Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
1931 HIGH POINT CIR, SARASOTA, FL 34236
$1,495,00057 Days on yellowkey MLS ID: A4690458
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1712 Built: 1940 Tax: $13,413 (2025)Community: Hudson BayouSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,413
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT. The interior features include refinished HARDWOOD FLOORS, double-paned windows, and an UPDATED KITCHEN equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a tray ceiling, gas fireplace and French doors leading to a private outdoor area and SALTWATER POOL, perfect for the Florida lifestyle. The fully FENCED professionally landscaped yard includes a PUTTING GREEN. Significant improvements offer peace of mind and long-term value, including a new standing seam METAL ROOF (2025), NEWER A/C system (2022)/mini-split (2024), and completely REPLUMBED with PVC. The air-conditioned TWO-CAR GARAGE features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. This property has a great rental history along with future bookings, please inquire for more details.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
5547 ASHTON LAKE DR #5547, SARASOTA, FL 34231
$299,50089 Days on yellowkey MLS ID: A4686214
3 Days Off yellowkey (back on 4/26/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1225 Built: 1990Monthly Fee: $550 Tax: $3,248 (2025)Community: Ashton Lakes 01 & 02Condo
Taxes:$3,248
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Location, Location, Location! Only 3.5 miles to the world-famous Siesta Key Beach. Close to I-75 and rte.41, shopping, hospital, schools and restaurants. A much sought after 2-bedroom, 2 bath, ground floor unit, garage, front porch, screened lanai with a captivating view of spring fed Sunnyside Lake and fountains can be yours. Bright & airy. Partially furnished. Ashton Lakes Community is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts & 4 pickleball courts, 2 heated pools, one large with a lap lane, shuffleboard, clubhouse, grilling stations, and other amenities. we are connected to Merchants mart shopping center by a foot bridge. Shops include CVS, ACE hardware, liquor, Dollar store, restaurants and the famous Detwillers farm market for your shopping convenience. Come, make this slice of heaven your paradise in the sun. Disclosures attached. Roof 2010, Water heater 2015, Air handler 2022.
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00047 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
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)
2632 SUNNYSIDE ST, SARASOTA, FL 34239
$395,00051 Days on yellowkey MLS ID: A4690325
3 Days Off yellowkey (back on 6/8/2026)
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: Under contract-accepting backup offers. 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)
5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$999,000193 Days on yellowkey MLS ID: A4673708
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,269 (2025)Community: Gulf & Bay Club Ph 2Condo
Taxes:$9,269
Elementary School: Phillippi Shores Elementary
Remarks: BEST VALUE AT SIESTA KEY BEACH GULF & BAY CLUB. Imagine living in Paradise…Welcome to your dream home on Siesta Key, where every day feels like a vacation. This beautiful beachfront corner unit in the prestigious GULF & BAY CLUB is located on the #1 Beach in America per Trip Advisor. Step into this stunning two-bedroom, two-bathroom unit, filled with natural light from expansive windows. Enjoy breathtaking sunrise and sunset views as part of your daily routine. The renovated interior features high ceilings, a gourmet kitchen with an office, modern bathrooms, smart storages and elegant details. Gulf & Bay Club is the gated resort community on the key. The serene property spans on 32 acres with 800 feet of private quartz sand beach, offering exceptional living. Beyond your home, Gulf & Bay Club offers world-class amenities, including scenic pathways to a freshwater lake with a rustic footbridge, a lush tropical courtyard with 3 heated pools, 6 pickleball courts, 4 tennis courts, 2 clubhouses and barbecue grills for social gatherings. Fitness enthusiasts can access a commercial gym, sauna, and media facility, while EV charging stations promote eco-friendliness. With an on-site rental management for one-month minimum rentals, this property is perfect for luxurious living and smart investment. Make this waterfront oasis your home where warm hospitality and serenity await.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Melanie Albaric (941-233-0957)
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00084 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
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 is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
300 GARDEN LN, SARASOTA, FL 34242
$2,790,000281 Days on yellowkey MLS ID: A4662830
REDUCED by $209,000 (7.0%) on 05/21/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,545
Tax Year: 2024
Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000346 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 is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
916 PATTISON AVE, SARASOTA, FL 34237
$399,90029 Days on yellowkey MLS ID: A4693771
REDUCED by $9,100 (2.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1044 Built: 1961 Tax: $4,185 (2025)Community: Robin Hood WoodsSpa: NoSingle Family
Taxes:$4,185
Elementary School: Alta Vista Elementary
Remarks: Don't let this one pass you by. Tucked in one of Sarasota's most sought-after locations, this beautifully updated single-family home offers the perfect blend of timeless neighborhood charm, modern comfort, and an active lifestyle — with no HOA to slow you down. Inside, a fully remodeled kitchen showcases quartz countertops, stainless steel appliances, and custom cabinetry, while two tastefully renovated bathrooms reflect the same attention to detail and designer touch found throughout. Natural light pours through the open layout, creating a warm, inviting atmosphere whether you're entertaining guests or simply settling in after a day at the beach. The big-ticket work is already behind you. A newer roof, updated HVAC, plumbing, and electrical mean you're stepping into genuine peace of mind — not a project. Outside, a spacious screened lanai and fenced backyard invite you to slow down, let the pets roam, tend the garden, or simply enjoy a warm Gulf evening in complete privacy. All of this, just minutes from the energy of downtown Sarasota — world-class dining, boutique shopping, pristine parks, and the Gulf's most celebrated beaches, world-renowned Yoders Marketplace, or a quick trip to the UTC area for outstanding retailers, Mote Marine, parks, walking trails, and more. Whether you're planning your starter home, escaping the winters, or adding a smart investment to your portfolio, this home checks every box. Stylish. Updated. Move-in ready. This is Sarasota living at its finest. Call today for your personal tour.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Kathleen Long (813-470-0047)
3800 FLORES AVE, SARASOTA, FL 34239
$4,495,00010 Days on yellowkey MLS ID: A4695844
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2026 Tax: $10,023 (2025)Community: GranadaSpa: YesSingle Family
Taxes:$10,023
Remarks: NEW CONSTRUCTION - Experience the pinnacle of Sarasota luxury in this newly completed, move-in-ready residence, ideally located within the City of Sarasota and attractively priced for today's market. Offering 4 bedrooms, a private den, 4.5 baths, and 4,106 square feet of thoughtfully designed living space, this exceptional home seamlessly blends contemporary elegance with relaxed coastal living. Crafted for effortless indoor-outdoor enjoyment, the home features two expansive lanais overlooking a private resort-style pool and spa, creating the perfect setting for entertaining or unwinding in complete privacy. Inside, refined finishes and modern conveniences abound, including engineered hardwood flooring, quartz countertops throughout, a chef-inspired kitchen with an oversized walk-in pantry, and the rare convenience of dual laundry rooms. Open-concept living spaces are filled with natural light and designed to accommodate both everyday living and grand-scale gatherings. Nestled in a peaceful, private setting, yet just minutes from world-famous Siesta Key Beach, premier golf courses, downtown Sarasota, St. Armands Circle, and an array of fine dining and cultural attractions, this residence offers the ideal balance of luxury, location, and lifestyle. A rare opportunity to own a brand-new custom home in one of Florida's most desirable coastal communities. (Some Photos are Virtually Staged)
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
4925 PRIMROSE PATH, SARASOTA, FL 34242
$1,795,00011 Days on yellowkey MLS ID: A4695589
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2609 Built: 1969 Tax: $16,475 (2025)Community: HarmonySpa: NoSingle Family
Taxes:$16,475
Remarks: Experience the best of waterfront island living in this exceptional 4-bedroom, 2.5-bath residence, perfectly positioned just minutes from the world-famous shores of Siesta Key Beach. Situated on a sprawling corner lot of approximately 19,055 square feet — with almost 80 feet of canal frontage — the property is enveloped by mature tropical landscaping that creates an incredibly private, resort-like sanctuary you have to see to believe. This home has been completely and thoughtfully updated — truly move-in ready with select furnishings included. New hurricane impact-rated windows and sliding doors (2023) provide both security and peace of mind, while the Tesla Solar System with battery backup delivers energy efficiency and independence. Step outside and discover your own private paradise. A tiki hut, freeform pool with cascading waterfall, and stunning outdoor living spaces make entertaining effortless, while your private dock with boat lift puts boating, fishing, kayaking, and paddleboarding right at your doorstep. The sheer size and lush privacy of this lot is a rare find — expansive, tranquil, and beautifully landscaped. No HOA. Just freedom, flexibility, and the Florida lifestyle at its absolute finest — minutes from the boutique shops, acclaimed dining, and laid-back charm of Siesta Key Village.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Stephen Johnston (941-302-8080)
2304 RINGLING BLVD #101, SARASOTA, FL 34237
$139,000225 Days on yellowkey MLS ID: A4670262
REDUCED by $6,000 (4.1%) on 05/11/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 552 Built: 1965Monthly Fee: $577 Tax: $1,641 (2024)Community: Garden AptsSpa: NoCondo
Taxes:$1,641
Remarks: **!! SELLER SAYS……SELL !!** Seller will cover the remaining monthly fees for the rest of 2026 with an acceptable offer. THE BUYER WILL SAVE OVER $3,000.00!! Welcome to this charming ground floor, 1 bed 1bath condo within walking distance of all of Sarasota’s splendor! This unit is in excellent condition and boasts tile floors throughout. Newer kitchen appliances, counter tops and cabinets. This condo is light, spacious and accessible. This home also has its own reserved parking space and there is guest parking on site. The association has just updated the laundry facility with brand new washers and dryers. It is perfect as a weekend get-a-way, or as your primary residence. It is also in a rental friendly community and has an excellent long-term rental history. Whether you are an investor or an empty nester, this condo is ready for occupancy!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
2110 MICHELE DR, SARASOTA, FL 34231
$2,525,000352 Days on yellowkey MLS ID: A4657130
REDUCED by $24,000 (0.9%) on 05/02/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4623 Built: 2025 Tax: $3,317 (2024)Community: MonticelloSpa: YesSingle Family
Taxes:$3,317
Remarks: OPEN, FLEXIBLE FLOOR PLAN designed to accommodate a variety of wishes and needs. New custom luxury home for sale in Sarasota Florida located on Coquina Island. This high-end Sarasota luxury estate features a private in-law suite, resort-style pool and spa, outdoor kitchen, and over 4,000 square feet of modern coastal living. One of a kind design to optimize the homesite, is located in the heart of Sarasota County offering luxury & timeless contemporary design. Just minutes from Phillippi Mansion Park, Siesta Key Beach, top-tier shopping, dining, Sarasota Memorial Hospital, Selby Gardens, and downtown Sarasota, this home enjoys a prime location. Key Features: 5 Bedrooms | 5 1/2 Bathrooms. 38' Wide Polyaspartic Garage with high ceilings, music speakers and 2 ceiling fans (space allows lifts in each bay). 13' High Ceilings in the great room. Gourmet Kitchen with sleek appliances, large island, cooktop hood, double wall ovens, coffee bar, and an expansive walk-in pantry with custom shelving and room for a full freezer or refrigerator. Truly a chef's delight! Spacious Master Suite with paver deck on main floor, his and hers huge walk-in custom closets, ensuite luxury bath. Private multiple decks and a large paver lanai overlooking the Pebble-Tec heated saltwater pool with spillover spa and outdoor kitchen Separate In Law Suite above the garage with a great room, full kitchen, bath, bedroom, laundry room, and balcony. Energy Efficient with Icynene insulation, soundproofed walls, and potential for solar power or generator. 3 HVAC units and zones. Instant hot water heater; separate water heater for in law suite, tankless hot water heater as well in main living spaces. Interior Highlights: High-end finishes and 2 custom-built open staircases. Wood and tile floors throughout. Floor-to-ceiling windows flood the home with natural light. Fully structured wiring for sound; 19 music speakers and 8 security cameras. Large laundry room with custom cabinetry, laundry sink, stone folding counter and hanging rod. Spacious pantry with custom shelves; electric dedicated circuit for additional freezer or refrigerator. Insulation in walls & ceiling for sound mitigation. WiFi mesh inside & out. Outdoor Oasis: Heated Saltwater Pool & Spa with spillover waterfall and floor clean system. 8 Security cameras. Outdoor Kitchen featuring marine-grade cabinets. Professionally designed tropical gardens with private well for the sprinkler system. LED Lit Circle Paver Driveway adds striking curb appeal. The home has been specifically designed for its setting, with eye appeal on all sides. Too many extra features to list! It is in a very quiet neighborhood, yet close to Sarasota. You will not be disappointed in this home!
Listing is courtesy of: FLORIDA HOME TEAM LLC (941-486-0012)
Listing Agent: John Ask (941-486-0012)
1794 CUNLIFF LN, SARASOTA, FL 34239
$2,997,00096 Days on yellowkey MLS ID: A4685523
REDUCED by $98,000 (3.2%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3377 Built: 2015 Tax: $39,491 (2025)Community: Bay View Heights AddSpa: YesSingle Family
Taxes:$39,491
Remarks: Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed in natural light. Oversized 10-foot doors frame every room, while hurricane-impact sliding glass doors seamlessly connect the interior to a resort-style outdoor oasis. The expansive pool deck showcases a stunning lighted fountain spilling from the spa into the oversized pool, a rainfall pergola, and lush tropical landscaping surrounded by a six-foot privacy fence—creating the ultimate setting for both relaxation and entertaining. Built with the signature craftsmanship of Allegra Homes, the residence features exceptional custom millwork, striking feature walls, designer lighting, and distinctive ceiling details throughout. Spanning 3,582 square feet, this thoughtfully designed home offers four spacious bedrooms, three luxurious bathrooms, a private den/office with a turret ceiling, and a versatile bonus room. The gourmet kitchen—one of Allegra’s most beloved layouts—is a true culinary showpiece, appointed with Sub-Zero and Wolf professional-series stainless steel appliances, including a five-burner natural gas cooktop, a second Sub-Zero beverage refrigerator, custom luxury cabinetry, rich 3cm granite countertops, and a glass tile backsplash with hidden electrical outlets Adjacent to the kitchen, the elegant dining room features a dramatic aquarium glass window overlooking the pool and gardens, along with a built-in buffet accented by a mirrored feature wall. The home’s split floor plan provides exceptional privacy. The serene primary suite is a private retreat, offering a spa-inspired bath with a walk-through shower, dual vanities, and a private water closet. A custom walk-in closet features built-in shelving, drawers, and a hallway dressing mirror. The bedroom is highlighted by an intricate custom ceiling design, designer lighting, and private access to the pool deck. On the opposite side of the first floor, you’ll find a built-in desk alcove, a spacious laundry room, a secondary bedroom with a walk-in closet, a full hall bath, and the bonus room with disappearing sliding glass doors that open to the screened pool area. The first level features rich porcelain wood-style flooring, while the second level is comfortably carpeted and hosts the third and fourth bedrooms, along with a media closet and additional HVAC storage. Bahama shutters and custom blinds complete the bedrooms and bathrooms. Situated on a 0.28-acre elevated lot, built above the flood plain in 2015, this exceptional residence offers privacy, luxury, and an unbeatable central location. Just minutes away are Sarasota Memorial Hospital, Southside Village, and top-rated Southside Elementary, with Siesta Key Beach, downtown Sarasota, Westfield Siesta Key Mall, and St. Armands Circle only a short drive away. This remarkable property may be purchased turnkey furnished, including original artwork, bronze sculptures, designer furnishings, and custom rugs, available under a separate bill of sale. Schedule your private showing today. Proof of funds required with all offers.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Jill Berg (941-315-1199)
3117 JAMAICA ST, SARASOTA, FL 34231
$369,900123 Days on yellowkey MLS ID: A4681988
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $9,600 (2.5%) on 06/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1800 Built: 1980 Tax: $1,935 (2025)Community: The WlySpa: NoSingle Family
Taxes:$1,935
Elementary School: Wilkinson Elementary
Remarks: Outstanding Sarasota location for this truly unique lakefront home, complete with a small private dock. Nestled on a wooded, private lot, the setting offers a peaceful retreat that feels worlds away—yet is just minutes from everything Sarasota has to offer. Inside, generous living areas and soaring ceilings create an open, airy atmosphere ideal for both everyday living and entertaining. There is ample space for gatherings, along with a versatile bonus area perfect for a study, den, or gallery. The main-floor primary suite features a walk-in closet for added comfort and convenience. The two-car garage is currently configured as a one-car garage with additional flex space that could serve as a bedroom or office and can easily be converted back to a full two-car garage. Two spacious upstairs bedrooms share a conveniently located bathroom. A large enclosed, air-conditioned lanai with French doors opens to a serene back patio, offering tranquil lake views and abundant wildlife. This home radiates warmth and character, reflecting years of cherished family and friend gatherings. Located just one block from Bee Ridge Park, which offers basketball, volleyball, softball fields, and a shaded playground, and within a highly sought-after school district for elementary, middle, and high school. Sarasota Memorial Hospital is only three miles away, downtown Sarasota just five miles, and world-famous Siesta Key Beach approximately seven miles away—featuring exceptional dining, shopping, and cultural attractions. This property has never flooded and sits well above sea level.
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
5420 EAGLES POINT CIR #406, SARASOTA, FL 34231
$769,0009 Days on yellowkey MLS ID: A4695955
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2165 Built: 1993 Tax: $4,683 (2025)Community: Eagles Point At The LandingsCondo
Taxes:$4,683
Remarks: Experience penthouse living in Eagles Point at The Landings, where expansive water views, vibrant amenities, and colorful sunsets create a true year-round retreat. This light and inviting top floor 3-bedroom residence offers spacious living areas, an additional foot of ceiling height, and an enclosed Florida room with hurricane-rated sliders and western exposure for enjoying sweeping views and beautiful evening skies. The open living and dining areas flow seamlessly together, while the kitchen features a granite-topped island, stainless steel appliances, and an eat-in area. The owner's suite opens to the Florida room and includes a fitted walk-in closet, dual-sink vanity, soaking tub, and separate shower. Two additional guest bedrooms enjoy eastern exposure and morning light, while the rare additional half bath not found in many other Eagles Point residences adds extra convenience for guests. Additional features include a spacious laundry room with utility sink, private storage, and two assigned parking spaces in the secure garage, a valuable benefit reserved for top-floor residences. Eagles Point residents enjoy a private pool and grilling area, while The Landings offers gated security, a vibrant social atmosphere, Racquet Club membership with Har-Tru tennis, pickleball, fitness, pool and spa, library, community room, kayak storage and launch, and a scenic trail to the Intracoastal fishing pier. Whether full-time or seasonal, Unit 406 offers an exceptional opportunity to enjoy penthouse views and The Landings lifestyle.
Listing Agent: Daniel Treiman (917-657-7495)
3246 MAIDEN LN, SARASOTA, FL 34231
$524,90072 Days on yellowkey MLS ID: A4688107
REDUCED by $24,600 (4.5%) on 06/05/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2170 Built: 1983 Tax: $4,622 (2025)Community: Kallas SubSingle Family
Taxes:$4,622
Remarks: **This is The One!** Prime Sarasota location just minutes to Siesta Key Beach, Downtown Sarasota, and more! This property offers strong potential as a primary residence, seasonal home, or investment opportunity. **NEW Roof in 2021** Functional layout with solid bones and opportunity to update or customize to maximize value. Private outdoor space and convenient access to shopping, dining, medical facilities, and I-75 add to the appeal. Ideal for buyers looking to capitalize on location and long-term upside in a highly desirable area. **NO HOA or Deed Restrictions** The Florida room provides the perfect spot to enjoy your morning coffee or unwind in the evening, and it opens to a spacious outdoor area—ideal for taking full advantage of Florida’s beautiful weather year-round. This property offers a versatile bonus space currently set up as a workshop **Potential to turn bonus space into living space/in-law suite with private entrance**, along with an additional climate-controlled room perfect for a home gym or flex space. Equipped with a 2-car attached garage PLUS an extra driveway on the side **Ample room for storing a Boat, Trailer, Lawn equipment, or other recreational vehicles.** Enjoy the freedom to truly make the space your own with endless possibilities. In addition, enjoy tons of storage space for all your holiday decorations and any additional items you may need to tuck away. Don't miss out on this incredible property - Reach out to schedule your private tour today! **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Ryan Miller (941-954-6925)
1255 E PEPPERTREE DR #201, SARASOTA, FL 34242
$499,000306 Days on yellowkey MLS ID: A4661191
2 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1460 Built: 1972 Tax: $5,890 (2024)Community: Peppertree Bay ISpa: NoCondo
Taxes:$5,890
Remarks: Under contract-accepting backup offers. Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedroom condo at Peppertree Bay, available at an unbeatable price! Experience resort-style living in this bayfront and beachside community. The interior boasts an open floor plan with spacious, welcoming rooms, tile and luxury vinyl plank flooring, and a generous 29-foot lanai. Peppertree Bay offers luxurious amenities, including under building parking, private beach access, two heated swimming pools, tennis and pickleball courts, two clubhouses, a fitness center, and a fishing pier. It’s like a vacation every day! When you want a change of pace, leave your car behind and take the trolley to all the wonderful restaurants and shopping Siesta Key has to offer. With onsite management and a rental desk, this Peppertree Bay condo serves as an ideal coastal getaway or a smart investment choice. Don’t let this one get away.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
1714 WALDEMERE ST, SARASOTA, FL 34239
$1,650,00075 Days on yellowkey MLS ID: A4688029
REDUCED by $150,000 (8.3%) on 06/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 2000 Tax: $4,256 (2025)Community: Hudson BayouSpa: NoSingle Family
Taxes:$4,256
Remarks: Rarely available 2001 built one story home on a 75 ft wide lot in the prime heart of West of Trail/ Southside Village area. One block to Sarasota Memorial Hospital and 3 blocks to the ever popular Southside Village shops and restaurants. A "true" neighborhood, Hudson Bayou is one of the most sought after areas to live in. This 4 bedroom (split bedroom plan) 3 full bath pool home has high ceilings and an oversized 2 car garage. The primary bathroom has a curbless oversized shower.
Listing Agent: Barbara May (404-822-9264)
2442 WOOD ST, SARASOTA, FL 34237
$449,000149 Days on yellowkey MLS ID: A4678152
REDUCED by $23,000 (4.9%) on 05/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1279 Built: 1951 Tax: $5,715 (2025)Community: Hudson ParkSingle Family
Taxes:$5,715
Remarks: Live in one of Sarasota’s most desirable neighborhoods! Priced to sell. This charming home offers two generously sized bedrooms plus a versatile third space that can serve as a sunroom, office, or private in-law suite/studio. This additional area includes its own bathroom, kitchenette, closet, and separate rear entrance—perfect for guests or rental potential. Inside, you’ll find a cozy layout with a welcoming kitchen nook and comfortable living area, ideal for relaxing and unwinding. The home has been thoughtfully updated with a remodeled kitchen, a newer roof (2018), granite vanity top and sink with brushed nickel fixtures (2020), a brand-new water heater (2025), upgraded lighting (2025), and numerous additional improvements throughout. Enjoy your morning coffee on the inviting front porch or entertain and relax on the back patio. The backyard features a two-car carport, storage sheds, and a newly completed, eye-catching stone fence that adds both ambiance and privacy. Conveniently located just minutes from downtown Sarasota, shopping, dining, and the world-famous Siesta Key Beach, as well as other nearby beaches, this home offers both comfort and accessibility. Additional highlights include RV parking and multi-family zoning, providing excellent flexibility and investment potential. Schedule your private showing today and experience everything this beautiful home has to offer!
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
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