18,358

Holiday, FL Homes

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  • /58

    $2,390,000

    • 5 Beds
    • 4.5 Baths
    • 4,006 Sq Ft

    3439 Brookfield Cir, Holiday, FL 34691

    Rarely available and updated Deerwood model in The Preserve at Emerald Hills, situated on a private corner lot with beautiful lake views. Now including a BRAND-NEW POOL in the purchase price, this modern organic home blends warm contemporary design with sophisticated finishes throughout. Home features 22-foot ceilings in the living room, oversized impact windows, and an open-concept layout filled

    Sabina Potack Douglas Elliman

    3439 Brookfield Cir, Holiday, FL 34691
  • /32

    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,208 Sq Ft
    • House for Rent

    2713 Capricorn Place, Holiday, FL 34691

    Welcome to this 3 bedroom, 2 bathroom home featuring a desirable split floor plan, with the primary suite located on the opposite side of the home for added privacy.This home offers a bright sunroom, an attached garage, and fresh carpet in all of the bedrooms. You’ll also enjoy the screened in front porch perfect for relaxing outdoors while staying comfortable inside your own home..Rental

    Ashley R. Williams LEGACY BUILDER REALTY AND DEVELOPMENT LLC

    2713 Capricorn Place, Holiday, FL 34691
  • /2

    $307,000

    Sold Aug 27, 2025

    3208 Brompton Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1970

    Last Sold Summary

    • $214/SF
    • 14 Days On Market

    Current Estimated Value $302,175

    Last Listing Agent Debbie Raimo FUTURE HOME REALTY INC

    3208 Brompton Dr, Holiday, FL 34691
    • /35

      Not Listed For Sale

      4699 Continental Dr Unit 95, Holiday, FL 34690

      • 2 Beds
      • 1 Bath
      • Built 1982
      4699 Continental Dr Unit 95, Holiday, FL 34690

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Lane Parks Gulf Breeze Mobile Home Sales, LLC

  • /32

    $200,000

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    1207 Lodestar Dr, Holiday, FL 34690

    The Home was owned and occupied, and well maintained exclusively by one family; never any tenants. The roof was replaced about three years ago. Living, dining, and kitchen have terrazzo flooring; bedrooms and baths are carpeted over terrazzo. All walls and ceilings are plastered white. All plumbing is in good condition and has been repaired or replaced as necessary. All existing blinds and

    Liz Piedra Horizon Palm Realty Group

    1207 Lodestar Dr, Holiday, FL 34690
  • /23

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • House for Rent

    3314 Trask Dr, Holiday, FL 34691

    ATTENTION RENTERS! Be the first to enjoy this stunning, fully remodeled 3-Bedroom, 2-Bathroom home in the heart of Holiday! Every inch of this home has been thoughtfully redesigned with high-end finishes and modern upgrades, offering a truly move-in-ready experience. From the moment you step inside, you'll appreciate the attention to detail, stylish design, and contemporary features that make

    3314 Trask Dr, Holiday, FL 34691
  • /2

    $225,000

    Sold May 19, 2026

    3307 Rosefield Dr, Holiday, FL 34691

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft
    • Built 1966

    Last Sold Summary

    • 10% Below List Price
    • $265/SF
    • 253 Days On Market

    Current Estimated Value $218,556

    Last Listing Agent Junie Cook FUTURE HOME REALTY INC

    3307 Rosefield Dr, Holiday, FL 34691
    • /33

      Not Listed For Sale

      4699 Continental Dr Unit 362, Holiday, FL 34690

      • 2 Beds
      • 1 Bath
      • Built 1986
      4699 Continental Dr Unit 362, Holiday, FL 34690

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Lane Parks Gulf Breeze Mobile Home Sales, LLC

  • /26

    $444,000

    $31K PRICE DROP Under Contract
    • 5 Beds
    • 3 Baths
    • 2,454 Sq Ft

    1220 Stover Ct, Holiday, FL 34691

    Under contract-accepting backup offers. Welcome to your own private oasis overlooking a beautiful lake. This completely remodeled five-bedroom, three-bathroom, one-car garage home offers exceptional space, versatility, and modern updates throughout. The property features a huge, detached workshop with electric, along with an attached storage building-perfect for hobbies, projects, or extra

    Allan Safranek, III RICHEY REALTY

    1220 Stover Ct, Holiday, FL 34691
  • /49

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • House for Rent

    3301 Rosefield Dr, Holiday, FL 34691

    Welcome to this three bed, two bath home ready for rent now! Freshly painted, new carpet, tile, and move in ready! First month's rent plus one month rent for security. No pets. No smoking inside. Must have stable income for last 6 months. Must make three times the rent or close to it. Owner will be looking at rental history and background. Tenant is responsible for water and electric and trash.

    Justin West RE/MAX MARKETING SPECIALISTS

    3301 Rosefield Dr, Holiday, FL 34691
  • /2

    $165,000

    Sold Oct 13, 2025

    3836 Staysail Ln Unit 3836, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,534 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $108/SF
    • 11 Days On Market

    Last Listing Agent Nicholas Vavoulis RE/MAX MARKETING SPECIALISTS

    3836 Staysail Ln Unit 3836, Holiday, FL 34691
    • /2

      Not Listed For Sale

      4341 Manton Ln, Holiday, FL 34691

      4341 Manton Ln, Holiday, FL 34691

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Carrissa Henshaw RE/MAX COLLECTIVE

  • /56

    $125,000

    • 1 Bed
    • 1 Bath
    • 880 Sq Ft

    3806 Staysail Ln Unit 704, Holiday, FL 34691

    Clean, Updated and Move in Ready, Non Flood Zone (X), and LOW HOA of $412/mo more than pays for itself! Welcome home to total ease and true maintenance-free Florida living at 3806 Staysail Ln, a beautifully updated, spacious single-story block construction villa in a peaceful 55+ community with no stairs to entry and no unit or neighbors above! Located in a non-flood zone, this home offers added

    Denvir Steele REALTY EXPERTS ASSOCIATES

    3806 Staysail Ln Unit 704, Holiday, FL 34691
  • /16

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft
    • House for Rent

    2552 Chancery Dr, Holiday, FL 34690

    Cute home with mature landscaping, fenced yard, garage, and large detached shed for storage or craft projects! Fresh paint, tile flooring, ceiling fans, plentiful storage. The kitchen has hardwood flooring that overlooks the nicely sized backyard with mature landscaping. The screened patio is a great outdoor space. Off-street parking is perfect for a trailer or boat. One-car attached garage.

    2552 Chancery Dr, Holiday, FL 34690
  • /2

    $375,000

    Sold Nov 26, 2025

    2427 Indian Key Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 2003

    Last Sold Summary

    • 13% Below List Price
    • $213/SF
    • 40 Days On Market

    Current Estimated Value $375,491

    Last Listing Agent Linda Forgues LOKATION

    2427 Indian Key Dr, Holiday, FL 34691
    • /38

      Not Listed For Sale

      4699 Continental Dr Unit 331, Holiday, FL 34690

      • 1 Bed
      • 1 Bath
      • Built 1987
      4699 Continental Dr Unit 331, Holiday, FL 34690

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Lane Parks Gulf Breeze Mobile Home Sales, LLC

  • /40

    $265,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,371 Sq Ft

    2146 Society Dr, Holiday, FL 34691

    Under contract-accepting backup offers. Virtually Staged. Tucked along the shores of Lake Conley, this turn key 2 bedroom, 2 bathroom home feels like the kind of place where mornings start slow with coffee on the porch and evenings end around the fire pit or swinging by the water under the stars. From the moment you arrive, the covered front porch with its welcoming bench invites you to sit down,

    Traci Pearson - Realtor KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

    2146 Society Dr, Holiday, FL 34691
  • /19

    $1,600 Per Month

    • 3 Beds
    • 2 Baths
    • 860 Sq Ft
    • House for Rent

    3323 Fairmount Dr Unit 17, Holiday, FL 34691

    Welcome to this three-bedroom, two-bathroom home in Holiday. The single-story layout offers flexible living space, three bedrooms, two full bathrooms, and a fenced yard for enjoying the outdoors.The property is conveniently located near shopping, restaurants, parks, Gulf Coast beaches, and US-19, providing easy access throughout Pasco and Pinellas counties.In addition to the advertised

    Chelsie Lewis WRIGHT DAVIS REAL ESTATE

    3323 Fairmount Dr Unit 17, Holiday, FL 34691
  • /28

    $290,000

    Sold Apr 16, 2026

    4250 Pinefield Ave, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft
    • Built 1980

    Last Sold Summary

    • $195/SF
    • 28 Days On Market

    Current Estimated Value $288,813

    Last Listing Agent John Blevins GENSTONE REALTY

    4250 Pinefield Ave, Holiday, FL 34691
    • /2

      Not Listed For Sale

      2021 Lullaby Dr, Holiday, FL 34691

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft
      • Built 1968
      2021 Lullaby Dr, Holiday, FL 34691

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Shelly Hayden BILTMORE GROUP INC

  • /33

    $208,988

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    1203 Chancellor Dr, Holiday, FL 34690

    Charming 2 bedroom 2 bath home with fenced yard located in the quiet neighborhood of Forest Hills. NO HOA or CDD. New carpet in both bedrooms and living room with tile in remaining areas. The Florida room is located off of the dinning room thru the new sliding doors that is cooled and heated for your comfort and can be used as a playroom, office, game room or TV room. Galley style kitchen with

    Richard Forgione COLDWELL BANKER REALTY

    1203 Chancellor Dr, Holiday, FL 34690
  • /2

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • 848 Sq Ft
    • House for Rent

    3315 Kinard Ln, Holiday, FL 34691

    Welcome Home to This Spacious 2-Bedroom, 2-Bath Home in Holiday, FL!Discover the perfect combination of comfort, space, and convenience in this inviting 2-bedroom, 2-bathroom home located in the heart of Holiday. With a versatile floor plan, spacious living areas, and a fully enclosed backyard, this home is ideal for anyone looking for extra room to live, work, and relax.Step

    3315 Kinard Ln, Holiday, FL 34691
  • /2

    $185,000

    Sold Nov 04, 2025

    4404 Beacon Square Dr, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,021 Sq Ft
    • Built 1967

    Last Sold Summary

    • $181/SF
    • 0 Days On Market

    Current Estimated Value $187,081

    Last Listing Agent Marcos Reyes CHARLES RUTENBERG REALTY INC

    4404 Beacon Square Dr, Holiday, FL 34691
    • /2

      Not Listed For Sale

      3220 Lanark Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1976
      3220 Lanark Dr, Holiday, FL 34690

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Kathleen Hernandez COLDWELL BANKER REALTY

  • /18

    $218,900

    $11K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    3619 Wiltshire Dr, Holiday, FL 34691

    Under contract-accepting backup offers. Welcome Home to this 3 bedroom/2 bath block home. Hard surface flooring and freshly painted throughout. NEW Septic System in 2026, Roof 2022, HVAC 2018, Water Heater 2018. Enjoy the Florida Room and spacious backyard. So close to the sun and fun on the Gulf, many restaurants, and shopping close by.

    Lynne Powers POWERS REAL ESTATE SOLUTIONS LLC

    3619 Wiltshire Dr, Holiday, FL 34691
  • /14

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • House for Rent

    1130 Powersong St, Holiday, FL 34690

    2 Bed/1 Bath Single-family Home-- AVAILABLE NOW!Beautifully updated 2 bedroom, 1 bath home with 1 car garage for rent in Holiday. This home is located on a corner-lot and features fresh paint and brand new wood laminate flooring throughout. The open kitchen has updated countertops and plenty of cabinet space. On the back of the home is a spacious, enclosed Florida room, and the large

    Kevin Byrne VALENCIA REALTY, LLC

    1130 Powersong St, Holiday, FL 34690
  • /2

    $229,900

    Sold Jul 24, 2026

    3521 Bigelow Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,164 Sq Ft
    • Built 1970

    Last Sold Summary

    • $198/SF
    • 59 Days On Market

    Current Estimated Value $226,597

    Last Listing Agent Dalton Robinson BIRCH HAVEN REAL ESTATE, LLC

    3521 Bigelow Dr, Holiday, FL 34691
    • /2

      Not Listed For Sale

      3641 Tiki Dr, Holiday, FL 34691

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1971
      3641 Tiki Dr, Holiday, FL 34691

      Last Sold Summary

      • 144 Days On Market

      Last Listing Agent Lisa Carroll MIHARA & ASSOCIATES INC.

  • /44

    $575,000

    • 5 Beds
    • 3 Baths
    • 3,072 Sq Ft

    1914 Oswego Dr, Holiday, FL 34691

    Welcome to this beautiful 5 bedroom 3 bathroom two-story home located in the highly desirable community of Key Vista. Upon entry you immediately feel welcome and at home with the large formal dining area and front living area with electric fireplace. The large kitchen boasts tall cabinetry and plenty of counter space with amazing views of the tree line that reflects along the waters edge. One

    Jason Scott INVESTMENT FLORIDA REALTY LLC

    1914 Oswego Dr, Holiday, FL 34691
  • /44

    $1,895 Per Month

    • 3 Beds
    • 1 Bath
    • 1,028 Sq Ft
    • House for Rent

    5913 Appletree Rd, Holiday, FL 34690

    Welcome home to this charming and well-maintained 3-bedroom, 1-bath single-family residence offering 1,028 square feet of comfortable living space. Designed for both convenience and functionality, this home features central heat and air to keep you comfortable year-round.The kitchen comes fully equipped with a refrigerator, oven, microwave, dishwasher, and electric water heater, making meal

    5913 Appletree Rd, Holiday, FL 34690
  • /2

    $114,000

    Sold May 27, 2026

    1850 Mary Ln, Holiday, FL 34690

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $108/SF
    • 44 Days On Market

    Last Listing Agent Cristina Taylor SIRROM REALTY LLC

    1850 Mary Ln, Holiday, FL 34690
    • /2

      Not Listed For Sale

      2108 Hoyle Dr, Holiday, FL 34691

      • 2 Beds
      • 2 Baths
      • 736 Sq Ft
      • Built 1984
      2108 Hoyle Dr, Holiday, FL 34691

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Sara Henk LA ROSA REALTY CENTRAL FLORIDA LLC

  • /11

    $214,900

    Pending
    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    4901 Picture Ave, Holiday, FL 34690

    Under contract-accepting backup offers. Move-in ready and beautifully updated, this Holiday home is packed with upgrades and ready for its new owner. From the moment you step inside, you'll notice the brand-new luxury vinyl flooring that flows throughout the home, creating a clean and modern feel. The completely updated kitchen features new shaker-style cabinets, quartz countertops, soft-close

    Nicholas Vavoulis RE/MAX MARKETING SPECIALISTS

    4901 Picture Ave, Holiday, FL 34690
  • /35

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • House for Rent

    2242 Pinewood Villas Dr, Holiday, FL 34691

    Welcome to your meticulously maintained 2-bedroom, 2-bathroom villa nestled in a serene community! Step inside and be greeted by an inviting open floor plan adorned with a cathedral ceiling and skylight, creating a bright and airy ambiance in the spacious living room and dining area. The master suite is a tranquil haven, complete with a walk-in closet and a master bath featuring a walk-in shower.

    JD Kaufman RE/MAX ALLIANCE GROUP

    2242 Pinewood Villas Dr, Holiday, FL 34691
  • /2

    $105,000

    Sold Jul 08, 2026

    3811 Sailmaker Ln, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1988

    Last Sold Summary

    • 28% Below List Price
    • $94/SF
    • 199 Days On Market

    Current Estimated Value $119,717

    Last Listing Agent Marcus Howard REALNET BROKERAGE

    3811 Sailmaker Ln, Holiday, FL 34691
    • /2

      Not Listed For Sale

      2050 Lullaby Dr, Holiday, FL 34691

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft
      • Built 1974
      2050 Lullaby Dr, Holiday, FL 34691

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Judi Pobst KELLER WILLIAMS REALTY- PALM HARBOR

  • /59

    $215,000

    $135K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,577 Sq Ft

    4233 Darlington Rd, Holiday, FL 34691

    Under contract-accepting backup offers. the craziest price ever!, Super motivated seller, it's now or never! Income-Generating Property - Investors, the Best Price!Appraisal Value $275.000 "Excellent investment opportunity in the Holiday market! This 3-bedroom, 2-bathroom property stands out for its generous size (2,628 sq. ft.) and excellent condition, including a brand-new roof (installed 1

    Francisco Rojas GLOBAL FORTUNE REALTY LLC

    4233 Darlington Rd, Holiday, FL 34691
  • /11

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • 1/1 Furnished with Lake View & Utilities in Tahitian Gardens a 55+ Community w/ Utilities Included

    4358 Tahitian Gardens Cir, Holiday, FL 34691

    (**NOT AVAILABLE ON FACEBOOK OR CRAIGS LIST**) 1/1 LAKE VIEW CONDO IN AN OVER 55 COMMUNITY. WAKE UP EVERY MORNING TO A LAKE VEIW!! CONDO BOASTS RECENTLY REDONE KITCHEN CABINETS, & FLOORS, FULLY FURNISHED WITH WASHER AND DRYER . COMMUNITY AMENITIES INCLUDE USE OF THE COMMUNITY POOL AND CLUBHOUSE AND PROPERTY IS LOCATED CLOSE TO 19 AND SHOPPING. *Electric / Water/ Sewer/ Trash/ Lawn

    4358 Tahitian Gardens Cir, Holiday, FL 34691
  • /2

    $237,500

    Sold Oct 24, 2025

    5033 Tammy Ln, Holiday, FL 34690

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $208/SF
    • 131 Days On Market

    Current Estimated Value $228,542

    Last Listing Agent Dan Risola RE/MAX REALTEC GROUP INC

    5033 Tammy Ln, Holiday, FL 34690
    • /2

      Not Listed For Sale

      3414 Chatford Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1980
      3414 Chatford Dr, Holiday, FL 34690

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY

Showing Results 241 - 280, Page 7 of 18

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