Location: Sarasota
Do Not Show Listings
217 S SHADE AVE, SARASOTA, FL 34237
$1,799,000462 Days on yellowkey MLS ID: A4628117
REDUCED by $100,000 (5.3%) on 05/12/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2561 Built: 2025 Tax: $4,777 (2023)Community: Terrace GardensSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,777
Elementary School: Alta Vista Elementary
High School: Sarasota High
Tax Year: 2023
Middle School: Booker Middle
Remarks: Introducing THE RETREAT, a stunning two-story residence. FOUR (4) bedroom, THREE (3) bath. Paver driveway, 3 CAR GARAGE, LVP flooring. Home has been professionally staged. Pool is complete; size 12 x 26 , leaving plenty of green space for pets in the backyard! This exceptional new build boasts superior block construction, a durable metal roof, impact-resistant windows, doors, and sliders. Inside is a thoughtfully designed open floor plan, featuring soaring 10-foot ceilings and elegant 8-foot solid core doors that enhance the home’s impressiveness. The gourmet kitchen is complete with a 6-foot island, luxurious quartz countertops, custom shaker cabinetry, and a top-of-the-line appliance package, perfect for both daily meals and entertaining. The primary bedroom, located on the main level, is a serene retreat with stunning tray ceilings, large his/her walk-in closets, double vanity, and a spacious walk-in shower. Bedroom #2, also on the first floor, is versatile and can serve as an additional bedroom or a home office. Upstairs, you'll find two more generously sized bedrooms that share a beautifully appointed full bathroom. The home’s detailed interior is complemented by luxury vinyl plank flooring throughout both levels, providing durability and style. Outdoors, a gas-heated saltwater pool and paver deck creates the ideal setting for relaxation and entertainment. Conveniently located with easy access to downtown Sarasota, the Legacy Trail, Payne Park, Sarasota Memorial Hospital, and the world-renowned beaches of Longboat and Siesta Keys, this home offers the perfect blend of luxury, comfort, and convenience for modern family living. Experience elevated living at its finest in "your RETREAT"!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Ingrid Caruso (941-539-6233)
300 GARDEN LN, SARASOTA, FL 34242
$2,790,000279 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
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Middle School: Brookside Middle
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)
8072 GLENBROOKE LN, SARASOTA, FL 34243
$531,000120 Days on yellowkey MLS ID: A4681070
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2090 Built: 1991Monthly Fee: $95 Tax: $3,114 (2024)Community: Vintage CreekSpa: YesSingle Family
Taxes:$3,114
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Welcome to your opportunity to own a move-in-ready pool home in Sarasota that delivers the space, flexibility, and Florida lifestyle buyers are searchin. From the moment you arrive, you’ll notice the lush tropical landscaping and inviting curb appeal, setting the tone for what’s inside. Step through the front door into a bright, open-concept living and dining area with vaulted ceilings, creating an airy feel that’s perfect for both everyday living and entertaining. The layout offers true flexibility, featuring multiple living areas and bonus spaces ideal for a home office, guest room, hobby space, or multi-generational living—something today’s buyers consistently need but rarely find at this price point. The kitchen flows seamlessly into the main living space, making it easy to stay connected while hosting or relaxing at home. Step outside and experience what Florida living is all about—your private screened-in pool and lanai, offering the perfect setting for morning coffee, weekend gatherings, or unwinding at the end of the day. The backyard provides additional space and privacy, with room to make it your own. Additional features include: Spacious bedrooms with great natural light Dedicated laundry area Two-car garage with ample storage Well-maintained interior ready for immediate enjoyment As a bonus, residents enjoy access to a community pool and amenities, giving them even more options for relaxation and socializing. Located on a quiet residential street, this home offers convenient access to shopping, dining, major roadways, and everything that makes Sarasota one of the most desirable places to live on Florida’s Gulf Coast. if you would like to change out any of the flooring it is all available locally. The owners have agreed to a flooring allowance.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)
Listing Agent: Patricia Baker (941-527-8669)
10193 CANAVERAL CIR, SARASOTA, FL 34241
$634,900157 Days on yellowkey MLS ID: A4675911
REDUCED by $10,000 (1.6%) on 05/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2064 Built: 2023Monthly Fee: $336 Tax: $6,059 (2025)Community: Grand ParkSingle Family
Taxes:$6,059
Elementary School: Lakeview Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: $10,000 price improvement! Better than new in Grand Park! A highly upgraded White Star floor plan by Neal Communities is ready for the most discerning buyers. It provides 2,064 sq. ft of luxury finishes, privacy and well thought out functionality in a light-filled open floor plan. Impact glass windows, hurricane shutters for the sliders and a ring doorbell add the security you are looking for. A whole-house water filtration and water softening system have been added. A large, screened lanai with custom pet door leads to the wrought iron fenced private yard. Inside, you’ll find elegant silver/crystal contemporary light fixtures, whitewash ceramic wood-look plank flooring throughout, neutral paint color, four ceiling fans with lights, and tray ceilings in the foyer, great room and primary bedroom. The chef’s kitchen includes a large quartz covered island with pendant lighting and breakfast bar, white linen 36” upper cabinets with crown molding, quartz counter tops, soft close doors and drawers, under-cabinet lighting, and tile backsplash. The stainless appliances include a gas stove (preferred by chefs), French-door refrigerator, dishwasher and microwave. Add to that a butler’s pantry to keep the chef organized and you’re ready to entertain in style! The primary bedroom is located in the rear of the house for privacy and includes two walk-in closets and an ensuite bathroom. A handheld shower head and heated bidet toilet seat add a touch of luxury. The guest bedrooms are in the front of the house with a guest bath with tub between them. A spacious den/office with double doors and a laundry room featuring an LG steam turbo washer/dryer with laundry sink complete the picture. The garage has an insulated garage door plus attic access with additional insulation and aluminum stairs/ladder. Grand Park is an amenity-rich community. The amenity center has two resort-style pools, fitness center, clubhouse, pickle ball and tennis courts, playground and dog park. Grand Park is conveniently located just East of I-75 and a short distance to Siesta Key Beach and downtown Sarasota with its arts venues and multiple restaurants.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Barb Standish (941-504-9458)
916 PATTISON AVE, SARASOTA, FL 34237
$399,90027 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
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)
2231 WOOD ST, SARASOTA, FL 34237
$1,999,000257 Days on yellowkey MLS ID: A4666469
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2731 Built: 2024 Tax: $4,662 (2023)Community: Poms Park 3Spa: YesSingle Family
Taxes:$4,662
Remarks: This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for a strong six figure range income annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
4323 PINE MEADOW TER, SARASOTA, FL 34233
$515,00031 Days on yellowkey MLS ID: A4692509
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 1978Monthly Fee: $25 Tax: $5,227 (2025)Community: Pine MeadowSpa: NoSingle Family
Taxes:$5,227
Elementary School: Ashton Elementary
Remarks: Under contract-accepting backup offers. You found it! A newly renovated pool home directly bordering the Legacy Trail and just a short drive to Siesta Key Beach! This home is in the highly sought-after community of Pine Meadow. Positioned on an oversized, private corner lot with an extended driveway, this property also offers direct and private access to the Legacy Trail through a custom door built into the fully fenced backyard. Extensive and thoughtful interior updates include a renovated kitchen with granite countertops, matching stainless steel appliances, and luxury tile flooring that flows seamlessly throughout the home. The split-bedroom floor plan complements the master bedroom, which offers an abundance of natural light and quaint charm. Accented by a modern farmhouse sliding door, this room features a large walk-in closet and an updated en-suite bathroom with a walk-in shower and floor-to-ceiling tile. Both additional bedrooms also feature large walk-in closets. The home was FULLY RENOVATED in 2019, receiving a new roof, fully updated electrical system, new hot water heater, custom 10x16 storage shed, new garage epoxy flooring, and a new garage door. The pool was also resurfaced and upgraded with a new pool cage and pump equipment. Embrace the private, tranquil backyard setting complemented by a variety of mature trees and lush landscaping. Enjoy the pool and lanai from the shaded, covered section, or soak up the warm Florida sun while relaxing poolside. This home is in a highly desirable Sarasota location, just 5.5 miles from Siesta Key Beach. It is assigned to all A-rated schools, offers direct access to the Legacy Trail, and provides quick access to I-75 and Sarasota Memorial Hospital.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Allen Smith, Iv (407-460-1564)
719 MALDIVES TRL, SARASOTA, FL 34234
$1,024,990330 Days on yellowkey MLS ID: A4659082
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2903 Built: 2024Monthly Fee: $185Community: Gracewater At SarasotaSpa: YesSingle Family
Taxes:$0
Elementary School: Emma E. Booker Elementary
High School: Booker High
Remarks: Current Model Home available , 6 month leaseback in the sought after Gracewater Community right in the heart of Sarasota. Our Bay Haven model home offers generous living space for the whole family to enjoy. With 4 bedrooms, 3.5 bathrooms, office and loft/bonus room, there’s plenty of room for everyone to have their own space. And when it’s time to come together, the open kitchen and great room provide the perfect setting for gathering and entertaining. The attached two-car garage offers convenience and peace of mind for storing vehicles and equipment. The lanai and double-entry laundry room add even more convenience to this already impressive home. And let’s not forget the bonus room – it can serve as a playroom, office, or whatever suits your needs.
Listing is courtesy of: PRIVADA REALTY (941-233-6000)
Listing Agent: Perry Pope (941-737-9124)
2424 ASHTON RD, SARASOTA, FL 34231
$2,442,50048 Days on yellowkey MLS ID: A4691268
REDUCED by $200,000 (7.6%) on 06/08/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2872 Built: 2026 Tax: $5,146 (2025)Community: Phillippi CrestSpa: YesSingle Family
Taxes:$5,146
Remarks: Pre-Construction. To be built. An extraordinary opportunity to create a one-of-a-kind luxury estate by E/M Custom Homes, set on a sprawling 1-acre homesite in a highly sought-after non-deed-restricted location with no HOA and located not in a Flood Zone. Offering the ultimate blend of privacy, flexibility, and upscale living, this premier property is further enhanced by its approved potential to be subdivided into four separate parcels, an exceptional investment opportunity for future development or multi-generational estates. The lot itself is offered at $900,000. This thoughtfully designed residence features an expansive open-concept floor plan with a stunning great room highlighted by coffered ceiling beams. The gourmet kitchen is the centerpiece of the home, complete with a large center island, quartz countertops, and premium wood cabinetry, perfect for both entertaining and everyday living. The layout includes three bedrooms, a dedicated den, and a versatile bonus room, allowing buyers to customize the space to fit their needs—ideal for a home office, gym, or media room. A three-car garage provides ample space for vehicles, storage, or recreational equipment. Enjoy Florida living at its finest with a covered lanai and summer kitchen, perfect for creating your own outdoor oasis. With no deed restrictions, there is plenty of room to expand, store boats or RVs, or design your ideal backyard retreat. Ideally located just 2.5 miles from Siesta Key, minutes to Downtown Sarasota, and offering easy access to Interstate 75, this property combines privacy with convenience. It is also situated within a top-rated school district featuring excellent magnet schools. E/M Custom Homes is known for quality craftsmanship and personalized design-build services, and there is still time for buyers to select finishes and customize the home to their exact vision. Photos are of a recently completed model and are for illustrative purposes only.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Pat Rodriguez (941-685-5805)
3656 OAK GROVE DR, SARASOTA, FL 34243
$849,90046 Days on yellowkey MLS ID: A4691432
REDUCED by $25,000 (2.9%) on 05/26/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4054 Built: 1981 Tax: $5,343 (2025)Community: Oak Grove ParkSpa: NoSingle Family
Taxes:$5,343
High School: Southeast High
Remarks: Under contract-accepting backup offers. Welcome to this non mandatory hoa neighborhood, beautiful 4 bedroom 3 full bath pool home featuring a 1 bedroom 1 bath mother in law suite with private access making it a total of 5 bedrooms 4 full baths. The mother in law suite has established itself as a successful vacation rental presenting an outstanding investment opportunity. Enjoy a Sarasota address while paying Manatee County taxes all while being conveniently located to everything this area has to offer. Situated on over an acre of land, this versatile property is perfect for those who need room to live, work and play... Bring your rv's, trailers, work vehicles or car collection... There is ample parking and no deed restrictions to limit your lifestyle. Even horses are welcome - with space to build a barn or custom collector garage. This home has a butler's pantry with stylish barn doors that add charm and functionality. Step outside to a private oasis - a large peanut shaped saltwater pool (8' deep) screened lanai (rescreened in 2025). The main house with generous room sizes has living area, kitchen, dining room and family room, master bedroom and 2nd bedroom on 1st level while upstairs there are 2 bedrooms with dual closets and a jack and jill bathroom to share. New metal roof (2019) 3 zone a/c system, 2 water heaters, 2 sets of stainless stell appliances, well irrigation system, hurricane shutters and VOLUNTARY HOA!! This is a unique opportunity to own a flexible, income producing property with space to expand in a prime Sarasota location.
Listing is courtesy of: AFFORDABLE REAL ESTATE (941-751-3000)
Listing Agent: Susan Harrison-Phipps (941-685-8349)
4867 HUNTLEIGH DR, SARASOTA, FL 34233
$499,00097 Days on yellowkey MLS ID: A4685110
REDUCED by $26,000 (5.0%) on 06/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1937 Built: 1980Monthly Fee: $29 Tax: $3,040 (2025)Community: Beneva PinesSpa: NoSingle Family
Taxes:$3,040
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. In the desired community of Beneva Pines in the heart of Sarasota, just five miles to the south bridge to the quartz sugar sand beaches of Siesta Key and Capt Curt's Restaurant and Tiki Bar! This smartly designed split plan home features an open plan, vaulted ceilings, and beautiful screened pool and lanai. The kitchen is the heart of this home and is surrounded by multiple gathering and dining areas. Impact sliders open off the Florida room to the pool. Most windows have been updated to impact rated as well. All four bedrooms are generous size and feature walk-in closets. The primary bedroom features an en-suite bath and two walk-in closets. Freshly painted inside, this home is ready for you to make it your own. Roof in 2022.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
5309 CHARLIE BROWN LN, SARASOTA, FL 34233
$749,00033 Days on yellowkey MLS ID: A4691590
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2768 Built: 2016Monthly Fee: $261 Tax: $6,961 (2025)Community: Luna BaySpa: NoSingle Family
Taxes:$6,961
Remarks: Opportunities like this are rare in Luna Bay, an intimate Sarasota neighborhood of just 21 homes—offering a true sense of privacy and community that’s hard to find. This beautifully appointed 4-bedroom, 3.5-bath residence is offered fully furnished, making it completely turnkey for immediate enjoyment or investment. The open floor plan features a desirable downstairs primary suite, a den/office and an upstairs loft ideal for a playroom, study area, or TV room. From the moment you arrive, the barrel tile roof, paver driveway, and covered front porch create impressive curb appeal. Inside, the home is bright and inviting with wood cabinetry, granite countertops, generous closet space, and numerous upgrades throughout. Step outside to a south-facing covered lanai overlooking the screened, heated pool with a paver deck, all set within a fenced backyard that offers complete privacy—perfect for relaxing, entertaining, or pets. Enjoy a low-maintenance lifestyle with HOA-covered yard maintenance. Ideally located within the highly sought-after Ashton Elementary school district and just minutes from top-rated Sarasota schools, this home also offers exceptional proximity to Siesta Key Beach, I-75, and a wide array of shopping and dining options. This is a rare opportunity to own a fully furnished home in a boutique community in one of Sarasota’s most desirable locations.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Quire (941-993-5706)
4442 HOLLYBROOK WAY, SARASOTA, FL 34233
$663,00024 Days on yellowkey MLS ID: A4694025
REDUCED by $22,000 (3.2%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2310 Built: 1994Monthly Fee: $80 Tax: $4,542 (2025)Community: GreenfieldSpa: NoSingle Family
Taxes:$4,542
Remarks: Beautifully updated and move-in ready 4-bedroom, 2-bath home in the highly desirable community of Greenfield, centrally located within top-rated school districts including Ashton Elementary School, Sarasota Middle School, and Sarasota High School. Greenfield offers low HOA fees and a peaceful setting with plenty of convenient shopping and dining amenities nearby and within short proximity to the white sand beaches of Sarasota. This meticulously maintained home is tucked along a quiet section of the neighborhood on an oversized quarter-acre lot. From the moment you arrive, you’ll appreciate the freshly painted exterior accented by timeless brick details and inviting curb appeal. Inside, the easy-living split floor plan offers 2,310 square feet under air with generous living spaces designed for both comfort and entertaining. This home is loaded with quality upgrades and recent improvements, including impact windows and sliders throughout (2025), luxury vinyl plank flooring, newer HVAC (2022), a fully updated kitchen (2022), recessed LED lighting, new ceiling fans (2026), and an impact-rated garage door (2020). The stunning gourmet kitchen features quartz countertops, stylish white shaker soft-close all-wood cabinetry with rollout drawers, stainless steel appliances, a large single-basin stainless sink, pantry storage, and both countertop seating and a dining area overlooking the pool. Just off the kitchen, the cozy living room centers around a charming wood-burning brick fireplace, creating the perfect gathering space for family and friends. The three guest bedrooms share a bathroom with convenient pool access, while the spacious primary suite offers privacy and comfort. Step outside to the generously sized screened lanai, an ideal outdoor retreat with ample shaded space for dining, relaxing, and grilling. The sparkling pool was resurfaced with a pebble finish in 2022 and features a newer Pentair pool pump, plus an outdoor shower for added convenience.The beautifully landscaped backyard is truly special, showcasing native Florida plants and flowering gardens designed for low-maintenance living. Enjoy Sunshine Mimosa ground cover, Mulberry trees, Elderberry, and a magnificent mature oak tree that provides natural shade and character. Additional exterior features include full irrigation and a new side fence installed in 2026. Every detail of this home reflects thoughtful design, exceptional upkeep, and high-quality craftsmanship, creating a stylish and worry-free property ready to be enjoyed for years to come.
Listing Agent: Heather Gehan (941-893-0213)
5301 SADDLE OAK TRL, SARASOTA, FL 34241
$1,999,000118 Days on yellowkey MLS ID: A4680226
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3978 Built: 2003Monthly Fee: $114 Tax: $10,477 (2025)Community: Saddle Oak EstatesSingle Family
Taxes:$10,477
Remarks: Under contract-accepting backup offers. Set on 6.34 private acres within the gated equestrian community of Saddle Oak Estates, this fully renovated estate has been reimagined for modern luxury living while preserving the rare sense of space and tranquility that defines the neighborhood. A long, impressive paver driveway introduces the nearly 4,000-square-foot residence, where estate privacy meets refined design just minutes from Sarasota’s everyday conveniences. Inside, wood-look tile flows seamlessly throughout the entire home, anchoring an open-concept layout designed for effortless indoor-outdoor living. The living room makes a striking first impression with a custom stone accent wall, fireplace, and built-ins that create a warm focal point for gathering. At the heart of the home, the chef’s kitchen is both elegant and functional, featuring a beautiful cabinetry with lighted upper cabinets, large island, gas range, stainless farmhouse sink, dine-in area, and a butler’s pantry that adds exceptional storage and prep space. A sunlit oversized dining room with custom cabinetry and high tray ceilings was designed for large family celebrations and entertaining. Walls of glass open directly to the pool terrace, blurring the line between inside and out. This impressive space is equally suited to function as a great room or media lounge, with the formal dining room positioned at the front of the home — currently styled as an inviting sitting area. A half bath is conveniently positioned here, and the second primary suite is located on this wing, creating the ideal setup for a private guest retreat or multigenerational living. The home offers two spacious primary suites, each with updated spa-inspired baths that feel like personal retreats. One suite includes a flexible den — perfect as a home office, gym, nursery or even a 5th bedroom. Two additional bedrooms and a full bath provide comfortable accommodations for family or guests. Thoughtful storage is built into every corner, including a cabinet-lined hallway leading to the oversized laundry room complete with granite counters, cabinetry, and utility sink. Plantation shutters, crown molding, and designer lighting elevate the interiors, adding warmth and sophistication throughout. Step outside to a true backyard oasis. The expansive paver patio surrounds a sparkling pool and flows into a large covered area with a wood-accent ceiling designed for lounging and outdoor dining. A pergola grilling area invites relaxed evenings entertaining under the stars, while a fenced dog run offers space for pets to roam. With flexible living spaces that adapt to your needs, expansive acreage, and the serenity of Saddle Oak Estates, this property delivers the rare combination of estate privacy and modern luxury, just minutes from Sarasota’s dining, shopping, and beaches.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Toma Milbank Pllc (941-720-5174)
2201 WEBBER ST, SARASOTA, FL 34239
$1,179,00034 Days on yellowkey MLS ID: A4692960
REDUCED by $11,000 (0.9%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2267 Built: 1953 Tax: $9,268 (2025)Community: South Side ParkSingle Family
Taxes:$9,268
Elementary School: None
High School: None
Middle School: None
Remarks: Exceptional opportunity to own a fully renovated, income-generating property with a strong track record of short-term rental success. This 4-bedroom, 3.5-bath home, located in the highly desirable Arlington Park area of Sarasota, was completely renovated in 2020, offering modern finishes, updated systems, and true turnkey condition for both personal use and continued rental income. For the past six years, the property has operated as a successful short-term rental, delivering consistent performance and strong guest demand. Even more compelling, there are future reservations already in place for 2026 and 2027, providing immediate, built-in income for the next owner. The spacious layout is ideal for accommodating larger groups, and the home has been meticulously maintained to meet guest expectations and maximize occupancy. Step outside to a private backyard retreat featuring a heated swimming pool, expansive deck, and a covered patio with a built-in outdoor grilling island—perfect for entertaining guests and enhancing the rental experience year-round. The listing agent is also the current property manager and has successfully managed the home over the past six years. For buyers seeking a seamless transition, professional management can continue in place, offering a true hands-off investment opportunity. Ideally situated less than 10 minutes to Downtown Sarasota and the world-renowned Siesta Key beaches, this location consistently attracts both vacationers and long-term visitors alike. 2201 Weber Street offers a rare combination of modern renovation, established income history, future bookings, resort-style outdoor living, prime location, and optional ongoing management—making it an exceptional opportunity for investors and second-home buyers alike.
Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)
Listing Agent: William Glade (941-356-1054)
5835 CALLA LILLY DR, SARASOTA, FL 34232
$475,000289 Days on yellowkey MLS ID: A4663252
REDUCED by $15,000 (3.1%) on 06/01/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2468 Built: 2020Monthly Fee: $75 Tax: $3,805 (2024)Community: Garden Village Ph 2Spa: NoSingle Family
Taxes:$3,805
Elementary School: Fruitville Elementary
Middle School: McIntosh Middle
Remarks: This exceptional five-bedroom, three-bathroom residence spans 2,468 square feet of living space, offering an inspired floor plan in the gated community of Garden Village. The partially oversized backyard provides ample room to create an outdoor oasis or a large pool. The heart of this remarkable home features a gourmet kitchen with an eat-in dining area, an expansive walk-in pantry, and an oversized island, perfect for entertaining. The first level conveniently offers a main-floor bedroom, while the second story houses the primary bedroom suite complete with an en-suite bathroom, plus three additional bedrooms. Recent updates elevate this home above others on the market, including freshly painted interiors, a new Samsung washer, dryer, and dishwasher installed in August 2025, a brand new AC system installed in March 2026, and a Mitsubishi mini-split system in the garage that provides both air conditioning and heat. Built in 2020, this Garden Village home offers low HOA fees, no CDD, and is not in a flood zone, complemented by modest homeowners association dues that will not strain your budget. The location provides quick access to Interstate 75, Downtown Sarasota, A-rated schools, shopping, and nearby beaches.
6961 SCRUB JAY DR, SARASOTA, FL 34241
$1,075,000147 Days on yellowkey MLS ID: A4677370
REDUCED by $25,000 (2.3%) on 05/28/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4177 Built: 2006Monthly Fee: $142 Tax: $9,513 (2024)Community: Red Hawk ReserveSpa: YesSingle Family
Taxes:$9,513
Middle School: Riverview Middle
Remarks: Welcome to 6961 Scrub Jay Drive, a beautifully maintained Sarasota pool home where the major updates have already been completed, allowing you to move in and immediately enjoy the Florida lifestyle. Freshly painted inside and out, this home offers a bright, clean feel from the moment you arrive. The kitchen is equipped with brand-new appliances, while a new hot water heater and new pool pump provide added peace of mind for years to come. Step outside to your private backyard retreat featuring a sparkling pool surrounded by attractive pavers, creating the perfect setting for entertaining, relaxing, or enjoying sunny Florida afternoons. A convenient pool bath adds functionality and makes hosting family and friends effortless, while the spacious pool deck provides plenty of room to create the outdoor kitchen of your dreams. Whether you envision a simple grilling station or a fully equipped outdoor entertaining space, the layout offers the flexibility to bring your vision to life. Adding even more value, the homeowner is willing to offer a concession toward updates, giving buyers the opportunity to personalize the home to their tastes while enjoying the confidence that many of the major mechanical and maintenance items have already been addressed. With the costly improvements already completed, 6961 Scrub Jay Drive offers the ideal blend of comfort, convenience, and outdoor living in one of Sarasota's most desirable locations. Simply unpack, settle in, and start enjoying everything this exceptional home has to offer.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Matthew Hickey (941-539-6773)
2207 WISTERIA ST, SARASOTA, FL 34239
$1,995,250100 Days on yellowkey MLS ID: A4683417
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3120 Built: 2017 Tax: $17,152 (2025)Community: GreenwichSpa: NoSingle Family
Taxes:$17,152
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. East of the Trail in Sarasota, this 2017-built concrete block pool home offers 4 bedrooms, 4 bathrooms, and a rare double-primary layout on an oversized gated and fully fenced lot just minutes from Siesta Key Beach, downtown Sarasota, Arlington Park, and Southside Village. Combining newer construction, Flood Zone X positioning, and a highly desirable central Sarasota location, this home delivers the features buyers are actively searching for today. Designed for both everyday living and entertaining, the open-concept floor plan features high ceilings, abundant natural light, and seamless indoor-outdoor flow. A three-panel sliding glass door connects the main living area to the covered lanai and screened pool, creating a true Sarasota indoor-outdoor lifestyle. A modern electric fireplace anchors the living space, while automatic entry blinds add convenience and privacy with additional plantation shutters throughout. The kitchen is built for functionality and gathering, complete with quartz countertops, a gas range, stainless steel appliances, slow close cabinetry, a large center island, and newly updated refrigerator, microwave, and wine refrigerator in 2025. The first-floor primary suite includes two walk-in closets and a spacious bath with marble flooring, soaking tub, walk-in shower, and dual vanities. A first-floor laundry room adds daily convenience. Upstairs, engineered hardwood flooring extends throughout, leading to a large bonus room ideal for a home office, media room, or fitness space. Two secondary bedrooms share a bath on one side, while a separate second primary suite with ensuite bath and walk-in closet offers privacy for guests, multigenerational living, or flexible use. Outdoor living is designed for real use, with a screened pool, covered lanai, outdoor kitchen, paver deck, and fenced yard with usable green space. Additional features include hurricane impact windows and doors, spray foam insulation, gas tankless water heater, and an epoxy-coated garage floor. Located within Sarasota city limits with close proximity to beaches, dining, shopping, and I-75, this home offers a compelling combination of location, construction quality, and flexible living. Potential short-term rental opportunities may be available, subject to city regulations and buyer verification.
Listing is courtesy of: LOYD ROBBINS & CO. LLC (941-957-9300)
Listing Agent: Ali Marks (941-321-5147)
2647 SYDELLE ST, SARASOTA, FL 34237
$699,00013 Days on yellowkey MLS ID: A4695270
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1954 Tax: $1,295 (2025)Community: Paver Park Estates 1St AddSpa: YesSingle Family
Taxes:$1,295
Remarks: Welcome to Paver Park Estates, one of Sarasota's fastest-growing and most sought-after neighborhoods, where modern renovations meet an unbeatable location. Just minutes from Downtown Sarasota, Sarasota Bay, Payne Park, and the Legacy Trail, this beautifully renovated 4-bedroom, 2-bath residence offers approximately 1,850 square feet of thoughtfully designed living space in the heart of the city. Completely transformed with extensive updates throughout, the home features a bright, open-concept floor plan highlighted by luxury vinyl plank flooring, recessed lighting, impact-rated windows, and a stunning shaker-style kitchen designed for both everyday living and entertaining. The kitchen boasts quartz countertops, a large center island, custom tile backsplash, and a full suite of Frigidaire appliances. The spacious primary and guest bathrooms have been tastefully updated with custom tile work, quartz countertops, and premium rain shower fixtures, creating a spa-like atmosphere. Additional improvements include shaker-style interior doors, updated lighting and ceiling fans, a new HVAC system with all-new ductwork, upgraded electrical service with underground power, and numerous modern finishes throughout. Step outside to your private backyard retreat featuring a newly constructed saltwater pool and spa, providing the perfect setting for relaxing, entertaining, or enjoying Sarasota's year-round sunshine. Located less than a mile from Downtown Sarasota, residents can easily bike or walk to the city's vibrant dining, shopping, arts, and cultural attractions, including the Sarasota Opera, Marina Jack, Bayfront Park, and countless restaurants and boutiques. The world-renowned beaches of Siesta Key and Lido Key are only a short drive away. Surrounded by new construction homes and luxury redevelopment, Paver Park continues to emerge as one of Sarasota's most exciting neighborhoods, making this property an exceptional opportunity for full-time residents, seasonal owners, or investors seeking a prime location with strong long-term upside.
Listing Agent: Randy Fallon (941-321-0997)
5347 MANG PL, SARASOTA, FL 34238
$475,00055 Days on yellowkey MLS ID: A4689588
REDUCED by $24,500 (4.9%) on 06/01/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2249 Built: 2012Monthly Fee: $236 Tax: $4,065 (2025)Community: Palmer Oaks EstatesSpa: NoSingle Family
Taxes:$4,065
Elementary School: K-8 At Clark And Lorriane
Middle School: K-8 At Clark And Lorriane
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained home in the highly sought-after, gated community of Palmer Oaks! Built in 2012, this spacious 4-bedroom, 2.5-bathroom residence offers 2,249 square feet of thoughtfully designed living space perfect for both everyday living and entertaining. Step inside to find a bright, open floor plan featuring tile flooring throughout the main level and fresh interior paint that gives the home a clean, modern feel. The kitchen seamlessly flows into the living and dining areas, creating an inviting space ideal for gatherings. Upstairs, you’ll find all four bedrooms along with a convenient laundry closet, providing both privacy and functionality. Enjoy peaceful mornings and relaxing evenings overlooking a beautiful fountain water view right from your backyard. The exterior has also been freshly painted, adding to the home’s curb appeal. Additional highlights include a newer HVAC system and maintenance-free living, allowing you to spend more time enjoying the community pool & incredible location. Location truly sets this home apart! With quick and easy access to I-75, commuting is a breeze. You’re just a short walk to Publix, Walmart, Chick-fil-A, Jimmy John’s, Applebee’s, Gecko’s, Ace Hardware, and numerous other shopping and dining options. Plus, world-renowned Siesta Key Beach, UTC Mall, Downtown Sarasota, and St. Armands Circle are all just a short drive away. This is the perfect opportunity to enjoy comfort, convenience, and the Florida lifestyle all in one place!
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Kevin Bruinsma (616-308-7965)
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