage provides flexible space for multi-generational living, a studio or fitness retreat. Throughout the home, refined details like solid-wood cabinetry, deep-trimmed windows and fine millwork reflect craftsmanship and quality. The great room impresses with a two-story ceiling and fireplace, while the kitchen showcases shaker cabinetry, quartz countertops, a center island, stainless-steel appliances and a walk-in pantry. Living in Granada Park provides the ease of a lock-and-go lifestyle in a gated, established neighborhood. This pleasant haven is conveniently just .3 miles from Publix, .5 miles to CineBistro, 1.3 miles to Southside Village, two miles to Sarasota Memorial Hospital, 2.6 miles to downtown Sarasota and five miles to Siesta Key Beach. It’s the best of Sarasota living, wrapped in a maintenance-free, West of Trail lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Andrew Tanner (941-539-0998)
1022 S OSPREY AVE, SARASOTA, FL 34236
$1,599,000207 Days on yellowkey MLS ID: A4666624
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2284 Built: 1922 Tax: $4,185 (2024)Community: Rigbys SubSingle Family
Taxes:$4,185
Remarks: Situated in the highly desirable West of Trail neighborhood of Hudson Bayou, this fully restored 1922 residence is the perfect blend of historic charm and modern conveniences. The property offers 2,284 square feet with two bedrooms and two bathrooms in the main house, plus a one-bedroom, one-bathroom guest house. Renovations include a 2006 conversion of the garage into a guest house with a stucco privacy wall and Chicago brick driveway. In 2018, a spacious primary suite with double closets, a large bath, and French doors to a screened lanai was added. High ceilings, oversized impact windows, and refinished hardwood floors (2024) add to the home’s appeal. Recent updates include a recoated roof with a 10-year transferable warranty (2025), A/C (2023), water heater (2024), encapsulated crawlspace with dehumidifier (2024), foundation reinforcement with new support jacks (2024/2025), and hurricane-rated windows. The kitchen and dining area were fully renovated, featuring custom Conestoga cabinetry and designer appliances (2024/2025). Additional features include recessed lighting, custom closets, a Murphy bed, and a natural gas fireplace. A wellness room with an infrared sauna (2025) completes the interior. Exterior highlights include enhanced landscaping, three all-weather sheds, a pergola with natural gas grill hookups, and a serene brick courtyard surrounded by mature landscaping for privacy. The location is unparalleled, with proximity to Southside Village, the downtown Sarasota bayfront, St. Armands Circle, and the world-famous beaches of Lido and Siesta Key.
Listing Agent: Barbara May (404-822-9264)
2960 SANDRINGHAM PL, SARASOTA, FL 34235
$525,000134 Days on yellowkey MLS ID: TB8453203
REDUCED by $15,000 (2.8%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2205 Built: 1991Monthly Fee: $700 Tax: $3,335 (2024)Community: Sandringham PlaceSingle Family
Taxes:$3,335
Remarks: Absolute stunner and an exceptional value. This fully remodeled (2025) 3-bedroom, 2-bath, 2-car garage home in The Meadows offers 2,205 sq. ft. of beautifully updated living space on just under a 1/3 of an acre (0.30-acre) lot. The property features an open, split-bedroom floor plan with 10-foot ceilings and a soaring cathedral ceiling in the great room. The brand-new kitchen includes stainless steel appliances, quartz countertops, new cabinetry, and updated lighting. Both bathrooms have been fully renovated with new tile, faucets, finishes, and fixtures. Additional upgrades include new laminate wood flooring throughout and fresh interior paint. The home offers a large living room with a fireplace, a formal dining room, and a spacious primary suite with an oversized walk-in closet, dual sinks, a large walk-in shower, and a stand-alone soaking tub. A 252 sq. ft. air-conditioned Florida room, a generous utility room with a sink, and an oversized garage provide added versatility and convenience. Enjoy a maintenance-free lifestyle with an HOA that covers landscaping, lawn care, irrigation, power washing, tree trimming, and exterior paint. The property is located in Flood Zone X, meaning flood insurance is not required—an excellent advantage for buyers. The Meadows is a highly sought-after, park-like community featuring extensive amenities, including social activities, miles of nature trails, three golf courses, 15 lighted tennis courts, pickleball and basketball courts, a new Lifestyle and Wellness Center, a Jr. Olympic pool and spa, and protected nature preserves. A professional, 24-hour vehicle-based security patrol provides added peace of mind. Ideally situated just minutes from the University Town Center Mall, boutique shopping and dining, Nathan Benderson Park, downtown Sarasota, and world-class Gulf beaches.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (813-259-0000)
Listing Agent: Lawrence Malloy (813-679-3990)
4341 NELSON AVE, SARASOTA, FL 34231
$415,00017 Days on yellowkey MLS ID: A4688886
0 Days Off yellowkey (back on 4/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1686 Built: 1998 Tax: $2,113 (2025)Community: Golf EstatesSingle Family
Taxes:$2,113
Remarks: Under contract-accepting backup offers. PROFESSIONAL PICTURES TO COME!! Welcome to 4341 Nelson Avenue—a well-loved single-family home full of charm, comfort, and thoughtful features. This inviting property offers generous closet space throughout, making organization easy and practical for everyday living. Enjoy peace of mind with a newer roof, adding value and durability to the home. The spacious primary bedroom provides direct access to a large lanai, creating the perfect private retreat to relax with your morning coffee or unwind in the evenings. Step outside to a beautifully landscaped yard filled with lush vegetation, offering a serene and natural setting. The partially fenced backyard provides both privacy and flexibility—ideal for pets, gardening, or outdoor entertaining. With its warm character, functional layout, and inviting outdoor spaces, this home is a wonderful opportunity to enjoy the best of Sarasota living.
Listing Agent: Daina Filiatreau (941-932-3414)
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