Oldsmar Villas for Sale by Neighborhood

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Newest Villas in Oldsmar by Neighborhood

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  • 25 TADS TRL, OLDSMAR, FL - MLS# TB8509080

    EAST LAKE WOODLANDS CLUSTER HOMES - TB8509080 - 25 TADS TRL, OLDSMAR, FL 34677
    8 Days on yellowkey

    $249,000 | Villa | 3 beds | 2.0 baths | 1 car

    Don’t miss out on an exceptional opportunity to own this 3 bedroom Maintenance Free Villa in the popular East Lake Woodlands Resort & Golf Community. This 1620 SF property includes an enclosed Florida room overlooking a beautiful peaceful backyard and is priced below appraised value so you can make it your own! The property boasts a brand new air conditioner and a 6 year old roof. The layout features a split bedroom plan, living and separate dining room, eating space in the kitchen and a fenced front patio to enjoy a morning cup of coffee! The spacious primary bedroom includes a walk-in closet, ensuite bath with dual sinks and sliders leading out to the lovely backyard. The second bedroom includes a Murphy Bed! This villa comes with an assigned carport space and a 5X6 outdoor storage room as well as a storage room in the rear lanai. John Chesnut Park on Lake Tarpon is directly across the street with a boat/jet ski ramp and is adjacent to the Pinellas Bike Trail! Conveniently located close to shopping fine restaurants, the sandy Gulf Beaches, popular Downtown Dunedin and only 20 minutes to Tampa Airport. Optional Ardea Country Club memberships provide access to two 18-hole golf courses, tennis, pools, fitness, dining and social amenities! Live the Florida Lifestyle at it’s best!!!

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    Listing is courtesy of: CHARLES RUTENBERG REALTY INC

  • 20 EVELYN CT, OLDSMAR, FL - MLS# TB8508719

    EAST LAKE WOODLANDS CLUSTER HOMES - TB8508719 - 20 EVELYN CT, OLDSMAR, FL 34677
    9 Days on yellowkey

    $259,000 | Villa | 2 beds | 2.0 baths | 1 car

    Tucked within the gated community of East Lake Woodlands, this beautifully refreshed 2-bedroom, 2-bath villa offers the perfect blend of low-maintenance living and Florida lifestyle appeal. Whether you are searching for a full-time residence, seasonal retreat, or lock-and-leave vacation home, this move-in ready property checks all the boxes. Inside, you’ll find an inviting open floor plan with split bedrooms for added privacy, fresh interior paint, and brand-new luxury vinyl plank flooring installed in May 2026. The spacious eat-in kitchen opens seamlessly to the main living area, creating an ideal space for entertaining or simply relaxing after a day at the beach or golf course. A screened lanai with additional storage extends your living space outdoors, while the private front courtyard is perfect for morning coffee, evening cocktails, or weekend BBQs. Major updates provide peace of mind, including a NEW HVAC system installed in May 2026 and a roof replaced in 2019. The freshly painted front door adds to the welcoming curb appeal. Additional features include a covered carport with storage room and convenient guest parking nearby. Residents of Cluster Homes enjoy maintenance-free living with exterior maintenance, grounds care, trash service, and basic cable all included. Ideally located near shopping, dining, medical facilities, award-winning beaches, top-rated schools, golf, and two international airports, this is your opportunity to enjoy the ease and convenience of the Florida lifestyle in one of Oldsmar’s most sought-after gated communities.

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    Listing is courtesy of: KELLER WILLIAMS ST PETE REALTY

  • 260 MICHAELS CIR, OLDSMAR, FL - MLS# TB8507054

    EAST LAKE WOODLANDS CLUSTER HOMES - TB8507054 - 260 MICHAELS CIR, OLDSMAR, FL 34677
    14 Days on yellowkey

    $280,000 | Villa | 3 beds | 2.0 baths | 1 car

    Spacious 3-bedroom, 2-bath villa offering 1,385 square feet of comfortable living in desirable East Lake Woodlands. This home features ceramic tile throughout the main living areas and cozy carpet in the bedrooms. The bright living room is lined with sliding glass doors that open to a screened lanai spanning the full length of the villa—perfect for enjoying indoor/outdoor Florida living. The primary bedroom and third bedroom both feature private patio door access to the screened lanai, while ceiling fans in the bedrooms add extra comfort. Enjoy additional outdoor space with a fenced front patio, plus extra storage located on the screened lanai. Your covered carport includes an additional storage unit and comes with one assigned parking space. Currently occupied by excellent tenants. For buyers looking to make this home their own, a lease termination may be negotiated.

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    Listing is courtesy of: DASHER RLTY & PROP. MANAGEMENT

  • 2034 MONTEGO CT, OLDSMAR, FL - MLS# TB8506783

    BAYSIDE MEADOWS PH II - TB8506783 - 2034 MONTEGO CT, OLDSMAR, FL 34677
    15 Days on yellowkey

    $225,000 | Villa | 1 beds | 1.0 baths | 1 gar

    Charming and low-maintenance 1-bedroom, 1-bath home tucked away on a quiet cul-de-sac in the highly desirable East Lake/Oldsmar area. This cozy residence offers an open and functional layout filled with natural light, creating a warm and inviting atmosphere from the moment you walk in. The living space flows seamlessly into the kitchen, which features ample cabinetry and workspace—perfect for everyday living. The spacious bedroom provides a comfortable retreat with generous closet space, while the full bath is conveniently located and well-appointed. Enjoy your own private outdoor space, ideal for relaxing or entertaining in Florida’s beautiful weather. With low HOA fees of just $160/month, you’ll appreciate the added value of community amenities including a pool and lawn service—making for truly easy, low-maintenance living. Located just minutes from Sheffield Park, you’ll have easy access to walking trails, playgrounds, and outdoor recreation. Whether you’re a first-time buyer, looking to downsize, or seeking a great investment opportunity, this home checks all the boxes. Conveniently located near shopping, dining, and just a short drive to the Gulf beaches. Affordable, well-located, and full of potential—don’t miss this opportunity!

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    Listing is courtesy of: RE/MAX ELITE REALTY





Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.