Holiday, FL Homes

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  /32

  $239,900

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft

  1958 Essex Dr, Holiday, FL 34691

  WELCOME HOME to this charming property situated on an OVERSIZED fenced lot with BOAT PARKING and a large side gate — perfect for all your outdoor toys and extra storage needs! This versatile 2-bedroom home also features a BONUS ROOM ideal for a home office, guest room, or potential third bedroom. Inside, you’ll find a refreshed kitchen complete with newer appliances and a spacious pantry for

  Heather Sandlin EXP REALTY LLC

  1958 Essex Dr, Holiday, FL 34691
• 

  

  /2

  $375,000

  Sold May 15, 2026

  3147 Mela Ct, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft
  • Built 2016

  Last Sold Summary

  • 3% Below List Price
  • $253/SF
  • 32 Days On Market

  Current Estimated Value $374,941

  Last Listing Agent Krystal Crichlow EXP REALTY LLC

  3147 Mela Ct, Holiday, FL 34691
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  /21

  Not Listed For Sale

  1929 Dixie Ln, Holiday, FL 34690

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

  1929 Dixie Ln, Holiday, FL 34690

  Last Sold Summary

  • 6 Days On Market
• 

  

  

  /24

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,587 Sq Ft

  3625 Richboro Dr, Holiday, FL 34691

  ***FEMA FLOOD INSURANCE PAID THROUGH NOVEMBER 2027***FULLY TRANSFERABLE TO THE NEW OWNER. INSTANT VALUE AND SAVINGS. DON’T MISS THIS PROTECTED HOME OPPORTUNITY. This beautifully updated 3-bedroom, 2-bath home features a spacious, open layout perfect for everyday living and entertaining. Enjoy ceramic tile floors throughout, remodeled bathrooms, and a modern kitchen with granite countertops and

  Maria Ospina PEOPLE'S TRUST REALTY

  3625 Richboro Dr, Holiday, FL 34691
• 

  

  /2

  $215,000

  Sold Jan 16, 2026

  5705 Mariposa Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $173/SF
  • 36 Days On Market

  Current Estimated Value $218,676

  Last Listing Agent Theo Malamoutsis SQUARE ONE REALTY

  5705 Mariposa Dr, Holiday, FL 34690
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  /8

  Not Listed For Sale

  5743 Cheyenne Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1977

  5743 Cheyenne Dr, Holiday, FL 34690

  Last Sold Summary

  • 7 Days On Market
• 

  

  /31

  $159,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft

  1804 Rising Sun Dr, Holiday, FL 34690

  Welcome to this 55+ community of Sunrise Square Villas! Check out this clean updated 2-bedroom, 2-bath condo that includes a 1 car carport. This condo features newer appliances, solid wood kitchen cabinets, a newer tankless hot water heater, a split floor plan and a relaxing Florida room. The living/dining room area has vaulted ceilings. Excellent location that is close to beaches, parks, Tarpon

  Dean Aaron Waters DALTON WADE INC

  1804 Rising Sun Dr, Holiday, FL 34690
• 

  /2

  $230,000

  Sold Feb 13, 2026

  4822 Panorama Ave, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Below List Price
  • $246/SF
  • 51 Days On Market

  Current Estimated Value $226,971

  Last Listing Agent Scarllet Silveira Rocha CHARLES RUTENBERG REALTY INC

  4822 Panorama Ave, Holiday, FL 34690
• 

  /2

  Est $133,039

  Not Listed For Sale

  4329 Tahitian Gardens Cir Unit C, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 768 Sq Ft
  • Built 1974

  4329 Tahitian Gardens Cir Unit C, Holiday, FL 34691

  Last Sold Summary

  • 144 Days On Market
• 

  

  /19

  $199,950

  $21K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  4642 Eastwood Ln, Holiday, FL 34690

  Move-in ready home for you in a quiet neighborhood, but very close to shopping and easy to commute. Nicely updated and very little lived in by the owner, who was coming only for a couple of months in winter time. Roof, windows and entry door were replaced in 2015. All floors are tiled, kitchen has nice wooden cabinets, like new appliances, and washer and dryer in the garage. Furniture is

  Maria Kastritsos OLYMPIC REALTY SERVICES LLC

  4642 Eastwood Ln, Holiday, FL 34690
• 

  /2

  $160,000

  Sold Apr 24, 2026

  5604 Cheyenne Dr, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • 1,323 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Below List Price
  • $121/SF
  • 57 Days On Market

  Current Estimated Value $176,767

  Last Listing Agent Ingrid Santaliz MARK SPAIN REAL ESTATE

  5604 Cheyenne Dr, Holiday, FL 34690
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  /52

  Not Listed For Sale

  2051 Waterview Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1978

  2051 Waterview Dr, Holiday, FL 34691

  Last Sold Summary

  • 7 Days On Market
• 

  

  /46

  $340,000

  • 2 Beds
  • 2 Baths
  • 1,730 Sq Ft

  3114 Summervale Dr, Holiday, FL 34691

  Welcome to this spacious 2-bedroom, 2-bath home with a 2-car garage offering over 1,700 square feet of living space, surrounded by lush tropical landscaping. An inviting arched doorway welcomes you into the open floor plan featuring a vaulted ceiling in the entryway and a warm living room with a fireplace. The separate dining area includes sliding glass doors leading out to the screened lanai and

  Jennifer Tobey RE/MAX CHAMPIONS

  3114 Summervale Dr, Holiday, FL 34691
• 

  /2

  $424,900

  Sold Aug 05, 2025

  1919 Oswego Dr, Holiday, FL 34691

  • 4 Beds
  • 2 Baths
  • 2,175 Sq Ft
  • Built 2004

  Last Sold Summary

  • $195/SF
  • 21 Days On Market

  Current Estimated Value $427,538

  Last Listing Agent Viral Doshi, PA. AMETHYST PROPERTY ADVISORS LLC

  1919 Oswego Dr, Holiday, FL 34691
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  /20

  Not Listed For Sale

  3128 Southport Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  3128 Southport Dr, Holiday, FL 34690

  Last Sold Summary

  • 2 Days On Market
• 

  

  /25

  $300,000

  $17K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  2453 Pleasant Hill Ln, Holiday, FL 34691

  Welcome to one of Holiday’s most sought after 55+ gated communities, where privacy, comfort, and an active Florida lifestyle come together seamlessly. This beautifully maintained 2 bedroom, 2 bath home in Key Vista offers 1,555 square feet of well designed living space, along with a versatile office/flex room that can easily serve as a third bedroom, hobby room, or dedicated workspace. Situated

  Ryan Retaleato LOKATION

  2453 Pleasant Hill Ln, Holiday, FL 34691
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  /2

  $240,000

  Sold Dec 09, 2025

  5038 Colonnade Ave, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1965

  Last Sold Summary

  • $250/SF
  • 0 Days On Market

  Current Estimated Value $238,273

  Last Listing Agent Stephanie Scarlette CHARLES RUTENBERG REALTY INC

  5038 Colonnade Ave, Holiday, FL 34690
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  /21

  Not Listed For Sale

  2049 Kona Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1982

  2049 Kona Dr, Holiday, FL 34691

  Last Sold Summary

  • 260 Days On Market
• 

  

  /40

  $165,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft

  4753 Sunny Loop, Holiday, FL 34690

  Welcome to this beautifully updated 2-bedroom, 2-bath villa nestled within a highly desirable 55+ community of Sunrise Square. This turn-key residence showcases meticulous care and thoughtful upgrades throughout, offering both comfort and style in a serene setting. Step inside to find easy flow from one room to the next. The kitchen features updated modern finishes that include, newer solid

  Warren Giese REALTY CONCIERGE SERVICES

  4753 Sunny Loop, Holiday, FL 34690
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  /2

  $82,000

  Sold Nov 20, 2025

  4331 Manton Ln, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 659 Sq Ft
  • Built 1965

  Last Sold Summary

  • 14% Below List Price
  • $124/SF
  • 8 Days On Market

  Last Listing Agent Penny Gould PENNY GOULD REALTY INC

  4331 Manton Ln, Holiday, FL 34691
• 

  

  /21

  Not Listed For Sale

  2101 Wailua Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1981

  2101 Wailua Dr, Holiday, FL 34691

  Last Sold Summary

  • 133 Days On Market
• 

  

  /25

  $284,900

  $5K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,189 Sq Ft

  3530 Windham Dr, Holiday, FL 34691

  **CONTRACT FELL THROUGH, BACK ON THE MARKET! ** 3 BEDROOM, 2 BATHROOM. 1 CAR GARAGE POOL HOME. COMPLETELY REMODELED!! BRAND-NEW ROOF 2026; BRAND-NEW HVAC 2026; BRAND-NEW GARAGE DOOR; BRAND-NEW WATER HEATER; BRAND-NEW SHAKER STYLE KITCHEN CABINETS; BRAND-NEW QUARTZ COUNTERTOPS; BRAND-NEW STAINLESS-STEEL APPLIANCES; BRAND-NEW LUXURY VINYL FLOORING THROUGHOUT; FRESH PAINT INSIDE AND OUT; BEAUTIFULLY

  Irina Dare STAR BAY REALTY CORP.

  3530 Windham Dr, Holiday, FL 34691
• 

  /2

  $278,000

  Sold Oct 31, 2025

  1351 Solar Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 1,079 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Above List Price
  • $258/SF
  • 13 Days On Market

  Current Estimated Value $272,739

  Last Listing Agent Oscar Huerta REALTY PROPERTY GROUP LLC

  1351 Solar Dr, Holiday, FL 34691
• 

  

  /23

  Not Listed For Sale

  2029 Kona Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  2029 Kona Dr, Holiday, FL 34691

  Last Sold Summary

  • 162 Days On Market
• 

  

  /61

  $265,999

  $4K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  5084 Forum Blvd, Holiday, FL 34690

  Welcome to this Stunning Townhouse, Built in 2023, Offering 1,634 square feet of Heated Living Space. This Beautiful Home Features Three Bedrooms and Two and a Half Baths, along with a One-Car Garage. Downstairs, you'll find an Open-Concept layout with a Bright Living Room, Dining area,and Kitchen, all adorned with elegant Ceramic Tile and High Ceilings. The Kitchen Boasts Stainless Steel

  Christina Vallianos RE/MAX REALTY UNLIMITED

  5084 Forum Blvd, Holiday, FL 34690
• 

  /2

  $215,000

  Sold Sep 25, 2025

  1663 Plum Tree Rd, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • 945 Sq Ft
  • Built 1972

  Last Sold Summary

  • 10% Below List Price
  • $228/SF
  • 29 Days On Market

  Current Estimated Value $218,436

  Last Listing Agent Daysi Malloy DAYSI MALLOY REALTY GROUP LLC

  1663 Plum Tree Rd, Holiday, FL 34690
• 

  

  /10

  Est $112,635

  Not Listed For Sale

  4338 Tahitian Gardens Cir Unit H, Holiday, FL 34691

  • 1 Bed
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  4338 Tahitian Gardens Cir Unit H, Holiday, FL 34691

  Last Sold Summary

  • 27 Days On Market
• 

  

  /51

  $499,900

  $99K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,761 Sq Ft

  1166 Chancellor Dr, Holiday, FL 34690

  Stunning fully remodeled 4-bedroom, 3-bath waterfront home offering privacy, functionality, and true Gulf-access living. This exceptional property has remained high and dry with no flooding during recent storms, providing peace of mind along with an unbeatable natural setting. Set along a scenic bend of the river, the backyard overlooks a private island preserve—meaning no rear neighbors, just

  Shawn Poole SNAP REALTY LLC

  1166 Chancellor Dr, Holiday, FL 34690
• 

  /2

  $219,000

  Sold Dec 30, 2025

  2229 Harrison Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1979

  Last Sold Summary

  • $203/SF
  • 11 Days On Market

  Current Estimated Value $223,312

  Last Listing Agent Louis Petruzzelli RE/MAX SUNSET REALTY

  2229 Harrison Dr, Holiday, FL 34691
• 

  

  /64

  Est $159,766

  Not Listed For Sale

  1123 Bowsprit Ln, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1983

  1123 Bowsprit Ln, Holiday, FL 34691

  Last Sold Summary

  • 72 Days On Market
• 

  

  /32

  $266,000

  $44K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,546 Sq Ft

  3202 Jackson Dr, Holiday, FL 34691

  Virtually Staged. Welcome home to this beautiful 3-bedroom, 2-bathroom home with a two-car garage situated on theserene shores of Lake Conley. As you step inside, you will immediately appreciate the bright, open feel ofthe home, enhanced by a neutral color palette that creates a warm and inviting atmosphere. Thespacious living room provides plenty of room for relaxing or entertaining

  Dawn Walls MARK SPAIN REAL ESTATE

  3202 Jackson Dr, Holiday, FL 34691
• 

  /2

  $245,000

  Sold Sep 05, 2025

  3032 Jacob Crossing Ln, Holiday, FL 34691

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft
  • Built 2021

  Last Sold Summary

  • 13% Below List Price
  • $170/SF
  • 98 Days On Market

  Current Estimated Value $255,999

  Last Listing Agent Jesenia Valdez BHHS FLORIDA PROPERTIES GROUP

  3032 Jacob Crossing Ln, Holiday, FL 34691
• 

  

  /17

  Not Listed For Sale

  1914 Mary Ln, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1979

  1914 Mary Ln, Holiday, FL 34690

  Last Sold Summary

  • 102 Days On Market
• 

  

  /29

  $124,900

  $5K PRICE DROP

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

  2049 Manoa Dr, Holiday, FL 34691

  Welcome to the highly sought-after Lake Conley (Lake Colony), a premier gated 55+ community where you own your land! This beautifully updated 2-bedroom, 2-bathroom manufactured home offers approximately 1,100 square feet of modern living space designed for comfort and the active Florida lifestyle. Step inside to find a spacious, open floor plan featuring fresh interior paint and brand-new

  Christopher Dufala SUNBELT REAL ESTATE FLORIDA

  2049 Manoa Dr, Holiday, FL 34691
• 

  /2

  $385,000

  Sold May 04, 2026

  2321 Wood Pointe Dr, Holiday, FL 34691

  • 4 Beds
  • 3 Baths
  • 2,429 Sq Ft
  • Built 2004

  Last Sold Summary

  • 21% Below List Price
  • $159/SF
  • 340 Days On Market

  Current Estimated Value $432,640

  Last Listing Agent Whitney Boland SIGNATURE REALTY ASSOCIATES

  2321 Wood Pointe Dr, Holiday, FL 34691
• 

  

  /15

  Not Listed For Sale

  3320 Chatford Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1979

  3320 Chatford Dr, Holiday, FL 34690

  Last Sold Summary

  • 34 Days On Market
• 

  

  /40

  $215,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,289 Sq Ft

  3320 Columbus Dr, Holiday, FL 34691

  Under contract-accepting backup offers. Looking for a home to entertain family and friends? This 2 Bedroom 2 Bath home with an oversized covered screened patio was made for it! Sliding glass doors from the Living Room, Family Room and Primary Bedroom open into the Patio area. Kitchen with closet pantry, opens into Family Room and has pass through window to Patio. Newer refrigerator, dishwasher

  Pamela Douberly KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

  3320 Columbus Dr, Holiday, FL 34691
• 

  /2

  $270,000

  Sold Dec 12, 2025

  5130 Chime Way, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $181/SF
  • 83 Days On Market

  Current Estimated Value $272,210

  Last Listing Agent Matt Sofarelli CHARLES RUTENBERG REALTY INC

  5130 Chime Way, Holiday, FL 34690
• 

  

  /18

  Est $316,466

  Not Listed For Sale

  2881 Jacob Crossing Ln, Holiday, FL 34691

  • 3 Beds
  • 2.5 Baths
  • 1,813 Sq Ft
  • Built 2020

  2881 Jacob Crossing Ln, Holiday, FL 34691

  Last Sold Summary

  • 33 Days On Market
• 

  

  /21

  $299,999

  Open Fri 3PM - 7PM $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  1715 Kenilworth St, Holiday, FL 34691

  Improved pricing! Seller is offering $3,000 in concessions and is highly motivated to get this home under contract this month! Welcome to 1715 Kenilworth Street in Holiday, Florida — a beautifully renovated NO HOA home that's move-in ready and packed with value. Featuring updated interiors, modern finishes, and a functional layout, this home is perfect for comfortable living and entertaining.

  Alejandro Conti LPT REALTY, LLC

  1715 Kenilworth St, Holiday, FL 34691

Showing Results 641 - 680, Page 17 of 18