Location: Sarasota , 34231
Do Not Show Listings
2233 MICHELE DR, SARASOTA, FL 34231
$649,900140 Days on yellowkey MLS ID: TB8453606
1 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 1970 Tax: $6,847 (2024)Community: Phillipe GardensSpa: NoApartment
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,847
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Fully remodeled Sarasota duplex for sale in highly desirable Phillippi Gardens—NO HOA and NO CDD fees—offering exceptional income potential and investment opportunity just minutes from world-famous Siesta Key Beach, consistently ranked among America's top white-sand beaches. This turnkey multifamily investment property features two spacious 2-bedroom, 1.5-bathroom units, each with an attached 1-car garage, private patio, screened lanai, and fully fenced backyard, delivering ideal privacy and separation for long-term tenants, short-term rental guests, or multigenerational family living. Both units have been thoughtfully and completely upgraded with brand-new luxury vinyl flooring, beautifully renovated kitchens featuring modern cabinetry and countertops, updated bathrooms, new stainless steel appliances including in-unit washers and dryers, all-new hurricane-impact windows and impact-rated garage doors, plus updated plumbing and electrical systems for true peace of mind. In a significant advantage for this market, the property experienced no interior flooding during the 2024 storms—a rare and valuable feature for Gulf Coast buyers. This Sarasota income-producing duplex is perfect for investors seeking strong long-term rental income, mid-term rental opportunities (buyer to verify local regulations), or a smart house-hacking strategy by living in one unit while renting the other to offset the mortgage. Ideally situated approximately 10 minutes from Siesta Key Beach, 12 minutes to Siesta Key Village, under 20 minutes to University Town Center (UTC), and conveniently close to US-41, Downtown Sarasota, waterfront dining, marinas, nightlife, championship golf, and premier shopping, this fully upgraded Phillippi Gardens duplex presents a rare opportunity to own a high-demand Sarasota multifamily investment property in one of the Gulf Coast's strongest rental markets, known for both consistent cash flow and long-term appreciation. Whether you're a seasoned investor expanding your portfolio, a first-time house-hacker, or a buyer seeking a flexible multigenerational property near the beach, this move-in-ready Sarasota duplex delivers location, upgrades, and income potential in one rare package—schedule your private showing today and secure your piece of the Siesta Key Gulf Coast lifestyle.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Mark Middleton (727-871-7653)
2411 GULF GATE DR, SARASOTA, FL 34231
$460,0002 Days on yellowkey MLS ID: A4690632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1291 Built: 1962Monthly Fee: $6 Tax: $4,318 (2025)Community: Gulf GateSingle Family
Taxes:$4,318
Elementary School: Gulf Gate Elementary
Tax Year: 2025
Remarks: Location, convenience, and charm! This delightful 2-bedroom, 2-bath home is ideally situated just two blocks from the shops and restaurants of the sought-after Gulf Gate community. Enjoy an open floor plan that flows seamlessly to a lovely screened-in pool area—perfect for relaxing or entertaining. The fully fenced yard offers plenty of space for pets to run and play. Features include terrazzo floors throughout, a circular driveway, and a freshly painted exterior. A wonderful opportunity to enjoy the Gulf Gate Lifestyle. Exterior of home is currently being painted. Professional pictures next week.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Ingrid Caruso (941-539-6233)
5436 S LOCKWOOD RIDGE RD, SARASOTA, FL 34231
$350,0002 Days on yellowkey MLS ID: TB8495570
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1484 Built: 1968 Tax: $1,903 (2025)Community: Sun HavenSingle Family
Taxes:$1,903
Remarks: You found it! A home that blends comfort, functionality, and Florida-style outdoor living—all with the freedom of NO HOA! This beautifully maintained single-family residence invites you in with a charming curb appeal featuring coach lights, gutters, and a decorative tile entryway that sets the tone from the moment you arrive. Enjoy the convenience of keyless entry and a thoughtfully designed garage with a side door to the exterior, perfect for easy access and added flexibility. Inside you’ll find a spacious, light-filled layout where everyday living and entertaining come together effortlessly. The living room is anchored by a custom media center, creating the perfect space for relaxing nights or hosting guests. The kitchen is both practical and inviting, offering an eat-in area, a separate dining space, and a unique pass-through serving window to the patio—ideal for seamless indoor-outdoor entertaining. Slide open multiple glass doors and step out to your private backyard oasis overlooking a tranquil pond view. Whether you’re enjoying your morning coffee, hosting a barbecue on the extended concrete slab, or soaking up the Florida sunshine, this outdoor space is designed to impress. Inside you’ll also find spacious guest bedrooms, each offering comfort and versatility, along with multiple double-door closets throughout the home—providing an abundance of storage options. Ceiling fans enhance comfort year-round, while hurricane shutters add peace of mind during storm season. This home truly checks all the boxes: VALUE, space, and smart features—all in a serene setting with no HOA restrictions. Seller offering a home warranty with approved offer …or add some updates to your own preference!
Listing is courtesy of: KEY TO FLORIDA REALTY (239-776-9260)
Listing Agent: Rhonda Ryals (813-368-6759)
5639 BLOUNT AVE, SARASOTA, FL 34231
$385,0006 Days on yellowkey MLS ID: A4690414
0 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1695 Built: 1984 Tax: $654 (2025)Community: Sarasota Venice Co 09 37 18Single Family
Taxes:$654
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Homes like this one do not come up often in this location at this price. 5639 Blount Avenue is a 3-bedroom, 2-bath, 1,695 square foot Sarasota home sitting on a generous, fully fenced lot just minutes from the world-famous white quartz sands of Siesta Key Beach. No HOA. No restrictions. No monthly fees. Just a well-built, character-filled Florida home with the space, the layout, and the location that buyers in this market have been searching for. Pull up and you immediately notice the lot. Large, lush, and fully fenced, the yard offers the kind of outdoor space that is increasingly rare inside Sarasota proper. Mature trees provide natural shade and a sense of privacy that makes the property feel like a private retreat tucked away from the pace of the city. Step inside and the home opens up. Vaulted ceilings lift the living spaces and flood the interior with natural light, creating an airy, welcoming feel that photographs cannot fully capture. You have to stand in it to understand how spacious it actually is. The living room features warm wood-paneled walls and a stone fireplace, the kind of old Florida charm that adds genuine character and personality to a home. Light wood floors flow throughout, tying the rooms together in a clean, cohesive aesthetic. The split floor plan is one of the most practical and desirable layouts in residential real estate, and this home executes it well. The primary suite is separated from the two guest bedrooms, offering true privacy for owners and guests alike. The primary bedroom is genuinely spacious, with vaulted ceilings, excellent natural light, and direct access to the rear of the home through French doors. The Florida room is a standout feature and one of the most versatile spaces in the home. Bright, open, and connected to the main living area via classic French doors, it functions beautifully as a second living room, a home office, a playroom, a creative studio, or a casual entertaining space. The possibilities are as flexible as you need them to be. The kitchen is well laid out with granite countertops, stainless steel appliances, and an abundance of cabinet storage. A window above the sink looks out to the lush greenery of the backyard, making even everyday tasks feel a little more Florida. The 2022 roof provides peace of mind and real value. The well and septic system eliminate monthly water and sewer utility bills entirely, a meaningful and ongoing financial advantage that adds up significantly over time. The garage provides covered parking and additional storage. The fully fenced yard is ready for pets, play, or simply enjoying the Sarasota sunshine in complete privacy. For buyers searching for a Sarasota home near Siesta Key with no HOA, a large yard, and strong bones at an attainable price point, 5639 Blount Avenue delivers exactly that. 5639 Blount Avenue · Sarasota FL 34231 · Sarasota County · Near Siesta Key Beach
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Traci Bolen (941-914-5159)
4301 S LOCKWOOD RIDGE RD, SARASOTA, FL 34231
$859,000153 Days on yellowkey MLS ID: A4672535
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3406 Built: 1970 Tax: $8,304 (2024)Community: Flora VillaSpa: NoSingle Family
Taxes:$8,304
Elementary School: Wilkinson Elementary
Remarks: A welcoming Sarasota residence that blends spacious indoor living with a true resort-style outdoor oasis, all positioned in one of the most convenient and desirable locations in Sarasota County. Thoughtfully decorated and beautifully maintained, this home opens with a charming courtyard entrance that sets an immediate tone of warmth and sophistication. Inside, Brazilian hardwood floors flow throughout the living spaces, complementing abundant natural light and an open, flexible layout. The home offers large bedrooms and two versatile flex rooms ideal for a den, office, playroom, hobby studio, gym, storage, or an additional guest suite. Upgraded interior doors add a refined touch, while the master bedroom features a custom built-in closet system for exceptional organization. The kitchen impresses with an epoxy river kitchen-island countertop paired with a copper farmhouse sink, creating a stunning focal point for both cooking and entertaining. Additional highlights include Mexican tile accents, a generous walk-in pantry, and thoughtful design that blends character with function. Step outside to discover the crown jewel of the property: a private, resort-style lagoon pool designed for the ultimate Florida lifestyle. This expansive 20,000-gallon saltwater pool showcases a rockwall waterfall, a dolphin fountain, bench seating, and a sun shelf for lounging. With outstanding sun exposure perfect for sunbathing, the pool is surrounded by an oversized pavered patio offering abundant space for lounge seating and entertaining. A 340-sq-ft screened lanai with a ceiling fan extends the indoor living space and provides a comfortable transition to the home’s breathtaking outdoor retreat. Mature tropical landscaping creates lush privacy, enhancing the serene ambiance and delivering the feeling of a secluded paradise. Completing the outdoor experience is a tiki bar with bartop seating and built-in lighting, ideal for evening cocktails, weekend celebrations, and memorable nights under the Florida sky. The property also includes a wired utility and workshop shed, plus an irrigation system for easy landscape maintenance. Beyond its impressive features, the location elevates this home even further. Residents are less than 10 minutes from Downtown Sarasota’s world-class dining, boutique shopping, waterfront parks, and vibrant cultural arts district. The world-famous Siesta Key Beach, renowned for its powdery white quartz sand, is approximately 10 minutes away, offering effortless beach days. The upscale UTC Mall and surrounding dining and entertainment district are about 15 minutes away, while St. Armands Circle and Lido Beach are roughly 20 minutes away for oceanfront dining and luxury leisure. Everyday conveniences, including Sarasota Memorial Hospital, grocery stores, parks, boat ramps, and I-75, are all within minutes, making this home a rare combination of comfort, style, and accessibility. Beautifully updated, move-in ready, and enhanced with an outdoor living experience rarely found in this location, this property presents an exceptional opportunity to embrace the best of Sarasota living! ROOF 2020. Two of three HVACs 2023. PVC plumbing throughout.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Janette Schafer (954-298-7791)
2144 OAK TER, SARASOTA, FL 34231
$475,0004 Days on yellowkey MLS ID: C7525020
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1769 Built: 1979 Tax: $4,601 (2025)Community: Harbor OaksSpa: NoSingle Family
Taxes:$4,601
Remarks: Single story home in move-in ready condition with an abundance of natural light throughout. The bedrooms are generously sized, and bathrooms are well maintained. The home also offers an oversized garage with additional storage potential. NO HOA FEES! Easy to show!
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: William Figueroa (305-662-1502)
5474 RIVERBLUFF CIR #V35, SARASOTA, FL 34231
$219,900183 Days on yellowkey MLS ID: A4669393
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1971 Tax: $2,363 (2024)Community: Strathmore Riverside IVilla
Taxes:$2,363
Remarks: Welcome to Strathmore Riverside Villas, a vibrant 55+ community perfectly situated in the heart of Sarasota. This spacious two-bedroom, two-bath villa offers the ideal blend of comfort, convenience, and endless potential. Light, bright, and airy, the home features an open-concept layout with generous room sizes and an inviting flow throughout. The enclosed lanai, complete with both windows and screens, provides a wonderful year-round living space; perfect for morning coffee, relaxing afternoons, or entertaining friends. The villa also includes a one-car carport and a separate storage and laundry area, offering privacy, security, and plenty of extra space. With just a touch of personalization, this residence can truly shine. The community itself is beautifully maintained and lushly landscaped, creating a serene and welcoming atmosphere surrounded by green space. Strathmore Riverside Villas is known for its active lifestyle and warm sense of community. Residents enjoy a wealth of amenities, including a heated geothermal pool overlooking the marina, clubhouse, fitness center, library, meeting rooms, sauna, and billiards. There’s always something happening here; social events, card games, bingo nights, potlucks, concerts, dancing, and more. Boat docks are available on a first-come, first-served basis for just $1,344 per year, and the community is pet-friendly. The location couldn’t be better; just minutes from shopping, hospitals, and the world-famous Siesta Key Beach, as well as the rich cultural attractions of downtown Sarasota, including opera, ballet, symphony, and live theatre. Whether you’re looking for a full-time residence or a seasonal getaway, this villa lives like a single-family home and offers the perfect opportunity to enjoy Florida’s relaxed coastal lifestyle. Don’t wait; schedule your private tour today and discover the charm of Strathmore Riverside Villas.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
2445 APACHE ST, SARASOTA, FL 34231
$540,000314 Days on yellowkey MLS ID: N6139245
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1253 Built: 2000 Tax: $5,364 (2024)Community: Jackson HighlandsSpa: YesSingle Family
Taxes:$5,364
Remarks: Location! Location! Location! NO FLOOD ZONE!SOLAR PANEL! NEW POOL CAGE!NEW FRONT FENCE PLUS SLIDING GATE! If you want total privacy, come check out this beautiful 3/2 Pool Home. This home has been almost fully updated, roof 12/2018 with transferable warranty, AC 6/2016, AC ducts 12/2018, bathrooms and flooring throughout the house 3/2017, water heater 2019, dishwasher 11/2020, full privacy fence 6/2020 and the house has been hooked up to public water 2019 and public sewer 2020. No need to worry about hurricanes. Hurricane Shutters have been installed 10/2020. You will find a tropical oasis in your totally private back yard. Pool with hot tub and large deck is surrounded by mature trees, including fruit trees, mango, Persian lime, bananas, papaya, avocado trees and pineapples. Walking distance to Riverview High School, shopping, 2 miles to the very famous and gorgeous Siesta Key Beach and just 10 minutes to beautiful downtown Sarasota. No deed restrictions.Conveniently located minutes away from I-75 and Tamiami Trail, this property offers excellent accessibility. Sarasota itself is a fantastic place to call home, with its central location providing easy access to shopping, dining, golfing, entertainment, medical facilities, award-winning beaches. Plus, you'll have effortless access to several airports, including Punta Gorda, Sarasota, Fort Myers, and Tampa.Experience the best of Florida with nearby beaches, golf courses, and outdoor recreational activities just a short drive away. Don't miss out on the chance to own this extraordinary home.
Listing is courtesy of: RE/MAX PALM REALTY OF VENICE (941-451-2025)
Listing Agent: Regina Melman (941-525-6818)
4313 MIDLAND RD, SARASOTA, FL 34231
$325,00030 Days on yellowkey MLS ID: GC538815
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1160 Built: 1957 Tax: $1,226 (2025)Community: Floral Park HomesteadsSingle Family
Taxes:$1,226
Remarks: Welcome to 4313 Midland Dr in beautiful Sarasota, a charming 3-bedroom, 1-bath home nestled in a **quiet, well-established community just minutes from the world-famous beaches of Siesta Key Beach. This beautifully updated home offers the perfect blend of comfort, style, and convenience. Step inside to find new tile flooring throughout, creating a clean and modern look while providing easy maintenance. The fully updated kitchen features elegant quartz countertops, offering both durability and a sleek contemporary feel—perfect for cooking and entertaining. The home has been freshly painted inside and out, giving it a bright and welcoming atmosphere. Outside, you’ll notice new landscaping that enhances the curb appeal and creates a relaxing outdoor space to enjoy Florida living. Located just minutes from shopping, dining, schools, and the white sands of Siesta Key Beach, this home is ideal as a primary residence, vacation getaway, or investment opportunity. Property Highlights3 Bedrooms / 1 Bathroom. Newly installed tile floors throughout. Updated kitchen with quartz countertops. Fresh interior and exterior paint. New landscaping and great curb appeal. Quiet neighborhood, Minutes to beaches, shopping, and dining. Don’t miss your opportunity to own a move-in ready home in one of Sarasota’s most desirable locations!
Listing is courtesy of: COASTAL REAL ESTATE PROFESSIONALS LLC (772-678-6017)
Listing Agent: Zachary Greenberg (561-310-9672)
5500 MERRIMAC DR, SARASOTA, FL 34231
$1,685,00051 Days on yellowkey MLS ID: A4684914
REDUCED by $85,000 (4.8%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 1974 Tax: $6,537 (2025)Community: Phillippi Gardens 08Spa: YesSingle Family
Taxes:$6,537
Remarks: Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
2571 RIVERBLUFF PKWY #V158, SARASOTA, FL 34231
$199,00091 Days on yellowkey MLS ID: A4678648
REDUCED by $16,000 (7.4%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1569 Built: 1971Monthly Fee: $725 Tax: $2,815 (2025)Community: Strathmore Riverside IiVilla
Taxes:$2,815
Remarks: VALUE PRICED! Villa 158 is a large C Model, originally built with a 12x30 screened porch/lanai, but professionally remodeled with screens, glass windows and air conditioned. This makes the square feet 1569 according to the Builder, the Paver Brothers. This villa has a new roof as of 2022. Tile floors throughout except for living room and Florida room ( former lanai ). The furniture is comfortable and negotiable. Villa is open and great for entertaining. It's just 4 blocks to the Clubhouse, Heated Pool and Marina. Less than 1/2 mile to shopping and even closer to the convenience store with one of the best egg salad sandwiches in town. The Community is one of the most socially active communities in the area. The happy community life offered here centers around the Recreation Complex. In the main building, a huge party-game-meeting room is equipped with dining tables, card tables, pool table, ping pong table, shuffle board table and audiovisual equipment and it's own complete kitchen. Poolside parties are easily accommodating, with one whole wall of sliding glass doors in the principal room leading you out to a full terrace, the Heated pool and shuffle board courts. The Clubhouse also has a lending library, card rooms, male and female saunas and two exercise rooms. Office manager is available 5 days a week. Villa 158 comes with it's own personal attached utility room for washer, dryer & water heater, and great for hobbyist or handyman. Villa 158 has a great location, approximately 2 miles to Siesta Key and 7 miles to Bayfront at Marina Jack's, Downtown Sarasota's restaurants and theatres. This Villa is hidden from traffic views. Boat docks are available with a rental fee of $1,344-a year, with direct access to over 4,000 feet of protected sea wall and docking for residential boats with easy access to Intercoastal Waterway, Bay and Gulf. And last but not least there are 2 pets welcomed; not to exceed 15" at the shoulder. If you are looking for a Spacious Villa This One is for You!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Marcia Morse (941-374-0442)
1884 SOUTHPOINTE DR, SARASOTA, FL 34231
$999,9009 Days on yellowkey MLS ID: A4689980
Bed: 6 Bath: 5.0 Liv Area Sq Ft: 2808 Built: 1972 Tax: $9,540 (2025)Community: Southpointe ShoresSingle Family
Taxes:$9,540
Remarks: A rare West of the Trail gem in Southpointe Shores, this beautifully updated 2,808 sq. ft. duplex captures the very best of Sarasota living, sun-soaked, private, and filled with opportunity. Whether you’re an investor seeking strong income potential, a homeowner looking to live in one side while the other helps offset the mortgage, or someone envisioning a future single-family coastal retreat, this exceptional property offers endless flexibility and long-term value. Each residence has been thoughtfully designed for comfort, privacy, and effortless modern living. With two private entrances, separate fenced backyards, and charming brick-paver patios, the layout creates the perfect blend of independence and connection, ideal for enjoying morning coffee beneath the palms or hosting intimate evenings under the stars. The left side, unit 1886, spans 1,639 sq. ft. and features 4 bedrooms, 3 bathrooms, a screened lanai, gas range, stainless steel appliances, luxury quartz countertops, elegant tray ceilings, and a versatile floor plan perfectly suited for families, guests, or long-term rental income. The right side, unit 1884, offers 1,087 sq. ft. with 2 bedrooms, 2 bathrooms, a light-filled sunroom, stainless steel appliances, quartz countertops, tray ceilings, and its own private fenced backyard, delivering warm coastal charm and easy everyday living. Both units include private indoor laundry rooms, backyards, and hurricane-impact windows, making this property truly move-in or rent-ready from day one. Beyond the home, Southpointe Shores welcomes you with quiet, tree-lined streets and optional HOA access to a private boat ramp and kayak launch perfect for sunset cruises, paddleboarding, or spontaneous days exploring Sarasota Bay. Just minutes away, enjoy the world-renowned shores of Siesta Key, the vibrant arts, dining, and culture of Downtown Sarasota, plus the boutique shopping and neighborhood charm of The Landings and Gulf Gate Village. More than a duplex, this is a lifestyle investment where location, versatility, and coastal elegance come together. Live beautifully. Earn effortlessly. Expand when the time is right. Own your piece of Sarasota magic in Southpointe Shores.
Listing Agent: Mark Klecka (941-348-9400)
3363 CROSS CREEK DR #3363, SARASOTA, FL 34231
$279,00085 Days on yellowkey MLS ID: A4680117
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1984Monthly Fee: $632 Tax: $2,727 (2025)Community: Crooked Creek Sec 7Condo
Taxes:$2,727
Remarks: Welcome to Crooked Creek, a hidden gem in Sarasota with its own private gated access to the Red Bug Slough Preserve. This beautifully maintained 2-bedroom, 2-bath 2nd floor residence was completely updated in 2021 and offers serene views of Crooked Creek, a charming wooden bridge, and lush park-like surroundings. The open and airy floor plan features hardwood floors and tile throughout, plantation shutters, a skylight at entry, and modern finishes. The updated kitchen includes white cabinetry, solid surface countertops with a large peninsula, tile backsplash, smart stainless steel appliances ( fridge and dishwasher 2025, oven and microwave 2021), a spacious pantry, and a garden window. Additional updates are water heater 2018, and reverse osmosis for kitchen sink 2025. The primary suite enjoys peaceful water, a walk-in closet, linen closet and sliding doors to a covered screened lanai. The updated bath has a washer/ dryer (2021)in separate laundry closet, as well as tile floors, a modern vanity, and tile shower . The guest bedroom offers flexible use with a built-in workstation and queen-size Murphy bed. Additional features include two screened covered lanais, reverse osmosis water system for kitchen sink, covered carport, and ample guest parking. Crooked Creek is a 78-unit community offering a heated resurfaced pool, updated poolside kitchen, gazebo with seating, gas and charcoal grills, tennis/pickleball court, community storage with individual lockers, newer roofs (2021), new carports, and recently painted buildings. HOA fees have been reduced by $69 per month from 2025, reflecting strong reserves and excellent financial management. Conveniently located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, and dining. A true nature lover’s paradise.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
1552 STICKNEY POINT RD #403, SARASOTA, FL 34231
$695,000470 Days on yellowkey MLS ID: A4634781
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982Monthly Fee: $1,007 Tax: $4,591 (2024)Community: The BoatyardSpa: NoCondo
Taxes:$4,591
Remarks: The Boatyard is a New England styled gated community of twenty one units located on the Intracoastal Waterway just across the south bridge from Siesta Key and its number one rated beach. Nearby are numerous opportunities for the shopping, dining, sports, and cultural activies that Sarasota is famous for. This furnished two bedroom, two bath unit features water views from most rooms, a bright open concept living/dining room with a tray ceiling and wood burning fireplace, an enclosed balcony overlooking a canal, updated kitchen and bathrooms, an oversized one car garage, and a ground level bonus room off the canal. In addition, the community amenities include a sundeck on the intracoastal waterway, a boardwalk along the canal, and a heated swimming pool. This is the Florida lifestyle you've been looking for.
Listing is courtesy of: ALAN J STEVENS (941-925-1818)
Listing Agent: Murphy Stevens (941-925-1818)
3541 WILKINSON WOODS DR #40, SARASOTA, FL 34231
$289,900157 Days on yellowkey MLS ID: A4672490
REDUCED by $5,000 (1.7%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1980 Tax: $3,658 (2025)Community: Wilkinson WoodsVilla
Taxes:$3,658
Remarks: One or more photo(s) has been virtually staged. Skip the renovation stress and discover an UNBEATABLE VALUE in this updated 2-bedroom, 2-bath attached villa, offering IMPACT WINDOWS, New A/C (2026) and NEWER APPLIANCES. Bathed in natural light, this home features elegant QUARTZ COUNTERTOPS throughout, designer LED-illuminated mirrors, and sleek, durable laminate flooring. Beyond the stylish interior lies a charming paver patio—a relaxing retreat for morning coffee or sunset breezes. Located in an enclave that feels like a hidden secret in South Sarasota, you are minutes from Siesta Key’s white sands, casual and world-class dining, entertainment...but miles from the stress of a fixer-upper. Experience just how effortless Florida living can be by taking this stylish, move-in-ready villa off your screen and scheduling your in-person tour today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Elisa Gersman (941-735-0595)
5800 TIDEWOOD AVE, SARASOTA, FL 34231
$3,149,000218 Days on yellowkey MLS ID: A4664806
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5167 Built: 2000 Tax: $25,244 (2024)Community: Baywood Colony Westport Sec 2Spa: YesSingle Family
Taxes:$25,244
Remarks: Welcome to ‘The Retreat at Tidewood’, a boater’s paradise nestled in one of Sarasota’s most desirable and secluded waterfront communities. Imagine living just minutes from downtown, fine dining, and shopping, all without the hassle of an HOA. This home offers the perfect blend of convenience and tranquility for those who love life on the water. Elevated 12 feet, this residence ensures peace of mind protection from flooding. Step inside to discover an updated gourmet kitchen with custom cabinetry and premium finishes, a spacious living and dining room, and a luxurious master suite with Venetian Plastering and his-and-hers closets. Every room on the ground floor opens directly to the pool, creating a seamless indoor-outdoor flow to over 2,500 sq. ft. of screened outdoor living — perfect for entertaining or relaxing in total privacy. For the avid boater, the property features a concrete seawall for easy canoe or kayak launching, making it effortless to explore the serene Intercoastal Waterway. Additionally, a boat yard just a short distance away accommodates larger watercraft and offers concierge services, ensuring your boating adventures are always within reach. Upstairs, a private “in-law suite” is accessible by elevator or stairs and includes three flexible rooms, full bath with tub/shower combo, kitchenette, a large walk-in closet, room to add an additional bathroom, and a screened porch overlooking the tranquil waterway, Siesta Key, and timeless sunsets. Surrounded by protected mangroves, the views are as peaceful as they are timeless. Designed for multi-generational living or hosting guests with ease, this home blends thoughtful functionality with waterfront luxury. Its location combines seclusion and convenience — tucked away in a peaceful community, yet close to everything Sarasota has to offer. The adjacent lot could also be purchased for additional acreage, offering even more space and potential. The ‘Retreat at Tidewood’ offers a once-in-a-lifetime opportunity to own a piece of paradise. This unique experience awaits you with the perfect blend of comfort, privacy, coastal beauty, and a lifestyle tailored for those who cherish the water.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Nancy Grenier (941-364-4000)
1621 MEMORY LN, SARASOTA, FL 34231
$3,980,000108 Days on yellowkey MLS ID: A4677041
Bed: 5 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 4626 Built: 2027 Tax: $16,466 (2025)Community: Not Part Of A SubdivisionSpa: YesSingle Family
Taxes:$16,466
Remarks: Pre-Construction. To be built. 1621 Memory Lane presents a rare opportunity to build a custom bayfront estate on Little Sarasota Bay in the Bayview Acres neighborhood, one of Sarasota’s most strategically positioned mainland waterfront communities. Situated on a quiet no-through street south of Stickney Point Road and west of Tamiami Trail, this expansive .47-acre parcel offers approximately 100 feet of direct frontage on the bay and the scale to design a significant coastal residence with generous outdoor living areas, pool, and the ability to construct a private pier, subject to permitting. The property is offered as a vacant lot for $1,480,000 or as a to-be-built custom residence by The Vision Group priced at $3,980,000, providing flexibility for buyers to bring their own builder or move forward with a fully designed plan. The setting delivers privacy and calm while remaining just minutes from the south bridge to Siesta Key and equally convenient to downtown Sarasota’s dining, arts, and cultural amenities. Continued investment along the U.S. 41 and Siesta Drive corridor, including Benderson’s planned retail and mixed-use development, further strengthens the long-term appeal of this location. The property is especially well suited for buyers transitioning off the barrier islands who want mainland accessibility without sacrificing water views, as well as inland residents ready to elevate to a true bayfront setting without HOA constraints. With limited remaining buildable bayfront parcels of this size and frontage—and new construction next door on a comparable lot estimated at $6 million in value—the economics present a compelling opportunity to build at a meaningful discount to neighboring new construction.
Listing Agent: Daniel Treiman (917-657-7495)
208 SOUTHWINDS DR, SARASOTA, FL 34231
$74,9003 Days on yellowkey MLS ID: A4690882
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 459 Built: 1966Monthly Fee: $195 Tax: $1,160 (2025)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,160
Remarks: Welcome to an incredible opportunity in the highly desirable Southwind's 55+ co-op community, ideally located in the heart of Sarasota just minutes from the world-renowned Siesta Key Beach. Whether you’re searching for a full-time residence, seasonal getaway, or investment opportunity, this property offers exceptional value in an unbeatable location. This one-bedroom, one-bath residence features a spacious and functional layout with abundant natural light throughout. The living area flows nicely, creating a comfortable and inviting space to relax or entertain. One of the standout features is the oversized lanai; perfect for enjoying the Florida lifestyle year-round and easily serving as additional living space. The home also offers a private driveway, a dedicated laundry area located in the shed, and ample storage space. While the unit could benefit from some updating, it is priced accordingly, presenting a fantastic opportunity to customize and make it your own. With a little vision, this property has the potential to truly shine; making it especially appealing for investors or buyers looking to add value. Located in an X flood zone, this property has had no flood or water damage from recent storms, offering added peace of mind. Southwind is a vibrant and friendly community known for its active lifestyle and impressive amenities, including a heated pool, shuffleboard courts, horseshoe pits, library, and recreation hall. The community also offers guest parking along with designated areas for RV and boat storage. With low monthly fees of just $195, which include water, sewer, cable, and lawn care, it’s one of the best values in Sarasota. Conveniently located just 10 minutes to Siesta Key, 20 minutes to downtown Sarasota and UTC Mall, and close to shopping, dining, and everything South Sarasota has to offer. Affordable opportunities like this in such a prime location are rare. Priced to sell and offered as-is with the right to inspect; don’t miss your chance to make this your own slice of paradise.
1680 STARLING DR #101, SARASOTA, FL 34231
$345,00050 Days on yellowkey MLS ID: A4684814
1 Days Off yellowkey (back on 3/24/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1712 Built: 1989Monthly Fee: $167 Tax: $4,502 (2024)Community: Landings South ViiCondo
Taxes:$4,502
Remarks: Under contract-accepting backup offers. Coveted end unit. Preserve views. Gulf Coast living at its finest. This ground-floor end unit coach home delivers the rare combination of privacy, natural light, and effortless indoor-outdoor living. South and west exposures bathe the space in sunshine, while serene preserve views set the backdrop from both the enclosed lanai and the expanded paver patio, ideal for relaxing or entertaining under the Florida sky. Inside, an open-concept layout connects the living and dining areas with the kitchen and flows seamlessly out to the lanai. Luxury vinyl flooring runs throughout, complemented by a white kitchen featuring raised panel cabinetry, decorative tile backsplash, solid surface counters, and a full stainless appliance package. The neutral palette is move-in ready. A split-bedroom floor plan ensures maximum privacy for owners and guests alike. The primary suite offers a generous bonus space perfect for a home office, along with an en-suite bath featuring an expansive shower and walk-in closet. The guest bedroom and bath create a welcoming retreat for visitors. Completing the home: a dedicated laundry room and single-car garage. Larger dogs are welcome; a rare find. Whether you're downsizing, snowbirding, or simply ready for a more relaxed pace, this home checks every box.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
2544 ORSOVA WAY, SARASOTA, FL 34231
$499,000188 Days on yellowkey MLS ID: A4668849
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1545 Built: 1964 Tax: $4,430 (2023)Community: Phillippi Gardens 14Single Family
Taxes:$4,430
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT TO $499,000. SELLER LOOKING FOR OFFERS!!! This amazing property is nestled in a highly sought-after South Sarasota location. It is located off Constitution Blvd. just south of Proctor Road. This unique location provides serenity and privacy yet close to endless dining options and shops. Located just 1 mile from Siesta Key’s world-renowned beaches! It’s a place where luxury meets practicality, creating a perfect balance for modern living. This cozy home is equipped with modern WALL TO WALL TILE, an upgraded SECOND BATH with no expense spared, a large heated pool (RECENTLY resurfaced), newly RESCREENED pool cage, a BRAND NEW ROOF ( FALL 2025) with 15 year warranty, new hurricane windows (FALL 2025), and lastly an over-sized two-car garage. One side of two-car garage is currently using a portion for a game room/ storage/office and can continue to be utilized in this manner or SELLER will remove the walls at buyers request to revert back to the standard garage. NEW PAINT and landscaping complete this wonderful home making it ready to call your own. It’s an ideal setting for hosting gatherings and creating unforgettable memories with friends and family. No HOA, no deed restrictions and no CDD. Some photos are virtually staged.Seller is updating MASTER BATH please be patient and cautions as work is in progress.
Listing is courtesy of: D'AGOSTINO REAL ESTATE CONSULTING LLC (941-320-0044)
Listing Agent: Kenneth Dagostino (941-320-0044)
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