Location: Sarasota , 34239
Do Not Show Listings
1394 HARBOR DR, SARASOTA, FL 34239
$7,750,00077 Days on yellowkey MLS ID: A4682309
REDUCED by $500,000 (6.1%) on 04/21/2026
Bed: 4 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5913 Built: 2004 Tax: $48,224 (2025)Community: Harbor AcresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$48,224
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Presenting a distinguished waterfront estate located in Sarasota’s premier bayfront community, Harbor Acres, widely regarded as the city’s most coveted neighborhood. Perfectly situated on a protected deep-water boat basin, this property offers immediate access to Sarasota Bay with the added benefit of a boat dock and lift on calm waters-ideal for larger vessels. With prized southern rear exposure, the home is bathed in natural light throughout the day, while capturing glowing sunsets across the water — a rare and highly desirable feature for waterfront living. The thoughtfully designed 4-bedroom, 6 bath floor plan offers exceptional flexibility and privacy, with distinct guest wings that function almost as private suites — ideal for hosting extended family, visiting friends, or even live-in arrangements without sacrificing personal space. The seamless flow between formal and casual living areas makes the home equally suited for elegant entertaining or relaxed everyday living. At the heart of the home, the chef’s kitchen features beautiful quartz countertops, island, abundant cabinetry, and premium appliances, opening effortlessly to the family room and outdoor living areas. A striking double-sided gas fireplace creates ambiance between key gathering spaces, enhancing both intimate evenings and larger gatherings. Enjoy the rare luxury of choosing between two primary suites. Both primary suites are serene retreats offering generous proportions, tranquil water views, and a spacious walk-in closets with custom built-ins designed for optimal organization. The spa-inspired baths provides a luxurious escape at the end of the day. Outdoor living is where this property truly shines. A fully equipped summer kitchen anchors the covered lanai, creating the perfect setting for waterfront dining and entertaining. The infinity edge pool, spa and outdoor lounge areas overlook the wide boat basin, where you can watch dolphins pass and boats glide by — all from the comfort of your own backyard.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
2215 DATURA ST, SARASOTA, FL 34239
$1,990,00083 Days on yellowkey MLS ID: A4681704
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2317 Built: 2018 Tax: $22,478 (2025)Community: GreenwichSpa: YesSingle Family
Taxes:$22,478
Remarks: Extraordinary Modern Sanctuary on a RARE DOUBLE LOT with Huge Saltwater Infinity-Edge Pool, Breathtaking Resort-Style Backyard Oasis & Brand-New Outdoor Kitchen! Crafted by Majestik Homes—one of Sarasota’s premier luxury builders—this stunning residence delivers innovative design, exceptional craftsmanship, and true resort-caliber living on one of the most desirable double-lot properties available. Boasting 4 bedrooms and 3 bathrooms with soaring 10-foot ceilings, 8-foot doors, and walls of hurricane-rated impact glass, the open-concept layout flows effortlessly from the chef’s kitchen (quartz counters, soft-close cabinetry, Sub-Zero refrigerator, induction cooktop, and premium appliances) into the expansive great room with perfect sightlines to the front and rear yards. The luxurious primary suite opens directly to the patio via sliding glass doors and features dual custom walk-in closets plus a spa-like bath. Three additional bedrooms offer high-end custom closets (two separated by a stylish barn door), while both guest baths are impeccably finished with frameless glass showers and elegant tilework. Premium upgrades include a new 16 SEER AC system, epoxy garage floors with built-in cabinetry, Tesla charging station, natural gas with generator hookup, auto drapes, architectural uplighting, and a private well for irrigation. The true showstopper is the jaw-dropping resort-style backyard on this rare double lot. Your own private Florida oasis awaits: a huge saltwater infinity-edge pool with integrated gas-heated hot tub — fully self-cleaning and self-draining for effortless year-round enjoyment. The expansive Shellock paver deck (cool-to-the-touch, slip-resistant, and ultra-durable) seamlessly connects to a spectacular just-installed (April 2026) custom outdoor kitchen by Paradise Professional Grills. Step into resort-style living with premium Paradise Professional stainless steel appliances—including a powerful built-in multi-burner grill, 3 outdoor refrigerators, and large stainless sink with protective cover. Finished with elegant Avellaero Stone Italian-engineered countertops, the expansive island offers ample prep and serving space, stainless drawers and cabinets, bar seating with footrest, and is perfectly positioned under the covered pergola with ceiling fan and large screen mounted TV. Overlooking the sparkling infinity pool and lush backyard, this entertainer’s dream is ideal for year-round Florida entertaining and al fresco dining. The entire oasis is fully enclosed by premium 6’ white vinyl privacy fencing and framed by mature tropical landscaping and palms for complete seclusion. A dedicated kids’ play area and large chicken coop add family-friendly charm. The second lot is the ultimate game-changer. With its own separate entrance off Hyde Park, this rare extra parcel offers endless possibilities: build a second garage, casita, home gym, pickleball court, expanded outdoor living area, RV/boat storage — whatever your vision demands. No HOA restrictions means total freedom to create your dream compound. Smartly scaled for low-maintenance living yet delivering an enormous, resort-caliber backyard with unmatched privacy and versatility. Just 1 minute to Sarasota Memorial Hospital, 5 minutes to downtown Sarasota, 10 minutes to Siesta Key, and minutes from top schools, beaches, shopping, and I-75. This is a rare opportunity to own a modern luxury home on a double lot!
Listing is courtesy of: RONNIE DEWITT AND ASSOCIATES (941-755-0011)
Listing Agent: Ronnie Dewitt (941-650-2154)
1775 STAPLETON ST, SARASOTA, FL 34239
$1,545,000183 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
Tax Year: 2024
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)
1541 FLOWER DR, SARASOTA, FL 34239
$1,870,000311 Days on yellowkey MLS ID: A4656365
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3302 Built: 1956 Tax: $7,456 (2024)Community: Harbor AcresSpa: NoSingle Family
Taxes:$7,456
Remarks: This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel was built in 1956 and was originally a 2/2. The original bathrooms are still in their original state and are in good condition providing a cool retro vibe. The original hardwood floors and fireplace exude warmth and sophisticated charm. The current owner purchased the home in 1989 and remodeled the kitchen and added a new wing on the house with 2 additional large bedrooms ensuite with baths. Copious amounts of storage in all 4 bedrooms and a huge laundry room with lots of closet space as well. The garage is oversize and there is a picturesque circular driveway for ample parking. There is plenty of room to put in a pool of your own design. The house was re-roofed in 2018. Some of the most beautiful homes in Sarasota are your neighbors in Harbor Acres. And Flower Drive is a special address with the highly sought after Southside Elementary School just 1-mile away, you can’t beat this property. In real estate it is all about Location, Location, Location. This home has plenty of room for the family, so, come on home!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kathleen Griffin (941-302-3979)
1661 S JEFFERSON AVE, SARASOTA, FL 34239
$1,250,00057 Days on yellowkey MLS ID: A4684656
1 Days Off yellowkey (back on 4/27/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2490 Built: 1953 Tax: $12,131 (2025)Community: Alfred ParkSpa: YesSingle Family
Taxes:$12,131
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. BUYER'S CONTRACT FELL THROUGH. So, back on the market. What a great opportunity! Live where mornings begin with coffee on the wide front porch beneath mature live oaks and evenings end with a swim in your own heated pool and spa, added by the current owner to elevate Florida living. Completely renovated down to the studs in 2021, this move-in-ready, three-bedroom, three-bath Arlington Park pool home with dedicated office, den/sunroom and bonus room blends timeless mid-century charm with modern systems and design. Major upgrades include a 2021 metal roof, newer plumbing, newer electrical wiring and panel, hurricane-rated windows, hurricane-rated garage door, LED lighting and hand-scraped engineered hardwood floors throughout, delivering both beauty and long-term peace of mind. Walls were thoughtfully opened to create bright, flowing living spaces anchored by a stunning Quartzite kitchen featuring an oversized island with seating, solid wood soft-close cabinetry, stainless KitchenAid appliances including under-counter microwave, full-height subway tile backsplash, ample pantry storage, and a built-in Quartzite-topped buffet with glass-front cabinetry and wine refrigerator in the dining area. The spacious living room and adjoining den/sunroom connect seamlessly to the private, fully fenced backyard oasis with multiple seating areas and professional landscaping. The owner’s suite offers a peaceful retreat with spa-style bath, Quartzite counters, glass-enclosed shower and private outdoor lounging deck, while two generously sized guest bedrooms, one ensuite, and two additional fully reimagined baths provide comfort and flexibility. A custom office with Quartzite and wood built-ins supports work-from-home ease, and the large bonus room is ideal for a gym, media room, or play space. Perfectly positioned on a prominent corner lot with circular driveway and side-entry two-car garage, this home is a short distance from Arlington Park and Aquatic Complex featuring a 50-meter lap pool, fitness center, indoor gymnasium, tennis and pickleball courts, basketball courts, playground, dog park and scenic walking trails, and is minutes to Downtown Sarasota’s restaurants, arts and waterfront, Southside Village shopping and dining, Sarasota Memorial Hospital and the world-famous beaches of Siesta Key. For buyers searching for a fully renovated Arlington Park pool home in Sarasota with modern upgrades, walkability and unbeatable proximity to parks, downtown and beaches, look no further.
Listing Agent: Roberta Tengerdy, Pa (941-321-2292)
2082 ORCHID ST, SARASOTA, FL 34239
$434,90014 Days on yellowkey MLS ID: A4690466
REDUCED by $14,100 (3.1%) on 04/24/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1958 Tax: $3,780 (2025)Community: South GateSpa: YesSingle Family
Taxes:$3,780
Remarks: Exceptional opportunity in the heart of Sarasota! Located within city limits, this 3-bedroom, 2-bath home offers a rare advantage with legal short-term rental allowance and an established rental history, making it ideal for both investors and primary homeowners. Offered turnkey furnished, this property is truly move-in or rental ready. Immediately walking in you are greeted with the open kitchen, living room, and dining room. Perfect for entertaining and enjoy a catch up of the day at the beach. The thoughtfully designed split floor plan provides privacy for the owner’s suite and guests, while a dedicated office overlooks the expansive backyard. The large, fenced lot creates the perfect setting for entertaining, complete with an open outdoor space and private jacuzzi for relaxing Florida evenings. Positioned in a highly desirable location, this home is walkable to shopping and dining along Siesta Drive, located within the sought-after Southside School District, and just minutes to downtown Sarasota and world-renowned Siesta Key Beach. Whether you’re seeking a full-time residence, vacation home, or income-producing property, this one offers versatility, location, and lifestyle all in one.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Kari Klein (941-961-7419)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$844,99977 Days on yellowkey MLS ID: A4681333
REDUCED by $19,001 (2.2%) on 04/23/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSpa: NoSingle Family
Taxes:$8,234
Remarks: Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
1642 BAHIA VISTA ST, SARASOTA, FL 34239
$3,995,000206 Days on yellowkey MLS ID: A4667508
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3809 Built: 2025 Tax: $10,995 (2024)Community: Seminole HeightsSingle Family
Taxes:$10,995
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning New Construction by Award-Winning Architect Dan Lear in coveted West of Trail Neighborhood** This meticulously designed luxury home offers the perfect blend of modern elegance and timeless sophistication. Near Selby Gardens, Morton's Market, and Sarasota Memorial Hospital, this exceptional property provides both convenience and style. Spanning over 3,800sqft of living area, this expansive residence boasts four spacious bedrooms, five full bathrooms, a enormous den with terrace, and a dedicated office space, all thoughtfully crafted for contemporary living. The grand, open-concept great room is the heart of the home, seamlessly floating over the pool area with a stunning large corner pocketing glass door that connects the interior to the beautifully landscaped outdoor oasis. The second floor features three guest suites, each with its own private terrace, offering tropical views and tranquility. The home's striking exterior showcases luxurious vein-cut travertine, creating a refined, sophisticated look. This is an extraordinary opportunity to move right in to a worry free one-of-a-kind masterpiece.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Victoria Lear (941-350-1064)
1671 ARLINGTON ST, SARASOTA, FL 34239
$2,995,00057 Days on yellowkey MLS ID: A4684899
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3564 Built: 2026 Tax: $10,197 (2025)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$10,197
Remarks: Located West of Trail, this beautiful new construction five-bedroom, five-and-a-half-bathroom residence captures the essence of Sarasota living. Designed with both comfort and entertaining in mind, the home features expansive sliding glass doors that open the main living areas to a private pool and outdoor gathering space, creating a seamless connection between indoor and outdoor living. Inside, generous living spaces, clean architectural lines, and refined finishes create a warm yet modern atmosphere. The open-concept layout centers around a spacious kitchen and living area, ideal for everyday living while also providing an elegant setting for hosting family and friends. Upstairs, well-appointed bedroom suites give privacy and flexibility, while the primary suite provides a peaceful retreat with a spa-like bath and thoughtfully designed closet space. Every detail of the home has been carefully considered to deliver both functionality and timeless style. Thoughtfully designed for comfort and ease, the property offers a low-maintenance lifestyle that appeals to both full-time residents and seasonal owners looking for a lock-and-leave Sarasota home. Ideally located just minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and the Gulf beaches, the home places you close to the best dining, shopping, and coastal experiences the area has to offer while maintaining the quiet charm that has long made West of Trail one of Sarasota’s most desirable neighborhoods.
Listing Agent: Steven Moore (401-767-7180)
1730 WISCONSIN LN, SARASOTA, FL 34239
$1,650,00032 Days on yellowkey MLS ID: A4687426
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2910 Built: 2024 Tax: $20,687 (2025)Community: BayviewSingle Family
Taxes:$20,687
Middle School: Sarasota Middle
Remarks: New Build. Seller Offering $40,000 Credit at Close. Located West of the Trail, this spacious modern home offers exceptional value in one of Sarasota’s most desirable in-city neighborhoods. Built in 2024, the residence features 4 bedrooms, 4.5 baths, and approximately 2,900 square feet of thoughtfully designed living space. Positioned within city limits, it provides flexibility for rental opportunities (7 Night Minimum) while still delivering a luxury lifestyle just minutes from Downtown Sarasota, Southside Village, and Siesta Key Beach. Close to Sarasota Memorial Hospital and the coveted Southside school district. The home blends clean contemporary design with energy-efficient construction, open living spaces, and seamless indoor-outdoor flow ideal for entertaining. Room for a pool, seller offering $40,000 credit towards pool. With limited new construction available in this area at this price point, it stands out as a strong opportunity for both end users and investors. A rare combination of location, modern design, and long-term value in the heart of Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Keith Kleppinger (941-525-2937)
2440 HILLVIEW ST, SARASOTA, FL 34239
$875,0006 Days on yellowkey MLS ID: A4691422
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1402 Built: 1964 Tax: $6,541 (2025)Community: Hyde Park Heights 2Single Family
Taxes:$6,541
Remarks: Rare opportunity in one of Sarasota’s most sought-after neighborhoods near the hospital district and 1 block from Arlington Park. This oversized ~13,728 sq ft lot offers exceptional potential for redevelopment or renovation, surrounded by multiple newly constructed luxury homes in the $2M–$3M+ range. The existing home features 3 bedrooms and 1 bathroom with large fenced in rear back yard. Home has been updated in side with new paint, new fixtures, and new kitchen quartz counter. Build your dream home, this property offers unmatched upside. Ideally located just minutes to downtown Sarasota, Siesta Key beaches, Sarasota Memorial Hospital, and Southside Village dining and shopping. Large lots in this area are increasingly rare—don’t miss this opportunity to secure a premium homesite in a rapidly transforming neighborhood. Property being sold for land value to build a new custom home.
Listing is courtesy of: AUTHORITY REALTY INC (941-752-0295)
Listing Agent: Jeffrey Wall (941-724-5333)
3310 MINEOLA DR, SARASOTA, FL 34239
$675,000116 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
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)
2155 WEBBER ST, SARASOTA, FL 34239
$315,0008 Days on yellowkey MLS ID: O6401903
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 970 Built: 1954 Tax: $5,099 (2025)Community: South Side ParkSingle Family
Taxes:$5,099
Remarks: Discover a rare opportunity in the heart of Sarasota — a historic 2-bedroom, 1-bath home on a lot offering over 4,700 sq ft of buildable space, priced at $315,000. Whether you're an investor, developer, or end-user ready to build your dream home, this property delivers serious upside. Ideal for a high-end single-family residence or a rent-by-the-room income strategy, the existing structure and generous lot give you the flexibility to execute your vision. Located just minutes from Sarasota Memorial Hospital and the world-famous Gulf Coast beaches, the parcel falls outside most flood plains — sitting in FEMA Flood Zone X — offering peace of mind and reduced insurance costs. Redfin Sarasota Memorial Hospital is less than one mile away, making this an especially attractive location for healthcare workers or medical tourism rentals. The property is situated in the Southgate neighborhood within ZIP code 34239 — one of Sarasota's most sought-after in-town corridors. Don't miss this investor-friendly opportunity in one of Southwest Florida's premier real estate markets.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Antoinette Munroe (786-252-8237)
3363 SHEFFIELD CIR, SARASOTA, FL 34239
$599,999166 Days on yellowkey MLS ID: A4672288
0 Days Off yellowkey (back on 4/25/2026)
REDUCED by $25,001 (4.0%) on 04/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1968Monthly Fee: $17 Tax: $2,925 (2024)Community: Village Green Club EstatesSpa: NoSingle Family
Taxes:$2,925
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. Major price reduction, priced to sell quickly. Experience quintessential Florida living in this spacious, light-filled pool home with a beautiful golf course backdrop—one of the largest pool homes in the highly sought-after Village Green Club Estates at Southgate. Offering over 2,240 sq. ft. of living space, this residence combines comfort, privacy, and classic Sarasota charm. Freshly painted exterior, New AC, The heart of the home is the inviting kitchen, showcasing granite countertops and a full wall of windows overlooking the lanai, sparkling pool, backyard, and golf course beyond. The kitchen flows seamlessly into the dining area/breakfast nook and spacious family room, anchored by a stunning fireplace with mantle. This open-concept layout feels both expansive and cozy—perfect for everyday living or hosting family and friends. A traditional living room and dining room extend from the other side of the kitchen, featuring an oversized sliding glass door that opens directly to the pool area. The split floorplan places the primary suite privately on this side of the home, offering separation from guests or grandchildren. The ensuite bathroom has been recently refreshed, and both bathrooms—as well as all tiled flooring—have been professionally cleaned for a pristine finish. Each bedroom enjoys direct access to the screened lanai and pool through sliding doors, and the second bathroom doubles as a dedicated pool bath for added convenience. The outdoor living area is where this home truly shines. The expansive lanai offers excellent privacy and is ideal for relaxing, entertaining, or simply enjoying the tranquil views. Take a dip in the cage-free 15,000-gallon pool, featuring a new pump and filter. The surrounding deck boasts a no-slip Chattahoochee Stone surface, recently resealed for durability and beauty. A true two-car garage provides ample space for two vehicles, a golf cart, and even extra storage. Residents of Village Green Club Estates enjoy a low HOA fee, **NO CDD fees**, and peace of mind in **Flood Zone X**, outside the 100- and 500-year flood plains. This prime location is just minutes to Downtown Sarasota, world-class beaches, SRQ Airport, and I-75—placing the best of the Suncoast right at your fingertips. Come see why this exceptional home stands out in one of Sarasota’s most established and beloved communities.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lee Brewer (941-724-3448)
1967 BROOKHAVEN DR, SARASOTA, FL 34239
$1,499,00044 Days on yellowkey MLS ID: A4686652
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2957 Built: 1969 Tax: $5,877 (2025)Community: Forest Lakes Cntry Club Estates UnSpa: NoSingle Family
Taxes:$5,877
Remarks: This completely reimagined residence in the desirable Forest Lakes Country Club community offers sweeping views of rolling greens and fairways. Every detail has been thoughtfully upgraded for modern luxury and effortless living. Located near the Legacy Trail, golf, and just minutes from Sarasota‘s vibrant arts, dining, and Gulf beaches, this home blends country club ambience with unmatched accessibility to everything that makes Sarasota exceptional. Step inside to discover a kitchen design for those who truly appreciate the art of cooking and entertaining. Entertaining here is a breeze with the separate bar and private powder room for guests. Custom oak cabinetry pairs beautifully with stunning Taj Mahal quartzite countertops and refined champagne hardware. Top tier, subzero refrigeration, and Bosch double ovens with induction cooktop elevate every meal. The entire home has been transformed including a new HVAC, updated electrical and plumbing systems, stone flooring throughout, and impact rated hurricane windows. Outside the newly upgraded pool and equipment invite you to unwind while soaking in the captivating golf course views. The garage and driveway feature sleek new epoxy flooring. Enjoy peace of mind with the dry elevation of approximately 19 feet, where flood insurance is not required offering financial savings and long-term security. This is more than a home, it’s a lifestyle anchored in quality, convenience and timeless appeal. Every upgrade has been completed with intention, every system refreshed to perform flawlessly for years to come. From the gourmet kitchen to the resort outdoor space, this home is ready to welcome its next chapter. Schedule your private showing and discover what modern Sarasota living truly looks like!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Ann Martin (941-356-7717)
1966 WISTERIA ST, SARASOTA, FL 34239
$3,400,000198 Days on yellowkey MLS ID: A4668324
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3934 Built: 2026 Tax: $9,291 (2025)Community: Desota ParkSpa: YesSingle Family
Taxes:$9,291
Remarks: Set within the coveted West of the Trail enclave, this newly constructed estate is a striking statement of contemporary design and quality craftsmanship. Thoughtfully designed with clean architectural lines and seamless indoor-outdoor flow. Exceptional attention to detail throughout the residence with 4-bedrooms + office/den + bonus loft and 6-bathrooms. European engineered hardwood and porcelain tile flooring, 9-foot interior doors, recessed ceilings and lighting, and a Level 5 wall finish. PGT impact-resistant, Low-E windows and expansive sliding glass doors flood the interiors with natural light. The open-concept great room is a dramatic focal point, featuring a soaring double-height ceiling and a striking slatted wood accent wall. State-of-the-art kitchen with premium Thermador appliance package, custom Studio Luxe cabinetry by Miralis, quartz countertops, and a waterfall island with designer breakfast bar seating. Opening seamlessly to the dining area and covered lanai, creating an ideal setting for entertaining. Large walk-in pantry, dedicated laundry room with Electrolux washer and dryer, elevator-ready storage space, and private office ensure everyday convenience is met with elegance. The main-level primary suite serves as a private retreat, featuring a spa-inspired bathroom and professionally designed, boutique-style custom closet. The second level offers three en-suite bedrooms, each with beautifully finished bathrooms and walk-in closets. Bathrooms are appointed with quartz countertops, LED mirrors, frameless glass shower enclosures, designer tilework, multiple shower heads, built-in niches, and integrated bench seating. A spacious loft lounge includes a wet bar with beverage refrigerator. Two expansive balconies provide additional space for relaxation or entertaining. Enjoy serene moments by the heated saltwater pool and integrated spa, covered lanai with summer kitchen, including grill, sink and refrigerator, and a dedicated poolside half bath. The backyard is fully enclosed with a six-foot privacy fence and includes green space suitable for pets or gardening. The pool area is screen-enclosure ready for year-round enjoyment. Ideally located just minutes from downtown Sarasota, top-rated schools, dining, shopping, and cultural attractions, this exceptional residence offers a rare opportunity to enjoy sophisticated West of Trail living with uncompromising design integrity and quality. Offering a one-year full developer warranty.
Listing Agent: Linda Driggs (941-374-2920)
2632 SUNNYSIDE ST, SARASOTA, FL 34239
$395,0008 Days on yellowkey MLS ID: A4690325
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 1957Monthly Fee: $17 Tax: $4,699 (2025)Community: South GateSingle Family
Taxes:$4,699
Remarks: Charming mid-century modern 3 bedroom, 2 bathroom home with an oversized 2-car garage, located in the established, deed-restricted South Gate neighborhood of Sarasota. Offering classic Florida style, the home features original terrazzo flooring throughout the home with the exception of ceramic tile in the kitchen and a functional layout with a spacious primary bedroom that includes an en-suite bathroom and walk-in closet. The living room features a built-in bookshelf, and an enclosed sunroom offers flexible space for a home office or additional family area. The home retains original features and offers ample storage throughout, plus a bonus workshop suitable for hobbies or projects. Recent updates include AC replacement (2023) a new garage door (2023), and brand-new toilets. Home is connected to county sewer and comes with Hurricane shutters. The optional South Gate Community Association offers access to a community pool and community center, including the architecturally significant Victor Lundy-designed property with events and weekly classes. Located in the highly sought-after Southside Elementary school district and near Southside Village, Sarasota Memorial Hospital, and just minutes to Siesta Key Beach, with convenient access to shopping, dining, and everyday amenities.
Listing Agent: Rachel Harvey (941-726-9300)
3280 SOUTHFIELD LN #804, SARASOTA, FL 34239
$219,900576 Days on yellowkey MLS ID: TB8309229
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 1969 Tax: $2,672 (2023)Community: South Gate Village Green 08Villa
Taxes:$2,672
Tax Year: 2023
Remarks: *UPDATED HOME IN SOUGHT OUT SOUTHGATE VILLAGE GREEN* Recently reduced and move-in ready, this charming villa offers an exceptional opportunity in one of the area's most sought-after 55+ communities. The home features a brand-new kitchen equipped with all modern appliances, fresh new carpeting in halwway and bedrooms, and stylish laminate flooring throughout living areas. A Bright and airy open floor plan complemented by freshly painted interiors and partially updated bathrooms. Residents enjoy convenient access to nearby shopping, parks, and scenic walkways in a relaxing and peaceful ambiance.. Pets welcome (under 20 lbs., subject to approval).
Listing is courtesy of: Y GROUP REALTY (800-386-2830)
Listing Agent: Nancy Yialouris (727-252-3631)
2068 SUNNYSIDE LN, SARASOTA, FL 34239
$895,00029 Days on yellowkey MLS ID: N6143339
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1722 Built: 1953 Tax: $2,984 (2025)Community: Hibiscus Park 1Spa: NoSingle Family
Taxes:$2,984
Remarks: One or more photo(s) has been virtually staged. Get ready to view and call your home in this pristine and immaculate kept move in ready. This stunning Mid-Century Modern residence located in the heart of the highly sought-after Southgate neighborhood! Minutes to Sarasota Hospital and Downtown Sarasota. This beautifully original quality 3-bedroom, 2-bathroom home with one bathroom is a pool bathroom. Original terrazzo flooring, solid wood doors, real wood cabinets and other quality designs with the history craftsmanship still installed of 1953 with updated functionality. As you walk around your home, feel the unique timeless design of a functional kitchen, all appliances included with even a gas stove. Move into your traditional spacious dining area for meals with family and friends. Wonder into the true comfort of an intimate family room, which leads into a spacious filled with natural light Florida room, air condition. Currently as an artist studio with many future possibilities. Open your French doors and seek out to an oversize Pool and lanai and enjoy a beautiful outside sanctuary retreat at the comfort of your home. But it does not end there. Walk out beyond your lanai to your well-kept private landscaping. Total property sits on 0.349-acre lot. Seamlessly blends timeless design with modern luxury and functionality. Step inside again and view your spacious master bedroom with two additional bedrooms. Recent upgrades provide peace of mind and exceptional value, including hurricane-impact windows, new roof installed in 2019. Recently re-plumbed and new water heater. This type of quality home is unmatched. Enjoy the freedom of no HOA fees while being conveniently located all of what Sarasota offers. This home is timeless quality with of style, comfort, and location in one of Sarasota’s most desirable neighborhoods. Schedule your private showing today and experience Southgate living at its finest.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Lenny Lesaltato (941-350-9238)
3020 HAWTHORNE ST, SARASOTA, FL 34239
$299,99080 Days on yellowkey MLS ID: N6142724
1 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1404 Built: 1962 Tax: $1,178 (2025)Community: Cottage In The PinesSingle Family
Taxes:$1,178
Remarks: Under contract-accepting backup offers. Cottage in the Pines, Great starter, downsizer or investment property. Florida Ranch in Quiet Well Established Neighborhood. Home features Comfortable living spaces, Open floor plan and is Move in Ready. Large Primary bedroom features newer wood plank flooring with lots of storage space and office nook. Newly finished 16X11 Bonus room makes a great Workshop or possible 3rd bedroom. Functional kitchen is a clean slate ready to update at new owners preference (price reflects). House updates include; Re-plumbing with PVC, Windows, Exterior door, Main Roof 2021, Flat roof with drip edge, Landscaping, Shell driveway, Storage shed, Septic and Drain field, Water filtration system. Conveniently Located in sought after Sarasota, just outside City limits for lower taxes and less restrictions. Nearby international airports, medical, vibrant downtown, Siesta Key and St Armands Circle.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Lauren Ward (941-875-0023)
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