5 Bedroom Homes for Sale in Dunedin, FL

5 Beds ⋅ 5 Baths ⋅ Spanish Trails SubDv.

Dunedin - Hidden beneath a canopy of majestic oaks along the peaceful banks of Curlew Creek, this extraordinary Spanish-inspired estate is a rare expression of architectural artistry, timeless craftsmanship, and refined Florida living. Situated on nearly 1.5 secluded acres in the coveted Spanish Trails community, the residence offers almost 5,300 square feet of beautifully curated living space where every detail has been thoughtfully designed to inspire. A private circular drive welcomes you to a home that immediately captivates with authentic character and enduring elegance. Rich reclaimed 114-year-old Pennsylvania oak floors, imported Spanish cedar doors, exposed pecky cypress beams, custom millwork, bay windows, and a magnificent wood-burning fireplace create an atmosphere that is both sophisticated and inviting. Thoughtfully renovated over the years, the home perfectly blends classic architecture with modern luxury. Designed for effortless entertaining and everyday living, the heart of the home is a gourmet chef's kitchen appointed with granite countertops, abundant custom cabinetry, a Sub-Zero refrigerator, and a Wolf gas cooktop. Multiple gathering spaces flow seamlessly throughout the home, while a hidden climate-controlled wine cellar with capacity for approximately 1,000 bottles is sure to impress the discerning collector. The private second level offers five spacious bedrooms, including a serene owner's retreat with two private balconies overlooking the lush grounds and tranquil creek—perfect for enjoying morning coffee or evening sunsets in complete privacy. Step outside to an exceptional outdoor sanctuary. An expansive screened lanai with Spanish tile flooring, a natural gas grilling station, and a granite serving bar overlooks the sparkling pebble-finish pool. Beyond, a freestanding entertainment pavilion with bar seating, an expansive deck, and a children's play area provides endless opportunities for gathering with family and friends. A charming bridge crosses picturesque Curlew Creek, leading to a private secondary green space where towering oaks and mature landscaping create the feeling of your own botanical park. Modern conveniences, including dual-zone Trane HVAC systems, updated electrical, and an oversized attached garage, blend seamlessly into the home's timeless design. Located in desirable Flood Zone X, this remarkable estate offers exceptional privacy just minutes from downtown Dunedin, marinas, boutique shopping, acclaimed restaurants, the Pinellas Trail, and the award-winning Gulf beaches. Homes of this caliber are seldom available. Rich in character, surrounded by nature, and crafted with uncompromising quality, this is more than an exceptional residence - it is a legacy estate. If you've been searching for a home that offers extraordinary privacy, timeless design, and a setting unlike any other in Dunedin, this is your opportunity. Schedule your private tour today and experience the beauty, serenity, and exceptional craftsmanship of 1850 Oak Creek Drive for yourself.

1850 Oak Creek Drive, Dunedin

$1,850,000

5 Beds ⋅ 3 Baths ⋅ Stirling Heights SubDv.

This home is a complete gem. You cannot duplicate this property, as it is nestled on an oversized 0.60-acre lot in one of Dunedin's most coveted enclaves. This exceptional waterfront residence embodies the rare marriage of timeless charm and spacious living. Majestic oak trees frame the property, while expansive, beautifully landscaped grounds set the stage for the dream that awaits. A wide front porch welcomes you upon arrival, offering plenty of space for rocking chairs and quiet mornings. Upon entering, a spacious hacienda-style first-floor layout reveals a gorgeous great-room floor plan with a fireplace and multiple sets of French doors that wrap around the home, providing beautiful views of the spring-fed lake and opening to the expansive enclosed pool, spa, and patio area. The custom kitchen includes ceramic tile floors, beautiful custom cabinetry, a center island, and granite countertops. High-end appliances complete the kitchen, along with a built-in desk and walk-in pantry. The oversized primary bedroom measures 14' x 37' and includes an area that can be used for exercise, yoga, an office, or a quiet sitting area. French doors lead out to the pool and patio area with views of the lake. The luxurious en-suite primary bath boasts a steam shower, separate his-and-her vanities, and a large soaking tub. The enormous primary closet is fully customized cabinetry, built-in drawers, and abundant storage. Off the kitchen is a large bonus room with direct pool access through French doors that can effortlessly transform into a bedroom, game room, art studio, or whatever your imagination desires. The oversized laundry room includes custom built-in cabinetry and a utility sink. There is also an office with uniquely designed custom cabinetry and a centrally located half bathroom. Upstairs, you will find three additional large bedrooms with dormer windows and plenty of closet space. The full bathroom is beautifully appointed. Step outside to your oversized pool and heated spa, surrounded by quartz tile pavers and completely enclosed within a screened lanai spanning 1,992 square feet. Multiple seating areas provide plenty of places to relax and entertain. Beyond the pool area lies your own private backyard sanctuary. Beautiful, mature oak, mango, Florida apple, and banana trees line a brick-paver path leading to the spring-fed lake, fire pit, and floating dock. You may spot otters, owls, and herons that call this area home. A large three-car garage provides ample space for vehicles, a golf cart, storage, or a workshop. Recent updates include a new spa heater, a whole-home generator installed in 2022 with its own propane tank, two new A/C units installed in 2025, freshly sealed pavers around the pool deck, and a 10-year roof sealant. Location! Ideally situated near Honeymoon Island State Park, the Pinellas Trail, and downtown Dunedin's charming shops, restaurants, and entertainment. The location even allows you to drive your golf cart into downtown Dunedin. This home is unique, unforgettable, and far from the typical cookie-cutter Florida property. A must-see!

1976 Dunloe Circle, Dunedin

$1,100,000

5 Beds ⋅ 3 Baths ⋅ Fairway Estates 4th Add SubDv.

Welcome home to a rare opportunity in Fairway Estates. Beautifully updated and situated on a rare 0.45-acre double lot, this 5-bedroom, 3-bath pool home offers 3,384 Sq Ft of thoughtfully designed living space with room to spread out both inside and out. Properties with this much usable yard space are seldom available, offering privacy, flexibility, and endless possibilities for outdoor living. Surrounded by mature trees and tropical landscaping, this home provides a peaceful setting while remaining close to everything you need. A private courtyard welcomes you to the front entrance. Inside, the spacious floor plan flows naturally from the living and dining rooms into the heart of the home, a large family room featuring a beautiful wood-burning fireplace with a travertine marble surround, creating a warm and inviting space for family gatherings or quiet evenings at home. The renovated kitchen blends style and function with custom wood cabinetry, granite countertops, double ovens, generous counter space, a breakfast area, and a movable granite-top island that's perfect for entertaining. Travertine marble flooring extends through the kitchen and dining room, while upgraded wood-look porcelain tile adds a fresh, modern feel to the living room and bonus room. The bonus room provides flexible space for a home office, playroom, fitness room, or media room. One of the home's standout features is the impressive 40-foot Florida room, creating an incredible extension of the living space with beautiful views of the screened pool and backyard. With multiple living and gathering areas throughout the home, there's plenty of space for everyone to spread out while still coming together for holidays, celebrations, and everyday life. At the end of the day, retreat to the oversized primary suite, thoughtfully updated with new porcelain tile flooring and a beautifully renovated en-suite bathroom featuring a double-sink vanity, designer finishes, and a spacious walk-in shower. Four additional bedrooms and three full bathrooms provide flexibility for growing families, guests, or multigenerational living. Step outside and enjoy your own backyard retreat. The covered screened lanai opens to a spacious screened pool enclosure, creating the perfect setting for relaxing or entertaining throughout the year. Situated on a rare double lot, the property offers an expansive side yard with the potential for boat or RV parking—an uncommon feature in this neighborhood. Whether you need extra space for your recreational vehicles, outdoor hobbies, pets, or simply want room to spread out, this property offers flexibility that's hard to find. Additional updates provide peace of mind, with a Fully renovated primary bathroom (2026), upgraded energy-efficient windows, fresh exterior paint (2026), upgraded 24-inch soffits, a new HVAC system with all-new ductwork and variable-speed air handler (2023), and new pool equipment (2023). Only minutes from Dunedin Golf Club, Downtown Dunedin, Dunedin Causeway & Honeymoon Island, Restaurants, Hospitals, Shopping and more. Whether you're looking for room to entertain, space for a growing family, or simply a property with features that are becoming harder to find, this Fairway Estates home offers an exceptional opportunity to make it your own. No Flood Zone

1350 Fairway Drive, Dunedin

$7,400,000

5 Beds ⋅ 7 Baths ⋅ Malones L H Sub SubDv.

MASTERFULLY REIMAGINED, THIS EXTRAORDINARY WATERFRONT ESTATE IS SET ON A SPECTACULAR 1.1-ACRE LOT OVERLOOKING THE INTRACOASTAL WATERWAY AND THE PRISTINE SHORES OF CALADESI ISLAND. Originally built in 2002 and extensively upgraded in 2026. Constructed with enduring quality and resilience, the residence features insulated concrete form (ICF) walls, rebar-reinforced hurricane-impact windows/doors, and a roof fortified by metal trusses—delivering exceptional structural integrity and peace of mind. Beyond the impressive gated entrance, a sweeping shellstone driveway and meticulously curated landscaping introduce a home of remarkable elegance and distinction. Inspired by Coastal Tuscan architecture, stately pillars frame a grand foyer with soaring 24-foot ceilings, creating a dramatic first impression. Exquisite porcelain flooring, artisan-crafted millwork, graceful archways, fluted columns, contemporary designer lighting, and smooth Level 5 walls combine to create a sophisticated and timeless aesthetic. The expansive waterfront living room flows seamlessly into a refined formal dining area, offering an ideal setting for entertaining. At the heart of the home, the chef’s kitchen is truly exceptional, showcasing dramatic double-slab translucent quartzite countertops with ogee-edge detailing, matching quartzite backsplash, custom raised-panel cabinetry with under-cabinet lighting, premium appliances, gas cooking, built-in refrigeration, and dual islands with bar seating—all opening effortlessly to the pool deck and waterfront beyond. The spacious family room enjoys sweeping water views and features a custom multi-level entertainment bar and serving center with Sub-Zero refrigeration and a dedicated ice maker. The executive office, also positioned to capture the stunning waterfront setting, is appointed with extensive custom built-ins and offers generous space for workstations and conference-style seating. The luxurious owner’s suite is a private waterfront sanctuary, featuring a spacious sitting area and two beautifully designed custom closet systems. The spa-inspired owner's bath is a showpiece of craftsmanship and luxury, finished in marble, quartzite, and translucent quartzite. Highlights include dual vanities, a dedicated cosmetics center, sauna, private rest room, freestanding microjet soaking tub, and a spectacular dual-entry walk-in rain shower with five additional body sprays, all enveloped in rich marble finishes. Each of the four guest suites offers exceptional scale and comfort, complete with walk-in closet systems and beautifully appointed en-suite baths finished extensively in marble. Outdoors, the estate evokes the glamour and grandeur of a private waterfront resort. A dazzling 5,000-square-foot elevated shellstone deck with elegant diamond-pattern design surrounds the pool/spa and is enclosed by custom cast-stone balustrades. Your terraced lounging areas descend to a beautifully landscaped waterfront lawn reminiscent of an Italian villa. Enjoy the rare luxury of a private white-sand beach and a composite dock equipped with a 16,000-pound boat lift. Setup provides quick and convenient access to Clearwater Beach, Caladesi Island, and Honeymoon Island, offering an unparalleled combination of waterfront recreation and beachside enjoyment. Brilliant sunsets, refreshing coastal breezes, and an unmatched setting complete this truly one-of-a-kind coastal offering—conveniently located within easy reach of downtown Clearwater.

1516 Bayshore Boulevard, Dunedin

$878,000

5 Beds ⋅ 4 Baths ⋅ Highwood Estates SubDv.

Virtually Staged. BIG PRICE DROP!!! LUXURY DUNEDIN RETREAT WITH TWO PRIMARY SUITES AND A THOUGHTFUL MULTI-GENERATIONAL DESIGN! Welcome to this beautifully appointed 5-bedroom, 4.5-bathroom residence offering 3,056 square feet of living space, a highly desirable split floor plan, and exceptional flexibility for today's lifestyle. Situated on a spacious homesite in Dunedin, this two-story home combines elegant finishes, generous living areas, and an abundance of indoor and outdoor entertaining space. Step inside to discover rich wood flooring, soaring ceilings, and an open-concept layout designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen serves as the heart of the home, featuring granite countertops, stainless steel appliances, custom wood cabinetry, a large center island with seating, built-in wall oven and microwave, decorative tile backsplash, and extensive storage and prep space. The kitchen overlooks the spacious family room, creating a seamless flow for gatherings of any size. One of the home's standout features is its dual primary suite design, offering a luxurious primary retreat on both the first and second floors. The downstairs primary suite provides privacy and convenience while featuring direct access to the covered rear patio, creating the perfect spot to enjoy morning coffee or unwind in the evening. The ensuite bath includes dual vanities, granite countertops, a spacious walk-in shower, and generous storage. Upstairs, the second primary suite offers its own private sanctuary complete with an ensuite bath and access to a covered balcony overlooking the property. The second floor also features a large loft area at the top of the stairs, ideal for a media room, playroom, home office, or additional living space. Two secondary bedrooms are connected by a convenient Jack-and-Jill bathroom, while an additional bedroom and full bath provide comfortable accommodations for family and guests. Outdoor living is equally impressive with a large covered rear patio overlooking the partially fenced backyard. The expansive yard provides plenty of room for pets, play, gardening, or the future addition of a pool, while still leaving ample space for entertaining and outdoor activities. Designed with both comfort and peace of mind in mind, the home features impact-resistant windows across the front elevation and storm shutters for the remaining windows and exterior doors, providing valuable hurricane protection and enhanced security. Additional highlights include a 2-car garage, spacious laundry room, abundant storage throughout, multiple living and gathering areas, and a versatile floor plan that easily accommodates multi-generational living, long-term guests, or work-from-home needs. Ideally located near Dunedin's vibrant downtown district, waterfront parks, beaches, dining, shopping, and recreational amenities, this exceptional property offers the perfect combination of space, flexibility, and Florida lifestyle living. Schedule your private showing today and experience everything this remarkable home has to offer.

2234 Highwood Court, Dunedin

$750,000

5 Beds ⋅ 3 Baths ⋅ Spanish Acres SubDv.

Welcome Home to Spanish Acres – One of Dunedin's Most Established and Desirable Neighborhoods! Nestled on an oversized fully fenced corner lot of more than ¼ acre, this spacious and versatile 5-bedroom, 3-bathroom pool-ready property with a 2-car garage offers a rare combination of size, flexibility, income potential, and future expansion opportunities that are becoming increasingly difficult to find in today's market. From the moment you enter, you'll appreciate the warm and inviting atmosphere of this thoughtfully designed home. The welcoming foyer opens to expansive living spaces that provide room for everyone, featuring two separate living rooms, a formal dining room, and an ideal layout for both everyday living and entertaining. The heart of the home is the updated kitchen, complete with stainless steel appliances, abundant cabinetry, and easy access to the dining and gathering areas. Whether you're hosting holiday dinners, family celebrations, or casual weekend get-togethers, this home was designed to bring people together. One of the most desirable features is the incredible flexibility for multi-generational living. The main home includes a spacious downstairs primary suite, an additional guest bedroom on the first floor, and ample room upstairs with 3 more bedrooms for family members, guests, hobbies, or home office space. Adding even more value to this amazing home is the opportunity to offer a private income-producing 1-bedroom, 1-bath apartment/in-law suite, complete with its own private entrance, full kitchen, living room, and separate bath. This is Perfect for extended family, adult children, guests, a caregiver, or long-term rental income. Step outside and discover your own private backyard retreat. The oversized fenced yard is dotted with delicious mature tropical fruit trees and offers endless possibilities for gardening, entertaining, pets, recreation, or future enhancements. Relax on the covered deck, enjoy outdoor dining and cookouts. With so much outdoor space, you'll have room to create the backyard oasis you've always envisioned. For buyers seeking future flexibility, the property has been approved to add a detached accessory dwelling unit (ADU), creating an incredible opportunity for additional living quarters, guest accommodations, rental income, a home office, studio, or private retreat. Major updates provide peace of mind, including: NO FLOOD INSURANCE NO HOA - Bring Your Big Boy Toys! NEW Roof (2025) AC 5 Ton (2023) Exterior Paint (2023) Updated Kitchen with wood cabinetry and stainless steel appliances (2023) Hurricane Impact Windows have a Lifetime Warranty Water Heater is Under Warranty Located in the highly sought-after Spanish Acres community, you'll enjoy the best of Dunedin living with convenient access to Downtown Dunedin, Honeymoon Island, the Pinellas Trail, waterfront parks, shopping, dining, breweries, marinas, golf courses, and some of Florida's most beautiful Gulf beaches. Whether you're searching for a forever family home, a multi-generational property, or an investment opportunity with built-in income potential and room for future growth, this exceptional property delivers a rare combination of location, flexibility, and value. Homes with this much space, versatility, and future potential rarely become available in Spanish Pines. Schedule your private showing today and experience everything this remarkable property has to offer.

3146 Carlos Drive, Dunedin

$764,900

5 Beds ⋅ 4 Baths ⋅ Acreage SubDv.

Rare Dunedin opportunity with two separate living structures, a screened pool, generous parking, and flexible living space designed for today’s multi-use lifestyle. Set on an oversized fenced parcel, the 2001-built main residence offers 2,526 square feet with 4 bedrooms, 2.5 bathrooms, a 2-car garage, formal living and dining areas, and a spacious family room with fireplace. The bright interior features soaring ceilings, oversized windows, an open flow between the main living spaces, granite kitchen counters, abundant cabinetry, tile flooring throughout the main level, and multiple areas for gathering, working, or relaxing from day one. The main home’s floor plan creates excellent separation between everyday living and private retreats. The oversized 24x12 primary suite provides room for a king-sized bed plus a sitting area, reading nook, or desk setup, while the upstairs landing with built-in shelving adds character and functional storage. Major confidence points include HVAC replaced in 2022, an insulated garage door, and a garage mini-split that makes the space ideal for a home gym, workshop, hobby area, or climate-controlled storage. The screened-in pool and covered outdoor areas extend the living space outdoors, creating an easy indoor/outdoor lifestyle for entertaining, relaxing, and enjoying Florida living. The detached 1953 guest house adds approximately 676 square feet of independent living space with 1 bedroom, 1 full bathroom, kitchen, living area, private entrance feel, and warm exposed wood beam ceilings that give it a charming cottage-style atmosphere. This second structure is ideal for in-laws, extended family, guests, adult children, a private office, creative studio, or potential long-term rental income estimated around $1,100–$1,300 per month. Public records reflect the property as single family with more than one house per parcel, with multi-family land use under 10 units. Located in highly desirable Dunedin, this property places you close to the lifestyle buyers are looking for: downtown Dunedin restaurants, breweries, boutique shopping, waterfront parks, TD Ballpark, the Pinellas Trail, Dunedin Causeway, Honeymoon Island, and Caladesi Island access. Honeymoon Island is known for Gulf views, sandy beaches, and nature trails, while the Pinellas Trail offers a dedicated corridor for biking, walking, jogging, and skating. Downtown Dunedin also offers year-round events, local markets, arts, dining, and spring training baseball, adding strong lifestyle appeal for full-time residents, seasonal owners, and investors. Enjoy convenient access to nearby beaches, shopping, grocery options, marinas, parks, US-19, downtown Clearwater, St. Petersburg, and Tampa International Airport. Dunedin is approximately 15 minutes from Honeymoon Island and about 30 minutes from Tampa International Airport, depending on traffic. With two living structures, a pool, flexible parking, income potential, and a location near some of Pinellas County’s most loved coastal amenities, this property offers a unique combination of comfort, versatility, and long-term value. Schedule your private showing today and experience all this Dunedin property has to offer.

3220 County Road 1, Dunedin

$1,625,000

5 Beds ⋅ 5 Baths ⋅ Dunedin Isles 1 SubDv.

Welcome to 236 San Salvador Drive, a truly exceptional Spanish-style estate located in the highly sought after Dunedin Isles community. Experience captivating views overlooking St. Joseph Sound. This fully remodeled property sits on an expansive 2¼ lots and offers a rare combination of luxury living, privacy, and outstanding income-producing potential. The stunning main residence features 3 bedrooms and 2 bathrooms, beautifully updated with high-end finishes throughout. The entire property has undergone an extensive renovation, including brand-new appliances, three new A/C units, and a newly constructed pool, creating a move-in-ready coastal retreat. Feel free to request sellers property disclosure regarding previous flood damage. Adding incredible versatility, the estate includes two separate private apartments, each with access to a dedicated laundry room, making them ideal for guest accommodations, multigenerational living, long-term rental income, or short-term vacation opportunities. Step outside to your own private oasis where a newly added pool and pool bath create the perfect setting for relaxing or entertaining. A charming brick-paved walkway winds through lush, mature landscaping, leading to multiple secluded sitting areas—perfect for enjoying Dunedin’s spectacular sunset views over the water. Privacy and curb appeal abound with a four-foot privacy wall surrounding the front and side of the property, while the oversized corner lot provides ample space for RV and boat parking—a rare find this close to the water. Whether you are seeking a luxury primary residence, a coastal compound, or an exceptional income-producing investment, this one-of-a-kind Dunedin Isles property offers endless possibilities in one of Florida’s most desirable waterfront communities. Buyer or Buyer's agent to confirm all leasing restrictions and rules with the City of Dunedin Room sizes are deemed reliable, but to be confirmed by Buyer(s).

236 San Salvador Drive, Dunedin

$1,395,000

5 Beds ⋅ 4 Baths ⋅ Oakland Sub SubDv.

One or more photo(s) has been virtually staged. THE BUILD IS DONE!! IF YOU HURRY-AN OPPORTUNITY BECKONS- BRAND NEW ALL BLOCK DUNEDIN CONSTRUCTION HOME W/5 BEDROOMS, 4 BATHS & 3,000 SQ.FT. AT THE FOUR CORNERS OF DUNEDIN’S SHOPPES, RESTAURANTS, GASTROPUBS AND LESS THAN 3/4 OF 1 MILE TO IT’S MARINA, WATERFRONT PARK, AND WATER ACCESS. Look at the photos of the home adjacent- This one sold in ‘24-I’ve attached the pics ... DUNEDIN, AND THIS REMARKABLE BUILD AWAIT YOUR FAMILY’S LEGACY

1040 Bass Boulevard, Dunedin

5 Bedroom Homes for Sale in Dunedin, FL

All 5 Bedroom Homes for Sale in Dunedin, FL

Joseph Sullivan Real Estate

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