OWNER MOTIVATED LOOKING FOR OFFERS! Positioned in highly desirable Oyster Bay Estates in the West of Trail area, this beautifully rebuilt 4-bedroom, 3.5-bath home sits on a high-and-dry spacious 1/3-acre lot in flood zone X where no flood insurance is required. Completely gutted and rebuilt from the studs in 2021 this residence is like new. The property includes a newly-built 484 sq ft detached guest house/ADU with private entrance. Lush, mature landscaping provides privacy and curb appeal to this lovely home. Relaxing Florida living is ensured with a covered luxury outdoor living space including an outdoor kitchen with grill, cooktop, refrigerator and sink ideal for entertaining and family life. Also part of the outdoor living space is the inviting heated saltwater pool and spa with travertine tile deck and new pool cage. The new open-concept kitchen boasts Dekton countertops, a light-wood island with built-in drawers, a gas range and closet pantry. All the bedrooms include ensuite bathrooms. The primary suite offers a custom walk-in closet and spa-style bath with dual vanities, quartz countertops, large walk-in shower, and Toto water closet. The A/C system was replaced in 2025 and provides individual thermostats in each bedroom for comfort. Other new features include wood-look tile flooring throughout, impact windows and doors, new roof, replaced PVC plumbing drains, updated electrical with new panel, sprayed insulation, smooth finished walls & ceilings, tankless water heater, natural gas hookup, new well and irrigation system, and $100,000 in upgraded landscaping. The oversized 2-car garage features epoxy flooring and an impact garage door. Surveillance cameras and security lighting is included for your well-being. Set back from the road, this home offers a quiet and private ambiance. Residents in Oyster Bay enjoy walking their dogs through the lovely treed neighborhood, biking to tennis, dining & the marina at the Field Club, and kids play or ride to Red Rock Park down the street. The home is in an excellent location just minutes to Siesta Key and downtown Sarasota, and walking distance to schools, Trader Joe’s, Publix, restaurants, and cafes. This is a fabulous opportunity!

Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wall ovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options.

This tastefully updated and remodeled single story home is ideally located within the sought after Bird Key neighborhood. Set on a large corner lot, it features a clean, contemporary style that feels both current and easy to live in. The home offers three bedrooms, two and a half bathrooms, and a two car garage, creating a comfortable and well balanced living environment. Inside, the open concept split floor plan provides both flow and definition, with separate living and family rooms suited to modern living. The remodeled kitchen features quartz countertops and sleek contemporary cabinetry and is centrally positioned to connect the main living, dining, and family spaces.
Both living areas open through impact sliding glass doors to the lanai and pool, creating an easy transition between indoor and outdoor living. Fully opening sliders from the living and family rooms extend the space onto the pool deck, making the home particularly well suited for entertaining. The primary suite includes a spacious bedroom, walk in closet, and an updated en suite bathroom. Two additional guest bedrooms and a bathroom are located on the opposite side of the home, offering privacy for family and guests. The generously sized family room easily incorporates a small home office area. Recent improvements include a new tile roof in 2025, whole house propane generator 2025, a newer air conditioning system in 2023, and impact windows for added security and peace of mind. Bird Key offers one of Sarasota’s most desirable locations, just minutes from downtown Sarasota, St. Armands Circle, and Lido Beach. Residents also benefit from the nearby Bird Key Yacht Club, currently undergoing a full redevelopment and expected to reopen early in 2027 as a premier destination for boating, tennis, and social activities. PLEASE NOTE FRONT DOOR ENTRY IS LOCATED ON BOBWHITE WAY.

Coastal Elegance on Phillippi Creek!
Custom-built by Coachman Homes, this exceptional waterfront residence blends timeless architecture, privacy, and an ideal Sarasota location. Set within an intimate gated enclave of just nine homes, the property spans nearly three-quarters of an acre and offers over 190 feet of private frontage on the scenic Phillippi Creek—an idyllic backdrop for daily living and entertaining. Notably, this house structure has had no history of water intrusion from any storm or hurricane.
Inside, approximately 3,500 square feet of living space unfolds in an open, light-filled layout with four bedrooms, a family room, and a dedicated office. A columned front porch and double-door entry lead into a grand living room featuring vaulted ceilings, a cultured stone fireplace, and a wall of glass doors that open to the screened lanai and pool. The adjacent dining room creates an elegant setting for gatherings, while the open-concept kitchen connects seamlessly to the family and casual dining areas—each overlooking the outdoor living space.
The chef’s kitchen features custom cabinetry with under-cabinet lighting, granite countertops, tile backsplash, breakfast bar, and stainless-steel appliances. A split-bedroom plan ensures privacy. The primary suite is a serene retreat with French doors to the deck, a large walk-in closet, and a spa-style bathroom complete with dual vanities, walk-in shower, soaking tub, and private water closet. A flexible office adjoins the suite, ideal for working from home or quiet reading. On the opposite wing, three guest bedrooms share two full baths, offering comfort for family and visitors alike.
Additional features include Lauzon hardwood floors throughout, recessed lighting, plantation blinds, hurricane shutters, two-zone A/C, brand-new Hayward Tristar 950 Variable Speed pool pump (2026), re-screened pool cage (2024), a spacious laundry with newer washer and dryer, and a three-car garage with abundant storage.
Outdoor living takes full advantage of Sarasota’s year-round sunshine. A large, screened lanai with swimming pool, spa, and waterfall fountain invites relaxation, while the full-length covered deck—with outdoor kitchen—encourages al fresco dining. Lush tropical landscaping guarantees privacy, and the large fenced portion of the backyard offers space for pets and play. A brick walkway leads to the private dock, equipped with water and electric. With only two bridges to Roberts Bay, boaters enjoy quick access to the Intracoastal Waterway and Gulf of Mexico.
This residence combines the serenity of a secluded estate with unmatched convenience—just minutes to Siesta Key Beach, Downtown Sarasota, and The Bay Park. Fine dining, boutique shopping, cultural venues, and waterfront recreation are all within easy reach. In this rare nine-home community, you’ll experience the perfect balance of coastal tranquility and city sophistication—a true Sarasota lifestyle.

One or more photo(s) has been virtually staged. Situated in the highly sought-after maintenance-free community of Queens Harbour, behind the gates of Bay Isles, this updated lakefront home perfectly captures the ease of Florida living. A 2023 tile roof adds peace of mind, while a smart split floor plan includes three en-suite bedrooms, a half bath, and a versatile den/office that can serve as a fourth bedroom. The interiors feel bright and welcoming with 12–15’ ceilings, neutral tones, and elegant architectural details. New wood-look porcelain tile flooring enhances the living room, dining room, den/office, and first-floor bedrooms, combining durability with style. The kitchen features stainless steel appliances, a center island with second sink, updated hardware, and a breakfast nook with bay window views of the pool and lake. The primary suite enjoys direct lanai access, tranquil water views, and a spa-like bath with dual vanities, soaking tub, and walk-in shower. Outdoors, the screened lanai offers a heated pool and spa with a peaceful lake backdrop, plus a refreshed covered sitting area with a new tongue-and-groove ceiling and accent wall—perfect for relaxing or entertaining year-round. Residents enjoy exclusive access to the Bay Isles Beach Club, with its private beachfront, cabanas, and members-only amenities, along with optional memberships for golf, tennis, and the Harbourside Marina with deepwater slips. This home sustained no hurricane damage or water intrusion. This is Longboat Key living made simple—beautiful, low-maintenance, and ready to enjoy.

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 strong income in $160K to $180K range 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. Seller Financing Available.

Welcome to your own piece of paradise in the prestigious Country Club Shores community on Longboat Key. This completely renovated 4-bedroom, 3-bath coastal retreat was taken down to the studs in 2012 and rebuilt with exceptional attention to detail—offering the rare combination of timeless style, modern infrastructure, and effortless move-in readiness on a tranquil canal.
From the ground up, every major system has been upgraded for peace of mind: new water and sewer lines, updated electrical throughout, impact-rated doors and windows, a resurfaced saltwater pool and with new pool heater. Newer seawall and dock, gas that was run to the house with no propane tank to worry about. No component was overlooked. The result is a home that lives like new yet radiates refined coastal charm, with most of the beautifully curated furnishings remaining with the property. Inside, you’ll be welcomed by a bright, open-concept design featuring beautiful, engineered wood floors, custom beadboard ceilings, with beams, elevated ceiling heigh in the main living room and a soothing palette of sea-glass blues and clean whites. The heart of the home is a gourmet kitchen outfitted with stainless steel appliances, designer pendant lighting, and stylish lattice-front cabinetry. A large island anchors the space, perfect for entertaining, while the adjacent living area boasts custom-built-ins, a sleek gas fireplace, and expansive views that flow effortlessly outdoors. Each bedroom is designed for comfort and privacy, with spa-inspired bathrooms that feature elegant tile work, modern fixtures, and soft lighting. The primary suite is a retreat of its own, with custom shelving, cozy window seats, and lush garden views through plantation shutters. Step outside to experience Florida living at its finest. The spacious screened lanai surrounds a sparkling heated saltwater pool and paved deck, creating a private oasis perfect for lounging, swimming, or dining alfresco in total comfort. Just beyond, a large, newer dock awaits, offering deep-water canal access—an ideal setup for avid boaters and water lovers. The deck overlooking the canal is a peaceful setting for morning coffee or an evening cocktail This home also offers exclusive deeded beach access, just a short walk or bike ride away, where you can soak in the soft white sands and turquoise waters of the Gulf. When it’s time to explore, the renowned boutiques and fine dining of St. Armands Circle are just down the street, offering vibrant nightlife, unique shopping, and gourmet experiences in a picturesque coastal setting. A short drive over the scenic Ringling Bridge takes you to downtown Sarasota, a cultural haven known for its art galleries, theaters, opera house, and waterfront dining. Whether you're strolling through the Saturday farmers market, taking in a performance at the Sarasota Opera, or enjoying waterfront cocktails at Marina Jack, the city provides an enriching blend of sophistication and coastal charm. With its ideal location, timeless design, and luxurious updates, this home offers the very best of Longboat Key living—a rare opportunity to enjoy both boating and beachside leisure in one of Florida’s most coveted communities.