Fenway On The Bay Homes for Sale in Dunedin - 5 homes

Remarks: Opportunity knocks only once! This 3-bedroom, 3-bathroom single-family home in Dunedin, FL, has sustained damage from Hurricane Helene and is being offered as a true renovation opportunity. The interior finishes were impacted, giving you a complete blank slate for improvements and customizations. Situated on an oversized lot just two blocks from downtown Dunedin, the home sits approximately half a block from Edgewater Drive and its scenic waterfront walking path, and one block from the Pinellas Trail. You’ll enjoy close proximity to local dining, shopping, and entertainment. The property offers potential views toward the Intracoastal Waterway from the front porch, which overlooks mature tropical landscaping. Located directly across the street from the historic Fenway Hotel—complete with on-site dining and rooftop seating—this is a rare chance to own in one of Dunedin’s most desirable locations. Buyer to verify all measurements, condition, and redevelopment requirements.

Listing is courtesy of: REK REALTY (727-584-0084)

Listing Agent: Robert Keller (727-638-6660)

Remarks: THIS PROPERTY IS BEING OFFERED 2 WAYS: 1) This property offers coastal living at its finest: Water views and downtown convenience.Discover your next home or project in the heart of Dunedin. Nestled on desirable Lyndhurst Street, this property at 224 Lyndhurst Street offers a rare chance to restore and customize the existing 1359 sq ft 3 BR 2 BA layout to your exact specifications and standards. The spacious 0.24 acre lot is in the sought after “Fenway-on-the-Bay” area, boasting views of St. Joseph Sound, beautiful sunsets and refreshing Gulf breezes. NO HOA. This residence sustained flood damage during Hurricane Helene. The property is being sold “As-Is” which presents a rare opportunity beyond the property’s potential. You are buying into one of Florida’s most vibrant and value proposition communities. You are steps away from: Downtown Dunedin, Toronto Blue Jays Spring Training ballpark, Pinellas Trail, and the Dunedin Public Library, You are walking distance to Jolly Trolley and City Bus. Don’t miss the chance to turn a rehab project into a coastal gem. 2) If you choose to demolish the existing structure and start with a clean slate. The existing home sustained flood damage from Hurricane Helene and the seller will provide demolition of the existing structure, offering a vacant lot ready for your custom coastal home. This oversized lot is approximately 0.24 acres. With roughly 75 feet of frontage and 139 feet of depth, there is ample room for a custom home, pool, outdoor kitchen or an expansive garden, Situated in the “Fenway-on-the-Bay” area, the property has a view of St. Joseph Sound and is famous for its sunset views. Just visit the property and you will be able to imagine the breathtaking water view from an upper deck on a 3 story home built on the property. No HOA. This property is a rare gem just waiting for you to make your dream home a reality.

Listing is courtesy of: GENSTONE REALTY (833-396-0092)

Listing Agent: John Blevins (443-250-1837)

Remarks: Price Improvement! Seller motivated! Welcome to a truly enchanting Dunedin retreat, where timeless character meets an unbeatable coastal lifestyle. Perfectly positioned on a sprawling corner lot at Broadway and Beltrees, just steps from the Pinellas Trail, one block from the Toronto Blue Jays Stadium, and around the corner from the historic Fenway Hotel and vibrant downtown Dunedin, this exceptional residence offers the very best of location, charm, and luxury. This completely updated home features 3 bedrooms, 3.5 baths, over 3,200 square feet of heated living space and nearly 4,000 square feet total, with thoughtful design and custom finishes throughout. From the moment you arrive, majestic oak trees and inviting curb appeal set the tone for what awaits inside. At the heart of the home, the stunning designer kitchen is both functional and beautiful, featuring a gas range, built-in refrigerator, custom two-tone cabinetry, a large center island with quartz countertops, and striking designer tile accents on the island that add warmth and character. A cleverly tucked-away laundry closet disguised as a pantry blends seamlessly into the cabinetry, keeping everyday living effortless and elegant. The expansive primary suite is a true sanctuary, offering two oversized walk-in closets and a spa-inspired bath with a large vanity and a beautifully designed walk-in shower. The secondary bath is full of charm and personality, showcasing a Victorian-style soaking tub, custom built-in vanity with Cambria quartz countertops, and exquisite designer tile. A stylish half bath is conveniently located just off the family room for guests. The living spaces are warm and inviting, with formal living and dining rooms, a spacious family room, and abundant custom built-ins that create the perfect setting for entertaining and everyday living. One of the most unique features of this property is the oversized three-car garage, which includes a full bath and ample space for all your toys, a workshop, or future expansion. This area offers the rare opportunity to easily connect it to the main home and create an additional living suite, guest quarters, or private retreat. Step outside into your private backyard oasis, where winding pathways, lush tropical landscaping, and a large paver patio create an ideal space for outdoor dining and entertaining. With plenty of room for a pool, this backyard is designed for both relaxation and hosting unforgettable gatherings. Meticulously maintained and full of character, this home offers a rare blend of historic charm, modern luxury, and an unbeatable Dunedin lifestyle — golf cart to downtown, stroll to the waterfront, trails, stadium, and restaurants, all from your front door. This is more than a home — it’s a truly special opportunity to own a piece of magical Dunedin. Homes like this rarely come available.

Listing is courtesy of: KATIE DUCHARME REALTY, LLC (727-492-8490)

Listing Agent: Katie Ducharme Procissi (727-492-8490)

Remarks: $100,000 UNDER APPRAISED VALUE! Elegant and sophisticated aptly describes this pristine 1927 Historic Landmark pool home with a Carriage House situated on over a 1/4 acre lot in the highly sought after Downtown Dunedin golf cart friendly Fenway-on-the-Bay neighborhood. This stylish home is for the discerning buyer with every attention to detail being addressed. Built in the same era, and within walking distance of the iconic Fenway Hotel, this home has been meticulously renovated with high-end modern luxuries while retaining its era charm. The main home boasts a welcoming living room with gas fireplace, dining room, family room, and a large renovated kitchen with striking granite countertops, a huge kitchen island, farm sink, wood shaker cabinetry, high-end commercial Wolf & Subzero stainless-steel appliances, and a 100+ bottle wine cooler.  Off of the kitchen is a charming Butler's pantry with copper sink, vintage window, built-in shelving and more spacious cabinetry. Open to the kitchen enjoy the family room, featuring its original refinished oak floor and unique raised ceilings and unparalleled view of the pool and backyard. The primary bedroom is spacious and bright and offers a built-in closet plus modern extra tall cabinet storage space. The second bedroom is currently being used as an office and it too offers a built-in closet. The pristine primary bathroom has a frameless glass shower surround, vintage-look vanity, lighted mirror, modern tiled floor, and a Vela Plus Self-Cleaning Smart Toilet/Bidet. Off of the dining room is an intimate bespoke cocktail lounge with lighted built ins, mirror shelving and deep storage cabinets, which could be transformed into an office. The home boasts wide wood plank and distinctive tile flooring, a neutral color palette, unique lighting fixtures, ample storage, all culminating into a truly historic feel with modern, luxurious updates. The fenced backyard is lush, private and offers a view of St Joseph's Sound and a tranquil 15x30 natural gas pebble tec, heated pool and spill over 8-person spa. There is a cabana with electricity and windows, currently used as a work shed. This backyard oasis is awesome and has been the scene of many events and festivities. The meticulous detail & size of this backyard oasis can only be appreciated in person. The light and bright Carriage House is separate from the main home and shares similar high-end finishes, with its tall ceilings, large tiled bathroom, a kitchenette, and spacious, sunny living area and bedroom offering a beachy vibe with ceiling fans, a 2 head mini-split a/c, painted wood flooring, & shiplap wall accents. This stunningly beautiful home is move-in ready and offers many notable efficient and structural features including LOW-E impact windows, whole house Generac generator, encapsulated crawl space, and a UV air purification system. With a home of this vintage, it is refreshing to see the renovations have been permitted through the City of Dunedin. Watch the attached VIDEO to fully appreciate this home. The location is also first class; walk or jump in your golf cart to nearby shops and restaurants; the Pinellas Trail intersects the street and is just a stroll away. Watch the sunset from your own exquisite backyard, or head downtown for dinner or to the many festivals and events. Couple this with excellent schools, pristine beaches and all that fabulous Dunedin has to offer, and you have the ultimate elegant Florida lifestyle home!

Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)

Listing Agent: Marina Kloppel, Pa (858-382-7499)

Remarks: A rare opportunity awaits on the prestigious Edgewater coastline—4.9 acres of elevated coastal elegance spanning two expansive lots with over 226 feet of prime water frontage. This estate is the embodiment of timeless sophistication and enduring craftsmanship, seamlessly blending classic architecture with thoughtful, modern refinement. With a proven history of resilience—remaining untouched by the 2024 storms—it offers peace of mind and enduring value. Each parcel allows for Intracoastal Waterway access, with the option to add a private dock, further enhancing the estate’s waterfront appeal. From the moment of arrival, grandeur and serenity abound. A newly constructed TEK composite porch leads into a residence rich with character—restored original hardwoods, custom millwork, and layered textures create a setting that is both stately and warmly inviting. Multiple living spaces, each imbued with their own ambiance, include a formal music room and a sitting room—both anchored by wood-burning fireplaces—a wraparound-windowed dining room, and a cozy family den complete with custom built-ins and a rolling library ladder. At the heart of the home, the chef’s kitchen is a culinary showcase: six-burner Thermador range, dual Sub-Zero refrigeration, wine fridges, a warming drawer, and a large central island adorned with Swarovski crystal hardware. Underfoot, linen tile floors lead through to a light-filled family room where sliding glass doors open to panoramic water views, creating a seamless transition to the outdoor oasis. Whether hosting grand soirées or enjoying quiet mornings, the home’s built-in bar, casual dining nook, and expansive entertaining areas are thoughtfully designed to elevate every moment. Upstairs, a loft-style corridor with tobacco-printed wallpaper guides you to the guest bedrooms—each spacious and unique—a cork-accented bath, and an elevator that serves all floors for ultimate convenience. The west-facing primary suite is a private sanctuary, complete with fireplace, private sunset balcony, and a spa-caliber ensuite featuring a marble walk-in shower, soaker tub, crystal-inlaid mosaic tiling, and a bespoke dressing room with center island storage. Beyond the main home lies a gracious guest house—with three bedrooms, balconies, a prep kitchen, and its own Generac generator—perfectly suited for visitors or extended stays. A Game Room House offers endless entertainment with a full bar, bath, and ample room for games, while a custom office with floor-to-ceiling cabinetry and balcony provides a serene space for productivity. Outdoors, the estate transforms into a private coastal retreat: a lighted tennis court, koi pond with cascading waterfall, gazebo for al fresco dining, and a resort-style swimming pool with diving board all set within lushly landscaped grounds and gas lantern-lit ambiance. A fully outfitted garage with new laundry, full bath, gym area, and abundant storage completes the offering. With restored windows, natural gas service, and curated luxury finishes throughout, this home is not just a residence—it’s a legacy. With its elevation, privacy, iconic location, and unyielding beauty, it offers a once-in-a-generation opportunity to own a piece of the coast that’s truly irreplaceable. Come see this unique property blocks from the Historic Fenway and 1 mile to downtown Dunedin.

Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-282-1788)

Listing Agent: Tiffany Spyridakos (727-641-9869)