Madeira Beach Homes with Courtyard Exterior Features

Madeira Beach Homes with Courtyard Exterior Features

Welcome to Madeira Beach, Florida – a hidden gem nestled in the heart of Pinellas County. Known for its stunning sandy shores, vibrant sunsets, and a laid-back coastal lifestyle, Madeira Beach offers a unique blend of relaxation and adventure. Whether you're strolling along the famous John's Pass Village and Boardwalk or enjoying the gentle breeze while fishing off the docks, this charming city captures the essence of Florida living at its finest.

Madeira Beach is not just about the sun and surf; it’s a community that thrives on its rich culture and friendly atmosphere. With an array of local shops, delicious seafood restaurants, and year-round events, there's always something to do. Families and retirees alike find solace in this picturesque locale, where the warm weather invites outdoor activities year-round.

If you're considering making Madeira Beach your home, you’ll be delighted to discover the unique properties available, particularly those featuring charming courtyard exteriors. These homes are designed to create an inviting atmosphere, often adorned with lush landscaping and private outdoor spaces perfect for entertaining or simply soaking up the sun. Imagine sipping your morning coffee in a tranquil courtyard, surrounded by the sights and sounds of nature, or hosting friends for a cozy evening under the stars.

In Madeira Beach, homes with courtyard features offer not just a place to live, but a lifestyle that embraces the beauty of coastal living. Whether you’re seeking a vacation retreat or a permanent residence, you’ll find that these properties embody the spirit of Florida’s beachfront paradise. Come explore the possibilities and discover your dream home in Madeira Beach today!

Newest Madeira Beach Homes with Courtyard Exterior Features

$1,300,000
5 Beds ⋅ 5 Baths ⋅ Gulf Shores 1st Add SubDv. ⋅ 33708 Zip Code
Located in the heart of Madeira Beach, FL, just one block from the Gulf beaches, 14135 Palm Street presents a rare opportunity to acquire a fully updated 5-unit income-producing property in one of the most desirable beach communities along Florida?s Gulf Coast. This solid block construction 5-plex consists of five well-designed 1-bedroom, 1-bathroom units with ample on-site parking, offering strong appeal to both long-term and seasonal tenants. What truly sets this property apart is its extensive hurricane-resilient construction and post-storm preparedness improvements. The building successfully withstood the major storms of 2024, demonstrating the quality and durability of the upgrades completed. Improvements include waterproof stucco interior wall systems, durable epoxy flooring throughout, elevated electrical connections, and water-resistant kitchen fixtures designed to minimize future storm vulnerability and maintenance concerns. In addition, the property features a newer roof, and all restoration and improvement work has been fully permitted and completed, providing added confidence for investors and lenders alike. The property offers flexible rental opportunities including annual rentals, seasonal leasing, workforce housing, or furnished beach rentals, creating multiple paths for maximizing income potential. With an attractive CAP rate, investors can benefit from both strong current cash flow and long-term appreciation in a highly supply-constrained beach market. Tenants will enjoy exceptional walkability and convenience. The property is located near Gulf Boulevard with easy access to the Pinellas Suncoast Transit Authority trolley and bus routes connecting residents to surrounding beach communities, downtown St. Petersburg, and area attractions. Nearby shopping, dining, and entertainment options include the popular John's Pass Village & Boardwalk, local restaurants, waterfront bars, grocery stores, marinas, and recreational activities including boating, fishing, and beach access. The location also provides convenient access to Treasure Island, Redington Beach, and the greater Tampa Bay area. This is an outstanding opportunity to own a proven storm-resilient multifamily asset in a premier coastal location with strong rental demand, attractive projected returns, and lasting tenant appeal.

14135 Palm Street, Madeira Beach
$475,000
2 Beds ⋅ 2 Baths ⋅ Boca Ciega Point East SubDv. ⋅ 33708 Zip Code
Welcome to this beautifully remodeled and move-in ready WATERFRONT 2-bedroom 2 bath VILLA with GARAGE, courtyard, private DOCK & BOAT LIFT! Nestled in the GATED 55+ Boating Community of Boca Ciega Point, this home boasts open water views, yet is located in a protected cove, ideal for boating, fishing, paddle-boarding, kayaking and dolphin & manatee watching. The new kitchen features “Lily Ann” gray custom wood cabinets with under cabinet lighting, modern back-splash, ample Quartz counter space, “Samsung” top of the line “smart appliances,” including a “quiet” dishwasher, upscale refrigerator, range, microwave and trash compactor. The primary suite includes a full bathroom, spacious walk-in shower with security handles and 2 walk-in closets, retractable blinds in lanai porch door - serene water views create a perfect spot to unwind at the end of the day. Other features include 2 skylights, ceiling fans throughout, new wood-plank laminate floors with 5” baseboards, remote-controlled sun shades in the spacious Florida room, a 3.5 ton superior “TRANE” HVAC system & water heater in 2024, double driveway, and best of all: SEWER LINES that were SLEEVED at a cost of $12,000! Association 14 roof replaced in 2017. Step outside and fall in love with the huge 15x11 ft composite deck, illuminated by night lights on remote control - storm-tested and built to last, for grand entertaining & fun on the water – watch the 4th of July fireworks from your backyard! An attached 1-Car Garage is finished with epoxy flooring, storage shelves, 160 Mile-rated garage door, water softener & washer/ dryer hook-up. The monthly HOA fees cover fiber-optic cable & internet, water, sewer, trash pickup, building- and flood insurance, exterior maintenance including seawall and roof, grounds-keeping, private roads, on-site management, heated/cooled community pool, tennis- & shuffleboard courts, bocce, 2 clubhouses with active social calendar, fitness center, card- & game rooms, library, along with ENVERA – a virtual gate security system. Pet-friendly – one pet up to 25 lbs permitted (Association 14 consists of only 40 units). Short commute to Publix & Walmart stores, restaurants, bars, Seminole City Center with movie theater, St. Pete College, Seminole Rec Center, Bay Pines Marina, VA hospital, Tyrone Mall, “The Legion”, Madeira Beach #1 tourist attraction “John's Pass Village” and world-renown white, sandy beaches. The vibrant downtown of St. Petersburg is only 13 miles away and 30 minutes' drive to Tampa International Airport. This true villa-style home – no one above or below you, and resort-style living awaits you to launch into the intracoastal lifestyle – hurry – seller is MOTIVATED!

542 Boca Ciega Point Boulevard N Unit 2108, Madeira Beach
$449,500
2 Beds ⋅ 1 Baths ⋅ Madeira Beach Yacht Club Condo SubDv. ⋅ 33708 Zip Code
Price just LOWERED!! $450,000 LOCATION! LOCATION! LOCATION! ATTN: INVESTORS AND BEACH LOVERS bring me your OFFERS! This 1st Floor unit presently has seasonable renters from 1/1/27 through 3/31/27. ALL BRAND NEW AND 5 STEPS TO THE POOL in this popular waterfront Madeira Beach community!! ******This beautiful 1st Floor, 750 Sq Ft, 2 bd/1 bath, condominium is 5 STEPS TO THE POOL! EVERYTHING IN THE ENTIRE CONDO IS BRAND NEW! Entire Kitchen: BRAND NEW!, Flooring: BRAND NEW!, Windows: BRAND NEW!, Ceilings: BRAND NEW!, Bathroom: BRAND NEW!, HVAC: BRAND NEW!, Lighting/fans: BRAND NEW! Roof: BRAND NEW! There is NOTHING for you to do in this condo unit, EXCEPT, to ENJOY your beautiful coastal condo AND/OR MAKE MONEY from your rental income as an investor. I themed my redesigned condo with a "coastal flare" in mind with SHIPLAP Walls and coastal lighting! This community is located just a 5 minute walk to the beach and restaurants and all the FUN, like watching the sunsets or taking a dip in the water or watching fireworks across the street at ROC park! THIS UNIT PRESENTLY HAS A REGULAR SNOWBIRD RENTAL FROM JAN 1ST, 2027 THRU MARCH 31, 2027, however, buyer will have the option to keep the renter or not. SOOOOOO, if you're an INVESTOR, this is a PLUS!! The Madeira Beach Yacht Club is an Coastal Community with lots of amenities such as 2 pools, 3 fishing Docks, private docks, clubhouse, canal walking path, dog friendly, and steps away from ROC PARK, where there are pickleball courts, basketball courts, walking trails around the canal, fireworks, festivals and music several times of the year! The $799 HOA Fee covers: water, sewer, building/roof insurance, cable/DVR, and more! You only pay ELECTRIC! Owners are allowed pet(s) 2 with a weight limit of 20lbs, or if the animal is needed as either a SA or an ESA support, then owners and rentals can have them, (no weight limit), however, providing the proper documentation will be needed., IE., a letter from a doctor. ASK YOU AGENT TO SHOW YOU THIS PROPERTY, OR CONTACT ME FOR A SHOWING! i

230 Medallion Boulevard Unit D, Madeira Beach
$465,000
3 Beds ⋅ 2 Baths ⋅ Gulf Shores Harbor Sub SubDv. ⋅ 33708 Zip Code
Welcome to your charming, fully remodeled beach cottage in the heart of Madeira Beach! Nestled just one block from the Gulf of America, 13707 Plymouth Street offers a rare opportunity to own a unique coastal retreat within walking distance of sugar-white sand beaches, waterfront dining, shopping, and entertainment. Recently updated from top to bottom, this beautifully renovated cottage blends timeless Old Florida charm with modern finishes and conveniences. Thoughtfully redesigned to maximize comfort and functionality, the home showcases a bright, inviting interior that perfectly captures the relaxed coastal lifestyle. Whether you're searching for a primary residence, vacation getaway, second home, or income-producing investment property, this one-of-a-kind beach bungalow is sure to impress. Located just steps from public beach access and approximately .8 miles to the world-famous John's Pass Village & Boardwalk, you'll enjoy easy access to waterfront restaurants, boutique shopping, fishing charters, dolphin cruises, live entertainment, and some of the area's most popular attractions. Spend your mornings walking the beach, afternoons boating or fishing, and evenings enjoying spectacular Gulf sunsets. The property's prime location provides convenient access to St. Pete Beach, Treasure Island, downtown St. Petersburg, Tampa International Airport, and all that Florida's Gulf Coast has to offer. With its unbeatable walkability, coastal character, and extensive recent updates, opportunities like this are increasingly rare. Experience the best of beach living in this charming and unique Madeira Beach cottage—where modern updates meet timeless coastal charm just steps from the sand.

13707 Plymouth Street, Madeira Beach
$479,900
3 Beds ⋅ 2 Baths ⋅ North Madeira Shores SubDv. ⋅ 33708 Zip Code
Virtually Staged. Priced to Sell – Exceptional Income-Producing Duplex in Madeira Beach This beautifully updated duplex offers outstanding versatility and strong cash flow in one of Tampa Bay’s most sought-after beach communities. Featuring a spacious 2-bedroom, 1-bath unit that rents for $2,500 per month and a cozy 1-bedroom, 1-bath unit at $2,000 per month, the property delivers a combined $4,500 monthly — that’s $54,000 in gross annual income. After Expenses your potential Net Income is $41,986 Whether you’re an investor looking for immediate dual income streams or an owner-occupant wanting to offset your mortgage by renting out one side, this turnkey opportunity checks every box. Both units have been storm-remediated and meticulously remodeled with premium finishes and modern systems, including a new roof, new water heaters, new A/C units, and numerous additional upgrades throughout. Each kitchen shines with elegant quartz countertops, crisp white shaker cabinets, and high-end stainless steel appliances. The exterior has been freshly painted and professionally landscaped, creating outstanding curb appeal. Out back, enjoy the low-maintenance turfed yard complete with charming string lighting — perfect for relaxing evenings or entertaining tenants and guests. The property also offers four dedicated parking spaces plus convenient street parking. Ideally situated in the heart of Madeira Beach, you’re just steps from the world-famous white-sand Gulf beaches, vibrant restaurants, shopping, nightlife, boating, and endless water activities. This prime location combines the relaxed beach lifestyle with easy access to everything the Tampa Bay area has to offer. A rare combination of income potential, quality upgrades, and unbeatable location — this is a true turnkey investment you don’t want to miss. Schedule your private showing today and secure this gem before it’s gone!

14906 N Bayshore Drive, Madeira Beach
$750,000
2 Beds ⋅ 2 Baths ⋅ Surfside South Condo SubDv. ⋅ 33708 Zip Code
Welcome to your dream coastal retreat! This lovely 2-bedroom, 2-bathroom CORNER UNIT offers the perfect combination of luxury, convenience, and serene beachfront living. Boasting mesmerizing views of the Gulf, this condo is ready to be updated any way you please adding your very own personal touches. This is one of the few units that has a full WRAP-AROUND PORCH and floor to ceiling windows at both the West and South orientations of the building providing an abundance of natural light. The hurricane shutters are electric operated. As you enter the unit, you’ll notice the beautiful beveled edge TRAVERTINE MARBLE FLOORS that cover the main living areas. Each bedroom has its own updated en-suite bathroom with newer granite countertop vanities. The kitchen is original, completely functional in its as-is condition, and waiting for you to customize it to your liking. This END UNIT is also one of the few that has a BONUS ROOM adjacent to the kitchen with electrical running to it. It could be used as an eat-in den, additional storage, or office space. You could very easily move the washer and dryer (currently in the kitchen) into this bonus space in order to expand the kitchen countertop and cabinets. The decision is yours! 2021 ELECTRICAL PANEL updated to the latest electrical standards. HVAC was replaced in 2018 and owner has it serviced every year. Other community features include heated pool and spa with beach views, private dedicated parking space with plenty of guest parking, elevator access, secure key access to the building, pet-friendly community (see association rules), 30-day minimum rental policy for great income potential (see association rules). This is a well-managed community. The roof was recently redone as well as the milestone inspection and reserve study. Maintenance-free living with spectacular sunset views and direct access to the magnificent Gulf of Mexico. What could be better! Easy access to John’s Pass, restaurants galore, public parks, grocery stores, hospitals. You will never run out of things to do! Schedule a showing today to take a look at this little slice of paradise.

14900 Gulf Boulevard Unit 401, Madeira Beach
Start Your Search