Location: Holiday
Do Not Show Listings
3519 WELLINGTON DR, HOLIDAY, FL 34691
$269,90072 Days on yellowkey MLS ID: TB8472616
0 Days Off yellowkey (back on 4/7/2026)
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 980 Built: 1968 Tax: $1,371 (2024)Community: Holiday Lake EstatesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,371
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Stunningly updated POOL home in the desirable Holiday FL! Featuring a brand NEW ROOF, all new interior and exterior paint, an open floor plan concept and many upgrades throughout. Your chef's kitchen awaits you with white soft-close cabinets, quartz countertops, and the best backyard views. Additionally, there are two spacious bedrooms and a newly updated bathroom. With 980 square feet of perfectly utilized space, this home feels larger than its listed size suggests and offers an open and spacious living area that flows seamlessly into the kitchen. Nestled in a quiet, established neighborhood with no HOA or CDD fees, this gem is just minutes from the Florida Gulf Beaches. Move-in ready and waiting for you, schedule your showing today!
Listing is courtesy of: URBAN CORE REALTY (813-418-0207)
Listing Agent: Monica Dudas (813-418-0207)
2726 BLOSSOM LAKE DR, HOLIDAY, FL 34691
$264,95011 Days on yellowkey MLS ID: TB8493805
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1200 Built: 1988 Tax: $3,775 (2025)Community: Holiday Lakes WestSingle Family
Taxes:$3,775
Tax Year: 2025
Remarks: Welcome to this charming 3-bedroom, 2-bath home located in the established community of Holiday Lakes West. Built in 1988, this well-maintained residence offers approximately 1,200 square feet of living space with a desirable split-bedroom floor plan and open-concept layout. Step inside to find vaulted ceilings and abundant natural light, creating a bright and spacious feel throughout the main living areas. The kitchen features ample cabinetry, a breakfast bar, and a pass-through to the dining area. Situated near US-19, offering quick access to Tampa, Clearwater, and St. Petersburg for work, dining, and entertainment. Just a short drive to Gulf beaches and waterfront parks, including Anclote River Park with boat ramps, fishing, and picnic areas.
Listing is courtesy of: THE SHOP REAL ESTATE CO. (727-593-7777)
Listing Agent: Terry Connors, Ii (727-452-6054)
1715 KENILWORTH ST, HOLIDAY, FL 34691
$319,99944 Days on yellowkey MLS ID: S5145157
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1442 Built: 1973 Tax: $4,454 (2025)Community: Holiday Lake EstatesSingle Family
Taxes:$4,454
Remarks: Welcome to 1715 Kenilworth Street in Holiday, Florida, a beautifully renovated home offering modern updates, functional living spaces, and the added benefit of no HOA restrictions. This move-in-ready property features refreshed interiors, contemporary finishes, and a layout designed for both everyday comfort and easy entertaining. The spacious backyard includes a private pool, creating the perfect setting to enjoy the Florida lifestyle year-round. The property is currently rented on a month-to-month basis. This is an excellent opportunity to own a renovated pool home with no HOA in a desirable Holiday location.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Alejandro Conti (321-424-8903)
3322 FAIRMOUNT DR, HOLIDAY, FL 34691
$279,000134 Days on yellowkey MLS ID: TB8451894
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1558 Built: 1972 Tax: $1,896 (2024)Community: Holiday Lake EstatesSingle Family
Taxes:$1,896
Remarks: Welcome to the established and friendly Holiday Lake Estates community, a quiet residential neighborhood just a stroll from the Anclote River and Gulf Coast beaches. This charming ranch-style home features 3 bedrooms, 2 bathrooms, and a convenient 1-car garage. With some recent updates and 1558 sq. ft. of living space, the home offers a comfortable floor plan perfect for families or those seeking serene Florida living. Enjoy proximity to local parks, fishing, and boating, with easy access to shopping, dining in Tarpon Springs. The spacious backyard provides the perfect space for outdoor relaxation or entertaining. Don't miss this opportunity to own this beautiful property!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Corey Auld (727-657-7977)
2150 MAUREEN DR, HOLIDAY, FL 34690
$225,00053 Days on yellowkey MLS ID: TB8478624
3 Days Off yellowkey (back on 4/7/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 956 Built: 1969 Tax: $428 (2025)Community: Holiday GardensSingle Family
Taxes:$428
Elementary School: Sunray Elementary-PO
High School: Anclote High-PO
Middle School: Paul R. Smith Middle-PO
Remarks: Under contract-accepting backup offers. Located in a quiet Holiday neighborhood East of US-19, this classic 2Bed/2Bath/1-Car garage Florida bungalow offers practical coastal living with its functional layout, private backyard and close proximity to Gulf beaches, shopping and major roadways. This property offers suburban comfort with easy access to waterfront recreation, combining a desirable mix of affordability with access to parks, marinas, fishing spots and easy commuting to Tarpon Springs and Clearwater. The home is block construction and features newly replaced Roof, Windows and Slider and A/C as well as a 2-Year Old Water Heater. This subdivision has No CDD, No HOA and No Deed Restrictions. Live the Florida dream with access to Anclote River Park for beach and boating, Key Vista Nature Park for trails and Gulf views, Tarpon Springs Sponge Docks for its renowned dining and cultural events, and bike or walk the Suncoast Trails. This home offers the Holiday advantage of affordable Florida living with strong coastal access and everyday conveniences, making it a practical choice for full-time or seasonal homeowners, first-time buyers or retirees. 2150 Maureen Drive is indeed a true Florida gem!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (813-907-8200)
Listing Agent: Sharon Cole (813-907-8200)
1238 FLOTILLA DR, HOLIDAY, FL 34690
$1,145,00036 Days on yellowkey MLS ID: TB8485598
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5360 Built: 1971 Tax: $8,869 (2025)Community: Forest Hills Un #22Spa: YesSingle Family
Taxes:$8,869
Remarks: Welcome to this one-of-a-kind exclusive waterfront home pool home in Holiday, set on 1.18 acres at the end of a quiet cul-de-sac on the Anclote River, with water on three sides and approximately 630 feet of waterfront. Surrounded by beautiful moss-draped oak trees, the property offers a private and scenic setting with incredible potential. Featuring Spanish and Mediterranean-inspired architecture, the home showcases arched openings, beamed ceilings, and stone and wood accents throughout. The spacious floor plan includes a sunken formal living room, family room, dining room, office/den and an updated kitchen with a large island, waterfall countertop, range, double oven, and walk-in refrigerator. A flex space with a wet bar and fireplace adds versatility, while the ground floor bath includes dual sinks, sauna with Jacuzzi tub and walk in shower. Two private primary suites, each with separate staircase access, offers comfort and privacy, and both feature private balconies with beautiful water views. Outdoor highlights include a covered deck, gazebo, lanai, oversized 3-car garage, and an expansive yard with room for boat or RV parking and possible tennis court restoration. Buyers will appreciate the opportunity to add a dock and boat lift for easy access to the Gulf of America, perfect for boating, fishing, and enjoying the waterfront lifestyle. This exceptional property offers a rare setting and endless opportunity for updating and personalized touches to create a truly spectacular waterfront retreat. With no HOA and convenient access to Tarpon Springs, beaches, shopping, and dining, this is a rare chance to make it your own.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Ruth Primeau, P.A (727-504-8000)
5300 FALCON DR, HOLIDAY, FL 34690
$179,99915 Days on yellowkey MLS ID: TB8491860
1 Days Off yellowkey (back on 4/7/2026)
Bed: 2 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1128 Built: 1972 Tax: $3,464 (2025)Community: Colonial HillsSingle Family
Taxes:$3,464
Elementary School: Anclote Elementary-PO
Remarks: Charming and thoughtfully upgraded 2-bedroom, 1.5-bath home offering 1,128 sq ft of comfortable living space in a convenient Holiday location. This move-in ready property showcases a beautifully updated kitchen and renovated bathrooms, complemented by new vinyl flooring throughout for a fresh, modern feel. Enjoy peace of mind with major system improvements including a new Rheem A/C with transferable warranty, a new hot water heater with transferable warranty, and electrical upgrades. The home also features hurricane-reinforced straps and a flat roof replaced adding durability and long-term value. At 39 feet above sea level, it’s not in a flooding zone. The inviting living space is enhanced by an electric fireplace with remote, creating a cozy focal point. Step outside to a private patio overlooking a fully fenced backyard perfect for entertaining, pets, or relaxation. Additional highlights include a newer garage with an oversized driveway, drop- down attic access with added flooring for storage, an outdoor shed, and exterior repaint completed in 2021. Ideally situated near local conveniences and attractions, this home offers easy access to shopping, dining, and major roadways including U.S. Route 19 for a smooth commute. Enjoy the Florida lifestyle just minutes from Anclote River Park, known for its scenic waterfront views, beach access, and boat launch. Explore nearby Key Vista Nature Park for walking trails and nature observation, or take a short drive to the historic Tarpon Springs Sponge Docks, famous for its waterfront dining, shops, and rich cultural heritage. Perfect for first-time buyers, downsizers, or investors, this home offers modern upgrades, solid infrastructure, and a prime location. This home is ready for its next owner to enjoy.
Listing is courtesy of: KELLER WILLIAMS SOUTH TAMPA (813-875-3700)
Listing Agent: Michele Herndon, Pa (813-856-9822)
5604 CHEYENNE DR, HOLIDAY, FL 34690
$163,00067 Days on yellowkey MLS ID: TB8474065
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 1974 Tax: $1,943 (2025)Community: Country EstatesSingle Family
Taxes:$1,943
Remarks: Rare opportunity with an assumable FHA loan—potential buyers can step into favorable financing, subject to lender approval Welcome to 5604 Cheyenne Drive, a cozy and inviting 2-bedroom, 1-bath residence ideally located in the heart of Holiday, Florida. This well-maintained home features a spacious sunroom that provides versatile living space—perfect for relaxing, entertaining, or creating a home office or hobby area. The interior offers a comfortable, functional layout filled with abundant natural light, creating a warm and welcoming atmosphere throughout. A standout opportunity, this property offers a 3.250% assumable FHA loan with Roam, making homeownership more accessible and affordable. Conveniently situated near shopping, dining, and major roadways, this home is well-suited for year-round living or a seasonal retreat. Don’t miss the opportunity to own a charming home with flexible space and an exceptional financing option in a prime location.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Ingrid Santaliz (941-962-1238)
3609 TRUMAN DR, HOLIDAY, FL 34691
$250,000172 Days on yellowkey MLS ID: TB8441905
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1536 Built: 1970 Tax: $3,650 (2024)Community: Aloha GardensSingle Family
Taxes:$3,650
Remarks: This beautifully maintained 3-bedroom, 2-bath home is perfect for first-time buyers looking for comfort, space, and affordability near Florida’s Gulf Coast. Located in the quiet Aloha Gardens neighborhood of Holiday, this home offers a great balance of convenience and relaxation — just minutes from beaches, shopping, and dining. Step inside to a bright, open floor plan with easy-to-maintain tile flooring throughout the main living areas. The spacious kitchen opens to the dining and living room, making it ideal for entertaining or family time. Each bedroom offers plenty of natural light and closet space, and the two full bathrooms provide functionality and privacy. Outside, you’ll enjoy a large fenced backyard, perfect for pets, weekend barbecues, or simply relaxing in your own space. The home also features a one-car garage and no HOA, giving you the flexibility and freedom many first-time homeowners are looking for.
Listing is courtesy of: BRIDGE HOMES (813-525-9014)
Listing Agent: Giancarlo Gonzalez (727-743-8541)
1205 CALVARY RD, HOLIDAY, FL 34691
$225,000122 Days on yellowkey MLS ID: TB8455069
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1701 Built: 1991 Tax: $394 (2024)Community: AcreageManufactured Home
Taxes:$394
Elementary School: Gulfside Elementary-PO
Remarks: Welcome to this charming Florida neighborhood three bedroom two bathroom mobile home in Holiday, 1,701 sq ft with NO HOA, where relaxed living and natural beauty come together to create the perfect place to call home. This inviting residence offers an ideal retreat to unwind after a long day, starting with the front wrap-around deck, a peaceful spot to enjoy your morning coffee while taking in the view of two mature oak trees gracing the front yard. Step inside and you’re welcomed by a spacious, light-filled kitchen featuring stainless steel appliances, large windows, a skylight, and an in-kitchen dining area—truly the heart of the home. The living room provides a cozy yet stylish atmosphere with a stone-faced fireplace. For dining, you’ll find both an intimate dining room accented with rustic wood paneling and a large window, as well as a family dining room designed for entertaining, complete with space for a large table, French doors, rustic wood paneling, and expansive windows that flood the room with natural light. The owner’s retreat is generously sized to accommodate a king-size bed and offers his-and-her closets, opening into a spacious bathroom highlighted by a skylight, wood-paneled ceiling, and dual-sink vanity. Two additional spacious bedrooms provide flexibility for a home office, guest room, or extra space. Outside, enjoy a fully fenced yard offering privacy and room to relax or entertain. Gather around the fire pit on warm Florida evenings to make s’mores and lasting memories. This property also includes a 12.5’ x 16’ air-conditioned and powered “Man Cave,” a 10’ x 24’ freestanding workshop, and an 8’ x 10’ utility shed, providing ample storage and workspace. Major updates include a new roof and water heater installed in 2017. The location is unbeatable—just 0.8 miles from the dog-friendly Anclote River Park, offering a boat launch, paved bike trails, playground, picnic shelters, hiking trails, swimming, kayaking, and fishing. Nearby are a bait and tackle shop, Anclote Village Marina, and Miss Vicki’s on the River restaurant, making this area a true outdoor enthusiast’s paradise. Plus, you’re only 7 minutes from the historic Tarpon Springs Sponge Docks.Whether you’re a fisherman, nature lover, or simply seeking a home with character and flexibility, this property offers something special. Schedule your private showing today and envision your future here.
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
2824 SUMMERVALE DR, HOLIDAY, FL 34691
$375,000190 Days on yellowkey MLS ID: TB8435387
2 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2499 Built: 1987Monthly Fee: $48 Tax: $7,148 (2024)Community: Amblewood Gulf TraceSingle Family
Taxes:$7,148
Elementary School: Gulf Trace Elementary
Remarks: Under contract-accepting backup offers. Welcome to this four-bedroom, three-bathroom pool home in the heart of Holiday in the Amblewood community of Gulf Trace, perfectly positioned on a tree-lined conservation lot offering both privacy and tranquility. Once the model home for the community, this residence showcases thoughtful design, spacious living, and just under 2,500 square feet of beautifully maintained space. Step inside through the foyer entrance with a convenient coat closet and be greeted by high ceilings and a light, bright interior filled with natural light from the large sliding glass doors overlooking the pool area. Enjoy entertaining in the formal dining area, while the galley kitchen - offering plenty of cabinet storage - opens to the family room and breakfast nook. The family room features a cozy wood-burning fireplace, creating a warm and inviting space for gatherings. The split floor plan provides both comfort and privacy, with a spacious primary suite featuring an en-suite bathroom complete with a dual-sink vanity, step-in glass-enclosed shower, and private water closet. A dedicated office is located just before the garage, perfect for working from home, and the laundry room includes additional storage for convenience. One of the back bedrooms includes an attached private bathroom, making it ideal for guests or multi-generational living. The additional bedrooms are nicely sized and share access to a third full bath. Step outside to your private screened-in pool area, ideal for year-round enjoyment. The outdoor space includes a covered area for al fresco dining, a wet bar, and a fenced backyard backing up to a peaceful conservation view - the perfect setting to relax or entertain guests. Located close to shopping centers, dining options, and just a short drive to the Gulf beaches, this beautiful Holiday home offers the best of Florida living - space, privacy, and convenience in one exceptional package. Schedule your private showing today!
2211 PLEASANT HILL LN, HOLIDAY, FL 34691
$315,00032 Days on yellowkey MLS ID: TB8485823
REDUCED by $10,000 (3.1%) on 04/06/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 2004Monthly Fee: $175 Tax: $1,954 (2025)Community: Key Vista Ph 03 Prcl 05Villa
Taxes:$1,954
Remarks: Welcome to Key Vista, one of Holiday’s most desirable 55+ gated communities, where comfort meets the best of the Florida lifestyle. This beautifully maintained 2-bedroom, 2-bath Bermuda model by Ryland Homes also includes a dedicated office that can easily function as a third bedroom. Perfectly situated on a private conservation lot with no rear neighbors, this home offers peaceful nature views and is located on the final lot developed in the community. Inside, you’ll find soaring ceilings, an open floor plan, and an abundance of natural light throughout. The main living areas feature tile flooring, while Berber carpet adds warmth and comfort in the living room, office, and bedrooms. The spacious living area is ideal for both relaxing and entertaining. The eat-in kitchen features solid-surface countertops, 42-inch wood cabinetry, a cozy breakfast nook, and brand-new stainless steel appliances installed in November 2024. The primary suite offers high ceilings, a large walk-in closet, and a private ensuite bath with solid-surface countertops, wood cabinetry, and a glass-enclosed shower. The guest bedroom and bath are equally welcoming, while the office located just off the foyer provides flexible space for working from home or accommodating guests. Additional highlights include an interior laundry room with washer, dryer, and utility sink, a two-car garage with epoxy flooring, a 2019 water heater, and a regularly serviced A/C system. Step outside to the screened lanai overlooking tranquil, tree-lined conservation views—perfect for enjoying your morning coffee or unwinding in the evening. Residents enjoy low HOA fees, no CDD, and access to two clubhouses: one exclusively for 55+ residents with its own private pool, plus the master clubhouse featuring a resort-style pool, spa, fitness center, tennis and pickleball courts, sand volleyball, playground, and more. RV and boat storage is also available for a small monthly fee. Ideally located near Key Vista Nature Park, you can take a short walk to the water to enjoy Florida’s spectacular sunsets or explore scenic nature trails. Conveniently close to parks, shopping, dining, and Gulf beaches. Schedule your private showing today and experience everything this beautiful Key Vista home has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Renee Gialousis (727-234-3353)
5404 FRONT DR, HOLIDAY, FL 34690
$289,90092 Days on yellowkey MLS ID: TB8464929
REDUCED by $5,100 (1.7%) on 03/31/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1966 Tax: $2,969 (2024)Community: Forest HillsSingle Family
Taxes:$2,969
Remarks: One or more photo(s) has been virtually staged. Must see WITH AN ASSUMABLE LOAN! Welcome to 5404 Front Dr in Holiday, FL, where space, style, and location come together on an oversized .21-acre lot with room to roam, expand, and even potentially add a pool. Best of all, there’s NO HOA or deed restrictions, giving you the freedom and flexibility today’s buyers dream of! Plus, this move-in-ready home is located in desirable Flood Zone X for added peace of mind. Inside, you’ll find approximately 1,240 sq ft with an additional 200 sq ft (approximate) under air, featuring 3 bedrooms plus a bonus 4th bedroom, 2 full bathrooms, and a garage conversion that offers extra living space—perfect for a primary suite, home office, or private guest retreat. The updated kitchen is sure to stop your scroll, showcasing refreshed cabinetry with new pulls, a stylish backsplash, sleek butcher-block countertops, a modern sink, stainless steel appliances, and durable LVP flooring—ideal for both everyday living and entertaining. The main bathroom is tastefully updated with beautiful new tile, classic subway tile, and updated fixtures, with no detail overlooked. The spacious enclosed Florida room (approximately 10x20) adds even more versatility and can easily serve as a family room, media room, playroom, or work-from-home space. Per records, major updates include a roof (2016), AC (2019), and several windows have been replaced! All of this is in a prime location with quick access to US Highway 19 for easy commuting, just minutes from the sugary sand Gulf beaches and the Jolley Trolley, and a short drive to the charm of the historic Tarpon Springs Sponge Docks. Opportunities like this don’t last—act fast and make this incredible home yours today!
Listing Agent: Gary Ubaldini (727-420-1765)
2945 WOOD POINTE DR, HOLIDAY, FL 34691
$345,00013 Days on yellowkey MLS ID: TB8494010
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1341 Built: 2004Monthly Fee: $175 Tax: $3,851 (2025)Community: Key Vista Ph 02Single Family
Taxes:$3,851
Remarks: Located within the 55+ area of the beautiful Key Vista gated community, this move-in-ready villa radiates pride of ownership through extensive upgrades and a cheerful, sun-drenched layout. The open floor plan features high ceilings, architectural niches, and brand-new luxury vinyl plank flooring complemented by fresh paint and elegant plantation shutters throughout. At the heart of the home, the kitchen boasts wood cabinetry, granite countertops, and newer stainless steel appliances, including a breakfast bar and a delightful dinette area. This space opens to a large, screened-in lanai with upgraded "no-see-um" screens and a pavered floor, offering a tranquil view of a serene pond and lush landscaping with no rear neighbors for ultimate privacy. The thoughtful design includes a split-bedroom layout for maximum comfort, along with a versatile den that can easily serve as a third bedroom or home office. For added convenience, the villa includes an indoor laundry room and a two-car garage. Living here means enjoying a maintenance-free lifestyle where the HOA covers exterior painting, cable, internet, and access to resort-style amenities. Residents can take advantage of two clubhouses, heated pools and spas, a fitness center, tennis and volleyball courts, and a playground, all within a beautifully manicured environment that even offers on-site storage for boats and RVs. The location is a true standout for outdoor enthusiasts, situated within a short walking distance of the Gulf of Mexico and the Key Vista Nature Park. You are just moments away from the Key Vista Waterfront Gulf Park, which offers a swimming area, kayak access, a 24-hour fishing pier, and miles of walking and bike trails. With the historic Tarpon Springs Sponge Docks, local marinas, and boat ramps at Anclote River Beach Park nearby, this home provides the perfect gateway to Florida's coastal lifestyle. NO FLOOD INSURANCE REQUIRED, NO CCD FEE, roof 2022, THE SOLAR PANELS WILL GIVE YOU AN IMMEDIATE SAVINGS AT ABOUT $100 A MONTH.
4720 BURNEY DR, HOLIDAY, FL 34690
$165,000153 Days on yellowkey MLS ID: W7880637
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1065 Built: 1981Monthly Fee: $143 Tax: $1,742 (2024)Community: Tanglewood Mobile VillageManufactured Home
Taxes:$1,742
Remarks: Under contract-accepting backup offers. Welcome to 4720 Burney Drive in the desirable 55+ Tanglewood Mobile Home Community! Where you OWN the land!! This water-view, corner-lot, beautifully updated 3-bedroom, 2-bathroom, beach-inspired furnished home is fully move-in ready for its next owners. Over $50,000 in updates and maintenance in the last five years ensures peace of mind and modern comfort from the moment you walk in. Step inside to an inviting open layout featuring a fully updated kitchen, new flooring, upgraded baseboards and moldings, and bright coastal finishes throughout. The spacious sunroom brings in tons of natural light — perfect for morning coffee, entertaining, or extra living space. A large storage shed gives you room for tools, beach gear, or hobby items, making this home as functional as it is charming. Located in one of the most sought-after 55+ communities, Tanglewood is known for its LOW HOA fee of just $143/month, which includes lawn maintenance. Residents also enjoy a vibrant and active community lifestyle with events like pancake breakfasts, social gatherings, shuffleboard, and more...plus a refreshing community pool to enjoy year-round. Whether you’re looking for a winter escape, a peaceful year-round home, or a fully furnished turnkey retreat, this property checks all the boxes. Don’t miss your chance to tour this beautiful water-view home. schedule your showing today!
Listing is courtesy of: MCCULLOUGH & ASSOC REALTY INC (727-237-4940)
Listing Agent: Sophia Arcese (727-744-2226)
3025 SHEPPARDS CROOK CT, HOLIDAY, FL 34691
$549,00014 Days on yellowkey MLS ID: TB8493709
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2218 Built: 2005Monthly Fee: $100 Tax: $4,909 (2025)Community: Ibis SubSingle Family
Taxes:$4,909
Remarks: One or more photo(s) has been virtually staged. Step into a sun filled oasis! Updated 3 bedroom, 3 bath, pool home offering tranquil, peaceful views; with a rare opportunity to live in a intimate private gated community. Home is full of natural light. Move-in ready, lovingly maintained. New roof, New water heater, New air conditioner, New flooring, updated baths, updated kitchen. Solar panel keep you electric bill very low. Large screened in Lanai with pool. Potential In-Law/Guest Suite. Gorgeous, memorable Sunsets. Backs up to a preserve on the Gulf of America. Workshop and built in storage adjacent to garage. Mature fruit trees. Elevation or the home is over 13 feet. Spacious Master bathroom with walk-in shower, garden tub, walk-in closet, new granite countertop. Don't miss this one, call for your private showing today! Discerning buyers know opportunities like this are few and far between!
Listing is courtesy of: AZURE WATERFRONT REALTY, LLC (239-872-9257)
Listing Agent: Brad Reddick (239-872-9257)
2138 BAYOU DR, HOLIDAY, FL 34691
$849,90065 Days on yellowkey MLS ID: TB8469784
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2583 Built: 1979Monthly Fee: $8 Tax: $6,034 (2024)Community: Baileys Bluff EstatesSingle Family
Taxes:$6,034
Remarks: One or more photo(s) has been virtually staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and share a beautifully appointed full bath with a tub/shower combination. A hallway linen closet with built-in shelving provides additional storage. The primary suite is a true retreat, featuring sliding-door access to the lanai and a spa-inspired bath complete with a step-in shower with sliding glass doors—also opening to the exterior—dual-sink vanity, private water closet, and a dedicated dressing hallway with abundant closet space. A separate pool-access bath with sink and toilet can be closed off from the primary suite for added privacy. A nearby washer and dryer closet enhances everyday convenience. The main living areas impress with soaring volume ceilings, recessed lighting, and a striking corner stone fireplace anchoring the space. The chef’s kitchen is as functional as it is beautiful, showcasing wood soft-close cabinetry, granite countertops, stainless steel appliances, a breakfast bar, pantry closets with extensive shelving, a built-in corner desk, and a sun-filled breakfast nook. Architectural details add warmth and character, including a barn-style sliding door allowing the kitchen to be closed off when desired, and a decorative wicker-accent opening that enhances the home’s charm. A flexible dining area offers the option of formal dining and opens through sliding doors to a charming brick patio. The bonus room provides exceptional flexibility—ideal as a home office, media room, or optional fourth bedroom—complete with a utility sink closet, additional storage, and direct garage access. Outdoors, the expansive screened-in lanai and pool create a private oasis perfect for entertaining, complemented by an outdoor shower. The generous fenced backyard leads to your waterfront dock area, where tranquil water views can be enjoyed from the living room, breakfast nook, dining area, and kitchen. Additional highlights include light wood luxury vinyl flooring throughout; tile flooring in all bathrooms, oversized windows providing abundant natural light, ample storage throughout, and an oversized two-car garage. Located just two blocks from the Coastal Anclote Trail, which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs. Enjoy easy water access via the bayou and creek with just a five-minute boat ride to the Gulf. The area is also ideal for kayaking. Pickleball courts with weekly league play are located within one mile. This exceptional waterfront property offers the perfect blend of lifestyle, comfort, and convenience. Schedule your private showing today.
Listing Agent: Vanessa Leonard (727-647-2706)
1955 DARTMOUTH DR, HOLIDAY, FL 34691
$435,00021 Days on yellowkey MLS ID: TB8490706
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1679 Built: 1974 Tax: $4,793 (2025)Community: Holiday Lake EstatesSingle Family
Taxes:$4,793
Remarks: “Attention investors and discerning buyers! This luxury property in Holiday is a once-in-a-lifetime opportunity just 7 min left to the beach! Completely rebuilt in 2026, everything is brand new: windows, doors, roof, air conditioning with modern lineal ducts—all completed in 2026. This home boasts a brand-new 2026 water heater, luxury ceramic bathrooms, and stunning ceramic flooring throughout. The terrace, with its wood finish and gazebo overlooking the water, is a private oasis. With three spacious bedrooms and three bathrooms, including a perfect in-law suite, every detail exudes sophistication. Modern cabinetry with quartz countertops creates a luxurious ambiance in the kitchen and throughout the open living space. The home also features a sleek modern garden, a fully updated electrical system (2026), and a brand-new electrical panel. This home is a smart home, with integrated speakers and a premium sound system for the ultimate living experience. This is a turnkey masterpiece—perfect for those seeking elegance, cutting-edge technology, and modern design. Don’t wait—schedule your tour today and join the elite who will call this home their own!”
Listing is courtesy of: SELLING USA, LLC (813-723-0086)
Listing Agent: Zuleidys Ares (813-723-0086)
5347 FLORA AVE, HOLIDAY, FL 34690
$215,00015 Days on yellowkey MLS ID: TB8493389
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1072 Built: 1969 Tax: $745 (2025)Community: Forest HillsSingle Family
Taxes:$745
Remarks: Welcome to this well-cared-for home in the Forest Hills community of Holiday, offering a great combination of updates, functionality, and outdoor space. With a comfortable layout and natural light throughout, this home is ideal for everyday living or investment.The interior features a bright living space and an updated kitchen that adds a modern touch while keeping things practical. The layout flows easily, making the home feel open and inviting.Step outside to a fully fenced backyard with southern exposure, providing sunshine throughout the day. This space is perfect for pets, entertaining, gardening, or creating your own outdoor retreat or future pool area.Several major improvements have already been completed, including a septic system approximately 5 years old, roof approximately 9 years old, A/C approximately 10 years old, windows approximately 10 years old, and a hot water heater just 1 year old, offering added peace of mind. Conveniently located near shopping, dining, beaches, and main roadways, this property offers both comfort and accessibility. Whether you are looking for a primary residence, seasonal home, or investment opportunity, this is a solid choice. Schedule your showing today and see the value for yourself.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ellie Lambert (813-690-0319)
3340 HONEYMOON LN, HOLIDAY, FL 34691
$238,00075 Days on yellowkey MLS ID: TB8471243
REDUCED by $1,000 (0.4%) on 04/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1334 Built: 1973 Tax: $3,199 (2024)Community: Beacon SquareSingle Family
Taxes:$3,199
Remarks: Beautifully remodeled 2 bedroom, 2 bathroom home with a 1-car garage located on a quiet street just minutes from the coast. This move-in ready property features a modern open layout, updated flooring throughout, fresh interior paint, and a fully renovated kitchen with stylish cabinets, updated countertops, and newer appliances. The spacious primary suite includes its own updated bathroom, and the additional bedrooms are generously sized, perfect for family, guests, or a home office. Both bathrooms have been tastefully upgraded with contemporary finishes. Enjoy the backyard—ideal for relaxing, entertaining, or adding outdoor features. The attached garage provides extra storage and convenience.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Alberto Delgado (813-380-2104)
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