Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
5295 ASHTON PINES LN, SARASOTA, FL 34231
$445,00097 Days on yellowkey MLS ID: A4678123
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1495 Built: 1987 Tax: $4,212 (2025)Community: Ashton PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,212
Elementary School: Wilkinson Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to Ashton Pines, a community of 11 homes conveniently located to everything Sarasota has to offer. The updates in this home are dramatic featuring an open floor plan with volume ceilings in the great room. The expansive kitchen has upgraded cabinets & appliances with marble(yes, MARBLE) counter tops. There is a spacious breakfast area. The expansive primary bedroom has volume ceilings and a large half round window for amazing natural light. In addition to a 7 x 5 walk in closet, there is an upgraded private bath. The oversize shower stall has 2 shower heads, one a rain shower. There is a private courtyard with a sliding glass door that brightens the whole room. The split plan has two bedrooms on the north side of the home along with the main bath. The kitchen, living room, & primary bedroom all have sliders to access the screened lanai and rear yard. The laundry room offers additional storage and access to the 2 car garage. The access to Siesta Beach(2 miles), I75(5 miles),and any shopping or restaurants on Clark Road & Tamiami Trail is available with a quick drive. This is a great location for a primary home, secondary home, or an investment property.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larry Brzostek (941-993-3125)
862 HUDSON AVE #862, SARASOTA, FL 34236
$925,000157 Days on yellowkey MLS ID: A4673143
REDUCED by $25,000 (2.6%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1362 Built: 1989 Tax: $10,348 (2025)Community: Hudson LandingsSpa: NoCondo
Taxes:$10,348
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: Located in Sarasota's coveted west-of-the-trail, canal-front enclave of Hudson Landings, this property offers a rare ground-floor residence with a deeded dock and direct bay access. Built in 1989 and spanning 1,362 square feet, this thoughtfully updated home features three bedrooms and two full baths, ideal for year-round living or a seasonal coastal retreat. An open layout connects the kitchen; featuring stainless steel appliances, granite countertops with seating opening to a spacious living and dining area highlighted by high ceilings and abundant natural light. The primary suite overlooks the bayou and pool area, creating a peaceful waterfront backdrop. Two additional bedrooms provide flexibility for guests, a home office, or a den. A screened patio captures soft southern light and frames a direct view of the water perfect for morning coffee or winding down in the evenings. Hudson Landings, an intimate community of just 12 residences, offers a heated pool, lush landscaping, and unbeatable proximity to downtown Sarasota, the marina, Marie Selby Botanical Gardens, and Southside Village. Notable upgrades include hurricane-rated windows and sliders, updated kitchen and bathrooms, a detached garage and boat-friendly amenities. This residence delivers the best of Sarasota living: downtown convenience in a quiet residential neighborhood paired with effortless waterfront access. Book your showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
1404 KENILWORTH ST, SARASOTA, FL 34231
$5,200,000105 Days on yellowkey MLS ID: A4672697
REDUCED by $450,000 (8.0%) on 04/06/2026
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5428 Built: 2007Monthly Fee: $333 Tax: $52,740 (2024)Community: Oyster Bay LandingsSpa: YesSingle Family
Taxes:$52,740
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Privately positioned in gated Oyster Bay Landings with water views stretching down a short canal to Sarasota Bay, this stunning iconic masterpiece from world-renowned architect Guy Peterson is a breathtaking example of the Sarasota School of Architecture’s style and vision. A comfortable modernistic ambiance flows freely throughout the 5,428 sq. ft. of open living where walls of glass capture spectacular displays of the cerulean blue water and evening skies of fiery beauty. No detail has been overlooked. No expense has been spared. Architecturally striking, this 4-bedroom, 4.5-bath waterfront residence is the ultimate indulgence offering rarity, cachet and grandeur. Dock with 2 lifts is conveniently situated on a waterway unencumbered by any bridge. Floor to ceiling windows frame expansive vistas and abundant natural light complements the thoughtfully-appointed and expertly-planned space. Over 4,000 square feet of outdoor area is inviting and festive, and presents unique vantage points to deliver an exhilarating experience. Expansive terraces promote seamless indoor-outdoor living. Covered entertaining is abundant among the verdant tropical gardens and immaculately manicured grounds. Resort-style amenities including an elevator, courtyard with fire pit and heated pool/spa, and breathtaking reflecting pool with fountain. The stunning kitchen is a culinary delight and complemented by an extravagant amenities package of top-tier appliances, island with seating for 6, 20-ft. long counter for 2 desk workstations, side-by-side but separate refrigerator and freezer, 2 dishwashers, and deep walk-in pantry. The family room is equipped with built-in entertainment wall and opens to a waterfront patio with outdoor cooking center. The great room has travertine floors and cypress ceiling detail, and the office provides a desk with stone countertops and plenty of solid wood cabinetry. A 400-bottle wine room is the highlight of the gaming area with wet bar, electric shades and unique glass chandelier. On the second level are spa-inspired en-suite bedrooms with custom closet systems and elevated ceilings. A 30-ft. bridge leads to the master wing highlighted by incredible water views, sitting room with morning bar, and home gym/office. The primary bath creates an immersive experience with a 16-ft. long dressing hall with a wall of built-ins and mirrors, large walk-in specialty closet, multi-faceted shower, deep soaker Jacuzzi tub, separate bidet and laundry chute. In addition, there are two laundry areas, an elevator from ground level to the 2nd and 3rd floors, Creston music and lighting system, Generac generator, and 4-car garage. In one of Sarasota’s most coveted locations along the waterfront, this home redefines coastal living is just minutes from beaches, golf, fine dining and downtown Sarasota’s beloved arts and cultural offerings. When scheduling your exclusive tour of this amazing MODERN waterfront estate, make sure to allow plenty of time for exploring its incredible features, both inside and out. It must be seen in person to be fully appreciated. Even the most discerning buyer will fall in love!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
6711 S LOCKWOOD RIDGE RD, SARASOTA, FL 34231
$529,000188 Days on yellowkey MLS ID: A4668944
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1816 Built: 1966 Tax: $4,379 (2024)Community: Gulf GateSingle Family
Taxes:$4,379
Elementary School: Gulf Gate Elementary
Remarks: Step inside this beautifully remodeled mid-century modern gem located in the highly sought after Gulf Gate community. This stylish 3-bedroom, 2 bath home also features two versatile bonus rooms, perfect for a home office, fitness room, Florida sitting room, or playroom, offering flexibility to fit your lifestyle. In keeping with its mid-century roots, the original Terrazzo flooring has been fully restored and polished, preserving the home's character while everything else has been reimagined with modern updates. The brand-new kitchen shines with custom cabinetry, granite countertops, stainless appliances, and an eat in kitchenette, creating an inviting space for everyday living and entertaining. Both bathrooms have been completely remodeled with new vanities, showers, fixtures and lighting for a fresh, contemporary look. Major upgrades include a new roof, new AC, and new Hot water heater, updated electric panel to 200 amps with new wiring to all light fixtures, main drain from house to sewer has been flushed, 2 large windows have been replaced with hurricane impact windows, all providing peace of mind for years to come. Enjoy Florida living at its best in the beautiful, fenced backyard, surrounded by mature landscaping and shade trees, ideal for relaxing or hosting gatherings, or a playground for your furry friends. Perfectly situated just a few miles from the world-famous Siesta Key Beach and only six minutes to Crescent Beach, Gulf Gate offers convenient access to schools, shopping, dining, downtown Sarasota, St. Armand's Circle, Lido Beach and Venice Beach, and is an Old Florida quiet neighborhood. This move-in ready home blends classic charm with modern luxury, a rare find in one of Sarasota's most desirable neighborhoods.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jennifer Bright (941-320-4989)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000195 Days on yellowkey MLS ID: A4668223
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $10,871 (2025)Community: CasarinaCondo
Taxes:$10,871
Remarks: Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling to this home. A wall mounted television with Sonos audio provides family entertainment. The spacious primary bedroom with a Closet Tech designed walk-in closet opens to a large bathroom with custom cabinets, dual sinks and large walk-in shower. A third bedroom was created during the recent remodel and includes a built-in under window desk. The full-sized laundry room allows for plenty of storage. Luxury vinyl flooring was installed in 2020 in all public rooms. Impact windows were added in 2016. Electric blinds can close off the sliding glass doors to the outside view while all other windows have custom designed plantation shutters. Crown molding and solid wood doors are found throughout the unit. Casarina is an 89-unit condominium complex that sits on 200 feet of private beach and encompasses 7 acres of tropical landscaping. The complex has a clubhouse with kitchen. Spend your days enjoying the beachside pool and spa, play a game of pickleball on one of the two lighted tennis courts, or relax on the island’s famous crystal sand beach. Hop on the free trolley to enjoy the dining, shopping and entertainment at Siesta Key Village. CASARINA ALLOWS OWNERS ONE SMALL PET.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000221 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
1473 LANDINGS CIR #44, SARASOTA, FL 34231
$468,888253 Days on yellowkey MLS ID: A4662144
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 1981 Tax: $6,233 (2024)Community: Landings TreehouseCondo
Taxes:$6,233
Remarks: Welcome to The Landings Treehouse, one of Sarasota’s most sought-after gated communities. This spacious 3-bedroom, 2.5-bath residence offers over 2,000 sq. ft. of living space with a thoughtfully designed open floor plan that balances comfort and style. The main level features a bright living and dining area with soaring ceilings, skylights, a cozy fireplace, and access to a private lanai surrounded by lush tropical landscaping. The updated kitchen boasts granite counters, a center island, breakfast bar, solid wood cabinetry, and stainless-steel appliances—perfect for both everyday living and entertaining. Upstairs, the primary suite offers a walk-in closet, high ceilings, and a spa-inspired bathroom with skylights that fill the space with natural light. Two additional bedrooms provide plenty of room for guests, one with its own en suite bath. Throughout the home, you’ll find luxury vinyl and tile flooring, designer finishes, and built-in features that enhance functionality. Set among mature trees and serene nature, The Landings Treehouse community is known for its exclusive amenities, including a heated community pool, tennis courts, walking trails, and private access to the Intracoastal Waterway through the Landings Racquet Club (membership optional). This desirable location places you just minutes from Siesta Key Beach, Downtown Sarasota, St. Armands Circle, and a variety of shopping, dining, and cultural attractions. With its generous floor plan, resort-style amenities, and unbeatable location, this home is the perfect opportunity to enjoy the relaxed yet vibrant Sarasota lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Michel (941-702-3889)
2303 LOMA LINDA ST, SARASOTA, FL 34239
$1,899,000122 Days on yellowkey MLS ID: A4676235
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2708 Built: 2025 Tax: $4,955 (2025)Community: Loma Linda ParkSpa: NoSingle Family
Taxes:$4,955
Elementary School: Alta Vista Elementary
Remarks: Fantastic $100,000 price reduction!!! In the well-established Loma Linda Park neighborhood in Sarasota, this new construction, Divald Homes custom-built two-story home offers a blend of modern design and traditional elements. The home is ideally near downtown Sarasota, Siesta Key and Sarasota Memorial Hospital, with no deed restrictions or HOA fees. The home features four bedrooms and three baths, including a spacious primary suite on the main floor. The open-concept floor plan featuring a 24-by-48-inch modern floor tile throughout, hurricane impact sliding doors and windows offers a light-filled welcoming space ideal for entertaining. The main floor includes a gourmet kitchen, dining area, living room, private den/bedroom 4, primary suite with an ensuite bath and a dedicated laundry room. The chef’s kitchen is a centerpiece, showcasing Bosch appliances, an oversized island with waterfall quartz countertop, and custom floor-to-ceiling full-overlay cabinetry in a beautiful honey-stained wood tone. The living room is highlighted by a striking tile accent wall with custom wood shelving and modern designed 42-inch linear electric fireplace. The living room opens seamlessly to the lanai, complete with an outdoor kitchen, including a gas grill, refrigerator and sink. You will also enjoy the pool with sundeck, oversized outdoor patio and a beautiful backyard with lush native plantings. A convenient pool bath offers direct access from the lanai and the private den. The dining area is elegant and inviting, featuring a statement iron chandelier and a wall of windows overlooking the backyard. Just off the kitchen, the main-floor primary suite serves as a private retreat with a luxurious en-suite bath featuring a marble stone accent wall, a large walk-in shower with seamless glass enclosure, a sculptural slipper tub, double vanity with quartz countertops, natural wood cabinetry, LED mirrors and a spacious walk-in closet with custom built-ins. The laundry room is conveniently near the oversized two-car garage with 12-foot ceilings, large windows for natural light and direct access to the side yard. Upstairs, an ornate wrought-iron and hardwood staircase leads to two additional bedrooms, a beautifully finished guest bath and a versatile flex room ideal for a game room, study or guest accommodations. This thoughtfully designed home offers refined finishes, flexible living spaces and an exceptional location, ideal for enjoying the Sarasota lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
3424 OLD OAK DR, SARASOTA, FL 34239
$1,195,00030 Days on yellowkey MLS ID: A4688216
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1953 Tax: $10,828 (2025)Community: Shoreland WoodsSpa: NoSingle Family
Taxes:$10,828
Remarks: Craving a low-maintenance, island-inspired lifestyle just moments from sparkling open water, world-famous beaches, and Sarasota’s most coveted destinations? This quaint Florida bungalow located in west of trail delivers the perfect blend of charm, location, and effortless living—just minutes to Siesta Key and steps from the coastal lifestyle you’ve been dreaming of. Tucked away in one of Sarasota’s most desirable “West of the Trail” neighborhoods, 3424 Old Oak Dr has been thoughtfully redesigned to preserve its original character while introducing timeless, modern updates. From the moment you arrive, the lush tropical landscaping, winding garden paths, and private courtyard-style entry create a warm, inviting ambiance that feels like your own hidden oasis. Inside, the home showcases a light-filled, airy design highlighted by vaulted wood-beam ceilings, soft coastal tones, and an open-concept layout that seamlessly blends comfort and style. The beautifully updated kitchen features granite countertops, open shelving, stainless steel appliances, and designer finishes, creating a space that is both functional and visually stunning. The living area centers around a charming wood-burning fireplace, adding warmth and character, while French doors invite natural light and connect indoor and outdoor living spaces effortlessly. The home offers flexible living spaces ideal for a primary residence, seasonal retreat, or income-producing property. Each room reflects a curated, coastal aesthetic with tasteful updates while maintaining the home’s unique bungalow charm. Step outside to your private backyard sanctuary, where a screened-in heated pool is surrounded by mature tropical landscaping, creating a serene and secluded environment perfect for relaxing or entertaining. An outdoor shower adds to the coastal lifestyle experience, while multiple seating areas and garden spaces enhance the home’s tranquil, resort-like feel. Located just minutes from Siesta Key Beach, Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and top-rated dining and shopping, this home offers unmatched convenience paired with a laid-back coastal lifestyle. Rarely does a property combine location, charm, income potential, and lifestyle so seamlessly. This is your opportunity to own a truly special Sarasota bungalow where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
1850 WEBBER ST, SARASOTA, FL 34239
$3,890,00034 Days on yellowkey MLS ID: A4686673
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026 Tax: $18,011 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$18,011
Remarks: One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing Agent: Kelly Gettel (941-315-2525)
1169 W PEPPERTREE DR #118A, SARASOTA, FL 34242
$649,00058 Days on yellowkey MLS ID: A4683913
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $4,521 (2025)Community: Peppertree Bay IiiCondo
Taxes:$4,521
Remarks: Discover this impeccable, light-filled second-floor End unit in Peppertree Bay, offering serene views of the tranquil pond. Meticulously remodeled and lovingly maintained over 20 years, this residence exudes pride of ownership. Featuring two bedrooms and two bathrooms, the unit is complete with impact windows throughout, ensuring safety and comfort. Every square inch of this home has been tastefully enhanced, and the furnishings are included for your convenience. Enjoy the added convenience of an in-unit washer and dryer. Residents of Peppertree Bay benefit from a wealth of resort-style amenities, including a private beach with lounge chairs, two heated swimming pools, a fitness center, saunas, tennis and pickleball courts, barbecue grills, a fishing pier, and dedicated on-site management. Ideally located just a short stroll from Siesta Village’s shops and dining, and a quick drive to Sarasota’s cultural attractions, this property embodies coastal living at its best. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity with rental income potential, this exceptional beachfront property meets all your needs. Don’t miss your chance to embrace the Siesta Key lifestyle—where every day feels like a vacation.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
1792 FLOYD ST, SARASOTA, FL 34239
$1,250,00062 Days on yellowkey MLS ID: A4684245
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2015 Built: 1951Monthly Fee: $2 Tax: $13,700 (2025)Community: Hudson Bayou/Midwood ManorSpa: YesSingle Family
Taxes:$13,700
Remarks: One or more photo(s) has been virtually staged. Great price for walled-in pool home in PRIME WEST OF TRAIL location, just a few blocks to Southside Village popular shops and restaurants and 1 block to Sarasota Memorial Hospital. The home was remodeled in 1996 and 2000 with vaulted ceilings, newer bathrooms and kitchen, split bedroom floor plan, pool (built in 2003 and Pebbletec resurfacing in 2026), interior laundry room and 1 car garage. Tile or wood floors throughout. Property re-piped in 2024, a/c 2019. Perfect for your residence or an easy investment property with weekly or monthly rentals allowed. Rental estimates range from $6k - 7.5k monthly depending on annual or weekly rental. Very limited rental availability in the area.
Listing Agent: Barbara May (404-822-9264)
1958 MORRIS ST, SARASOTA, FL 34239
$1,195,000113 Days on yellowkey MLS ID: A4677121
REDUCED by $100,000 (7.7%) on 04/03/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2362 Built: 1957 Tax: $7,088 (2025)Community: HartsdaleSpa: YesSingle Family
Taxes:$7,088
Remarks: One or more photo(s) has been virtually staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite bathroom—ideal for multigenerational living, extended guests, or a private home office retreat. Light-filled living spaces flow effortlessly, creating an inviting atmosphere for both everyday living and entertaining. The functional layout offers privacy where you want it and openness where it matters most, making the home equally suited for relaxed coastal living or hosting family and friends. NEW ROOF 2025. NO STORM DAMAGE. Step outside to your private fenced backyard oasis, where an oversized sparkling swimming pool takes center stage—perfect for year-round enjoyment in Florida’s sunshine. Located West of the Trail, this home places you in one of Sarasota’s most desirable areas. Enjoy the convenience of being just minutes from Downtown Sarasota, with its vibrant arts scene, dining, and waterfront attractions. The popular Morton's Market and Hillview shops and restaurants are close by for everyday errands and casual nights out, "A" rated Southside Elementary School just around the corner, Siesta Key Beach and Sarasota Memorial Hospital are only moments away, adding peace of mind and unmatched accessibility. Whether you’re searching for a full-time residence, seasonal getaway, or smart investment, this home stands out with its versatile floor plan, unbeatable location, and outstanding value. Opportunities like this in such a sought-after Sarasota setting—are rare. Schedule your private showing today and experience the lifestyle this property has to offer.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Jon Patella (941-228-1613)
1723 OAK ST, SARASOTA, FL 34236
$1,999,999168 Days on yellowkey MLS ID: A4671825
REDUCED by $49,001 (2.4%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2862 Built: 2004 Tax: $15,094 (2024)Community: Burns RealtySpa: NoSingle Family
Taxes:$15,094
Remarks: The best of both worlds awaits in historic Laurel Park: a walkable downtown lifestyle paired with the privacy and comfort of a single-family home. 1723 Oak Street is a rare offering: an elevated, concrete-block residence with a character-rich Spanish Colonial exterior and nearly 2,900 square feet of light-filled living space. From the picture-perfect front porch, you’re welcomed into the main level, where high ceilings and hurricane-rated French doors and windows flood every room with natural light. The kitchen is a true showpiece, blending upscale finishes with coastal-inspired design. A 36” Wolf range and built-in refrigerator complement the Calacatta marble countertops and exotic wood topped island, while an expansive walk-in pantry provides coveted storage. A beverage refrigerator on the island makes entertaining effortless. The semi-open floor plan flows seamlessly between the dining and living areas, creating the perfect environment for gathering in style. A flexible den, ideal as a study, playroom, or media space, is enclosed by French doors. Upstairs, the spacious primary suite offers a private balcony, dual walk-in closets, and a spa-like bath with marble countertops, a soaking tub, and an oversized walk-in shower. Two additional bedrooms share a beautifully appointed full bath and a balcony overlooking the property. The laundry is conveniently located on the same level as the bedrooms. Outside, discover an unexpected oasis in the heart of downtown: a heated PebbleTec plunge pool, brick paver patio, mature tropical landscaping, and lush turf that creates a serene, low-maintenance retreat. A detached structure at the rear of the property provides exceptional flexibility. The upper level hosts a self-sufficient guest suite complete with kitchen, bath, and built-in queen Murphy bed. Below, a two-car garage with a sleek impact-rated glass door not only offers prized garage space but has been finished and air conditioned to function as a home office, fitness studio, or creative flex space (this bonus space is not included in square footage). The property is fully fenced and includes off-street parking in addition to the garage. Located in one of Sarasota’s most desirable neighborhoods, you’ll enjoy dozens of restaurants, shops, and cultural venues just steps from your door, along with easy access to the waterfront, farmers markets, and year-round festivals and shows. Few homes combine modern quality, neighborhood charm, and exceptional indoor–outdoor living quite like this one. Don’t miss this rare opportunity to experience the very best of Laurel Park.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Nick Gard (941-500-4273)
1705 FIELD RD, SARASOTA, FL 34231
$2,499,000176 Days on yellowkey MLS ID: A4671008
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2409 Built: 1975 Tax: $9,575 (2024)Community: Oyster Bay EstatesSingle Family
Taxes:$9,575
Remarks: Welcome to this stunning, fully reimagined residence in one of Sarasota’s most sought-after neighborhoods West of the Trail. Comprehensive back to studs renovation with an effective build date to Florida building codes of 2020. No detail has been overlooked in this comprehensive luxury renovation, offering the perfect blend of timeless coastal elegance and modern sophistication. This home is offered fully furnished. Step inside to discover brand-new wood flooring, custom millwork, and an open-concept layout that seamlessly connects living, dining, and entertaining spaces. The gourmet kitchen is a showstopper, featuring designer cabinetry, quartz countertops, high-end appliances including SubZero and Wolf, luxury faucets from Perrin and Rowe and an oversized island perfect for gathering with family and friends. This exceptional home offers four spacious bedrooms, three full baths, and two half baths, providing ample room for comfort and privacy. Every bathroom has been beautifully appointed with premium finishes and spa-inspired details. Enjoy peace of mind with all-new electric, plumbing, roof, siding, and hurricane-impact windows and doors—including an impact-rated garage door. Outside, the property shines with fresh landscaping, new patios, and elegant walkways, creating a serene retreat for outdoor living and entertaining. Perfectly situated West of the Trail, this home places you minutes from Sarasota’s vibrant downtown, St. Armands Circle, world-class beaches, and top-rated schools, dining, less than a block to the Field Club and close to shopping. Buyer and Buyer's Agent to confirm room dimensions.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Albert Joerger (941-685-6145)
4626 GLEASON AVE, SARASOTA, FL 34242
$695,00090 Days on yellowkey MLS ID: A4680372
REDUCED by $35,000 (4.8%) on 04/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1144 Built: 1955 Tax: $6,783 (2025)Community: Ocean BeachSingle Family
Taxes:$6,783
Remarks: You're about to miss it...coming off the market 6/1. A perfect blend of old-school cool and 2026 finishes, this mid-century modern bungalow is a true "buy it and move-in tomorrow” type home. Most importantly, no high condo/HOA fees. Polished terrazzo floors, vaulted ceilings, it’s just fun all over. Fully renovated with crisp coastal selections. It has a nice sunroom for a large party gathering or workout room, art studio, play area. Carport equipped with RV hookups and motor court driveway. Plenty of parking space for bikes, scooters, and golf carts. The landscaping is immaculate, professionally designed by the owner including an advanced drainage system helping keep you dry 24/7/365. Not far from the Village, close to the beach, and minutes to North bridge. Clean, affordable, easy beach living. Being offered turn-key furnished.
Listing Agent: Jason Skowronski (941-812-6090)
1690 ASSISI DR #12, SARASOTA, FL 34231
$1,779,00014 Days on yellowkey MLS ID: A4690125
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3097 Built: 2007Monthly Fee: $388 Tax: $15,103 (2025)Community: Portofino On The BaySingle Family
Taxes:$15,103
Remarks: Don’t miss this stunning Mediterranean-Tuscan-style residence, perfectly situated just steps from the Intercostal. This gated Sarasota estate home located in Portofino on the Bay includes its own DEEDED boat slip and remote controlled 10,000 LB. boat lift. Experience being near waterfront without the need for any flood insurance or stress of flooding, but still have your boat in your backyard with Bay access. This model-home-ready property features a private feeder dock slip, offering effortless access to the open water for boating. The Bay opens almost directly across from the newly opened midnight pass with Caribbean worthy turquoise water. Inside, the home has been completely renovated with top-of-the-line appliances and designer finishes throughout, blending luxury with comfort in every detail. The luxury chefs kitchen was renovated in 2023 leaving nothing out, complete with Fulgor Milano appliances. Enjoy the convenience of a first floor master with en suite and his and her wardrobes, a large home office and 10 foot-high ceilings with arched entryways throughout and a 25 foot high foyer with impressive feature wall and fireplace. The upstairs features impressive Cumaru wood flooring and stairs, three large bedrooms and a newly renovated bathroom with tub. The guest suite shows off with a Juliet balcony overlooking the private back yard. The open and inviting layout flows seamlessly into a serene private courtyard - perfect for relaxing or entertaining guests. Unwind in the soaking spa and enjoy the convenience of being just a short drive to downtown Sarasota, world-famous Siesta Key Beach, The Legacy Trail and the newly developing Sarasota Square, placing shopping, dining, and entertainment right at your doorstep. The Portofino on the Bay community has a Kayak Launch, kayak storage and a guest slip for daily visitors passing through. This exceptional home combines timeless architecture with modern elegance in a prime near waterfront location. Don’t miss out on this one.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Alexandra Lawson-Baker (703-963-4887)
2806 UPPER TANGELO DR, SARASOTA, FL 34239
$499,00034 Days on yellowkey MLS ID: A4687698
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1538 Built: 1958Monthly Fee: $17 Tax: $4,501 (2025)Community: South GateSingle Family
Taxes:$4,501
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after South Gate neighborhood of Sarasota, ideally located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Situated on a highly desirable corner lot, this move-in ready home offers exceptional curb appeal with a newly installed 8-ft vinyl fence, along with a new roof, fascia, and gutters completed in 2023. Step inside to an inviting, light-filled living space where large windows create a bright and airy atmosphere. The flexible layout flows seamlessly into a versatile bonus area—perfect for a home office, sitting room, or additional entertaining space. The updated eat-in kitchen is the heart of the home, featuring freshly painted cabinetry, quartz countertops, stainless steel appliances, and a stylish backsplash—designed for both everyday living and hosting. A dedicated laundry room with built-in shelving doubles as a convenient pantry for added storage, and the home includes a new washer and dryer. French doors lead to the screened lanai, with upgraded wood tile flooring, creating a warm and inviting outdoor living space perfect for relaxing or entertaining. The fully fenced yard, mature canopy, and producing lychee tree contribute to a setting that feels both established and quietly distinctive. This backyard also offers room for play and possibly a pool for the future owner. The primary suite offers a peaceful retreat with an updated ensuite bathroom, featuring a new vanity and walk-in shower. Additional upgrades include fresh interior and exterior paint, new landscaping, vinyl flooring throughout, and added attic insulation (2024) for improved energy efficiency. This home is equipped with hurricane shutters, a 360-degree security system, and surge protection in the electrical panel for added protection and peace of mind. Furniture is available for purchase separately, making this a potential turnkey opportunity. Residents have the option to join the voluntary HOA, which provides access to the South Gate Community Association pool—an added perk that enhances the neighborhood lifestyle. Enjoy an unbeatable Sarasota lifestyle just minutes from shopping, dining, and entertainment, with easy access to the Legacy Trail, Siesta Key and St. Armands Circle. Whether you're searching for a primary residence, seasonal retreat, or investment property, this South Gate home offers the perfect blend of location, upgrades, and lifestyle. The property is maintained with consistent professional care, supporting long-term integrity. Schedule your private viewing today!
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
35 SANDY COVE RD #2A, SARASOTA, FL 34242
$975,000212 Days on yellowkey MLS ID: A4653716
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1254 Built: 1970 Tax: $7,373 (2025)Community: Sandy CoveCondo
Taxes:$7,373
Remarks: Sandy Cove – Mid-Century Modern Gulf Front Paradise: Period-preserved mid-century architecture meets breathtaking Gulf front water views in this exceptional Siesta Key residence. Located in Sandy Cove, a hidden gem and distinguished 1970s development of villas and mid-rises, this fifth-floor residence offers a panoramic vista over Big Pass to Lido, Bird Key, and downtown Sarasota—a guaranteed "wow" moment. Sandy Cove Condos was designed in 1969 by Frank Folsom Smith with James Holliday and James Durden, earning a 1970 AIA Florida Award for architectural excellence. This light-filled, architecturally preserved residence is over 1,200 square feet with two bedrooms, two bathrooms, and a thoughtful split floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home. Step inside and be captivated by the spectacular living room featuring soaring vaulted ceilings that provide ample natural light and an airy, open ambiance. Enjoy breathtaking Gulf water views from your living room and kitchen sliders, which open seamlessly to your private patio. The sliders pull back to welcome Gulf breezes throughout the entire residence, connecting to several delightful porches and patios—including an additional private palm tree patio with IPE decking. A rare and highly coveted feature: this residence includes a private one-car garage. Gulf front residences in Sandy Cove rarely become available, making this a unique chance to own a piece of Siesta Key's architectural history. The home has potential to be sold furnished and is offered in as-is condition, presenting an opportunity for buyers to customize their personal vision. Ideally situated close to Siesta Key Village—just a short distance away, this truly unique location offers a natural private beach exclusive to the community, along with a fishing pier. Come see this truly "if you know, you know" treasure on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mickey Kiernan (941-402-9115)
225 LITTLE POND LN, SARASOTA, FL 34242
$4,450,000202 Days on yellowkey MLS ID: A4668094
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3867 Built: 1987Monthly Fee: $125 Tax: $28,385 (2024)Community: Siesta Es Boyds RepSpa: NoSingle Family
Taxes:$28,385
Remarks: Experience coastal luxury with confidence in Siesta Key’s exclusive Cocoanut Bayou. Further enhancing peace of mind, the entire property—including seawall, pool, and home—has recently undergone a comprehensive inspection by a highly regarded firm, confirming its exceptional condition. Buyers are encouraged to request a copy of this detailed report from their agent, as it will be available within the MLS. This extraordinary waterfront estate rests on nearly three-quarters of an acre of meticulously landscaped grounds adorned with mature Royal Palms and lush tropical greenery, blending sophistication with relaxed island living. Completely reimagined and reinvented, the home showcases striking new design elements including a new roof, Hardie board siding, new stucco, and three new AC systems—offering the rare comfort of new-construction quality in an established, sought-after enclave. Inside, expansive living spaces are bathed in natural light through new impact-rated windows and doors that frame sweeping waterfront views. This five-bedroom residence boasts two designer-appointed primary suites for ultimate privacy and comfort. The stunning chef’s kitchen features Thermador appliances, double dishwashers, dual sinks, wall and speed ovens, a 36-inch induction cooktop, and a 48-inch built-in refrigerator—crafted to inspire culinary artistry and effortless entertaining. A custom lounge bar with built-in refrigeration and icemaker invites refined gatherings overlooking serene Bayou waters. Step outside to a 2024 resort-style pool and shaded architectural lounge with Cypress wood inlay ceiling, pre-wired for a Jacuzzi, creating your own waterfront sanctuary. The expansive marine-grade dock, two new boat lifts (12,000-lb. and 20,000-lb.), and quick access to open waters with no fixed bridges elevate the boating experience. Residents of the 54-home Cocoanut Bayou community enjoy gated, private beach access across the street with tiki hut, gathering area, and a wide white-sand beach for Siesta Key’s world-famous sunsets. Refined. Verified. Ready—Welcome home to the ultimate in island living.
Listing Agent: Thomas Netzel (941-539-0633)
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