Holiday, FL Homes

• 

  

  

  /23

  $219,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  3630 Winder Dr, Holiday, FL 34691

  Step into a bright and inviting home where contemporary style meets everyday comfort. Thoughtfully upgraded and move-in ready, this property offers a warm, welcoming feel from the moment you enter. The open-concept layout creates an effortless flow between the living spaces, while sleek plank flooring adds a polished touch throughout. The kitchen serves as a natural gathering place with crisp

  Adriana Echevarria ORCHARD BROKERAGE, LLC

  3630 Winder Dr, Holiday, FL 34691
• 

  

  /2

  $200,000

  Sold Jan 30, 2026

  4111 Moog Rd, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1966

  Last Sold Summary

  • 11% Below List Price
  • $159/SF
  • 301 Days On Market

  Current Estimated Value $204,887

  Last Listing Agent Laney Balis ELEVATED REALTY

  4111 Moog Rd, Holiday, FL 34691
• 

  

  /2

  Est $301,095

  Not Listed For Sale

  3056 Inlet Breeze Way, Holiday, FL 34691

  • 3 Beds
  • 2.5 Baths
  • 1,813 Sq Ft
  • Built 2021

  3056 Inlet Breeze Way, Holiday, FL 34691

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Kirk Budd KELLER WILLIAMS REALTY- PALM HARBOR
• 

  

  

  /18

  $89,900

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft

  3204 Channing Dr, Holiday, FL 34690

  Need a handicap accessible home for winter or year-around living, then stop and look at this neat and clean 1 bedroom, 1 bath updated home in a 5-star 55+ very Active Community with low monthly fee of $143.00 includes, lawn maintenance, garbage service, maintenance of year-around heated pool clubhouse, and common areas taxes.Home comes nicely furnished and enclosed front porch, nice outside

  Stella Wooster CITY BREEZE ACTION REALTY

  3204 Channing Dr, Holiday, FL 34690
• 

  

  /2

  $435,000

  Sold Jul 31, 2026

  5904 Springrun Ct, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 2,284 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $190/SF
  • 24 Days On Market

  Current Estimated Value $442,470

  Last Listing Agent Marie McLaughlin CENTURY 21 ALLIANCE REALTY

  5904 Springrun Ct, Holiday, FL 34690
• 

  

  /10

  Not Listed For Sale

  2316 Prestige Dr, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1973

  2316 Prestige Dr, Holiday, FL 34690

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Melissa Horn FLORIDA LUXURY REALTY INC
• 

  

  /18

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  1300 Maybury Dr, Holiday, FL 34691

  Virtually Staged. 3 bedroom, 2 bathroom, 1,316 sq ft home. Features an open living area with plenty of room to create comfortable living and dining spaces. The kitchen offers existing wood cabinetry, tile flooring, and a layout ready for a fresh update. Primary bedroom features an en-suite bath, and the floor plan provides flexibility for everyday living, guests, or a home office.The

  Anthony Masso LAMAR PROPERTIES, INC.

  1300 Maybury Dr, Holiday, FL 34691
• 

  /2

  $57,000

  Sold May 21, 2026

  2110 Orange Dr, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 460 Sq Ft
  • Built 1959

  Last Sold Summary

  • 24% Below List Price
  • $124/SF
  • 47 Days On Market

  Last Listing Agent Jackie Little KELLER WILLIAMS REALTY- PALM HARBOR

  2110 Orange Dr, Holiday, FL 34691
• 

  /2

  Not Listed For Sale

  2033 Manoa Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,082 Sq Ft
  • Built 1979

  2033 Manoa Dr, Holiday, FL 34691

  Last Sold Summary

  • 200 Days On Market

  Last Listing Agent Diana Schlafley CHARLES RUTENBERG REALTY INC
• 

  

  /36

  $255,000

  $10K PRICE DROP

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

  2578 Charlan Ct, Holiday, FL 34690

  Virtually Staged. INVESTMENT PROPERTY. SOLD WITH AMAZING TENANT IN PLACE.NEW PRICE- SELLER MOTIVATED!Beautiful, three bedroom townhome in well maintained community. Townes at Darlington is close to everything! Built in 2023 the community is practically new! Lower level with living room, dining area, kitchen with breakfast bar, pantry and sliding access to covered rear patio with

  Lorina Smith BEST OF THE GULF REALTY INC

  2578 Charlan Ct, Holiday, FL 34690
• 

  /2

  $148,000

  Sold Mar 26, 2026

  5616 Golden Nugget Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1979

  Last Sold Summary

  • 20% Below List Price
  • $131/SF
  • 9 Days On Market

  Current Estimated Value $178,581

  Last Listing Agent Justin Brandon, PA RE/MAX ALLIANCE GROUP

  5616 Golden Nugget Dr, Holiday, FL 34690
• 

  

  /14

  Not Listed For Sale

  2051 Hoyle Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 410 Sq Ft
  • Built 1958

  2051 Hoyle Dr, Holiday, FL 34691

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Sal Urso EXIT ELITE REALTY
• 

  

  /55

  $314,900

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  2229 Roselawn Dr, Holiday, FL 34691

  Virtually Staged. Beautifully Renovated Home with Luxury Finishes & Exceptional Curb AppealWelcome to this beautifully renovated home, where modern style, comfort, and thoughtful upgrades come together. From the moment you arrive, the impressive curb appeal sets the tone with an extended driveway offering plenty of parking with custom artificial grass design, a welcoming front porch, and

  Yisel Diaz Cruz VITA LUXURY REALTY LLC

  2229 Roselawn Dr, Holiday, FL 34691
• 

  /2

  $239,900

  Sold May 26, 2026

  3150 Beacon Square Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 998 Sq Ft
  • Built 1969

  Last Sold Summary

  • 7% Below List Price
  • $240/SF
  • 331 Days On Market

  Current Estimated Value $234,387

  Last Listing Agent Artemis Kousathanas FLORIDA PREMIERE REALTY

  3150 Beacon Square Dr, Holiday, FL 34691
• 

  

  /26

  Not Listed For Sale

  2113 Manoa Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1981

  2113 Manoa Dr, Holiday, FL 34691

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Analia Leon DENNIS REALTY & INV. CORP.
• 

  

  /35

  $283,900

  $21K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  3314 Columbus Dr, Holiday, FL 34691

  Virtually Staged. Down payment assistance might be available for qualified buyers. Zero-down payment program might be available for qualified buyers. Owner is motivated. Welcome to your remodeled coastal retreat in Holiday, Florida, just moments from the Gulf of America's stunning beaches. This home is not in a flood zone. This immaculate property boasts a spacious open concept, perfect for

  Lazaro Borrego SUNSET LAKES REALTY, LLC.

  3314 Columbus 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 $423,644

  Last Listing Agent Gigi Gauthier TRUE REALTY GROUP

  5253 Boardwalk St, Holiday, FL 34690
• 

  

  /25

  Est $235,462

  Not Listed For Sale

  5135 Sandalwood Dr, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Built 1969

  5135 Sandalwood Dr, Holiday, FL 34690

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Randall Patrick WESTBAY REAL ESTATE
• 

  

  /70

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,004 Sq Ft

  1031 Conoley Ln, Holiday, FL 34691

  Welcome to 1031 Conoley Ln, a beautifully maintained and thoughtfully updated 3-bedroom, 1-bath home in the desirable Holiday Lake Estates community of Holiday, Florida! Offering 1,004 square feet of comfortable living space on a spacious 5,663-square-foot lot, this home delivers an ideal combination of updates, functionality, and Florida living. From the moment you arrive, the pride of ownership

  Alex Caballero IMPACT REALTY TAMPA BAY

  1031 Conoley Ln, 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 $117,675

  Last Listing Agent Steve Diller PARADISE WEST REALTY, INC

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

  

  /40

  Est $237,233

  Not Listed For Sale

  3149 Bluebird Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,310 Sq Ft
  • Built 1973

  3149 Bluebird Dr, Holiday, FL 34690

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Demi Katechis EXP REALTY LLC
• 

  

  /30

  $217,500

  $18K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,004 Sq Ft

  5046 Farley Dr, Holiday, FL 34690

  Virtually Staged. New Price! Welcome to 5046 Farley Drive, where you can simply move in and enjoy! This charming concrete block home has been beautifully renovated and is in exceptional condition, offering peace of mind from the moment you walk through the door. Best of all, there are no HOA fees, no deed restrictions, and the home is not in a flood zone. Recent updates include: gorgeous

  Terra Brady BRADY ADVANTAGE

  5046 Farley Dr, Holiday, FL 34690
• 

  /2

  $245,000

  Sold Aug 14, 2026

  1301 Viking Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,136 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $216/SF
  • 11 Days On Market

  Current Estimated Value $239,931

  Last Listing Agent Janina Wozniak FUTURE HOME REALTY

  1301 Viking Dr, Holiday, FL 34691
• 

  

  /24

  Not Listed For Sale

  1939 Speck Dr, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1972

  1939 Speck Dr, Holiday, FL 34691

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Analia Leon DENNIS REALTY & INV. CORP.
• 

  

  /22

  $200,000

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 988 Sq Ft

  3246 Brookfield Dr, Holiday, FL 34691

  Under contract-accepting backup offers. This well-maintained 2-bedroom, 1.5-bath home offers 988 square feet of comfortable living space and an impressive list of recent updates. Major improvements include a newer A/C system (2024), and newer water heater (2023), and roof (2014) providing peace of mind for years to come. The home also features hurricane shutters for every window, a PVC privacy

  Abigail Jonas GULF COAST EXECUTIVE REALTY

  3246 Brookfield Dr, 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 $377,115

  Last Listing Agent Ernie Fuentes, Jr. ERNIES REAL ESTATE

  1945 Blue River Rd, Holiday, FL 34691
• 

  

  /41

  Est $132,189

  Not Listed For Sale

  4344 Tahitian Gardens Cir Unit G, Holiday, FL 34691

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

  4344 Tahitian Gardens Cir Unit G, Holiday, FL 34691

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Michael McAuley COASTAL FLORIDA REAL ESTATE
• 

  

  /42

  $119,000

  $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,318 Sq Ft

  3960 Sailmaker Ln, Holiday, FL 34691

  Welcome home to Holiday Lake Villas, a welcoming 55+ community in Holiday, Florida. This one level end unit villa is move in ready and offers 2 bedrooms, 2 full baths, and approximately 1,316 square feet of comfortable, easy living.The kitchen is a standout, with abundant cabinet space, and it overlooks the bright living room where vaulted ceilings and natural light create an open, airy feel.

  Catalina Cooper PALM PARADISE REALTY GROUP

  3960 Sailmaker Ln, 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 $463,184

  Last Listing Agent Patrycja Henderson LUXURY & BEACH REALTY INC

  3311 Hearthstone Ct, Holiday, FL 34691
• 

  

  /18

  Not Listed For Sale

  4901 Plymouth Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 882 Sq Ft
  • Built 1972

  4901 Plymouth Dr, Holiday, FL 34690

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY
• 

  

  /30

  $239,900

  • 2 Beds
  • 1 Bath
  • 744 Sq Ft

  1310 Mandarin Dr, Holiday, FL 34691

  Welcome to this 2 bedroom, 1 bath, 2 car garage home located in Holiday Lakes West — and no flood insurance required! Both bedrooms are roomy in size and the bathroom has been completely updated featuring a tiled walk-in shower and brand new vanity. The covered patio features a huge concrete slab perfect for grilling or entertaining. The fully fenced yard backs up to no rear neighbors, offering

  Samuel Caudle LPT REALTY, LLC

  1310 Mandarin Dr, Holiday, FL 34691
• 

  /2

  $270,000

  Sold Sep 04, 2026

  3340 Wilson Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,268 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $213/SF
  • 19 Days On Market

  Current Estimated Value $264,352

  Last Listing Agent Edward Mikhail CHARLES RUTENBERG REALTY INC

  3340 Wilson Dr, Holiday, FL 34691
• 

  

  /28

  Not Listed For Sale

  4308 Morlock Ln, Holiday, FL 34691

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

  4308 Morlock Ln, Holiday, FL 34691

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Tom Wibirt RE/MAX CHAMPIONS
• 

  

  /45

  $190,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft

  3230 Lanark Dr, Holiday, FL 34690

  Under contract-accepting backup offers. This absolutely charming home is nestled in the sought-after Tanglewood Mobile Village Condominium. Unlike many similar subdivisions, the land is owned, not leased. A 55+ community, residents will enjoy a multi-amenity lifestyle that includes a safe, pet-friendly park along with shuffleboard and horseshoe courts, a heated community pool and a clubhouse.

  Lori Crawford RE/MAX ACTION FIRST OF FLORIDA

  3230 Lanark Dr, Holiday, FL 34690
• 

  /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 $175,689

  Last Listing Agent Katherine Congdon KELLER WILLIAMS REALTY- PALM HARBOR

  4140 Castlewood Dr, Holiday, FL 34691
• 

  

  /26

  Not Listed For Sale

  2023 Oahu Dr, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1979

  2023 Oahu Dr, Holiday, FL 34691

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Ashley Quaife RE/MAX CHAMPIONS
• 

  

  /31

  $270,000

  Open Sat 11AM - 2PM $20K PRICE DROP

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

  3543 Rockaway Dr, Holiday, FL 34691

  Welcome Home!! From the moment you pull up to your new home, you’ll appreciate the inviting curb appeal and a driveway offering plenty of room for parking and everyday convenience. Lots of recent improvements & updates for this BEAUTIFUL home that include a Newer Re-Roof (2025), Newer HVAC System (2025), Newer Water Heater (2025), and Newer Stainless Steel Appliances. Step inside through the

  Andrea Ansley KELLER WILLIAMS REALTY- PALM HARBOR

  3543 Rockaway 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 $209,602

  Last Listing Agent Jansz Umboh LOKATION

  4326 Westwood Dr, Holiday, FL 34691
• 

  

  /77

  Est $165,744

  Not Listed For Sale

  1141 Bowsprit Ln Unit 1001, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1981

  1141 Bowsprit Ln Unit 1001, Holiday, FL 34691

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Bob McCaffery BHHS FLORIDA PROPERTIES GROUP
• 

  

  /47

  $285,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft

  5633 Andrea Dr Unit 1, Holiday, FL 34690

  Virtually Staged. Stunning Move-In Ready Home! Welcome to 5633 Andrea Dr — a beautifully updated gem in the heart of Holiday! This charming home features brand-new flooring and a fully remodeled master bathroom with modern finishes that create a true spa-like retreat. Enjoy an open, light-filled floor plan perfect for entertaining or relaxing with family. The kitchen offers ample cabinet space

  Brandi Smith EXP REALTY LLC

  5633 Andrea Dr Unit 1, Holiday, FL 34690

Showing Results 521 - 560, Page 14 of 18