Holiday, FL Homes

• 

  

  

  /50

  $222,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  3441 Eisenhower Dr, Holiday, FL 34691

  Move-in ready opportunity in Holiday! This beautifully maintained home features 2 bedrooms, 2 bathrooms, central HVAC, and vinyl flooring throughout. Enjoy a fenced backyard, patio area, and a one car garage. Conveniently located near everyday shopping, dining, and entertainment with easy access to major roadways and the Gulf Coast. Easy to show!

  William Figueroa SOVEREIGN REAL ESTATE GROUP

  3441 Eisenhower Dr, Holiday, FL 34691
• 

  

  /2

  $440,000

  Sold Mar 05, 2026

  5253 Boardwalk St, Holiday, FL 34690

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $238/SF
  • 213 Days On Market

  Current Estimated Value $428,427

  Last Listing Agent Gigi Gauthier TRUE REALTY GROUP

  5253 Boardwalk St, Holiday, FL 34690
• 

  

  

  /42

  Not Listed For Sale

  1909 Kepner Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 672 Sq Ft
  • Built 1966

  1909 Kepner Dr, Holiday, FL 34691

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Judi Pobst KELLER WILLIAMS REALTY- PALM HARBOR
• 

  

  

  /11

  $159,000

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  3303 Eisenhower Dr, Holiday, FL 34691

  Welcome to this charming one-story home located in the Aloha Gardens community of Holiday. Offering 3 bedrooms, 2 bathrooms, and approximately 1,116 square feet of living space, this home provides a functional layout with plenty of potential to make it your own. The spacious living room is ideal for relaxing or entertaining, while the open-concept kitchen flows seamlessly into the dining area and

  Jesse Carriedo REALTYCITY INC

  3303 Eisenhower Dr, Holiday, FL 34691
• 

  

  /2

  $118,000

  Sold Feb 19, 2026

  4321 Tahitian Gardens Cir Unit A, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $154/SF
  • 72 Days On Market

  Current Estimated Value $117,351

  Last Listing Agent Steve Diller PARADISE WEST REALTY, INC

  4321 Tahitian Gardens Cir Unit A, Holiday, FL 34691
• 

  

  /19

  Not Listed For Sale

  4356 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Built 1968

  4356 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Pamela Bass COASTAL PROPERTIES GROUP INTERNATIONAL
• 

  

  /17

  $229,900

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,346 Sq Ft

  3208 Kilburn Rd, Holiday, FL 34691

  Don’t miss this charming 2-bedroom, 2-bath solid block and stucco home featuring a separate Florida room plus a spacious bonus room that can easily be converted into a third bedroom and includes a wood-burning fireplace. The garage has been converted into a large bonus space, offering excellent flexibility for a home office, guest suite, or additional living area. Recent updates include a newer

  Julie Mueller THE BOUTIQUE REAL ESTATE GROUP

  3208 Kilburn Rd, Holiday, FL 34691
• 

  /2

  $382,000

  Sold Sep 18, 2025

  2452 Big Pine Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 2003

  Last Sold Summary

  • 7% Below List Price
  • $218/SF
  • 108 Days On Market

  Current Estimated Value $380,016

  Last Listing Agent Robert Hodge COLDWELL BANKER REALTY

  2452 Big Pine Dr, Holiday, FL 34691
• 

  

  /38

  Not Listed For Sale

  4347 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Built 1973

  4347 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Michael McAuley COASTAL FLORIDA REAL ESTATE
• 

  

  /49

  $225,000

  $5K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,047 Sq Ft

  3049 Kilburn Rd, Holiday, FL 34691

  Seller motivated! Don't miss this fantastic opportunity to own this charming 3-bedroom, 1.5-bathroom home featuring a 1-car garage and a versatile detached shed with electricity perfect for a workshop, hobby space, extra storage, or a home office. This well-maintained home also features a newer roof and A/C, providing added peace of mind for years to come. Step outside to enjoy the fully paved

  Jasmin Cabral LIFESTYLE INTERNATIONAL REALTY

  3049 Kilburn Rd, Holiday, FL 34691
• 

  /2

  $380,000

  Sold Feb 26, 2026

  1945 Blue River Rd, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft
  • Built 2005

  Last Sold Summary

  • 13% Below List Price
  • $201/SF
  • 103 Days On Market

  Current Estimated Value $378,253

  Last Listing Agent Ernie Fuentes, Jr. ERNIES REAL ESTATE

  1945 Blue River Rd, Holiday, FL 34691
• 

  

  /18

  Not Listed For Sale

  2330 Baron Dr, Holiday, FL 34690

  • 1 Bed
  • 1 Bath
  • 630 Sq Ft
  • Built 1971

  2330 Baron Dr, Holiday, FL 34690

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Tom Emundi SUNCOAST GROUP REALTORS LLC
• 

  

  /23

  $229,900

  $40K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,519 Sq Ft

  3105 Pinon Dr, Holiday, FL 34691

  Under contract-accepting backup offers. Auction Property. Short Sale. * * FANTASTIC OPPORTUNITY * * Welcome to this 3-bedroom, 2-bath POOL HOME located in the heart of Holiday, FL. This home offers the perfect blend of comfort, style, and indoor-outdoor living. Step inside to find a bright, open floor plan with abundant natural light, spacious living and dining areas, and a thoughtfully designed

  Matthew Brashear RE/MAX ELITE REALTY

  3105 Pinon Dr, Holiday, FL 34691
• 

  /2

  $472,500

  Sold Oct 21, 2025

  3311 Hearthstone Ct, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft
  • Built 1991

  Last Sold Summary

  • 4% Below List Price
  • $215/SF
  • 65 Days On Market

  Current Estimated Value $473,919

  Last Listing Agent Patrycja Henderson LUXURY & BEACH REALTY INC

  3311 Hearthstone Ct, Holiday, FL 34691
• 

  

  /5

  Not Listed For Sale

  0 Mariposa Dr, Holiday, FL 34690

  0 Mariposa Dr, Holiday, FL 34690

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Steve Diller PARADISE WEST REALTY, INC
• 

  

  /19

  $119,900

  $9K PRICE DROP

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

  3807 Staysail Ln, Holiday, FL 34691

  Motivated seller. Come join this 55+ community and all the amenities it has to offer including clubhouse, pool area and shuffleboard courts. This ground level unit comes with parking out front of unit and an outside storage. Kitchen has been updated and comes with washer and dryer. The large step down sun room has plenty of light for reading or shut the blinds for privacy. This unit offers split

  Garth Marsh BEST BEACH RENTALS & SALES PA

  3807 Staysail Ln, Holiday, FL 34691
• 

  /2

  $271,000

  Sold Sep 22, 2025

  2431 Pinetta Ct, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Above List Price
  • $179/SF
  • 6 Days On Market

  Current Estimated Value $277,379

  Last Listing Agent Katie Gawel COASTAL PROPERTIES GROUP INTERNATIONAL

  2431 Pinetta Ct, Holiday, FL 34691
• 

  

  /60

  Not Listed For Sale

  2336 Prestige Dr, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2004

  2336 Prestige Dr, Holiday, FL 34690

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Denise Wooley RE/MAX ALLIANCE GROUP
• 

  

  /3

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,032 Sq Ft

  4338 Beacon Square Dr, Holiday, FL 34691

  Charming 3-bedroom, 2-bath single-family home offering a comfortable floor plan with spacious living areas and plenty of natural light. The home features an attached one-car garage, a fully fenced backyard ideal for outdoor enjoyment, and a functional layout designed for everyday living. Close to Anclote River Park, for a true Florida water-living experience.

  Cliff Glansen FLATFEE.COM

  4338 Beacon Square Dr, Holiday, FL 34691
• 

  /2

  $170,000

  Sold Jan 16, 2026

  4140 Castlewood Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $138/SF
  • 33 Days On Market

  Current Estimated Value $176,109

  Last Listing Agent Katherine Congdon KELLER WILLIAMS REALTY- PALM HARBOR

  4140 Castlewood Dr, Holiday, FL 34691
• 

  

  /24

  Not Listed For Sale

  4345 Tahitian Gardens Cir Unit J, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Built 1979

  4345 Tahitian Gardens Cir Unit J, Holiday, FL 34691

  Last Sold Summary

  • 120 Days On Market

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
• 

  

  /18

  $90,000

  $25K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 552 Sq Ft

  1837 Lullaby Dr, Holiday, FL 34691

  This 3 bedroom, 1 and a half bathroom home is nestled on a spacious, oversized lot, offering room to roam, play, and entertain. The true highlight is its incredible location. You're just a short distance from everything you need and love: from trendy shops and delicious restaurants to exciting entertainment venues and, of course, the stunning nearby beaches.

  Asteropi Tsalickis PREMIER REALTY CONSULTANTS

  1837 Lullaby Dr, Holiday, FL 34691
• 

  /2

  $210,000

  Sold Jun 05, 2026

  4326 Westwood Dr, Holiday, FL 34691

  • 3 Beds
  • 1 Bath
  • 1,023 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $205/SF
  • 51 Days On Market

  Current Estimated Value $209,850

  Last Listing Agent Jansz Umboh LOKATION

  4326 Westwood Dr, Holiday, FL 34691
• 

  

  /39

  Not Listed For Sale

  2139 Kepner Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,205 Sq Ft
  • Built 1959

  2139 Kepner Dr, Holiday, FL 34691

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Mike Del Grande 1% LISTS CENTRAL FLORIDA
• 

  

  /12

  $90,000

  • Land
  • 16,988 Sq Ft
  • $230,769 per Acre

  1504 Jackson Dr, Holiday, FL 34691

  Discover the perfect setting for your custom waterfront dream home on this expansive .39-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering ample space for a variety of home designs, outdoor living areas, and landscaping possibilities, this oversized property provides a rare opportunity to create your ideal Florida retreat. An added bonus - the adjacent lot is also available

  Jeffrey Borham EXP REALTY LLC

  1504 Jackson Dr, Holiday, FL 34691
• 

  /2

  $255,000

  Sold Aug 26, 2025

  3250 Coldwell Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,214 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Below List Price
  • $210/SF
  • 21 Days On Market

  Current Estimated Value $245,144

  Last Listing Agent Robert Bello DALTON WADE INC

  3250 Coldwell Dr, Holiday, FL 34691
• 

  

  /20

  Not Listed For Sale

  6331/6325 Lost Trail, Holiday, FL 34690

  6331/6325 Lost Trail, Holiday, FL 34690

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Bernard Champagne CENTURY 21 ALTON CLARK
• 

  

  /26

  $225,000

  $10K PRICE DROP Pending

  • 2 Beds
  • 1.5 Baths
  • 984 Sq Ft

  4948 Genesis Ave, Holiday, FL 34690

  This 2 Bedroom 1.5 Bath Home with a 1 Car Garage on a Corner Lot has Low Maintenance wood-look tile floors throughout! Entertaining is easy with the Open Floorplan that also offers creative options for placing your furniture! Kitchen has modern cabinets with subway tile backsplash, stainless steel appliances and buffet area for added serving space. Indoor Laundry Area with Washer and Dryer.

  Pamela Douberly KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

  4948 Genesis Ave, Holiday, FL 34690
• 

  

  /40

  $29,900

  Sold Jan 02, 2026

  4699 Continental Dr Unit Lot 584, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • Built 1987

  Last Sold Summary

  • 33% Below List Price
  • 302 Days On Market

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

  4699 Continental Dr Unit Lot 584, Holiday, FL 34690
• 

  

  /22

  Est $269,911

  Not Listed For Sale

  3027 Victoria Inlet Dr, Holiday, FL 34691

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 2024

  3027 Victoria Inlet Dr, Holiday, FL 34691

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
• 

  

  /49

  $300,000

  $1K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft

  4344 Oak Bluff Ave, Holiday, FL 34691

  NEW ROOF TO BE INSTALLED BEFORE CLOSING!!!!!!Welcome to 4344 Oak Bluff Avenue in Holiday, Florida — a beautifully updated home offering comfort, flexibility, and peace of mind with major improvements already completed. This move-in-ready property features an oversized primary suite that provides the perfect private retreat with plenty of space to relax and unwind. The fully finished garage is

  Chris Gonzalez HOMEXPRESS REALTY, INC.

  4344 Oak Bluff Ave, Holiday, FL 34691
• 

  /2

  $65,000

  Sold Dec 12, 2025

  1814 Hoyle Dr, Holiday, FL 34691

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

  Last Sold Summary

  • 13% Below List Price
  • $82/SF
  • 32 Days On Market

  Last Listing Agent Penny Gould PENNY GOULD REALTY INC

  1814 Hoyle Dr, Holiday, FL 34691
• 

  /2

  Not Listed For Sale

  3309 Tiki Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 720 Sq Ft
  • Built 1971

  3309 Tiki Dr, Holiday, FL 34691

  Last Sold Summary

  • 196 Days On Market

  Last Listing Agent Bob McCaffery BHHS FLORIDA PROPERTIES GROUP
• 

  

  /34

  $228,500

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  3240 Briar Cliff Dr, Holiday, FL 34691

  Gulf Coast beaches and the iconic Tarpon Springs Sponge Docks just minutes away. This is the kind of Florida lifestyle first-time buyers dream about, and this home puts it within reach. This 3-bedroom, 2-bathroom home with a 1-car garage sits in a non-flood zone community and offers a comfortable, functional layout with genuine upgrades already in place. The kitchen is already the kind most

  Michele Strong ENGEL & VOLKERS BELLEAIR

  3240 Briar Cliff Dr, Holiday, FL 34691
• 

  /2

  $482,000

  Sold Oct 06, 2025

  2310 Wood Pointe Dr, Holiday, FL 34691

  • 5 Beds
  • 3 Baths
  • 2,429 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $198/SF
  • 112 Days On Market

  Current Estimated Value $482,029

  Last Listing Agent Maggie Loving FUTURE HOME REALTY INC

  2310 Wood Pointe Dr, Holiday, FL 34691
• 

  

  /55

  Not Listed For Sale

  5707 Silver Spur Dr, Holiday, FL 34690

  • 1 Bed
  • 1 Bath
  • 4,424 Sq Ft
  • Built 1974

  5707 Silver Spur Dr, Holiday, FL 34690

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Brande Greenlee GREENLEE HOME SALES OF TRINITY
• 

  

  /17

  $235,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 936 Sq Ft

  Unlisted Address

  If you appreciate a home that has been loved and flawlessly cared for, this is the one. This light and bright 2-bedroom, 1.5-bathroom home shines with pride of ownership and features NO HOA restrictions. Enjoy complete peace of mind with major mechanical and structural updates, including a newer roof (2018), updated electrical panel (2022), new plumbing throughout, a new water heater, and fresh

  Team Papin FLORIDA LUXURY REALTY INC

  Unlisted Address
• 

  /2

  $121,000

  Sold Jun 15, 2026

  2101 Kona Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $115/SF
  • 46 Days On Market

  Last Listing Agent Gail Small FUTURE HOME REALTY INC

  2101 Kona Dr, Holiday, FL 34691
• 

  /2

  Not Listed For Sale

  1908 Viceroy Ln, Holiday, FL 34690

  • 1 Bed
  • 1 Bath
  • 216 Sq Ft
  • Built 1958

  1908 Viceroy Ln, Holiday, FL 34690

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Joyce Ratliff RE/MAX ALLIANCE GROUP
• 

  

  /28

  $244,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  3920 Beacon Square Dr, Holiday, FL 34691

  Virtually Staged. Rare opportunity! Qualified buyers may assume the existing FHA mortgage at approximately **3.625%**, offering the chance to secure yesterday's interest rate on today's home. This exceptional financing advantage is becoming increasingly difficult to find in today's market. Welcome to this inviting 2-bedroom, 2-bath home in the established Beacon Square community, offering a

  Keisha Allen HOMESMART

  3920 Beacon Square Dr, Holiday, FL 34691

Showing Results 561 - 600, Page 15 of 18