Featured Properties

Some or all of the listings below are provided by the Longboat Key office.
$2,249,000 (USD)
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Osprey Area Single Family Home

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362 Macewen Drive Osprey, FL 34229

4 Bed
4 Baths
4117 sqft
MLS# A4676567
Virtual Tour
Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Steve Abbe
$2,195,000 (USD)
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Longboat Key Area Condominium

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455 Longboat Club Road 402 Longboat Key, FL 34228

3 Bed
3 Baths
2410 sqft
MLS# A4686984
Virtual Tour
Gulf-front living takes on a refined sense of scale in this beautifully renovated residence at The Pierre, an intimate waterfront community of just 66 residences set behind the gates of the Longboat Key Club. With 2,400+ sq. ft. of thoughtfully updated living space, the residence offers a seamless blend of comfort, style and presence in one of the island’s most desirable locations. From the moment you enter the foyer, the tone is set with diagonal tile flooring, high ceilings, crown molding and tray accents that create a sense of openness and quiet sophistication. The great room unfolds with ease, connecting living, dining and kitchen spaces in a way that supports both everyday living and entertaining. A full wall of glass in the living area draws in natural light and frames views of the Gulf and manicured grounds, while a custom built-in adds both function and visual interest. The dining area sits adjacent, wrapped in glass and oriented toward the view, creating a natural setting for gatherings. The kitchen has been remarkably reimagined with black stone countertops, off-white cabinetry with glass panel accents, high-end appliances and generous counter space with a breakfast bar. A slider opens to the terrace, allowing for easy indoor-outdoor flow. A private office with double glass doors and a tray ceiling with custom lighting provides a quiet and versatile workspace. The primary suite is spacious and serene, featuring a breath taking view, terrace access and a large bath designed with both comfort and flexibility in mind. Dual water closet areas and a distinctive glass-enclosed circular shower with detailed tilework add a unique architectural element. Guest accommodations are well-sized and welcoming, and an in-residence laundry room adds everyday convenience. Residents of The Pierre enjoy a full complement of amenities, including concierge service, under-building parking, 24-hour security, a fitness center, 2 guests suites, heated pool, spa, children’s pool, Har-Tru tennis courts, shuffleboard courts and private beach access. Membership opportunities at the Longboat Key Club offer access to championship golf and fine dining, all within proximity to St. Armands Circle and Sarasota’s vibrant downtown.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Bruce Myer
$2,150,000 (USD)
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Osprey Area Single Family Home

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642 Trenton Way Osprey, FL 34229

4 Bed
5 Baths
3939 sqft
MLS# A4686927
Virtual Tour
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.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Steve Abbe
$2,150,000 (USD)
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Sarasota Area Single Family Home

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430 Bird Key Drive Sarasota, FL 34236

3 Bed
3 Baths
2498 sqft
MLS# A4691206
Virtual Tour
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.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Yvette Sellyn
$2,149,000 (USD)
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Sarasota Area Single Family Home

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3930 Elysian Woods Lane Sarasota, FL 34231

4 Bed
3 Baths
3531 sqft
MLS# A4668774
Virtual Tour
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.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Roger Pettingell
$2,050,000 (USD)
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Longboat Key Area Single Family Home

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3617 Fair Oaks Place Longboat Key, FL 34228

3 Bed
4 Baths
2950 sqft
MLS# A4663935
Virtual Tour
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.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Ryan Ackerman
$1,999,000 (USD)
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Sarasota Area Single Family Home

Active

2231 Wood Street Sarasota, FL 34237

4 Bed
4 Baths
2731 sqft
MLS# A4666469
Virtual Tour
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.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Rinat Sikdar