Displaying: For Sale
Location: Holiday
Property Type(s): Villas
Beds: 2 to 2
Do Not Show Listings
Holiday - 6 properties found
2214 OAK WIND DR, HOLIDAY, FL 34691
$183,500313 Days on yellowkey MLS ID: TB8417286
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $5,500 (2.9%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1985Monthly Fee: $50 Tax: $1,597 (2024)Community: Pinewood VillasVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,597
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Serene Pinewood Villas neighborhood is close to shopping and dining for convenience. This two bedroom two full bath home has tile flooring throughout. Extra living area makes this one of the larger units in the community with an extra large side lot for gathering with friends. Main living area has high ceilings with windows allowing for extra light. Community has sparkling pool, clubhouse and shuffleboard with picnic tables for grabbing lunch by the pool. Low HOA fee makes this a affordable place to live. Hot water heater replaced 2020. Newer kitchen faucet and garbage disposal. Washer just one month new. Thermostat fully programable and newer. Call to make an appointment today.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Jennifer Hallett (727-686-6969)
2216 OAK WIND DR, HOLIDAY, FL 34691
$169,90082 Days on yellowkey MLS ID: TB8492620
REDUCED by $10,000 (5.6%) on 06/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1986Monthly Fee: $50 Tax: $2,500 (2025)Community: Pinewood VillasVilla
Taxes:$2,500
Tax Year: 2025
Remarks: Welcome home to this charming 2 bedroom, 2 bathroom villa with newer ROOF in the highly desirable Pinewood Villas community in Holiday, Florida. One of the biggest highlights of this adorable unit is the EXCEPTIONALLY LOW HOA fee of just $50 per month...an INCREDIBLE VALUE that makes ownership both affordable and stress-free. Even better, this is not a 55+ community and pets are welcome, making it the perfect fit for a variety of buyers. Ideally located near shopping, libraries, the post office, beaches, and the historic waterfront town of Tarpon Springs, this home offers easy access to dining, parks, marinas, and the Gulf Coast lifestyle so many buyers are looking for. Whether you enjoy boating, local seafood restaurants, sponge docks, or relaxing beach days, you’re close to it all. Inside, this cute and inviting villa features walk-in closets in both bedrooms, an expansive vaulted ceiling, and abundant natural light from the high windows spanning the living room wall. The kitchen overlooks the dining and living areas, creating an open and comfortable layout perfect for everyday living or entertaining guests. Enjoy additional space in the large enclosed porch with storage closet, plus a separate shed for even more storage. The property also includes a 2-car carport with an additional parking space. Each lot is individually owned and maintained by the owner, adding to the pride of ownership throughout the community. Residents enjoy access to a recreational building, community POOL, and shuffleboard area, all while benefiting from one of the lowest HOA fees around.
Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)
Listing Agent: Shawna Liotine (813-407-8011)
1027 BOWSPRIT LN, HOLIDAY, FL 34691
$165,000146 Days on yellowkey MLS ID: TB8470035
REDUCED by $4,900 (2.9%) on 04/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1534 Built: 1984Monthly Fee: $613 Tax: $2,361 (2024)Community: Holiday Lake Villas CondoVilla
Taxes:$2,361
Remarks: Welcome to 1027 Bowsprit Lane, a well-maintained residence located in the heart of Holiday, Florida. This unit boasts of 1,534 SF and contains 2 bedrooms, 2 bathrooms, brand new kitchen (remodeled 2025), living room, laundry area, walk-in closet, walk-in pantry, and glass-covered lanai. This villa also has a small storage shed outside, parking for one car is assigned under a carport, and guest parking is available close to the entrance. The home features an updated kitchen with ample cabinetry and workspace, ideal for everyday living and entertaining. Spacious living and dining areas create a warm and welcoming atmosphere, while the thoughtfully designed layout maximizes functionality. The monthly maintenance fee of $613.00 covers building exterior, roof, water and sewer service, rubbish removal, basic cable TV, landscaping maintenance, escrow reserves, and insurance of the structure and common elements (a community owned clubhouse with heated pool). Conveniently located near shopping, dining, parks, and major roadways including US-19, offering easy access for commuting and daily errands. Whether you are downsizing, or looking for an excellent investment opportunity, this property presents great value in a growing area. Schedule your private showing today and experience all this home has to offer. Furniture negotiable. The community rules do not allow trucks, boats and motorcycles. Water heater 2022, AC 2023, don't miss this amazing opportunity, schedule your private showing today!
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Brie Burch (813-863-1986)
2211 PLEASANT HILL LN, HOLIDAY, FL 34691
$300,000100 Days on yellowkey MLS ID: TB8485823
REDUCED by $15,000 (4.8%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 2004Monthly Fee: $175 Tax: $1,954 (2025)Community: Key Vista Ph 03 Prcl 05Villa
Taxes:$1,954
Remarks: Welcome to Key Vista, one of Holiday’s most desirable 55+ gated communities, where comfort meets the best of the Florida lifestyle. This beautifully maintained 2-bedroom, 2-bath Bermuda model by Ryland Homes also includes a dedicated office that can easily function as a third bedroom. Perfectly situated on a private conservation lot with no rear neighbors, this home offers peaceful nature views and is located on the final lot developed in the community. Inside, you’ll find soaring ceilings, an open floor plan, and an abundance of natural light throughout. The main living areas feature tile flooring, while Berber carpet adds warmth and comfort in the living room, office, and bedrooms. The spacious living area is ideal for both relaxing and entertaining. The eat-in kitchen features solid-surface countertops, 42-inch wood cabinetry, a cozy breakfast nook, and brand-new stainless steel appliances installed in November 2024. The primary suite offers high ceilings, a large walk-in closet, and a private ensuite bath with solid-surface countertops, wood cabinetry, and a glass-enclosed shower. The guest bedroom and bath are equally welcoming, while the office located just off the foyer provides flexible space for working from home or accommodating guests. Additional highlights include an interior laundry room with washer, dryer, and utility sink, a two-car garage with epoxy flooring, a 2019 water heater, and a regularly serviced A/C system. Step outside to the screened lanai overlooking tranquil, tree-lined conservation views—perfect for enjoying your morning coffee or unwinding in the evening. Residents enjoy low HOA fees, no CDD, and access to two clubhouses: one exclusively for 55+ residents with its own private pool, plus the master clubhouse featuring a resort-style pool, spa, fitness center, tennis and pickleball courts, sand volleyball, playground, and more. RV and boat storage is also available for a small monthly fee. Ideally located near Key Vista Nature Park, you can take a short walk to the water to enjoy Florida’s spectacular sunsets or explore scenic nature trails. Conveniently close to parks, shopping, dining, and Gulf beaches. Schedule your private showing today and experience everything this beautiful Key Vista home has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Renee Gialousis (727-234-3353)
3811 SAILMAKER LN, HOLIDAY, FL 34691
$117,450215 Days on yellowkey MLS ID: TB8449382
1 Days Off yellowkey (back on 6/9/2026)
REDUCED by $4,450 (3.7%) on 05/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1114 Built: 1988 Tax: $702 (2024)Community: Holiday Lake Villas Ph 2Villa
Taxes:$702
Elementary School: Gulfside Elementary-PO
High School: Anclote High-PO
Middle School: Paul R. Smith Middle-PO
Remarks: Under contract-accepting backup offers. Welcome to the low maintenance Florida style living! This inviting first floor, 2-bedroom, 2-bath villa in Holiday, FL, offering comfort, convenience, and a gorgeous pond view right from your backyard. This home features an open floor plan that fills the living area with natural light and creates a spacious, welcoming feel—perfect for relaxing or entertaining. Enjoy tranquil mornings on your private patio overlooking the water, and appreciate the ease of covered parking right at your doorstep. Both bedrooms are generously sized, and the split layout offers privacy for guests or family members. Located close to shopping, dining, beautiful Gulf beaches, and scenic county parks, this villa puts you near everything you need while still offering a peaceful, low-maintenance lifestyle. Was just recently painted outside front and back! Whether you're looking for a seasonal escape or a full-time Florida home, this charming villa is a must-see. X flood zone NO FLOOD insurance.
Listing is courtesy of: REALNET BROKERAGE (727-753-8555)
Listing Agent: Marcus Howard (727-421-0055)
2907 FEATHERSTONE DR, HOLIDAY, FL 34691
$194,900164 Days on yellowkey MLS ID: W7881997
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1159 Built: 1987Monthly Fee: $570 Tax: $1,241 (2024)Community: Edgewood Gulf Trace RepVilla
Taxes:$1,241
Remarks: price adjustment and a very motived seller,,,Move-in ready and full of potential! This 2-bedroom, 2-bath home features an open floorplan with vaulted and cathedral ceilings, creating a bright, spacious feel throughout. The living room/dining room combo is perfect for everyday living and entertaining, while solid wood cabinets and solid surface counters add lasting quality to the kitchenEnjoy a split bedroom layout for privacy, walk-in closets, and ceiling fans for year-round comfort. Conveniently located near shopping, dining, and major roadways, this Holiday home delivers space, function, and value in one smart package.
Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)
Listing Agent: Donna Kroll (813-444-5777)
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