Location: Sarasota
Do Not Show Listings
2111 FAIRFIELD AVE, SARASOTA, FL 34232
$349,90016 Days on yellowkey MLS ID: O6414126
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1166 Built: 1978 Tax: $3,813 (2025)Community: Sarasota SpgsSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,813
Elementary School: Brentwood Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: This charming 3-bedroom, 2-bathroom single-story home offers a highly functional, stairs-free layout that ensures broad, long-term market appeal. The heart of the home features an efficient kitchen beautifully equipped with a sleek suite of stainless steel appliances, perfectly paired with durable, low-maintenance laminate countertops. Moving through the residence, the private quarters serve as a warm and quiet retreat, with plush carpeting in all the bedrooms to provide maximum comfort and sound dampening underfoot. Complete with an attached 1-car garage that provides secure parking and excellent extra storage space, this classic ranch-style home is designed for easy, comfortable living.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
221 DADE AVE, SARASOTA, FL 34232
$575,00016 Days on yellowkey MLS ID: A4696280
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1534 Built: 1978 Tax: $1,790 (2025)Community: Greers Homeland RepSpa: NoSingle Family
Taxes:$1,790
Elementary School: None
High School: None
Middle School: None
Remarks: 221 DADE AVE. 4bd/2ba $575,000 4 bedroom, 2 bath home features an extra large circular driveway and sits on 1/3 of an acre. No deed Restrictions with plenty of room to build out and/or park vehicles, RV and boat. This one of a kind built home on a cul-de-sac has been fully remodeled inside and out. The house opens to a vaulted ceiling in the large living area and features a tongue in groove ceiling in cedar. Most renovations have been completed in the last 5 years. Brand New Oversized European Eat -In Kitchen with finished cabinet interiors and granite countertops. Mined Stone Slate tile from India throughout. 4th bedroom can be an office or den with coordinated laid stone tile work. Ikea and Floor and Décor Remodeled bathrooms and New Carpeting and new plush padding in all the bedrooms, New Modern Hunter Ceiling fans in every room and 3 fans outdoors in the screened pool lanai. Double walk in closets in the Master and Easy entry walk-in shower with floating glass wall and waterfall showerhead. New woodwork, carpentry and fixtures throughout. New Windows and Upgraded window coverings for all windows and sliding doors included for immediate privacy in this like new home built perfectly for a family. Newly completed $7,000.00 garage remodel with new ceiling and epoxy flooring. New pool surface and New pool cage 2022. Roof is less then 10 years old and a brand new electrical panel replaced with room on the panel for additions. Features a new Kinetico whole home water purification system and RO purified water in the kitchen. Kitchen Sliding doors to the pool and patio with room for an outdoor kitchen. The home comes equipped for RV hookup on the side of the house. Expansive backyard with landscape built out like the start of a tropical sanctuary. A hundred species of birds have visited the creek at the back end of the property. Home sits minutes from right between Downtown Sarasota and UTC. 14 blocks to the oceanfront, 3 miles to Lido Beach. Upgrades do not reflect on the appraisal. This is not a cookie cutter house with plastic floors and discount cheap material updating. House is solid and built with higher standards. Like stepping into Florida life with a beautifully appointed home for parties and entertaining. Home is move in ready, meticulously clean. Some furnishings may be left for an additional price and at the buyers request. No Lowball offers. Cash Buyers Welcome.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
2119 & 2125 MONTCLAIR DR #1 & 2, SARASOTA, FL 34231
$990,00016 Days on yellowkey MLS ID: A4696057
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 4972 Built: 2007 Tax: $4,981 (2025)Community: Montclair VillasApartment
Taxes:$4,981
Remarks: Montclair Villas offers a rare opportunity to own a 2007 masonry construction duplex in the Coquina Island area, just minutes from Siesta Key. The property features two spacious, two-story 3-bedroom / 2.5-bathroom units, each with an open living area, tile flooring, sliding glass doors, recessed lighting, decorative tray ceiling with crown molding, private swimming pool, screened patio, private yard, and two-car garage. Each unit also includes spacious bedrooms with decorative tray ceilings, crown molding, recessed lighting, and ceiling fans. All utilities are separately metered and paid directly by tenants, helping reduce owner-paid expenses. Additionally, each unit and the common area have separate parcel IDs, offering potential future flexibility through an individual condo sell-off strategy. Given its proximity to Siesta Key, the property may also be well-positioned for potential vacation rental use, providing multiple paths for future ownership flexibility. With quality construction, private outdoor amenities, garage parking, and a highly desirable location, Montclair Villas offers a compelling blend of residential appeal and long-term investment upside.
Listing is courtesy of: THE MULTIFAMILY FIRM LLC (941-444-6160)
Listing Agent: Phil Ginexi (631-404-6060)
1006 DE LEO DR, SARASOTA, FL 34243
$325,00019 Days on yellowkey MLS ID: A4696192
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1345 Built: 1972 Tax: $2,416 (2025)Community: Whitfield Country Club Heights Un 5Single Family
Taxes:$2,416
Remarks: Charming and ideally located in Whitfield Estates, this 2-bedroom, 2-bath home offers the perfect blend of character, comfort, and convenience. Inside, you’ll find original wood floors that add warmth and timeless appeal, while major system updates provide peace of mind for years to come. The home features hurricane impact windows and doors, a newer HVAC system, a recently updated water heater, and fully paid-off solar panels that help keep electric costs remarkably low currently averaging less than $40 per month. With 1,345 square feet of living space, the layout is both functional and inviting, making it an excellent option for first-time homebuyers, seasonal residents, or investors seeking rental flexibility. Whitfield Estates allows short-term rentals, creating an opportunity for personal enjoyment and income potential. Location is everything, and this home delivers. Situated just minutes from IMG Academy, Abel Elementary School, Sarasota-Bradenton International Airport, downtown Sarasota, St. Armands Circle, and the area’s world-renowned Gulf Coast beaches, you’ll enjoy easy access to everything that makes Sarasota one of Florida’s most desirable destinations. Sara Bay Marina is also nearby, offering convenient dry dock storage and access to Sarasota’s waterfront lifestyle. Whitfield Estates also offers a voluntary neighborhood association for only $40/year, providing culinary access to the Sara Bay Country Club. Whether you’re searching for a primary residence, winter retreat, or investment property, this charming Whitfield Estates home is ready to welcome its next owner.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Jessie Bonner (941-356-3182)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00058 Days on yellowkey MLS ID: A4690742
2 Days Off yellowkey (back on 6/9/2026)
REDUCED by $35,000 (5.0%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1439 Built: 1960 Tax: $6,132 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,132
Elementary School: Southside Elementary
Middle School: Brookside Middle
Remarks: A rare offering within Sarasota’s desirable South Gate community, this meticulously restored Atomic Ranch embodies the essence of authentic Mid-Century Modern design. Revered as one of the foundational architectural styles of the 20th century, this residence has been thoughtfully preserved and elevated by discerning owners who understood the importance of honoring its original integrity. Ideally positioned in the heart of Sarasota, the home offers effortless access to world-class beaches, premier shopping and dining, top-rated schools, Sarasota Memorial Hospital, and the vibrant downtown district. The residence unfolds with a seamless, open-concept design, featuring three spacious bedrooms and two bathrooms, an inviting eat-in kitchen area, and expansive living areas designed for both comfort and entertaining. Walls of vintage sliding glass doors dissolve the boundary between indoors and out, opening to a generous pool terrace. Both covered and open-air, this creates a true indoor-outdoor lifestyle synonymous with classic Florida modernism. Authentic details remain beautifully intact, including original terrazzo flooring throughout, vintage architectural elements, and curated mid-century finishes that speak to the home’s heritage. An oversized garage, along with substantial fenced exterior space, provides flexibility for additional parking, including room for a boat or recreational vehicles. The home has been featured on Sarasota’s renowned “MOD Tour,” celebrated for its originality and preservation. As noted during the tour, the residence showcases vintage sliding glass walls, vibrant period kitchens and baths, and a fluid connection to the pool area. Carefully selected furnishings that reflect the era enhance the spirit of 1960s design. This is a truly special opportunity to own a piece of architectural history. Thoughtfully restored, exceptionally located, and ready to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
346 ANDROS DR, SARASOTA, FL 34233
$170,00062 Days on yellowkey MLS ID: A4691142
REDUCED by $29,000 (14.6%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 2003Monthly Fee: $178 Tax: $2,425 (2025)Community: Windward IslesManufactured Home
Taxes:$2,425
Elementary School: Ashton Elementary
High School: Riverview High
Middle School: Sarasota Middle
Remarks: WELCOME TO WINDWARD ISLES – ONE OF SARASOTA’S MOST DESIRABLE RESIDENT-OWNED 55+ COMMUNITIES! This WELL-MAINTAINED 2 BEDROOM, 2 BATH DOUBLE-WIDE HOME offers the perfect blend of comfort, convenience, and FLORIDA LIFESTYLE LIVING. Built in 2003 and featuring APPROXIMATELY 930 SQ FT OF HEATED SPACE, this home sits on a nicely sized lot with COVERED PARKING, A PRIVATE DRIVEWAY, AND ADDITIONAL STORAGE SHED. Step inside to find a LIGHT AND BRIGHT FLOOR PLAN with LAMINATE FLOORING THROUGHOUT MAIN LIVING AREAS, a SPACIOUS LIVING ROOM, and a FUNCTIONAL KITCHEN equipped with CONVECTION OVEN, REFRIGERATOR, MICROWAVE, and more. The PRIMARY SUITE includes a WALK-IN CLOSET and EN-SUITE BATH, while the SPLIT BEDROOM DESIGN offers privacy for guests. Enjoy your morning coffee or evening relaxation from MULTIPLE OUTDOOR SPACES INCLUDING A SCREENED PORCH, FRONT PORCH, AND REAR PATIO—perfect for taking in Sarasota’s year-round sunshine. WINDWARD ISLES IS A LAND-OWNED CO-OP COMMUNITY offering residents access to a HEATED COMMUNITY POOL, RECREATIONAL FACILITIES, AND A FULL CALENDAR OF SOCIAL ACTIVITIES. The LOW HOA FEE (APPROX. $178/MONTH) INCLUDES WATER, TRASH, LAWN MAINTENANCE, AND COMMUNITY AMENITIES, making this an EXCEPTIONAL VALUE. Ideally located just minutes from SHOPPING, DINING, MEDICAL FACILITIES, AND WORLD-FAMOUS GULF BEACHES, this property offers both PEACEFUL COMMUNITY LIVING and EASY ACCESS TO EVERYTHING SARASOTA HAS TO OFFER. Whether you're looking for a SEASONAL RETREAT or a FULL-TIME RESIDENCE, this home is a fantastic opportunity to own in a HIGHLY SOUGHT-AFTER COMMUNITY. SCHEDULE YOUR PRIVATE SHOWING TODAY.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Jeff Simpson (941-504-5552)
6266 MIDNIGHT PASS RD #404, SARASOTA, FL 34242
$1,170,00063 Days on yellowkey MLS ID: A4691031
REDUCED by $10,000 (0.8%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1263 Built: 1980 Tax: $10,169 (2025)Community: Excelsior Beach To BayCondo
Taxes:$10,169
Remarks: RARELY AVAILABLE INCOME PRODUCING EXCELSIOR GULF FRONT UNIT This large unit has been completely updated and renovated with Impact windows and new HVAC in 2025, Upgraded kitchen and all appliances, plantation shutters, and Hunter Douglas window shades, in-unit washer/dryer, custom tile throughout, tastefully appointed with fine furnishings and all the accoutrements for the Siesta Beach lifestyle. The under-building covered parking and elevators are conveniently located the spacious gulf front patio is the perfect place to relax and enjoy the fabulous views. Excelsior is your Gulf to Bay resort residence with a Private White Sand Beach, Two Large Heated Swimming Pools, Poolside Restrooms / Hot Water Showers, Shuffleboard, Two Heated Whirlpools, Two Lighted Tennis Courts, Two Pickle Ball Courts, Fitness Center, Large Gulfside Sun Deck, Beach Loungers and Chairs, Lounges & Sunbathing Parapets' Outdoor Barbecues / Picnic Areas, Intercoastal Fishing Pier / Shaded Viewing Area, Community Room and monthly community events', Library' Walk to Shopping, Dining, Bike & Boat Rentals Located just a half mile to the S village shops, dining and marina makes this a great spot to enjoy all the best that world famous Siesta Key has to offer.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Bob Stahlschmidt Ii (941-266-2684)
$1,170,00023 Days on yellowkey MLS ID: A4695534
Bed: 2 Bath: 0.0 Liv Area Sq Ft: 1263 Built: 1980 Tax: $10,169 (2025)Community: Excelsior Beach To BayApartment
918 LA COSTA CIR #3, SARASOTA, FL 34237
$139,900120 Days on yellowkey MLS ID: A4683613
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $5,000 (3.5%) on 05/22/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 865 Built: 1972 Tax: $2,335 (2025)Community: Park ViewSpa: NoCondo
Taxes:$2,335
Elementary School: Tuttle Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Priced to sell, this beautifully furnished 2-bedroom, 1-bath condo is conveniently located just half a mile from Downtown Sarasota’s Main Street and only 4 miles to Lido Beach and St. Armands Circle. Perfect for a second home to escape those cold winters, or make it an investment property ready to rent and produce income, if you have 1031 exchange the sellers are ready to accomodate a quick closing, or make it your primary residence, you can't find a better priced condo this close to all downtown Sarasota has to offer as well as it's close proximity to the world famous white sandy beaches of Siesta Key and Lido. Situated in a secure gated community with a serene, park-like setting, residents enjoy access to two community pools (one heated), a community room with full kitchen, and a well appointed exercise room. The condo is being sold **fully furnished**, offering an easy move-in experience in one of Sarasota’s most convenient locations. The kitchen and bathroom have granite counter tops. The water heater was replaced within the past year. Don’t miss this opportunity! HOA includes water/sewer/trash and exterior maintenance.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Julie Kell (330-309-7022)
4396 WOODMANS CHART #146, SARASOTA, FL 34235
$347,00096 Days on yellowkey MLS ID: A4686620
REDUCED by $28,000 (7.5%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1551 Built: 1977 Tax: $3,023 (2025)Community: Woodmans Chart - The MeadowsVilla
Taxes:$3,023
Remarks: Elegant, delightful and move-in ready with serene pond views! This 3 bedroom, light filled end-unit villa with no shared walls offers the easy, maintenance-free lifestyle buyers are looking for; perfect for enjoying Sarasota year-round or locking up and leaving with peace of mind. Even better, the big-ticket items are already taken care of: 2025 exterior paint, 2024 roof, 2022 A/C and water heater. A private atrium, vaulted ceilings, transom windows, and an open floor plan create a bright, airy feel from the moment you enter. You’ll love the stone-look tile flooring, no-popcorn ceilings, and beautifully updated kitchen with solid-wood cabinetry, Santa Cecilia granite countertops, stainless-steel appliances, and breakfast bar. The oversized screened lanai overlooks peaceful wooded and pond views—ideal for morning coffee, relaxing, entertaining, or birdwatching. Additional highlights include an interior laundry room, abundant storage in the stand-up attic, an oversized two-car garage, block construction, and a desirable Flood Zone X location above the flood plain. Homes with this combination of privacy, updates, views, and maintenance-free convenience are hard to find; don’t miss it! All in The Meadows, a sought-after 1,600-acre park-like community just 15 minutes from downtown Sarasota. Residents enjoy 14 miles of scenic trails and access to a fitness center, Junior Olympic pool, pickleball, golf, and Har-Tru tennis. You’ll also be minutes from award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, the Legacy Trail, Mote SEA Aquarium, the future Sarasota Orchestra Music Center, and University Town Center’s shopping, dining, and entertainment. A fabulous Florida lifestyle awaits!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Fernando Viteri, Pa (941-400-7676)
830 HAMMOCKWOOD CT, SARASOTA, FL 34232
$500,00054 Days on yellowkey MLS ID: A4691916
3 Days Off yellowkey (back on 6/8/2026)
REDUCED by $50,000 (9.1%) on 05/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2131 Built: 1986Monthly Fee: $65 Tax: $6,286 (2025)Community: Woodland ParkSingle Family
Taxes:$6,286
Elementary School: Fruitville Elementary
Remarks: Under contract-accepting backup offers. -Rare one-story, cul-de-sac lot backing directly to a private nature preserve — one of Woodland Park’s most secluded settings. -Upon entering you will find vaulted ceilings, rich Brazilian cherrywood floors, and walls of windows that frame preserve views from nearly every room. -A wood-burning fireplace and custom staircase anchor the main living area, while skylights flood the space with natural light throughout the day. -The outdoor living is equally impressive — a private covered and screened pool deck creates a year-round retreat that’s as suited for quiet mornings as it is for entertaining. -Recent updates include a BRAND-NEW ROOF and a replacement AC system installed in 2024, so the big-ticket items are already handled. -Low HOA fees of just $65/month. -Woodland Park — oak-canopied streets, nature preserve access, and Old Florida character that’s increasingly rare to find.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Barry Brodsky (941-313-4590)
4913 ALMANZA AVE, SARASOTA, FL 34235
$419,90034 Days on yellowkey MLS ID: A4694051
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1640 Built: 1980 Tax: $3,822 (2025)Community: De Soto LakesSingle Family
Taxes:$3,822
Elementary School: Emma E. Booker Elementary
Remarks: Ideally located near shopping, dining, the new Mote Marine Aquarium at UTC and the Sarasota-Bradenton International Airport, this move-in ready home offers the perfect blend of comfort, convenience, and freedom. Just minutes from Nathan Benderson Park with miles of walking and biking trails, kayaking, rowing, and year-round community events. Enjoy true Florida living with NO CDD fees, NO HOA fees, NO deed restrictions, and NO flood insurance required — not located in a flood zone. Bring all your Florida toys with plenty of room for your RV, boat, jet-skis, and more! This spacious 3-bedroom, 2-bath split floor plan features both living & family rooms, an updated kitchen & bathrooms and a private primary suite with walk-in closet and en-suite bath. Recent major updates include a NEW roof and NEW AC in 2026, NEW hot water heater 2020, plus repiping completed in 2020 for added peace of mind. Step outside to the lanai overlooking a large fenced backyard — perfect for entertaining or pets. Complete with a 2-car garage and centrally located near Sarasota’s best amenities, this property is ideal for full-time residents, seasonal owners, or investors alike.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Mike Bridges (941-316-6530)
2839 OLYMPIC ST, SARASOTA, FL 34231
$426,000141 Days on yellowkey MLS ID: A4680914
REDUCED by $13,900 (3.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1955 Tax: $2,877 (2025)Community: Sarasota Venice Co 09 37 18Single Family
Taxes:$2,877
Remarks: Beautiful!! Completely rehabbed with nice finishes throughout,New Ac and much more , this move-in-ready home offers modern updates, quality craftsmanship, and a bright, welcoming interior. Ideally located near top Sarasota schools, shopping, and dining, and just minutes from Siesta Key Beach, this property delivers both comfort and convenience in one of Sarasota’s most desirable areas. The neighborhood features new construction homes selling at significantly higher prices, making this an exceptional value. Enjoy a spacious, fully fenced patio—including the front yard—for absolute privacy, with plenty of room for an RV, multiple vehicles, or a boat. Schedule your showing today and explore the possibilities for yourself.
Listing is courtesy of: GENESIS JC REALTY LLC (941-281-8829)
Listing Agent: Juan Reyes (941-281-8829)
3543 65TH AVENUE CIR E, SARASOTA, FL 34243
$323,00034 Days on yellowkey MLS ID: A4694314
REDUCED by $6,000 (1.8%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1211 Built: 1988Monthly Fee: $29 Tax: $2,737 (2025)Community: Centre Lake SubSpa: NoSingle Family
Taxes:$2,737
Elementary School: Kinnan Elementary
High School: Southeast High
Middle School: Braden River Middle
Remarks: Welcome to this charming 3 bedroom home featuring an open floor plan and inviting indoor-outdoor living spaces. Once you walk in, you'll appreciate the seamless flow between the living room, dining room, and kitchen, while the vaulted ceiling creates a bright and airy feel throughout the main living area. Enjoy Florida living from both the screened lanai and adorable screened front porch - perfect for relaxing with morning coffee or unwinding in the evenings. Additional features include a newer roof, washer, dryer, stove, and dishwasher. With an HOA of only $350/year, you'll enjoy affordability along with convenience and charm. Ideally located just 6 miles from both downtown Bradenton and Sarasota, 8 miles from Lido Beach and St. Armands Circle, and only 5 miles from all of the shopping and dining at UTC—this home offers an amazingly convenient location while still feeling like a peaceful retreat. Full of character, this home is ready for its next owner to add their personal touches. **This property qualifies for a Lender Credit of 1% Discount Point that can be used towards closing costs or buying down the rate if using preferred lender. Inquire for more details** Schedule your showing today!
Listing Agent: Kristy Gentile (941-720-6699)
7549 WESTMORELAND DR, SARASOTA, FL 34243
$549,000112 Days on yellowkey MLS ID: A4684919
REDUCED by $20,000 (3.5%) on 06/08/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1410 Built: 1956Monthly Fee: $3 Tax: $2,912 (2024)Community: Whitfield Estates Unit 1Single Family
Taxes:$2,912
Tax Year: 2024
Remarks: West of the Trail in Whitfield Estates, this mid-century gem captures the charm and character that define classic Florida architecture. From the original terrazzo floors to the preserved kitchen design, the home reflects the clean lines and simplicity that make mid-century residences so desirable. The spacious great room with fireplace serves as the heart of the home, offering natural light and comfortable gathering space while maintaining its authentic architectural appeal. Situated on a rare double lot, the property offers exceptional flexibility and long-term potential. Expand the footprint, design a custom pool, add a detached garage, or simply enjoy the privacy and space that are increasingly rare west of the Trail. Located on sought-after Westmoreland Drive, just across from multi-million-dollar bayfront estates, this property blends historic charm with premier positioning. Residents of Whitfield Estates have the unique opportunity to enjoy dining at nearby Sara Bay Country Club. For an optional annual HOA fee of just $35, owners may obtain a culinary membership granting full access to the clubhouse for dining and social events (golf privileges not included; membership subject to club approval). Minutes to Sarasota Bay, IMG Academy, SRQ Airport, and downtown Sarasota — this is authenticity, land, and lifestyle in one of the area’s most established West of the Trail neighborhoods.
Listing Agent: Lisa Kartz (941-587-3602)
4306 MADEIRA CT #3335, SARASOTA, FL 34233
$269,00048 Days on yellowkey MLS ID: TB8506253
REDUCED by $20,999 (7.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1998Monthly Fee: $418 Tax: $2,555 (2025)Community: Casa Del Sol SarasotaSpa: NoCondo
Taxes:$2,555
Middle School: Oak Park School South
Remarks: AMAZING AND RARE OPPORTUNITY TO OWN A FIRST FLOOR END UNIT WITH NO STAIRS!!! THIS APARTMENT AT 4306 MADEIRA CT UNIT 3335 SARASOTA FL 34233, FEATURES 2 BEDROOMS 2 BATHROOMS AND 1083 SQFT, FULLY RENOVATED WITH MARBLE COUNTERTOPS, CALACATTA FLOORS, SPACIOUS CLOSETS. LAUNDRY WITH BRAND NEW APPLIANCES. JUST 10 MINUTES AWAY FORM FLORIDA FINEST BEACHES AND NATIONWIDE FAMOUS SIESTA KEY BEACH, CLOSE TO SHOPPING, RESTAURANTS, GOLF COURSES, THE HOSPITAL, DOWNTOWN, SARASOTA AIRPORT, AND 5 MINUTES AWAY FROM UTC MALL. ONLY ONE MILE AWAY FROM EXIT 207 OF I 75, THE ASSOCIATION IS A PET FRIENDLY COMMUNITY, ADMIRAL WALK IS FULLY GATED COMMUNITY, WITH SECURITY ENTRANCE. HOA HAS RESONABLE FEES THAT ALSO INCLUDES WATER & SEWER UTILITY. THERE IS A LOVELY CLUB HOUSE WITH LAKE VIEW, POOL AND SPA, FITNESS ROOM, BATHROOMS, GAME ROOMS AND TENNIS COURT. CALL TODAY FOR A SHOW, YOUR IDEAL HOME AWAITS!!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Karelys Diaz (813-997-6775)
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00095 Days on yellowkey MLS ID: A4687031
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2217 Built: 1998Monthly Fee: $1,985 Tax: $13,269 (2025)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$13,269
Elementary School: Phillippi Shores Elementary
Remarks: Under contract-accepting backup offers. Experience endless panoramic views of downtown Sarasota and Sarasota Bay from the climate-controlled balcony of this newly renovated top-floor residence in the gated community of Dolphin Bay on Siesta Key. This spacious condo offers over 2,200 square feet of beautifully updated living space, featuring 2 bedrooms, 2 bathrooms, and a den, all enhanced by vaulted ceilings that create an open and airy coastal atmosphere. Enjoy stunning sunsets over Siesta Key Beach from the front entryway each evening, and wake to beautiful sunrises from the primary bedroom and lanai—an exceptional feature of this remarkable home. Residents of Dolphin Bay enjoy a true waterfront lifestyle with access to a private community dock, clubhouse, tennis courts, fitness center, and a resort-style pool. A private one-car garage, with epoxy flake floors, is conveniently located just steps from the elevator. Perfectly situated within minutes of the beach, shops, and restaurants, this residence combines luxury, convenience, and the best of Siesta Key living. Enjoy the waterfront lifestyle at its finest in this exceptional move-in-ready home. Contact me for a private showing today.
Listing Agent: Maryana Zilinskiy (941-744-6065)
5257 MYRTLE WAY #29, SARASOTA, FL 34235
$290,00091 Days on yellowkey MLS ID: A4687062
REDUCED by $8,500 (2.8%) on 06/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1239 Built: 1981 Tax: $2,584 (2025)Community: MeadowsSpa: NoCondo
Taxes:$2,584
Remarks: Welcome to 5257 Myrtle wood unit 29, a beautifully updated 2-bedroom, 2 bath condo with high ceilings and an open flowing floor plan in a serene setting. This unit includes a covered carport and relaxing private screened walk out porch, overlooking a tranquil pond. Spacious bedrooms, modern finishes, and peaceful views. Enjoy essentially a turnkey property with low maintenance and a focus on natural beauty and relaxing in a desirable private location. Enjoy amenities like a pool, 14 miles of scenic walking trails and still maintain a central location to the UTC area, world class shopping, entertainment and dining. This rare property is 6-8 miles (15-20 minutes) from Famous Lido Beach or Bird Key Park. Making this condo your perfect Florida retreat.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Cg Wolynski (860-671-0026)
2259 PALAZZA DR #78, SARASOTA, FL 34238
$149,900147 Days on yellowkey MLS ID: TB8470014
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 960 Built: 1974Monthly Fee: $190 Tax: $1,523 (2025)Community: Venetian EstatesMobile Home
Taxes:$1,523
Remarks: New Price! This beautifully updated two-bedroom, two-bathroom home, located in the heart of the Venetian Park Estates Mobile Home Community, is move-in ready. The charming décor and open floor plan are perfect for entertaining or relaxing at home. The home is fully furnished, providing everything needed for easy Florida living. Both spacious bedrooms feature private, updated bathrooms. Venetian Park Estates is an active, over-55 community, offering amenities such as a heated pool, relaxing spa, and shuffleboard. The clubhouse features many activities, including Bingo, Trivia, Game Night, Cards and Coffee Socials.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Katie Strand (941-928-1023)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000357 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing Agent: Derek Edwards (941-929-3183)
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