Location: Holmes Beach
Keyword(s): Manatee High
Keyword(s) High School: Manatee High
Do Not Show Listings
3014 GULF DR, HOLMES BEACH, FL 34217
$1,095,00097 Days on yellowkey MLS ID: A4678029
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1320 Built: 1977 Tax: $12,953 (2024)Community: IlexhurstSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,953
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $130k in rental revenue in 2025. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!
Listing is courtesy of: PINEYWOODS REALTY LLC (813-225-1890)
Listing Agent: Amanda Cornett (941-807-2811)
5200 GULF DR #302, HOLMES BEACH, FL 34217
$749,000101 Days on yellowkey MLS ID: A4677566
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 832 Built: 1970Monthly Fee: $1,297 Tax: $4,263 (2024)Community: Martinique Apts SouthSpa: NoCondo
Taxes:$4,263
Remarks: GULF FRONT - Spacious and Beautifully Maintained and Renovated 1 Bedroom/1 Bath Condo in the Heart of Holmes Beach. Breathtaking Gulf Views to behold from every room. The kitchen, windows and sliding doors have been updated and the AC was replaced in 2025. This unit features a covered, open balcony allowing for your own Private Outdoor Space while relishing in the balmy Gulf breezes. Commodious Open living/dining area is painted in calm, neutral colors and ceramic tile flows throughout. The bedroom features full gulf views, a large walk-in closet and ensuite bath with separate vanity area and combination tub/shower. The updated kitchen provides plentiful and aesthetic cabinetry, a closet pantry, newer appliances, desk area and Washer and Dryer. Martinique South offers a Gulf side pool, tennis/pickle ball courts, an elevator, secure entrance, large Community living space with full Gulf Views, a complete kitchen, bathrooms, and outdoor covered patio. The Community Room is ideal for parties and large gatherings. Pride of ownership shines in this community where friends are neighbors and neighbors are friends. This lovely unit is offered turn-key furnished, with room for your personal touches as well as a carport and storage room. Located within walking distance of Holmes Beach amenities. Magnificent sunsets, strolls along the white sand beach, passing dolphins, the cry of the seabirds and the comforting sound of the surf await...
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Adele Holland (941-587-6328)
203 72ND ST, HOLMES BEACH, FL 34217
$2,649,000219 Days on yellowkey MLS ID: A4664948
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2153 Built: 1971 Tax: $27,767 (2024)Community: West Wind ShoresSpa: NoSingle Family
Taxes:$27,767
Remarks: Welcome to Tidal Daze, an exceptionally decorated and fully furnished 4-bedroom, 3.5-bathroom island retreat in the heart of Holmes Beach. This thoughtfully designed home offers flexibility and comfort with dual living spaces – both the upper and ground levels feature 2 bedrooms and 2 bathrooms, ideal for multi-generational living or guests who prefer single-level accommodations. Open & Airy Interior Living At the heart of the home, the second-floor open-concept layout combines the kitchen, dining, and living areas into a welcoming gathering space. The kitchen includes a pantry, spacious island, and modern finishes, seamlessly connecting to the dining area for everyday living and entertaining. Coastal-inspired décor and abundant natural light create a relaxed yet refined atmosphere throughout. Resort-Style Outdoor Oasis Step outside to your private backyard sanctuary complete with: Oversized heated pool with sun shelf and color-changing lights Large turf play area and 3-hole putting green Covered patio with mounted TV for outdoor enjoyment Custom outdoor shower for post-beach refreshes Private parking for up to 6 vehicles, plus a garage for storage and golf cart Location & Lifestyle Just 200 yards from the Gulf’s sugar-sand beaches, Tidal Daze offers the perfect balance of small-town charm and coastal beauty. Holmes Beach is known for its vibrant dining, boutique shopping, and endless outdoor activities – from boating and paddleboarding to biking along the island. With a proven 5-star rental history, this home is also an excellent investment opportunity for buyers seeking a property with income potential.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
2913 GULF DR, HOLMES BEACH, FL 34217
$1,099,00039 Days on yellowkey MLS ID: A4684724
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 1940 Tax: $13,580 (2024)Community: IlexhurstSingle Family
Taxes:$13,580
Remarks: You must see this charming 1940s Craftsman cottage tucked into the historic heart of Anna Maria Island! This beautifully renovated two-bedroom, two-bath homestead blends timeless Old Florida character with effortless coastal charm. The home’s distinctive pecky pine exterior pay homage to its heritage while creating a warm, inviting island aesthetic that reflects the relaxed spirit of Anna Maria’s historic beach community. Inside, the home opens into a light-filled open floor plan designed for easy coastal living and effortless entertaining. The living, dining, and kitchen areas flow seamlessly together, creating a welcoming gathering space filled with natural light and breezy island ambiance. Whether enjoying a quiet morning coffee or hosting friends after a day at Anna Maria’s beautiful beaches, the layout makes the home feel both spacious and intimate. A convenient indoor laundry room is thoughtfully tucked away, adding modern practicality to this historic retreat. The home features a well-designed split floor plan, offering privacy and comfort for residents and guests alike. The primary bedroom suite includes a private ensuite bath, creating a peaceful retreat at the end of the day. On the opposite side of the home, the second bedroom features charming built-in bunks, perfect for family or visiting guests, with easy access to the second full bath. Step outside to discover a beautifully landscaped private pool enclosure, surrounded by lush tropical greenery that creates a tranquil island oasis. It’s the perfect spot to relax, unwind, and soak in the peaceful rhythm of Anna Maria’s laid-back island lifestyle. All of this is located just two blocks from Anna Maria’s world-famous sugar-sand beaches, and only moments from the island’s beloved restaurants, charming boutiques, and local shops. Spend your days biking to breakfast cafés, strolling to dinner with sunset views, or exploring the unique coastal storefronts that make Anna Maria so special. This lovingly restored cottage offers a rare opportunity to own a piece of historic island charm paired with modern comfort in one of Florida’s most treasured beach communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
504 58TH ST, HOLMES BEACH, FL 34217
$1,450,00047 Days on yellowkey MLS ID: A4685187
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1540 Built: 1962 Tax: $10,386 (2025)Community: Holmes Beach Fourteenth UnitSingle Family
Taxes:$10,386
Tax Year: 2025
Remarks: Recently renovated 3 bedroom, 2 bath canal front home on a beautiful, deep water, natural-lined mangrove canal with a boat dock. This meticulously cared for home is located on a very quiet street in Holmes Beach. A shady, private paver lined courtyard sits canal side and is a serene spot to escape. PGT Hurricane rated windows & doors installed Oct. 2021, new metal roof installed 2025, new A/C, ductwork & insulation 2025 and all new appliances 2025. Centrally located on the island just steps from Holmes Beach City Park & Public Event Venue, with pickleball courts, a dog park and The Island Library. Walking distance to great dining options & local shopping boutiques. Hop on your golf cart to enjoy the pristine beach & Gulf located just minutes from your door! One car garage and ample driveway parking. This great home is truly "island living" at its best.
Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)
Listing Agent: Marianne Norman-Ellis (941-685-3393)
511 BAYVIEW DR, HOLMES BEACH, FL 34217
$5,290,000111 Days on yellowkey MLS ID: A4675904
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3353 Built: 2020 Tax: $24,007 (2024)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$24,007
Remarks: Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
408 71ST ST, HOLMES BEACH, FL 34217
$1,799,000189 Days on yellowkey MLS ID: A4668595
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2037 Built: 1966 Tax: $16,372 (2024)Community: Bay Palms AddSpa: NoSingle Family
Taxes:$16,372
Remarks: Welcome to paradise at Coco Cay! This beautiful 4 bedroom 4 bathroom home has been completely remodeled top to bottom. Brand new hurricane impact windows and doors, a new roof, kitchen, appliances, bathrooms, flooring, paint, furnishings, and even a new pool! This island oasis is move-in ready and only a few blocks from the world-famous beaches of Anna Maria Island. You will notice coastal décor as soon as you step into this island gem. The home provides a spacious open living area with teal accents, stainless-steel appliances, quartz countertops, and a game room conveniently adjacent to the kitchen with a pool table and dartboard. Outside you'll enjoy a screened in porch accessible from the living room, a seating area complete with a firepit, and a huge covered lanai for cooking and dining poolside. Weekly rentals are allowed. Make an appointment for your private showing and see what makes Coco Cay an excellent full-time home or investment property.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Don Purvis (901-240-2180)
603 EMERALD LN, HOLMES BEACH, FL 34217
$4,340,000344 Days on yellowkey MLS ID: A4652348
Bed: 5 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 3700 Built: 2024 Tax: $21,278 (2023)Community: Key Royale 11Th AddSpa: YesSingle Family
Taxes:$21,278
Tax Year: 2023
Remarks: Stunning turnkey new construction on Anna Maria Island, located on a serene and rare double channel lot in the Key Royale neighborhood. This spacious residence features 5 bedrooms, 2 on the main level and 3 upstairs, all with en suite and walk-in closets offering ample space for family and guests. The main floor’s primary suite includes a large bathroom with steam shower and beautiful marble tile flooring. Enjoy 2 living spaces, one on the main level and another with a large balcony overlooking the canal on the second floor. The elevator provides easy access to both levels. Convenient laundry with 4 washers and 4 dryers, 2 upstairs and 2 on the main level. Upgraded finishes throughout with wide plank engineered walnut flooring, marble tile in the bathrooms, quartz countertops, 8' high extra thick upgraded doors, and upgraded trim package. The modern kitchen boasts brand new high-end Sub-Zero and Wolf paneled appliances and upgraded cabinetry. Step outside to enjoy covered seating and dining areas, a large saltwater pool and spa with breathtaking canal views, and 2 new composite wood docks with new seawall on this home's rare corner channel access, ideal for water enthusiasts. The property also features garage spaces to accommodate 4 vehicles, and new mature landscaping. The home's interiors are thoughtfully designed with hand-curated, beach inspired furnishings which are included in the sale.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
6005 GULF DR #219, HOLMES BEACH, FL 34217
$739,90085 Days on yellowkey MLS ID: A4679762
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1980 Tax: $7,704 (2025)Community: Playa EncantadaCondo
Taxes:$7,704
Remarks: New Price Adjustment! Enjoy Coastal Living on Anna Maria Island ! This 2 bedroom, 2 bath, 2nd floor, turnkey furnished condo is located in one of the best & most sought after complexes on the Island. Heated swimming pool, spa, pickleball/tennis courts, shuffleboard court, building elevator & beach are just a few of the condo amenities. The condo overlooks the tennis courts with updated stylish kitchen, quartz countertop, stainless appliances & an open/airy floor plan. Large lanai, crown molding throughout & all tile floors accent this gorgeous condo. Washer & dryer are located inside the unit, plus there is an owner's storage room on the ground level. Kitchen appliances & A/C system new in 2021. Just walk across the street to enjoy the white sandy beach & blue green waters of the Gulf of Mexico. Enjoy living the Florida lifestyle!
Listing Agent: Thomas Nelson (941-448-4465)
205 HAVERKOS CT, HOLMES BEACH, FL 34217
$1,525,00055 Days on yellowkey MLS ID: A4683517
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1599 Built: 1975 Tax: $12,097 (2024)Community: Haverkos CourtSingle Family
Taxes:$12,097
Remarks: Welcome to your slice of paradise on beautiful Anna Maria Island! This 3-bedroom, 2-bath island retreat is ideally located just 2.5 blocks from the sugar-sand beaches of the Gulf of Mexico, offering the ultimate coastal lifestyle in one of Florida’s most sought-after destinations. Designed for relaxation and entertaining, the home features an amazing ground-level pool with spa — your own private tropical oasis perfect for soaking up the Florida sunshine or unwinding after a day at the beach. The spacious layout comfortably accommodates family and guests, making every stay feel like a vacation. Enjoy being within walking distance to all that Anna Maria has to offer — charming local shops, great dining, grocery options, and more. Leave the car behind and embrace the true island lifestyle. In addition to being a wonderful personal getaway or primary residence, this property is a great rental home with strong appeal to vacationers seeking location, comfort, and exceptional outdoor living. Its proximity to the beach, walkability, and desirable pool/spa amenities make it highly attractive for short-term rental opportunities. Whether you're looking for an island escape, investment property, or both — this home delivers the very best of Anna Maria Island. Come live your Anna Maria Life!
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
7000 GULF DR #115, HOLMES BEACH, FL 34217
$1,395,00085 Days on yellowkey MLS ID: A4679118
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1978Monthly Fee: $1,150 Tax: $11,730 (2024)Community: Tiffany PlaceCondo
Taxes:$11,730
Remarks: Imagine waking up to views of sugar sand beaches and the turquoise waters of the Gulf. Imagine no longer as you can enjoy this beachfront lifestyle from this 2 bedroom, 2 bath condo in the Beachfront Condominium complex, Tiffany Place. From the moment you enter the unit you will realize its many upgrades: the polished porcelain tile in the foyer and kitchen, the engineered hardwood flooring throughout the remainder of the unit, the plantation shutters, new kitchen cabinets, Jenn Aire Range, stainless steel appliances, remodeled bathrooms and custom cabinets in the primary bedroom. In 2022 a new air conditioner and electric panel were installed and a new hot water heater in 2025. In 2023, all the windows were replaced with Hurricane Impact proof windows, which prevented any damage from the two 2024 hurricanes and provided a discount in insurance and lowered AC costs significantly. As the condo is in the north wing of the complex, you can enjoy the morning sun while drinking your coffee on the balcony and comfortable shade for your afternoon tea or cocktails. The unit has 2 additional storage closets. Tiffany Place is close to the free Island Trolley which can take you to the many unique shops and restaurants on the island and the Library. Or stay put and just enjoy the beachfront living from your new home. .
Listing is courtesy of: A PARADISE INC REALTOR (941-778-4800)
Listing Agent: Helen Ross (941-524-8214)
101 73RD ST #2, HOLMES BEACH, FL 34217
$700,000166 Days on yellowkey MLS ID: A4669721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 810 Built: 1980 Tax: $3,478 (2025)Community: Princess Martha AptsCondo
Taxes:$3,478
Remarks: One or more photo(s) has been virtually staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home use as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof was installed in 2025, and the air-conditioning unit in 2022. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Shellie Young, Pa (941-713-5458)
6500 FLOTILLA DR #126, HOLMES BEACH, FL 34217
$685,00095 Days on yellowkey MLS ID: A4678773
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1185 Built: 1978 Tax: $9,027 (2024)Community: Westbay Point & Moorings IiCondo
Taxes:$9,027
Remarks: Beautifully renovated FURNISHED SECOND FLOOR bayfront condominium offering expansive, unobstructed views of Anna Maria Sound in the highly desirable Westbay Point & Moorings community. Positioned to capture sweeping water vistas, this residence delivers the quintessential Florida waterfront lifestyle with sunrise and sunset views, gentle bay breezes, and panoramic scenery visible from nearly every room. The interior has been thoughtfully updated with wood-look tile flooring, two remodeled bathrooms and a guest bath featuring glass-enclosed shower doors. The bright, coastal-inspired kitchen showcases white cabinetry, quartz countertops, and stainless steel KitchenAid appliances, creating an open, airy space ideal for entertaining. Roof and air conditioning system were replaced in 2025 adding comfort and peace of mind. In 2020, the screened lanai was enclosed with HURRICANE IMPACT RATED WINDOWS, enhancing year-round living while maintaining stunning waterfront views. French doors lead directly to the primary suite, where tranquil bay views set the tone for relaxation. The elevated second floor vantage point that truly sets this home apart. Outdoors Westbay Point & Moorings offers resort-style amenities, including tennis and pickleball courts, a heated waterfront pool, a second pool with spa. The community is situated on a private peninsula with lush, park-like tropical landscaping and enjoys one of the highest elevations on Anna Maria Island, a notable advantage for coastal living. The Association is fully reserved, professionally managed with a long-term on-site manager, and the property includes established rental history, with multiple rentals already in place for 2026. The Holmes Beach dog park, skate park, basketball, tennis and pickleball, public boat launch, playground and community activities are just around the corner. The public library, many restaurants, art galleries and shops are very convenient to this location. The world famous sandy beaches of Anna Maria Island are a short drive, bike ride or stroll away. A rare opportunity to own a bayfront residence on Anna Maria Island combining luxury updates, resort amenities, and enduring rental appeal.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Linda Moore (941-737-3581)
6250 HOLMES BLVD #56, HOLMES BEACH, FL 34217
$849,90058 Days on yellowkey MLS ID: A4681823
REDUCED by $15,100 (1.7%) on 03/31/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1536 Built: 1992Monthly Fee: $855 Tax: $10,907 (2024)Community: North Beach Village IiiCondo
Taxes:$10,907
Remarks: BEACHY KEEN… Just steps from the pristine shores of Anna Maria Island, this exceptional townhome is ideal as a weekend escape, a seasonal retreat from Old Man Winter, or a smart investment while retirement plans are still taking shape. Whether you’re tired of renting, dreaming of a coastal getaway, or looking to diversify with Florida real estate, this property checks all the boxes. Inside, you’ll find an updated kitchen designed to delight the family chef, featuring newer stainless-steel appliances, rich granite countertops, and classic shaker cabinetry. Stunning Brazilian rosewood flooring flows throughout the open, inviting floor plan, complemented by a dedicated dining area perfect for relaxed gatherings. A conveniently located first-floor powder room offers added convenience for guests. The expansive lanai off the living area is ideal for outdoor entertaining and provides easy access to the community pool. Upstairs, two spacious ensuite bedrooms each feature a private bath and their own balcony—perfect for morning coffee or unwinding at the end of the day. A two-car garage offers ample space for vehicles and other island essentials. Located less than 500 yards from the Gulf, your new home away from home invites daily beach walks, refreshing coastal breezes, and spectacular sunsets. Enjoy the island’s charming shops, restaurants, and community amenities including tennis, pickleball, and a baseball field. Come for the weekend, stay for the season, or plan for the future—either way, you’ll be glad you made this move.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Richard Capps (941-920-7500)
101 73RD ST #3, HOLMES BEACH, FL 34217
$725,000166 Days on yellowkey MLS ID: A4669729
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1980 Tax: $3,151 (2025)Community: Princess Martha AptsCondo
Taxes:$3,151
Remarks: One or more photo(s) has been virtually staged. This is your golden moment. Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home or to use as a weekly rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
213 84TH ST, HOLMES BEACH, FL 34217
$2,250,00068 Days on yellowkey MLS ID: TB8475905
1 Days Off yellowkey (back on 4/2/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2193 Built: 1986 Tax: $23,426 (2025)Community: Holmes Beach 34Th UnitSingle Family
Taxes:$23,426
Remarks: Under contract-accepting backup offers. Positioned on a naturally elevated homesite for enhanced drainage and reduced flood exposure, this custom-built Anna Maria Island retreat delivers the perfect blend of luxury, flexibility, and proven investment potential. Offered turnkey furnished, the residence features 4 bedrooms, 3 full baths, and a layout designed for effortless full-time living or high-performing vacation use. The light-filled main living level showcases soaring cathedral ceilings, an open-concept great room, and retractable glass doors that create seamless indoor-outdoor living to the expansive deck. The chef’s kitchen is built to impress with double ovens, commercial-size refrigerator, custom cabinetry, soapstone countertops, large island seating, and a brand-new ZLINE gas cooktop, all enhanced by suspended track lighting. Recent improvements include fresh interior and exterior paint, fresh sod and landscaping, an upgraded irrigation system, and a new pool heater and pump — delivering true move-in-ready peace of mind. The private primary suite offers a balcony retreat, walk-in closet, soaking tub, and walk-in shower. Two additional upstairs guest rooms share a spacious bath, while the fourth bedroom on the lower level provides direct pool access and an additional full bath — ideal for guests or multi-generational living. Outdoor living steals the show with a heated pool and spa, waterfall feature, gas firepit, built-in seating, and lush tropical landscaping for maximum privacy and year-round enjoyment. Zoned R1 with 30-night minimum rentals and a strong established rental history, this property offers exceptional flexibility for personal use, seasonal escapes, or income production. Located moments from the Gulf beaches, dining, and shopping of Anna Maria Island, this elevated, furnished coastal home is the total package.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
101 73RD ST #1, HOLMES BEACH, FL 34217
$675,000166 Days on yellowkey MLS ID: A4669608
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1980 Tax: $3,402 (2025)Community: Princess Martha AptsCondo
Taxes:$3,402
Remarks: One or more photo(s) has been virtually staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated one-bedroom, one-bath unit is a first-floor corner unit that has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf. This is a rare opportunity as unique buildings like this are few and far between. It could be the ideal place to call home or as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
624 DUNDEE LN, HOLMES BEACH, FL 34217
$2,295,000209 Days on yellowkey MLS ID: A4665745
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1799 Built: 1967 Tax: $21,626 (2024)Community: Key Royale 9Th AddSingle Family
Taxes:$21,626
Remarks: Welcome to Southern Exposure! One of the best things about coming to sunny Florida from the cold North is a home with Southern Exposure so you can bask in the sun by this amazing pool all day long! Tranquil, private waterfront sanctuary — 624 Dundee on Key Royale is an impeccably renovated residence offering modern-luxe living by the water. This refined 3-bedroom, 2-bath pool home blends effortless flow with elevated finishes throughout. Meticulous landscaping and elegant paved walkways welcome you, while thoughtful attention to detail is evident in every room. Outdoors, a perfectly scaled heated pool and generous sun terraces are complemented by covered lounge space for sophisticated alfresco living and dining. A fully equipped dock with a 10,000 lb lift invites effortless access to open water, fishing, kayaking, or paddleboarding amid abundant coastal wildlife. Entertain beautifully: a sleek, brand-new kitchen with island opens to the dining area and elongated living room, creating seamless indoor-outdoor flow. The primary suite sits poolside with a private ensuite—ideal for morning swims or coffee on the lanai with sunshine all day! Two additional bedrooms share a well-appointed bath and can easily convert to a chic home office or guest quarters. Perfectly positioned on the island, this home captures the quintessential Anna Maria lifestyle—relaxation, sunlit days, and waterfront adventures—ready to be enjoyed as an exquisite primary residence or a sophisticated addition to your investment portfolio.
3018 GULF DR, HOLMES BEACH, FL 34217
$1,500,000343 Days on yellowkey MLS ID: A4651692
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2320 Built: 1920 Tax: $14,695 (2024)Community: IlexhurstApartment
Taxes:$14,695
Remarks: This property is best suited for buyers seeking short-term rental income, a multi-unit investment, or a flexible owner-occupant strategy in a prime Holmes Beach location on Anna Maria Island. This income-producing triplex is located just steps from the Gulf beaches with no busy streets to cross and offers three separate rental units, including a 3-bedroom, 1-bath residence upstairs, plus a 2-bedroom, 1-bath unit and a studio apartment on the main level, allowing for multiple income streams, full-time investment use, or a live-in-one, rent-the-others approach. Currently operating as an active short-term rental, the property benefits from strong year-round demand driven by its proximity to the beach, dining, and entertainment near Bridge Street, as well as convenient access off the island via the Manatee Avenue Causeway. The central location also provides easy reach to IMG Academy, University Town Center, Lakewood Ranch, Downtown Sarasota, and both Sarasota-Bradenton International Airport and Tampa International Airport, making it attractive for owners, guests, and investors alike. Whether held as a turnkey short-term rental, positioned for a 1031 exchange, or used as a coastal residence with income, this Holmes Beach triplex offers a rare combination of location, flexibility, and proven rental performance.
Listing Agent: Brooke Doucett, Llc (941-586-3522)
208 PEACOCK LN, HOLMES BEACH, FL 34217
$1,250,000343 Days on yellowkey MLS ID: A4651677
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1738 Built: 1976 Tax: $10,455 (2024)Community: Aufra RepApartment
Taxes:$10,455
Remarks: This property is best suited for buyers seeking short-term rental income, a flexible second home, or a long-term investment in a desirable Holmes Beach location on Anna Maria Island. This well-maintained duplex is ideally located near the island’s renowned Gulf beaches, dining, and shopping, with each side offering 2 bedrooms and 2 bathrooms designed for comfortable island living. Currently operating as an active short-term rental, the property provides immediate income potential while allowing personal use as desired, making it attractive to investors and vacation-home buyers alike. Both sides feature spacious private backyards with room to enhance outdoor living and the potential to add a pool (subject to city approval), offering additional upside in both enjoyment and rental performance. With its proven rental history, flexible use options, and sought-after island setting, this duplex presents a compelling opportunity to own income-producing property on Anna Maria Island.
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