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Homes with a Pool in Holiday, FL

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3 beds

26 listings

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Homes with a Pool in Holiday, FL

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24 of 26 Listings

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24 of 26 Listings

Your Holiday agent

LPT Realty

Call LPT

29Active
$399,000
3 bd · 2 ba · 1,502 sqft
1117 Rushmore Dr, Holiday, FL
Gene Morales · TMWRK BROKERAGE LLC
57Active
$1,299,999
4 bd · 4 ba · 4,204 sqft
3143 Pineview Dr, Holiday, FL
Jennifer Tobey, PA · RE/MAX CHAMPIONS
44Active
$579,900
4 bd · 4 ba · 3,553 sqft
5657 Oceanic Rd, Holiday, FL
Nicole Volentine · DALTON WADE INC

35Active
$499,900
3 bd · 2 ba · 1,758 sqft
2530 Arrowpointe Dr, Holiday, FL
Jeffrey Borham, PA · EXP REALTY LLC
42Active
$244,900
2 bd · 2 ba · 948 sqft
3748 Redwood Dr, Holiday, FL
April Nyemah · REALTY ONE GROUP BEYOND
1Active
$229,000
2 bd · 2 ba · 1,383 sqft
2144 Harrison Dr, Holiday, FL
Thomas Ambrose-emundi · SUNCOAST GROUP REALTORS LLC
20Active
$182,150
2 bd · 2 ba · 988 sqft
4640 Tropical Ln, Holiday, FL
Ramon Arteaga · MR BIGGS LLC
50Active
$449,000
3 bd · 3 ba · 1,762 sqft
1324 Chancellor Dr, Holiday, FL
Beth Belloise · TROPICAL LIFE REALTY, INC.
15Active
$284,900
3 bd · 2 ba · 1,354 sqft
2641 Flintwood Dr, Holiday, FL
Robert Salmons · ENTERA REALTY LLC
34Active
$459,500
3 bd · 2 ba · 2,151 sqft
3225 Hearthstone Ct, Holiday, FL
Bobbie Coleman · SUNCOAST GROUP REALTORS LLC
Price Reduced19Active
$249,999
3 bd · 2 ba · 1,326 sqft
3349 Overland Dr, Holiday, FL
Joseph Buchi · DENNIS REALTY & INV. CORP.
Price Reduced33Active
$289,000
2 bd · 2 ba · 1,386 sqft
1332 Flotilla Dr, Holiday, FL
Harris Gruman · REALNET FLORIDA REAL ESTATE
27Active
$379,000
3 bd · 2 ba · 1,346 sqft
1346 Chancellor Dr, Holiday, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
Price Reduced57Active
$545,000
4 bd · 3 ba · 2,462 sqft
2309 Swordfish Ave, Holiday, FL
Greg Palumbo · KELLER WILLIAMS REALTY- PALM HARBOR
24Active
$252,000
2 bd · 2 ba · 1,136 sqft
3221 Roxbury Dr, Holiday, FL
Roy Barnhart · BAM REALTY ADVISORS INC
Price Reduced36Active
$210,000
2 bd · 2 ba · 1,125 sqft
3153 Moog Rd, Holiday, FL
Rose Parsons · DALTON WADE INC
Price Reduced60Active
$525,000
4 bd · 3 ba · 2,857 sqft
3225 Glenwood Cir, Holiday, FL
Jocelyn Carbonelli · VANDERLEELIE & ASSOC.RE ESTATE
Price Reduced29Active
$379,900
4 bd · 3 ba · 2,002 sqft
3708 Holiday Lake Dr, Holiday, FL
Paola Millan · MY REALTY GROUP, LLC.
Price Reduced35Active
$475,000
4 bd · 2 ba · 2,366 sqft
2811 Ravendale Ln, Holiday, FL
Alissa Caputo · FUTURE HOME REALTY INC
Price Reduced63Active
$579,000
3 bd · 4 ba · 2,367 sqft
3020 Sheppards Crook Ct, Holiday, FL
STEVE DeMatos · RE/MAX ALLIANCE GROUP
Price Reduced43Active
$499,999
4 bd · 3 ba · 2,861 sqft
2210 Bayou Dr, Holiday, FL
Peter Ingrasselino · DEAL HOUSE REALTY LLC
Price Reduced37Active
$364,988
3 bd · 3 ba · 1,416 sqft
3645 Overland, Holiday, FL
Taylor Sparling · SELECT PROPERTIES INC
30Active
$380,000
2 bd · 2 ba · 1,691 sqft
3110 Shadow Oaks Dr, Holiday, FL
Chelsea Vecchio · FUTURE HOME REALTY INC
Price Reduced37Active
$319,900
3 bd · 2 ba · 1,967 sqft
3206 Pinon Dr, Holiday, FL
Philip Shaw · LEERDAM PROPERTIES INC.

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Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Holiday housing market

August 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 38 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $180,000$126,589–$268,000 typical range
Price per sq. ft.: $156
Sales: 74
Paid in cash: 48.7%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 42 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -2.8%

Holiday, FL community profile

Area: 21.2 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Your Holiday agent

LPT Realty

Call LPT

New construction
With a pool

Your Holiday agent

LPT Realty

Call LPT

Holiday, FL community profile

Area: 21.2 sq. mi.

Source: HJN community data

Holiday housing market

August 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 38 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $180,000$126,589–$268,000 typical range
Price per sq. ft.: $156
Sales: 74
Paid in cash: 48.7%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 42 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -2.8%