Featured Properties

Some or all of the listings below are provided by the St. Armands office.
$2,275,000 (USD)
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Sarasota Area Single Family Home

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1585 South Drive Sarasota, FL 34239

3 Bed
4 Baths
2764 sqft
MLS# A4666035
Virtual Tour
Welcome to 1585 South Drive, a timeless cottage-style residence in the beloved West of Trail community of Cherokee Park. Thoughtfully updated and rich with character, this home seamlessly blends historic charm with modern comfort. Refinished white oak floors, abundant natural light, stylish finishes, and a gracious, contemporary layout make it truly move-in ready. Elevated more than 10 feet above sea level yet just three houses from the bay, the home enjoys both beauty and peace of mind on a corner lot at the quiet end of the street.

From the inviting brick front porch, step into a foyer with custom board-and-batten detailing. To the right, a generous living room encourages gathering; to the left, a versatile office, den, or sitting room is tucked behind sliding doors for a quieter retreat. Expansive windows frame leafy views and bathe the interiors in light.

At the heart of the home, the oversized kitchen impresses with a large central island, abundant counter space, walk-in pantry, wet bar, and KitchenAid appliances. The adjoining dining room opens to the backyard and screened porch, creating seamless indoor-outdoor living.

The primary suite is privately situated on the main level, offering a spacious walk-in closet, serene ensuite bath, and direct screened porch access. Nearby, a second bedroom with its own hall bath serves perfectly as a guest suite, children’s room, or home office. Upstairs, a private retreat includes a large bedroom with dormer windows, built-in window seats, an ensuite bath, and extensive storage.

Additional highlights include a recently remodeled marble powder room, a well-equipped laundry room, an irrigation well, and an attached two-car garage. The generously sized lot offers ample room for a pool, guest house, or future expansion.

Sarasota's West of Trail neighborhoods are coveted for their proximity to Sarasota Memorial Hospital, downtown, and the sugar white sands of Siesta Key. Cherokee Park is perhaps the most prized of these, celebrated for its stately homes, wide tree-lined streets with sidewalks, walkability to Southside Village and Southside Elementary, and cherished traditions — from bustling Halloweens to twinkling luminaries and carriage rides at the holidays. While the surrounding streets boast their share of impressive new construction, this well-proportioned and well-preserved original stands apart for its enduring charm, turnkey livability, and exceptional value. Designer furnishings by Pecky Interiors are optionally available.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Nicholas "Nick" Gard
$1,750,000 (USD)
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Osprey Area Single Family Home

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422 Blue Garden Lane Osprey, FL 34229

3 Bed
4 Baths
3872 sqft
MLS# A4664436
Virtual Tour
A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool and waterfall feature. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna complete the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. Ownership includes membership in The Oaks Club, Sarasota’s premier golf and country club, featuring two championship courses, tennis, WellFit center, fine dining, and a vibrant year-round social calendar—all in the heart of South Sarasota.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe
$1,750,000 (USD)
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Sarasota Area Single Family Home

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1719 Kenilworth Street Sarasota, FL 34231

5 Bed
5 Baths
4432 sqft
MLS# A4665777
Virtual Tour
1719 KENILWORTH -WEST OF TRAIL- where space, elegance, and Sarasota’s most desirable lifestyle converge—all at a price that represents remarkable value in this highly coveted corridor. With more than 4,400 square feet of thoughtfully designed living space, this 5 Bedroom, 5 Bathroom (4 En Suite) home delivers a perfect balance of sophistication and comfort, crafted for both everyday living and memorable entertaining.
Step inside and be immediately struck by the voluminous ceilings that create a grand sense of space. A wide impressive wood staircase adds character and expansive hallway provides a graceful introduction to the home’s flowing layout. Sunlight pours through the sliders and windows, illuminating the formal and casual living areas and highlighting the seamless transition from indoor spaces to the gorgeous outdoor retreat.
At the heart of the home, the chef’s kitchen features double ovens, a generous center island, and a built-in coffee station, making it perfect for everything from weekday breakfast to weekend entertaining. A convenient downstairs En Suite Bedroom is perfect for multigenerational living, visiting guests, or main-level accessibility. Sliding doors open to the outdoor living space, where a saltwater, solar-heated pool and spa take center stage, framed by lush landscaping and low-maintenance turf. This private oasis is ideal for morning swims, quiet afternoons, or lively evenings under the stars.
Upstairs, the spacious owner’s suite offers a serene retreat with dual walk-in closets and a spa-inspired bath featuring dual vanities and an oversized shower. Three additional En Suite Bedrooms provide comfort and privacy for family or guests, while a versatile loft adds flexibility for work, study, or hobbies.
Premium finishes reinforce the home’s exceptional value: ceramic tile floors on the main level for timeless style and easy care, and luxury vinyl floors upstairs for warmth, comfort, and durability. Additional upgrades including impact windows, a three car garage, dual HVAC system, and a sprinkler system.
Life West of Trail is about more than location; it is a lifestyle defined by privacy, convenience, and access to Sarasota’s best. From this tranquil residential setting, you are just 3.7 miles from Siesta Key Village, offering world-famous white sand beaches, vibrant arts, and dining options. Additionally, the charming Southside Village is nearby, featuring Morton’s Gourmet Market, restaurants and a variety of boutique shops. Selby Gardens and downtown with all that the city offers is just 5 minute drive. Homes of this size, quality, and location seldom come to market at this price point, making this an exceptional opportunity for discerning buyers.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Danelle Haag
$1,347,000 (USD)
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Sarasota Area Single Family Home

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1738 Siesta Drive Sarasota, FL 34239

4 Bed
3 Baths
2131 sqft
MLS# A4657081
Newer (2013) “West of Trail” offering with the perfect blend of charm and peace of mind — elevated 22 feet above sea level (X flood zone) with quick access to Siesta Key and zoned for the highly sought-after Southside Elementary. Thoughtfully designed for modern living, it features 3 bedrooms plus a flexible 4th bedroom, office, or gym, along with a versatile downstairs bonus room ideal for hobbies, a dining space, or a cozy hangout. Tasteful curb appeal with Key West charm and a durable metal roof invite you to your slice of Florida living — conveniently located on the mainland. Preferred southern exposure fills the coastal-casual great room and updated kitchen with natural light and frames views of the sparkling saltwater pool and lush tropical oasis. Pocketing sliders create seamless indoor-outdoor flow, connecting multiple gathering spots — whether sun lounging by the pool or dining beneath the flowering plumeria canopy. Artificial turf and custom, low-maintenance landscaping offer a year-round backdrop for enjoyment, whether you’re here seasonally or full-time. All of it paired with the peace of mind (and lower insurance costs) that comes with newer construction — with only a few coconuts lost in the busy 2024 storm season. A two-car garage includes a Tesla charger and plenty of space for a golf cart or bikes for the quick ride to Southside Elementary, Red Rock Park, or Southside Village for gourmet groceries and dining. The historic Granada neighborhood blends 100 years of character and charm, with an eclectic mix of architecture and a quiet, tucked-away feel — right in the heart of Sarasota. Stroll tree-lined sidewalks to Bonita Park, breakfast cafés, croissants, or Shakespeare’s neighborhood pub. Ideally located between the white sands of Siesta Key and vibrant Downtown Sarasota — just 10 minutes to either — you’ll feel like you’re on vacation every day. Within the City of Sarasota, the property also offers excellent weekly rental potential for long-term investment or seasonal flexibility. This is your low-stress entry into “West of Trail” living. Furnishings are available to make the move even easier — reach out today to schedule your tour!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Adamson
$1,250,000 (USD)
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Sarasota Area Single Family Home

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321 Gowdy Road Sarasota, FL 34237

3 Bed
4 Baths
2443 sqft
MLS# A4665965
Virtual Tour
Fully furnished! Modern Style Meets Downtown Sarasota Convenience.
Welcome to this beautifully designed three-story townhome, a residence that offers the best of city living with a warm and inviting feel. From its prime location across from Payne Park to its thoughtful upgrades and spacious layout, this home was created to complement both an active lifestyle and moments of quiet retreat.
Step inside and discover a bright and versatile first level, featuring a private bedroom with en-suite bath—ideal as a guest suite, home office, or creative studio. The main living level showcases soaring ceilings and a seamless open concept, where natural light pours in from every angle. At the heart of the home, the chef’s kitchen impresses with quartz counters, full-height cabinets, a large island, and premium stainless steel appliances. Whether you’re hosting friends for dinner or enjoying a quiet night in, this space is equal parts functional and stylish.
The adjoining living and dining areas create an easy flow for entertaining, with oversized windows framing views of Payne Park. A private balcony extends your living space outdoors, perfect for morning coffee or sunset cocktails.
The top floor is home to a serene primary suite designed as a true retreat. Complete with custom closets, a spa-like bath featuring a glass-enclosed shower and soaking tub, and tall tray ceilings, this space feels luxurious yet comfortable. An additional bedroom with its own private bath completes the third level, offering privacy for family or guests.
Additional highlights include plank flooring throughout, designer fixtures, smart home features, a private elevator, and a two-car garage with epoxy flooring. Outside, enjoy the low-maintenance lifestyle of Payne Park Village, with resort-style amenities including a heated pool, spa, cabana, BBQ area, dog park, and turf play area. 
When you’re ready to explore, Sarasota’s vibrant downtown is at your doorstep—boutiques, award-winning dining, theaters, and the weekly farmers market are all just minutes away. Hop on the Legacy Trail for a bike ride, spend the afternoon at St. Armands Circle, or unwind on the world-famous beaches of Siesta Key and Lido.
This home blends modern comfort, designer details, and unbeatable convenience—making it the perfect choice for those ready to embrace the Sarasota lifestyle.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ashley Goldstein
$1,200,000 (USD)
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Longboat Key Area Single Family Home

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4968 Gulf Of Mexico Drive Villa 22 Longboat Key, FL 34228

3 Bed
2 Baths
1422 sqft
MLS# A4650036
Breathtaking Sarasota Bay views can be yours! This rare to find 3BR/2BA waterfront villa offers unobstructed water views and a dream coastal lifestyle. With an extraordinary location on a serene peninsula, this ground-level, maintenance-free residence lives like a single-family home—without the upkeep or the price. Step outside to your private waterfront patio, with dolphins, manatees, and seabirds as your daily companions. Just across the street, enjoy your choice of three beach accesses, making sun and sand part of your everyday routine. Inside, discover a bright and open floor plan featuring a great room and bonus room with windows on three sides, welcoming in bay breezes, moonlit water views, and peaceful tropical vibes. The kitchen is a chef’s delight, with granite countertops, stainless appliances, breakfast bar, and ample storage. Tile floors flow throughout, offering easy maintenance and a clean, coastal feel. The split-bedroom layout ensures privacy, ideal for hosting guests or working from home. The primary suite overlooks the marina and features a walk-in closet and beautifully updated ensuite bath with granite vanity and custom glass shower. The two guest bedrooms share an equally impressive bathroom with a granite topped vanity and large, tiled shower. An in-unit laundry room with full sized Washer/Dryer, 2018 roof, 2024 HVAC, and Hurricane-Impact Windows/Doors offer peace of mind year-round. Enjoy covered parking right at your door and soak up all that this amenities rich community offers including 2 marinas with first-come boat slips ($40/month or $45/month with an owner supplied lift), 2 heated pools (one is suitable for laps), kayaking, floating kayak launches and storage, tennis, pickle ball, fitness center, saunas, clubhouse, BBQ grills, fire pits, and a ½-mile of private walking paths. The HOA fee of $1,292/month covers building, flood, and hurricane insurance in addition to CATV and internet, sewer/water/trash and building maintenance, providing excellent value and low-stress ownership. With only 151 residences sharing 26 acres and ½ mile of direct Bay front land, this community feels peaceful, private and exclusive yet it’s just minutes from championship golf, top-tier marinas, fine dining, boutique shopping, and the vibrant cultural scenes of downtown Sarasota and St. Armands Circle. Pet-friendly? Absolutely. This community allows 2 pets (75 pounds max each) even for renters - an in demand and rare-to-find rental niche. This is Florida home ownership at its finest!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Deborah "Debbie" McHardy
$1,199,000 (USD)
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Sarasota Area Single Family Home

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3716 Camino Real Sarasota, FL 34239

3 Bed
3 Baths
2023 sqft
MLS# A4639409
Discover a rare, expansive property nestled in one of Sarasota’s most coveted “West of Trail” neighborhoods. This .35-acre property sits gracefully above special flood zones and offers convenient access to Downtown Sarasota, Siesta Key, and the prestigious Field Club. Located within the esteemed Southside Elementary School District, this home combines the quiet charm of the Granada neighborhood with easy access to Sarasota’s growing attractions. Follow the winding red brick path inside to a welcoming living room featuring a wood-burning fireplace and cozy atmosphere. The updated kitchen boasts quartz countertops, custom cabinetry, and sunlit views across the serene back courtyard. A distinctive sitting room with tongue-and-groove ceilings, a café dining area, and a peaceful reading nook overlooks one of the many tranquil courtyard settings. In the primary suite, you will find vaulted ceilings, a spacious ensuite bath, and French doors that open onto a pergola-adorned back deck. Two guest bedrooms—one currently configured as an office—are thoughtfully positioned across the home with convenient access to an additional guest bath. Completing this graceful estate is a generously sized screened pool nestled under mature oaks—a perfect backdrop for leisurely outdoor entertaining. This tranquil courtyard residence may serve as your gateway into one of Sarasota’s most cherished neighborhoods, or its impressive 128 feet of lot frontage could provide a remarkable canvas for your forever home. Enjoy the comforts of mainland living while being just minutes away from the powdery sands of Siesta Key beaches and the cultural attractions of downtown Sarasota.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Adamson
$1,100,000 (USD)
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Sarasota Area Single Family Home

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7198 Westwood Way Sarasota, FL 34241

4 Bed
3 Baths
2464 sqft
MLS# A4663691
Virtual Tour
Welcome to this beautifully updated equestrian estate located in Westwood by Myakka Valley Ranches. Nestled on 5.8 private, high-and-dry acres on a quiet cul-de-sac street, this 4-bedroom (+bonus room), 2.5-bathroom home with 2,464 sq.ft. of living space combines modern updates with country charm, offering a private pool, 12-stall barn, and covered riding arena—everything you need for both comfortable living and an equestrian lifestyle. Inside, the home features a renovated kitchen with newer cabinets, quartz countertops, a center island, and upgraded 2023 LG appliances including a microwave, dishwasher , refrigerator, and oven. Additional updates include a LG washer & dryer (2023), chimney renovation (2023), utility room and half-bath renovation (2023), and new upstairs carpet (2024). Comfort is assured with two Lennox A/C systems installed in 2023, with a Haylo air purifier downstairs, plus a new water heater (2025) and water treatment system (2022). The exterior has been extensively upgraded in 2023 with James Hardie cement siding, fascia and soffit, impact-resistant windows and doors, exterior paint, and a brand-new shingle roof (2022). The backyard oasis includes an inviting pool with a rock formation and updated pool pump and equipment (2024). The septic system was upgraded with a new tank (2025). Horse lovers will be impressed by the 12-stall barn with a new metal roof, fascia, soffit, and electric panel (2025), plus a 4,800 sq.ft. covered riding arena completed in 2024 with clay footing. The property is fully fenced with multiple pastures, offering ample space for horses, trailers, or RV storage. Westwood is located inside Myakka Valley Ranches, Sarasota's largest equestrian community, featuring miles of accessible horseback riding trails. It also borders Myakka State Park, the largest state park in Florida. This property is just a short drive to A+ rated schools, shopping, Lakewood Ranch, and Sarasota’s beautiful beaches. Acreage in Sarasota will be priceless one day—so bring your horses, llamas, golf cart, toys, dirt bikes, 4-wheelers, RV, or boat. This land has room for it all! Host parties, ride horses, camp under the stars, or simply watch the wildlife. As an added bonus, the seller is including a home warranty with an accepted contract—providing extra peace of mind. Your life will change once you own this special property in Sarasota.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roni-Marie "Roni" Gold
$925,000 (USD)
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Osprey Area Single Family Home

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21 Bayhead Lane Osprey, FL 34229

3 Bed
2 Baths
2216 sqft
MLS# A4664085
Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with leaded glass and step into the light-filled interior. Here you will find everything you need for comfortable Florida living. There is a dedicated home office off the entryway, with plantation shutters and a ceiling fan. The formal dining area features a lovely decorative ceiling, and a beautiful built-in buffet with glass-fronted cabinetry. The great room features another gorgeous piece of built-in furniture; floor to ceiling sliding glass doors connect the screened lanai and this room, making it bright and airy. The open kitchen, with breakfast bar, features beautiful new granite counters, stainless appliances, a chef’s desk, built-in wine and beverage cooler. The adjoining breakfast nook is flooded with natural light that streams through the aquarium window and offers an amazing view over the pool and spa. The master suit is huge and has a sitting area with a built-in window seat and large walk-in closets with glass front storage. The spacious master bedroom has been updated with granite countertops, and features dual sinks, a tub and separate shower and has marble wall accents. The two guest bedrooms are good sized and offer ample closet space. The second bathroom has been tastefully updated with granite counter and marble accents. The 2 car garage, with epoxy floor, is air conditioned with plentiful storage. Situated in the Bishopscourt neighborhood, behind the secure gates of The Oaks Preserve, this beautiful home backs a lush, tropical preserve providing privacy for the sparkling pool and spa. The lanai has two separate areas surrounding the pool. A large, covered area with an outdoor kitchen and ceiling fan, the perfect place for al fresco dining in the shade, and pool and spa area, covered by a cage, allowing for frolicking in the sunshine. Or meet your neighbors for a dip in the Bishopscourt community pool. The Oaks Club amenities include two championship golf courses, an award-winning tennis program, pickle ball and croquet courts, and a state-of-the-art fitness center. With three outstanding restaurants, and a wide variety of social and recreational options, there is no need to look any further than here for the perfect place to enjoy the best of Florida country club living. Club membership is required with homeownership.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe