Fenway-On-The-Bay Real Estate, Homes, Condos for Sale in Dunedin, FL

3 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

LOCATION, LOCATION, LOCATION — it truly doesn’t get any better than this! Welcome to 215 Edgewater Drive, Dunedin, FL — a charming SINGLE-FAMILY HOME perfectly situated JUST OFF THE GULF with breathtaking panoramic WATERFRONT VIEWS. This coastal retreat features 2 spacious bedrooms, 2 full bathrooms, and a versatile BONUS ROOM that can easily serve as a third bedroom, private office, or entertainment space. ORIGINAL HARDWOOD FLOORS flow throughout, preserving the timeless character and coastal charm of this VINTAGE DUNEDIN HOME. Sitting on OVER HALF AN ACRE of prime waterfront land, the property offers ABUNDANT OUTDOOR SPACE to live the ultimate Florida lifestyle — whether you choose to enjoy peaceful mornings by the water, host SUNSET GATHERINGS under the palms, or explore the ENDLESS POTENTIAL to renovate, expand, or build your custom coastal dream home. A RARE OPPORTUNITY TO OWN prime real estate within WALKING DISTANCE TO DOWNTOWN DUNEDIN’s vibrant shops, award-winning restaurants, and local breweries, as well as the iconic Fenway Hotel, where you can enjoy live music and rooftop sunsets over the gulf. Don’t miss your chance to secure a piece of paradise in one of Dunedin's most coveted locations!

215 Edgewater Drive, Dunedin

$650,000

3 Beds ⋅ 3 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

Nestled along one of Dunedin's most scenic waterfront corridors, this rare flood-damaged property presents an exceptional opportunity to renovate, reimagine, or build new on an oversized 75 x 139-foot lot totaling more than a quarter acre. With picturesque views of St. Joseph Sound and the Intracoastal Waterway, this is a prime location for investors, builders, or buyers seeking to create a custom residence in one of Tampa Bay's most beloved coastal communities. The existing home offers nearly 2,000 square feet of living space with three spacious bedrooms, each featuring its own private bath, roof (2020), hurricane shutters, along with a two-car garage and a large fenced backyard shaded by mature landscaping. Whether you choose to restore the home to its former charm or design a new coastal retreat, the possibilities are extraordinary. Location is everything, and this address delivers the very best of Dunedin living. Situated steps from iconic Edgewater Drive, just two blocks from the vibrant downtown district and only one block from the Pinellas Trail, you are moments from boutique shopping, award-winning restaurants, breweries, the Dunedin Marina, waterfront parks, and the TD Ballpark, spring training home of the Toronto Blue Jays. Directly across the street, the historic Fenway, Autograph Collection offers waterfront dining, live music, and a rooftop bar with breathtaking sunset views. From this coveted location, you can stroll to nearly everything that makes Dunedin so special, hop aboard the Trolley for an easy ride to Clearwater Beach or Tarpon Springs, and enjoy spectacular sunsets over the water each evening. Opportunities like this are increasingly rare. Bring your vision and unlock the tremendous potential of this premier Dunedin waterfront location.

220 Lyndhurst Street, Dunedin

$985,000

2 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

Welcome to the heart of Downtown Dunedin at Fenway On The Bay — one of the most coveted addresses on the coast. This cottage-style two-bedroom, one-and-a-half-bath retreat sits on an oversized 85x150 corner lot with a detached side-loader two-car garage. Four thousand square feet of premium pavers (2023) wrap the entire property, with room for an RV, a large boat, and up to six vehicles. The private courtyard is the showpiece: a koi pond, soaking tub, built-in bar, and outdoor TV make it an entertainer's dream under the Florida sky. A second patio out front extends the living space into a lush garden setting. Inside, enjoy wood floors and tile throughout, plantation shutters, and a generous kitchen with solid wood cabinets and newer stainless appliances. A new roof (2023), fresh exterior paint (2024), and epoxy garage floors (2024) mean the big-ticket items are already handled. Step outside and the town is yours. The Fenway Hotel, downtown shops and restaurants, the Marina, the VFW, Blue Jays spring training, and waterfront parks are all a short stroll away. The Pinellas Trail runs directly behind the property, draped in mature trees and tropical plantings. Catch the Jolly Trolley to Clearwater Beach or Tarpon Springs, or hop the Water Taxi across the bay. And the upside is real: build up, add on, or use the included architectural plans for an accessory dwelling unit next to the garage — flexible space for a studio, guest quarters, or income potential.

501 Broadway, Dunedin

$600,000

3 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

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.

224 Lyndhurst Street, Dunedin

$965,000

3 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

One or more photo(s) has been virtually staged. Welcome to the definitive Dunedin experience! Nestled on a sprawling quarter-acre lot in the city's most coveted neighborhood, this 3-bedroom, 2-bath historic residence perfectly balances architectural charm with modern security. Framed by tropical landscaping, this haven lives larger than the enchanting exterior portrays. Step through the screened lanai and imagine relaxing, sipping a beverage and waving hello to your friendly neighbors. Natural light pours through French double doors, illuminating a home built for both grand entertaining and quiet reflection. The interior unfolds with graceful arched doorways and the warm glow of the original parquet flooring, while an artisanal stone fireplace anchors the front living area. Calm mornings and cozy evenings with friends and family start here. The thoughtfully arranged kitchen is illuminated by a skylight, providing Florida sunshine for your recipes. The custom solid wood cabinetry features pull-out shelving and built in organization, to optimize storage. Brilliant new quartz counters and stainless steel appliances elevate the culinary experience, while the kitchenette window perfectly showcases the vibrant blooms outside. The wide doorway and pass through window connects to your secondary living area. Entertaining will naturally spill over into this room and then out into the lush landscaped oasis of your deep (and secluded feeling) backyard. Paver walkways and a wide sweeping patio give guests space to roam and relax. Beyond the living spaces, you have a perfect split floor plan. The expansive primary suite, complete with classic basketweave tile in the primary bathroom and walk-in closet are at the back of the home. Plus the residence offers large guest bedrooms and spacious walk-in closets, unique in a historic home. True luxury is found in having peace of mind. The current owners invested in the structural integrity of this home so you don't have to. A Brand New Roof (2025), Hurricane Resistant Impact Rated Windows (2018), High Efficiency HVAC (2020 and 2024), and a new Water Heater (2024). Electrical updates were also done, including the Electrical Panel (2014). Additionally, your new home offers a substantially-sized workshop with high wood framed ceilings, and with a lot this deep you have ample room to install a custom pool (we have plans we can share). Lastly, location is key here. This neighborhood is highly desired by the locals. Positioned to easily stroll or take a golf cart to the shops, restaurants and premier micro breweries of Downtown Dunedin. Only one block to the pedestrian friendly Pinellas Trail, you can cycle to Honeymoon Island or all the way to Downtown St Pete! When evening approaches, take a short stroll to the end of Aberdeen Street to watch the sunset over the Gulf off Edgewater Drive. Make your appointment for a private tour to make this home yours and have the very best of Florida at your doorstep. Preferred Lender offering $10,000 credit and waived appraisal fee.

250 Aberdeen Street, Dunedin

$1,225,000

3 Beds ⋅ 4 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

Price Improvement! Seller motivated! Below appraised value! 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. No past storm damage or flooding from any past hurricanes! 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.

400 Broadway, Dunedin

$1,575,000

3 Beds ⋅ 3 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

$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!

225 President Street, Dunedin

$850,000

2 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

PRICE REDUCED, SELLER SAYS SELL IT!!!!!!...... RARE OPPORTUNITY to own a true unicorn in Downtown Dunedin!! Entertainers dream come true! Welcome home to this meticulously maintained and thoughtfully updated 2-bedroom, 2-bathroom masterpiece that has never flooded. From the moment you arrive, your eyes won’t know where to look first. Will it be the breathtaking views of St. Joseph Sound, the custom-fabricated metal roof, new copper oversized gutters, custom pecky cypress garage doors with matching shutters, or the award-winning native Florida landscaping surrounding the property? Step out onto the newly poured concrete driveway, listen to the tranquil water feature, and follow the hand-laid flagstone pavers to the matching pecky cypress front door. Open the door and prepare to be amazed. The front porch, poured with a 16' slab, features storefront high-impact glass on all windows and its own A/C unit for year-round comfort—perfect in every season. Inside, you’ll immediately notice the wide-open layout with gorgeous Spanish-style ceramic tile flowing throughout the home. The primary bedroom showcases a custom Moroccan tile accent wall and a solid iron claw-foot tub, while the second full bath features a beautifully curved stone shower—each space highlighting the home’s distinctive craftsmanship. Continue through the living area to the kitchen, where solid maple cabinetry, brand-new stainless-steel appliances, and a suspended pot rack create a perfect blend of functionality and style. The adjoining second living room, filled with natural light, features a custom-tiled fireplace and French doors leading to your private backyard oasis. Out back, a deep covered porch with a custom cypress pergola and a designer concrete-and-flagstone water feature provides a serene setting for relaxing or entertaining. Sitting on nearly a quarter acre, this lot offers plenty of space to add a pool if desired. Don’t miss this rare opportunity to make 266 Lyndhurst Street your new home.

266 Lyndhurst Street, Dunedin

$650,000

2 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

Rare opportunity for a beautifully renovated Delightful Dunedin home settled among historic bungalows, stately live oaks and within 3 blocks to downtown Main Street. This truly delightful 2 bedroom, 2 bath, 1 car garage, 1 golf cart pavered carport home offers charm, fun, location and so many newer and desirable features. The pavered driveway, walkway, and covered front porch welcome you into this inviting home. When you enter you will love the open feeling, the designer touches, the wood-look porcelain tiles throughout and great floor plan. The Living Room is perfect for TV with extra space for your guests who will love to come visit. The Dining Room can seat a large family and has a view of the historic neighborhood. Enjoy the updated kitchen with newer cabinets, appliances, gas range with hood exhausted to the outside, drawer microwave, quartz counters and peninsula pass-through to the Dining area. Bedrooms are spacious, have roomy closets, are off a hallway offering privacy and share a fully renovated bath. Additional upgrades, improvements and features are numerous and include: in-home natural gas, on-demand tankless hot water heater, all new doors, lighting fixtures, whole house fan and yard is fully fenced. A second bath and laundry room is conveniently accessed off the covered lanai and features a newer washer and dryer, updated laundry sink, toilet and exterior window. Relax sitting in the screened lanai overlooking your artfully landscaped back yard. Meander the park-like walkway through the tropical foliage enjoying the patio, cooling shade, perfect place for a hammock and verdant sitting areas. A custom shed with a charming front porch adds to the enticing space. Conveniently backing to the Pinellas Bike Trail will put you just a short walk or bike ride to downtown, the gorgeous waterfront overlooking Clearwater Beach, the Blue Jays Stadium, Hale Activity Center, Dunedin Library, restaurants, craft breweries, shopping and all Dunedin offers within just a few blocks in this Golf Cart approved city. Enjoy the festivals, spring training, open air markets, parks, beaches, Community Center, City Pool, Dunedin Golf Club, State Parks, Marina, Boat Ramp to the Intercoastal Water way and Gulf. Easy commute to the Tampa Airport, the Arts, Cruise Terminals and Championship Sports. This home and lot remains high and dry and did not sustain any flood/water damage during the 2024 hurricanes. Come live a true Florida Lifestyle! Wine Fridge in Dining Room does not convey.

525 Broadway, Dunedin

$504,000

2 Beds ⋅ 1 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

Adorable 2BR/1BA Home in Prime Dunedin Location! Just 800 feet from the Intracoastal Waterway and a few short blocks from TD Ballpark—spring training home of the Toronto Blue Jays—this charming concrete block home offers the perfect mix of coastal living and convenience. Step inside to discover a warm and inviting main living area featuring a stunning wood ceiling that adds character and charm. Enjoy fresh new carpet throughout, ceiling fans for added comfort, and elegant French doors that separate the living and dining spaces. The home also boasts a beautifully landscaped yard and a tidy back patio—ideal for relaxing or entertaining. The 1-car garage includes a washer and dryer for added practicality. Whether you're seeking a full-time residence, seasonal escape, or investment opportunity, this Dunedin gem offers timeless appeal in a highly desirable waterfront community.

417 Broadway, Dunedin

$970,000

3 Beds ⋅ 2 Baths ⋅ Fenway-On-The-Bay SubDv. ⋅ 34698 Zip Code

RARE OPPORTUNITY to live in the "Number One" rated coastal town of Dunedin by Southern Living Magazine for 2022, in sought-after HISTORIC DISTRICT of "Fenway-on-the-Bay" - desirable Aberdeen Street, known for its unique Estate Homes & quirky mailboxes, just steps away from breathtaking sunsets over St. Josephs Sound (Gulf of Mexico) on Edgewater Dr. This 1949-built block home features 2,109 heated sqft, 3 spacious bedrooms, 2 baths, a functional eat-in kitchen with newer Whirlpool appliances, pantry & storage space, a cozy living room with parquet and tile floors, a wood-burning fireplace, an oversized INSIDE laundry room that doubles as sewing or hobby room - cabinets galore, and an inviting Florida room with wooden ceilings, two French doors overlooking a large deck and tropical backyard oasis. Other features include a new LG Smart Inverter, ductless & efficient A/C system, newer windows, interior window shutters, roof from 2014, ceiling fans, custom-built bookcase and shelves, a remodeled guest bath, newer hot water heater (2), a generator and a 1.5 Car garage (440 sqft) - all on 0.34 acre fenced lot, inclusive a storage shed and a boat carport. Walk along tree-lined country roads to historic Dunedin with its trendy shops, eateries, pedestrian downtown with Community & Fine Arts Center - offering festivals, concerts, exhibits, carnivals, art shows, a library, micro-breweries & bars along the 47-Mile Fred Marquis Pinellas Trail, spring training at nearby Blue Jay Stadium, Championship Golf communities, ferry & trolley rides to nearby Honeymoon Island or Dunedin Marina (fishing pier, boating, excursions) with iconic Fine-Dining restaurant "Bon Appetit" and the nearby landmark FENWAY HOTEL! Hurry, this one-of-a-kind property won't last!

244 Aberdeen Street, Dunedin

Browse All Fenway-On-The-Bay Properties for Sale

Fenway-On-The-Bay Real Estate & Homes