Location: Sarasota
Do Not Show Listings
5917 OLIVE AVE, SARASOTA, FL 34231
$412,99959 Days on yellowkey MLS ID: O6411402
REDUCED by $36,000 (8.0%) on 07/09/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1957 Tax: $3,209 (2025)Community: Golden AcresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,209
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Virtually Staged. Located in the desirable coastal community of Sarasota, this inviting home offers a relaxed Florida lifestyle with a comfortable layout and bright, open living spaces. The interior features a functional flow designed for everyday living and easy entertaining, with well-sized bedrooms and versatile common areas. Outdoor space provides room to enjoy the warm weather year-round, whether relaxing, gardening, or hosting gatherings. Conveniently situated near Gulf beaches, shopping, dining, and cultural attractions, this property delivers both lifestyle and location in one of Sarasota’s most sought-after areas.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
2817 HAWTHORNE ST, SARASOTA, FL 34239
$341,99948 Days on yellowkey MLS ID: O6413863
REDUCED by $8,000 (2.3%) on 07/16/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1383 Built: 1954 Tax: $5,194 (2025)Community: Rio Vista ResubSingle Family
Taxes:$5,194
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: Virtually Staged. Located in a highly desirable Sarasota area, this residence offers a comfortable layout with inviting living spaces and a functional floor plan designed for everyday living. The interior provides a natural flow that works well for both relaxation and entertaining. This home presents a great opportunity for a buyer looking to personalize and make improvements. Outdoor space adds flexibility for gardening, outdoor activities, or future enhancements. Conveniently situated near shopping, dining, beaches, and downtown Sarasota, this property offers access to some of the area’s most sought-after amenities.
5005 CANTERBURY DR, SARASOTA, FL 34243
$719,40032 Days on yellowkey MLS ID: A4698046
REDUCED by $25,350 (3.4%) on 07/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2451 Built: 1981 Tax: $6,537 (2024)Community: De Soto Lakes Country Club 1Single Family
Taxes:$6,537
Elementary School: Kinnan Elementary
High School: Braden River High
Tax Year: 2024
Middle School: Braden River Middle
Remarks: Rare Palm Aire opportunity offering the freedom, flexibility, and Florida lifestyle so many buyers are looking for. Perfectly positioned along the second hole of the Champions Course at Palm Aire Country Club, this beautifully renovated home offers serene golf course views with NO HOA and NO deed restrictions — giving you the ability to keep your boat, RV, golf cart, work vehicle, or other recreational equipment right at home. Renovated in late 2023, this charming two-story Cape Cod-style residence blends timeless character with thoughtful modern updates. The main level features durable luxury vinyl plank flooring, while the staircase and entire second floor showcase rich hardwood floors. The open kitchen and family room create an inviting everyday living space, complete with granite countertops, soft-close cabinetry, and views out to the pool and golf course beyond. The first-floor primary suite offers comfort and convenience, featuring a spacious walk-in closet and a beautifully updated en-suite bath. Upstairs, two additional bedrooms and a full bathroom provide flexible space for guest rooms, office space, hobbies, fitness, media, or additional storage. Step outside and enjoy your own private Florida retreat. The pool deck was refreshed in 2024 with new brick pavers, creating a beautiful setting for relaxing, entertaining, or enjoying the peaceful golf course backdrop. With no HOA fees and no deed restrictions limiting how you use your property, this home offers a level of flexibility that is increasingly hard to find. Furniture is negotiable, making this move-in-ready home even easier to enjoy from day one. Whether you are looking for a full-time residence, seasonal escape, or flexible home base with room for your Florida lifestyle, this property delivers the perfect combination of location, updates, views, and freedom.
Listing is courtesy of: DANIELLE GLADDING & CO. REALTY (941-539-8535)
Listing Agent: Alison Kanter (941-306-9786)
1675 LANDINGS LN, SARASOTA, FL 34231
$1,930,0007 Days on yellowkey MLS ID: O6426507
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4214 Built: 1987Monthly Fee: $167 Tax: $11,309 (2025)Community: The LandingsSpa: YesSingle Family
Taxes:$11,309
Elementary School: None
High School: None
Middle School: None
Remarks: Virtually Staged. Tucked beneath a canopy of sweeping mature oaks in one of Sarasota's most coveted gated communities, this gracious two-story home strikes the perfect balance between timeless elegance and Florida ease. The brick paver driveway, bay window entry, and lush manicured lawn set an inviting first impression that the interior effortlessly sustains. Step inside to soaring vaulted ceilings with exposed beam detail, gleaming hardwood floors, and a stunning crystal chandelier that anchors the grand living room. A classic white marble fireplace, plantation shutters, and an open staircase with white balusters and rich wood railing give the space a warmth and architectural character rarely found at this price point. The kitchen is bright and functional — white cabinetry with glass-front uppers, an island with cooktop, double wall ovens, stainless steel appliances, and a picture window framing the lush greenery outside. A perfect canvas for the cook who wants both form and function. The screened pool and spa with brick paver deck and mature oak surround deliver complete privacy and the quintessential Florida outdoor lifestyle — whether you're entertaining or simply unwinding after a day at the beach. Located in The Landings, Sarasota's premier gated community known for its racquet sports complex, nature trails, and unbeatable proximity to Siesta Key Beach, top-rated dining, and the vibrant arts and culture scene downtown Sarasota is celebrated for.. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
4040 CROCKERS LAKE BLVD #1717, SARASOTA, FL 34238
$220,000184 Days on yellowkey MLS ID: A4679678
0 Days Off yellowkey (back on 7/23/2026)
REDUCED by $9,000 (3.9%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1350 Built: 1989 Tax: $2,117 (2025)Community: Vintage GrandCondo
Taxes:$2,117
Remarks: Under contract-accepting backup offers. Through no fault of the seller or property, this sought-after condo is back on the market and ready for its next owner. Turnkey Vacation Home. Fully remodeled and ready to move in. This unit is being sold with high end furnishings including a 50 bottle wine cooler and tropical designer decor. This great investment opportunity offers exceptional value. This spacious Floreta floor plan is one of the largest units in Vintage Grand, offering 3 bedrooms, 2 baths with no stairs. This condo has been lightly used and was foreigner owned, the guest bedrooms have hardly been used at all. Vintage Grand has recently completed a full exterior renovation, featuring hurricane-rated energy-efficient windows, enhanced stucco, new gutters, and refreshed landscaping—ensuring lasting value as improvements near completion. The location is unbeatable: walk to Costco right across the street. Explore miles of nearby trails, including the Legacy Trail, or enjoy world-famous Siesta Key Beach just minutes away. Community amenities include two resort-style pools, spas, tennis courts, clubhouse, and a fully equipped fitness center. This is the nicest unit within Vintage Grande. Schedule your showing today
Listing is courtesy of: YORKSHIRE INTERNATIONAL R.E. (941-366-0000)
Listing Agent: Jules Roman (941-366-0000)
4820 KESTRAL PARK CIR #18, SARASOTA, FL 34231
$499,00066 Days on yellowkey MLS ID: A4694438
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1570 Built: 1982 Tax: $5,710 (2025)Community: Landings Carriagehouse IiCondo
Taxes:$5,710
Elementary School: Phillippi Shores Elementary
Remarks: Welcome to one of The Landings' best-kept secrets. Tucked inside the intimate Carriage House community, this 2-bedroom, 2-bath plus spacious den residence delivers the feel of a single-family home wrapped in the ease of maintenance-free living and its move-in ready. Inside, tile flooring flows throughout, anchoring a bright, open layout that feels larger than its footprint suggests. The updated kitchen impresses with a modern aesthetic, solid surface counters, and finishes that feel fresh and intentional, not dated. Both bathrooms have been thoughtfully remodeled, featuring solid surface counters and elegant tile enclosures. A wood-burning fireplace adds warmth and character, making this home as livable as it is lovely. The very spacious den offers the flexibility to serve as a home office, guest room, or hobby space, whatever your lifestyle calls for. An additional den space provides even more room to spread out, work, or create. Your private one-car garage sits just beyond a charming paver driveway shared with only one neighbor — a quiet, neighborly setup that feels nothing like a typical condo. When it comes to outdoor living, this home truly delivers: an expansive screened-in patio sets the stage for year-round enjoyment, while a separate open-air patio offers a sun-drenched spot to relax, garden, or simply soak in the Florida lifestyle. Peace of mind comes standard: a brand-new 2026 roof means this home is as solid as it is stylish. Offered unfurnished and ready for immediate occupancy. Residents of Carriage House II enjoy access to a beautiful pool and clubhouse, all set amid lush, manicured grounds surrounding a tranquil lake with fountains, turtles, and ducks. Membership to The Landings Racquet Club is available but not included or required — a wonderful option for those who want the full lifestyle package. The Landings' coveted location west of the Trail puts everything within easy reach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
7373 S SERENOA DR, SARASOTA, FL 34241
$950,00018 Days on yellowkey MLS ID: A4699588
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 1998Monthly Fee: $170 Tax: $6,153 (2025)Community: Serenoa Ph 3Spa: YesSingle Family
Taxes:$6,153
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Many home buyers dream of a neighborhood like the gated community of Serenoa... it is a quiet street, canopy lined with mature trees and plenty of breathing room. The lots here are HALF-ACRE+, the streets are calm with beautiful, quality homes throughout. It's a gated community with lakes, plenty of green space tennis and pickleball courts with a golf course where MEMBERSHIP IS OPTIONAL. This spacious home is in a perfect location, close to TOP-RATED SCHOOLS, Siesta Key beach, UTC for shopping and dinner, Lakewood Ranch, downtown Sarasota, hospitals and five airports all within about an hour. The house itself is a 4 bedroom, 3 bath, with a den, with a POOL AND SPA. It offers many nice touches including tray ceilings, arched doorways, built-ins, and large windows and many pocketing sliders that let in a plethora of natural light. The TILE ROOF IS YOUNG, INSTALLED IN 2023, POOL RESURFACED IN 2023, NEWER AC SYSTEMS (2023 AND 2024), AND THE HOUSE WAS COMPLETELY REPIPED IN 2024... all of these improvements give the next homeowner peace of mind. Hard flooring spans throughout the home, so it's easy to keep clean and is perfect for pets. In the entry area, there is a formal dining room, sitting area/flex room with pool views and a den. The kitchen is at the center of the house, where the heart of the home should be, and it opens directly up to the family room and a breakfast nook area, where entertaining or family relaxing time is easy. Light colored cabinets, a big island and breakfast bar, a dry bar, a built-in desk, and a walk-in pantry big enough for real grocery runs are gifts that this home offers. You have pool views from the kitchen and family room as well. You will enjoy the large, NEWLY SCREENED, NEWLY PAINTED lanai where there is plenty of room for family and friends, and where you can sit to enjoy watching our Florida wildlife while sipping your coffee or cocktail. The pool is surrounded by landscaping AND plenty of space between homes that gives the wonderful feeling of privacy. The master bedroom is split from the extra bedrooms for privacy. The primary suite has its own pool access, an expansive walk-in closet, and a bathroom with two vanities, a soaking tub, a separate shower, and its own water closet. Two of the other bedrooms share a Jack-and-Jill bath, and the fourth bedroom is off by itself with its own full bath and a door out to the lanai... good setup if you've got guests or family staying with you. The garage fits three cars and is extra deep, with a wide driveway to match. Storage isn't an issue anywhere in this house. This solid, well-built home is in a sought-after neighborhood where people love living. Come visit in person... come see, come sigh, come make this home your own.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
4478 STREAMSIDE CT #1506, SARASOTA, FL 34238
$315,000110 Days on yellowkey MLS ID: A4689139
REDUCED by $7,000 (2.2%) on 06/30/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1554 Built: 2005 Tax: $4,008 (2025)Community: Arielle/Palmer Ranch Sec IvCondo
Taxes:$4,008
Remarks: Under contract-accepting backup offers. NEW PRICE! TURNKEY FURNISHED! $5,000 SELLER CREDIT! MOTIVATED SELLER! Welcome to Arielle on Palmer Ranch, where everyday living feels like a private retreat in one of Sarasota's most desirable gated communities. Now offered at $315,000, this beautifully maintained ground-floor residence with no stairs combines comfort, convenience, and low-maintenance Florida living. Recent improvements include brand-new luxury vinyl plank flooring installed in May 2026 throughout the main living areas, primary bedroom, and enclosed den, along with a new Carrier Performance Series HVAC system installed in 2025 featuring a smart thermostat and a transferable warranty available to the buyer (subject to warranty transfer requirements). Being offered turnkey furnished, the home includes quality furnishings, housewares, and everyday essentials. Highlights include a Natuzzi leather sofa and recliner, king-size beds in both bedrooms, and a Flexsteel sleeper sofa in the enclosed den. With 1,554 square feet under air, this spacious two-bedroom plus enclosed den, two-bath residence lives like a single-family home. The enclosed den offers flexibility as a private office, media room, hobby room, or third bedroom. An oversized one-car garage, extended driveway accommodating two additional vehicles, and abundant guest parking provide exceptional convenience. Three sets of sliding glass doors fill the home with natural light and open to a screened lanai overlooking a peaceful preserve with pond and creek views. The primary suite features two walk-in closets and tranquil preserve views. Residents enjoy maintenance-free living with the HOA covering water, internet, basic cable, exterior maintenance, roof maintenance, and professional landscaping, along with a heated pool, spa, poolside restrooms, barbecue area, and gated entry. The Legacy Trail is just outside the community entrance. Located less than five miles from Siesta Key Beach and just minutes from downtown Sarasota, St. Armands Circle, Lido Key, Nokomis Beach, championship golf, dining, shopping, and cultural attractions. The seller is offering a $5,000 credit at closing that may be used toward closing costs, an interest rate buy-down, or future updates. Motivated seller welcomes serious offers.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Tanya Agle (484-904-5588)
4557 KINGSMERE #23, SARASOTA, FL 34235
$277,000132 Days on yellowkey MLS ID: A4685751
REDUCED by $10,000 (3.5%) on 07/10/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1188 Built: 1987 Tax: $3,813 (2025)Community: Kingsmere - The MeadowsVilla
Taxes:$3,813
Remarks: Spectacular golf course views, partially furnished and priced to sell! Easy living in this spotless, maintenance-free one-story villa with natural light and tranquil golf views in The Meadows, a park-like oasis in a phenomenal location. A canopied street and charming pergola welcome you home. Inside, you will love the cathedral ceilings, new skylights that bathe the great room with soft light, and a relaxing Florida room overlooking the golf course with a preserve in the distance. No neighbors in sight. The kitchen features stainless steel appliances, white shaker cabinetry, Mykonos White quartz countertops and direct access to the private grilling patio. The primary suite pampers you with a walk-in closet and a gorgeous zero-entry Roman shower with mosaic flooring. All just 100 feet to the heated pool, 1.5 miles to Whole Foods and Trader Joe’s and convenient to all The Meadows has to offer. Set on 1,600 park-like acres, The Meadows is a resort-style community only 15 minutes from downtown Sarasota. Residents enjoy 14 miles of scenic biking and walking trails, and, for a low resident fee, a new fitness center, Junior Olympic-size pool, pickleball courts, golf courses and a top Har-Tru tennis complex. Plus, close to the country's award-winning beaches, remarkable arts and culture, and just two miles from Nathan Benderson Park, the new Mote SEA Aquarium, the future Sarasota Orchestra and The Mall at University Town Center, a world-class fashion and dining destination. A fabulous Florida lifestyle awaits. With 2024 shingle roof and above flood plain in zone X.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Fernando Viteri, Pa (941-400-7676)
4725 GREENCROFT RD, SARASOTA, FL 34235
$594,000182 Days on yellowkey MLS ID: A4679547
REDUCED by $15,000 (2.5%) on 05/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2300 Built: 1978 Tax: $5,502 (2025)Community: The MeadowsSpa: NoSingle Family
Taxes:$5,502
Remarks: A home you can truly feel good about. Welcome to this sustainable, tranquil pool home with sweeping golf course views, in The Meadows, a 1,600-acre park-like oasis in one of Sarasota’s most desirable locations. Major structural systems already upgraded, including fully owned solar system (no lease), professionally epoxy-lined sewer pipes (2022), newer HVAC (2019), and electrical panel replacement, providing rare long-term cost stability and peace of mind. Set on a quiet, tree-lined street, a circular drive and charming front porch invite you into this eco-conscious residence where solar panels provide abundant power, saving an estimated $3,000+/year, while Florida-friendly landscaping conserves water and minimizes environmental impact. Inside, you’ll find gorgeous matte Romana porcelain tile flooring throughout, soaring beamed cathedral ceilings in the family room, and spacious interiors filled with natural light. The heart of the home is the updated kitchen, featuring solid maple cabinetry, thick Baltic granite countertops, stainless steel appliances, and a convenient pass-through window to the pool deck perfect for effortless entertaining. Step outside to the inviting screened lanai and pool, ideal for relaxing, swimming, or gathering with friends and family, all framed by lush greenery and serene golf course vistas. Residents of The Meadows enjoy a true resort-style lifestyle set across 6,600 lush acres, just 15 minutes from downtown Sarasota. Community amenities include 14 miles of scenic walking and biking trails, a vibrant social calendar, fitness center, junior Olympic pool, 10 pickleball courts, three 18-hole golf courses, and a premier tennis complex all available at a very reasonable fee. Ideally located near award-winning beaches, cultural attractions, Nathan Benderson Park, Mote Marine Aquarium, Whole Foods, Trader Joe’s, and The Mall at University Town Center: a world-class destination for shopping, dining, and entertainment. A fabulous Florida lifestyle awaits. Notable Updates: 2022 owned photovoltaic solar panels & electrical panel, 2022 epoxy-lined sewer pipes, 2019 HVAC system, 2016 Pool cage, 2004 Tile roof, above flood plain in Flood Zone X
6006 MIDNIGHT PASS RD #48, SARASOTA, FL 34242
$325,00085 Days on yellowkey MLS ID: A4691484
REDUCED by $25,000 (7.1%) on 07/23/2026
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 420 Built: 1960 Tax: $2,987 (2025)Community: Casa MarSpa: NoCondo
Taxes:$2,987
Remarks: PRICE IMPROVEMENT! Private Beach Access and exceptional value on Siesta Key! Rare opportunity to own in highly desirable Casa Mar and create your own island retreat with outstanding value-add potential. This studio unit presents one of the most compelling opportunities to own on Siesta Key. The unit already features updated lower kitchen cabinetry, quartz countertops, and a stainless-steel sink, providing an excellent foundation for customization. Ready for a new owner to install appliances and replace the A/C, the unit is priced accordingly and offers tremendous potential for investors, seasonal residents, or buyers seeking an affordable entry into one of Florida's most sought-after beach communities. Ideally situated within the community, this premium location places the pool directly behind the unit and provides convenient access to the private beach path leading to Siesta Key's world-famous powdery quartz sand beaches and stunning Gulf waters. Spend your days enjoying the sunshine, taking peaceful walks along the shoreline, and ending each evening with breathtaking Gulf Coast sunsets just steps from your door. Casa Mar permits weekly rentals, creating excellent income-producing potential and flexibility for owners. The condominium association fee includes cable, internet, water, sewer, building insurance, exterior maintenance, and grounds care, making ownership simple and convenient. Whether you're searching for an investment property, vacation getaway, or future beachside escape, this is an opportunity to secure a piece of Siesta Key at an attractive price point. Private beach access, weekly rentals, and endless possibilities.
Listing Agent: Susan Beaver, Llc (732-489-3727)
2121 PALM TER, SARASOTA, FL 34231
$599,000145 Days on yellowkey MLS ID: A4684433
REDUCED by $16,000 (2.6%) on 07/23/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1681 Built: 1950 Tax: $5,120 (2025)Community: Harbor OaksSingle Family
Taxes:$5,120
Remarks: Backyard retreat + income-producing detached studio + steps to Trader Joe’s! Quiet dead-end street near Siesta Key & Downtown Sarasota—privacy meets prime location. Extensively updated and ideally located, this Sarasota home offers the perfect blend of lifestyle and convenience—just minutes to Downtown, Siesta Key Beach, Sarasota Memorial Hospital, and SRQ Airport. The private backyard is a true highlight, featuring lush landscaping, custom hardscaping, a pergola, and a striking mural—fully fenced (2023) for privacy and perfect for entertaining or relaxing outdoors year-round. Inside, the home is move-in ready with fresh paint, custom feature wall, built-in closets, blackout blinds, and hurricane-rated windows and doors for peace of mind and natural light. The kitchen includes a Bosch dishwasher (2025), Samsung range and microwave (2023), plus LG washer/dryer (2023). Additional upgrades include whole-home water filtration with reverse osmosis (2022), air purification (2024), generator with transfer switch (2025), updated plumbing, maintained HVAC, and a new 28-gallon water heater (2026). The upgraded garage features waterproof flooring, built-ins, insulation, and mini-split AC (2025)—ideal for a gym, workshop, or flex space. The detached studio adds exceptional versatility with a private entrance, outdoor space, kitchenette, full bath, washer/dryer, and dedicated AC (2023). The studio has been successfully rented, offering strong income potential or flexibility for guests or a private office. A rare opportunity combining privacy, flexibility, and a highly desirable Sarasota location.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Samantha Markbreit (845-558-4828)
5456 HAMPSTEAD HEATH #20, SARASOTA, FL 34235
$278,00080 Days on yellowkey MLS ID: A4692963
REDUCED by $17,000 (5.8%) on 06/24/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1241 Built: 1989 Tax: $3,626 (2025)Community: Hampstead Heath - The MeadowsVilla
Taxes:$3,626
Remarks: Fabulous location and views! Tranquil pond and golf course views from this bright end-unit in The Meadows, a park-like oasis 15 minutes from downtown. In the desirable maintenance-free Hampstead Heath community, canopied streets and a private front patio welcome you home. Inside, vaulted ceilings, tall windows and walls of sliders bring in the outdoors, creating a bright and tranquil ambiance. You’ll enjoy the spacious great-room layout, ample kitchen with breakfast nook with access to grilling patio, and the relaxing glassed-in lanai showcasing a daily parade of bird life there just to entertain you! The primary suite features a walk-in closet, double vanities and walk-in shower. All just half a block to the heated pool and convenient to all The Meadows has to offer. Set on 1,600 park-like acres, The Meadows is a resort-style community just 15 minutes from downtown. Enjoy 14 miles of scenic trails and available fitness center, Junior Olympic pool, pickleball, golf, and Har-Tru tennis. You’ll be minutes to award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, Mote SEA Aquarium, Legacy Trail, the future Sarasota Orchestra and University Town Center, a favorite shopping, entertainment and dining destination. Furniture available separately, 2026 exterior paint, 2024 shingle roof, 2023 hot water heater, 2021 A/C system, and above flood plain in Zone X.
5475 CHANTECLAIRE #58, SARASOTA, FL 34235
$525,00048 Days on yellowkey MLS ID: A4695707
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985 Tax: $5,106 (2025)Community: Chanteclaire - The MeadowsVilla
Taxes:$5,106
Remarks: One of a kind! Welcome to this beautifully updated villa on the 14th fairway of the Meadows Golf Course. Enjoy stunning golf course views from the builder’s choice lot in Chanteclaire. Fully updated in 2023, the interior features luxury vinyl flooring, crown molding and abundant natural light. The open kitchen boasts stainless-steel appliances, Malibu quartz countertops, a new tile backsplash and Oxford Maple soft-close cabinetry with direct access to the grilling patio. Perfect for entertaining, the living room includes new custom cabinetry, a matching quartz countertop and a built-in wine fridge. The spacious primary suite serves as a true retreat, complete with a custom walk-in closet and a sliding door that opens to peaceful nature views. The present owners have added extensive premium updates for ultimate comfort and peace of mind. The home features full-height, custom PGT hurricane-rated windows and doors throughout, powered aluminum hurricane shutters and plantation shutters in the dining room and bedrooms. Mechanical and structural upgrades include a high-efficiency Trane variable-speed HVAC unit and a new shingle roof installed in 2025 with 71 additional joist clips for enhanced wind protection. This property sits at a 33-foot elevation in Flood Zone X, making it the perfect choice for a secure, lock-and-leave Florida lifestyle. Outside, a quiet cul-de-sac location, paver driveway and charming courtyard welcome you home. Mature shade trees, colorful sunsets and a daily parade of local birds frame the golf course views. The villa is also just a short distance from two heated community pools. The comprehensive HOA fee covers exterior insurance, maintenance-free yard care, irrigation, pest control, exterior cleaning and painting, roof maintenance, dryer vent cleaning, neighborhood pools and basic cable. Set within the 1,600 park-like acres of The Meadows, this resort-style community offers an active social calendar, 14 miles of scenic trails, championship golf courses, a junior Olympic pool, pickleball, Har-Tru tennis and a fitness center. You are just 15 minutes from downtown Sarasota, Bradenton, Lakewood Ranch and Sarasota International Airport and mere minutes from Whole Foods, Trader Joe’s, Nathan Benderson Park, the Legacy Trail and premier dining at University Town Center. Experience worry-free Florida living at its finest!
3757 COUNTRYSIDE RD, SARASOTA, FL 34233
$649,00084 Days on yellowkey MLS ID: A4692427
REDUCED by $31,000 (4.6%) on 07/17/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2694 Built: 1981Monthly Fee: $50 Tax: $5,257 (2025)Community: Country PlaceSpa: NoSingle Family
Taxes:$5,257
Elementary School: Wilkinson Elementary
Remarks: Nestled on an oversized, oak-shaded lot in the highly sought-after Country Place subdivision, this exceptional 3-bedroom, 3-bathroom home delivers Sarasota charm with serious modern peace of mind. The property has been meticulously updated, highlighted by a complete replumb and brand-new flooring throughout the main living areas and primary suite in 2025, plus impact-resistant windows in the Florida room, a roof replaced in 2018, and dual A/C units replaced in 2017 and 2021. Outdoors, a heated screened-in pool anchors a lush backyard retreat maintained effortlessly by an in-ground sprinkler system on a private well. The thoughtful floor plan offers exceptional privacy, with walk-in closets in all three bedrooms, a primary suite with pool access, and a second en-suite with its own private entrance and patio, ideal for guests or multi-generational living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Inbal August (917-957-8111)
2070 59TH ST, SARASOTA, FL 34243
$599,00090 Days on yellowkey MLS ID: A4691713
0 Days Off yellowkey (back on 7/12/2026)
REDUCED by $45,000 (7.0%) on 07/11/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1745 Built: 1984 Tax: $6,039 (2025)Community: Desoto AcresSingle Family
Taxes:$6,039
Remarks: Under contract-accepting backup offers. Tucked away on 2.15 private acres in the heart of DeSoto Acres, this One-of-a-Kind 3-bedroom, 3-bath property captures the essence of “Country Estates in the Heart of Town.” Spanning more than 850 acres of 2+ acre homesites, DeSoto Acres—renamed in 1945—remains Sarasota County’s largest RE-1 low-density community, celebrated for its rustic charm, canopy roads, and equestrian-friendly lifestyle just minutes from city conveniences. This inviting home offers exceptional versatility, making it an ideal primary residence, investment opportunity, or income-producing rental. Step inside to a welcoming, light-filled Florida sunroom that flows seamlessly into a screened patio—perfect for enjoying peaceful mornings and breezy evenings surrounded by nature. The thoughtfully designed layout includes a spacious primary suite with an en suite bathroom, large walk-in closet and a slider door that provides access to the tranquil side yard. A guest bedroom features a bonus den with direct access to a screened rear porch—an ideal retreat overlooking the shady, tree-filled preserve where birdsong and natural beauty abound. Adding even more value is a private 1-bedroom, 1-bath apartment with a kitchenette and separate entrance (completed in 2024), offering excellent potential for rental income, guest accommodations, or multigenerational living. The cozy main living area is anchored by a striking rock hearth fireplace and complemented by a Vermont Castings wood-burning stove, creating a warm and welcoming atmosphere. Recent upgrades include impact entry doors and a newer hot water heater for added peace of mind. Practical features abound with a 2-car carport, an attached 2.5-car garage, and ample storage space. Outdoors, the expansive property truly shines—featuring a 20' x 10' livestock corral ready for chickens, mini cows, or even a horse. With no deed restrictions, you’ll enjoy unmatched freedom, privacy, and the flexibility to create your own country lifestyle. This is a rare opportunity to own a slice of Old Florida charm with room to grow, invest, and live freely—all in a highly sought-after Sarasota location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Heather Gehan (941-893-0213)
5507 CONTENTO DR, SARASOTA, FL 34242
$1,599,999157 Days on yellowkey MLS ID: A4683288
REDUCED by $125,001 (7.2%) on 07/07/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSpa: NoSingle Family
Taxes:$15,484
Remarks: A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
539 AVENIDA DEL NORTE, SARASOTA, FL 34242
$5,690,0006 Days on yellowkey MLS ID: A4700498
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4195 Built: 2026 Tax: $7,935 (2025)Community: Archibald ResubSpa: YesSingle Family
Taxes:$7,935
Remarks: Virtually Staged. Exquisite new construction on Siesta Key redefines island luxury! Substantial progress has already taken place to complete this masterpiece. This is a rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. Siesta Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its famous powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. Just moments from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity: your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock—a true island luxury! This thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate incredible craftsmanship and fine detail, the home offers 4,195 square feet of interior living space and an additional 3,756 square feet of outdoor living, seamlessly blending indoor and outdoor environments. The chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. Two beautifully appointed bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or the private elevator one level up to access the primary suite, featuring a truly custom bath with bespoke tile, designer finishes, a soaking tub, and a spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper level. Flexible, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any lifestyle, from multi-generational living to a dynamic entertainer’s paradise. Imagine a home where the luxuries of island beach life blend perfectly with a private, resort-style retreat. Step outside to your inground pool and spa for cooling off or casual lounging, head up to the rooftop deck for sunset cocktails and starlit conversation, or enjoy your private boating access just steps from your front door. When you are ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. This is more than a home; it is an invitation to own your piece of the new Siesta Key lifestyle—elevated, effortless, and extraordinary!
Listing Agent: Andrew Azzarello (941-266-6084)
2050 EUCLID TER, SARASOTA, FL 34239
$2,395,000122 Days on yellowkey MLS ID: A4687473
Bed: 5 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 3991 Built: 2026 Tax: $4,305 (2025)Community: Euclid SubSpa: YesSingle Family
Taxes:$4,305
Remarks: Some homes impress. This one creates a lifestyle. Thoughtfully designed for the way todays families live, this exceptional 3,991 sq. ft. contemporary residence offers 5 bedrooms, 6 full bathrooms, a private office, and a flexible second-floor bonus room perfect as a game room, gym, or media lounge. Every detail was designed with comfort and connection in mind. The open-concept floor plan is filled with natural light and flows effortlessly into a private outdoor retreat featuring a saltwater pool and spa, outdoor grill, covered lanai, and spacious backyard with room for children, pets, and unforgettable family gatherings. Located in Arlington Park, one of Sarasota's fastest-growing and most desirable neighborhoods, this home offers more than luxury, it offers a lifestyle. Tree-lined streets, beautiful parks, highly rated schools, and a welcoming sense of community have made Arlington Park one of the city's premier destinations for new construction. Enjoy the convenience of being just minutes from Southside Village, Sarasota Memorial Hospital, downtown Sarasota, Siesta Key, and Lido Key, while coming home to a neighborhood that continues to grow in value and demand. With striking modern architecture, expansive indoor-outdoor living, a covered carport, premium finishes, and thoughtfully designed spaces throughout, this home stands out as one of Arlington Parks most distinctive new residences. Come experience the lifestyle, design, and quality that make this home truly unforgettable.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Alberto Rueda Ramirez (701-314-6916)
2010 HYDE PARK CIR, SARASOTA, FL 34239
$2,175,000122 Days on yellowkey MLS ID: A4687471
REDUCED by $24,000 (1.1%) on 06/11/2026
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3515 Built: 2026 Tax: $4,305 (2025)Community: Purtz SubSpa: YesSingle Family
Elementary School: Alta Vista Elementary
Remarks: Rarely does a new construction offer this combination of space, design, and functionality. Situated on an oversized 10,200 sq. ft. corner lot, this two-story residence features a private elevator, two luxurious primary suites, one on each level, and one of the best values in Arlington Park. Designed by Courtyard Modern Development LLC, this exceptional home offers 3,515 sq. ft. of living space, 4 bedrooms, 5 full bathrooms, 1 half bath, and an attached 2-car garage, thoughtfully designed for modern living. The first floor (1,825 sq. ft.) features a spacious primary suite, private office, laundry room, chef’s kitchen, and expansive open-concept living areas that seamlessly connect to the outdoor entertaining spaces. Upstairs, the 1,690 sq. ft. second level includes a stunning primary suite with a large private balcony, two additional guest bedrooms, and elevator access connecting both floors. The backyard is designed to embrace the Florida lifestyle, featuring a heated saltwater pool and spa, generous green space, natural landscaping, and multiple areas for entertaining, relaxing, or enjoying time with family and friends. Every space has been carefully planned to create a seamless indoor-outdoor living experience. Whether you’re searching for a primary residence, seasonal retreat, or investment opportunity, this property offers flexibility with potential for both short-term and long-term rentals, making it an outstanding option for a variety of buyers. Located in one of Sarasota’s most desirable neighborhoods, this home combines privacy, oversized lot size, contemporary architecture, and luxury finishes with exceptional value. Opportunities to own a newly built home on a corner lot of this size, with two primary suites and a private elevator, are becoming increasingly rare. Schedule your private showing today and experience why this is one of Arlington Park’s most compelling new construction opportunities...
Listing Agent: Jason Coy Turner (205-612-4353)
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