Oldsmar Homes with Gated Amenities

Oldsmar Homes with Gated Amenities

Welcome to Oldsmar, Florida, a charming city nestled in the heart of Pinellas County that perfectly balances the tranquility of suburban living with the vibrancy of nearby urban attractions. Known for its picturesque landscapes, Oldsmar boasts a rich history and a strong sense of community, making it an ideal place for families, retirees, and everyone in between. With its proximity to the stunning Gulf Coast beaches, top-notch shopping, and a variety of recreational activities, residents enjoy a lifestyle that is both relaxed and engaging.

One of the standout features of Oldsmar is its selection of homes with gated amenities. These exclusive communities offer a sense of security and privacy that is highly sought after. Imagine returning home to your beautifully designed residence, surrounded by lush landscaping and serene surroundings, all while knowing that you are part of a safe and welcoming neighborhood. Gated communities in Oldsmar often come equipped with a range of luxurious amenities, such as sparkling swimming pools, fitness centers, and clubhouses, providing residents with opportunities for leisure and socialization right at their doorstep.

Whether you’re looking for a cozy single-family home or a spacious luxury villa, Oldsmar's gated properties cater to various lifestyles and preferences. The combination of community spirit, access to nature, and modern conveniences makes Oldsmar a hidden gem in Florida’s real estate market. Discover your dream home in this delightful city and embrace a lifestyle that is both enriching and fulfilling. Welcome to Oldsmar, where your perfect home awaits!

Newest Oldsmar Homes with Gated Amenities

2063 Warwick Drive, Oldsmar
$895,000
4 Beds ⋅ 3 Baths ⋅ Warwick Hills SubDv. ⋅ 34677 Zip Code
SPECTACULAR PRESERVE VIEW! Enjoy the privacy and solitude of this beautiful home backing to the 8500 acre Brooker Creek Preserve with frequent sightings of dear and wildlife. Great curb appeal with custom glass front doors, landscaping and lighting. The interior of the home features a split floor plan with 4 bedrooms, an office and 3 full baths. The back bedrooms would also make a great in-law suite or media room. Entertain formally in the living and dining room with preserve view or casually poolside with heated pool and spa. The gourmet kitchen is the heart of the home with granite counters, abundant cabinets and counter space, stainless appliances and a breakfast nook. The kitchen opens to the family room and the outdoor pool and preserve view. The owner’s suite is a retreat with pool and patio access, walk in closet with custom shelving, crown molding and plantation shutters. The en-suite bath is complete with granite counters, double sinks, garden tub and walk in shower. Additional features include a security system, crown molding, in home vacuum, motorized window coverings, gas fireplace, outdoor lighting and plantation shutters. Live the Florida lifestyle! Take a dip in the heated salt pool, soak in the spa or unwind on the expansive deck overlooking the preserve. The outdoor kitchen has a gas grill and sink. An additional patio in the backyard is great for entertaining. The expansive backyard is private and perfect for sports, children and pets. LOCATION! Live on a quiet street in the Warwick Hills subdivision of Eastlake Woodlands. Eastlake Woodlands is a golf and tennis community with two renowned golf courses and clubhouse. Membership in the newly remodeled premiere Ardea Country Club is required to enjoy golf, tennis, pickle ball, swimming pools, child activity center and newly refurbished gym. Eastlake Woodlands is central to all dining, shopping and highly rated schools. A short drive will take you to all area beaches, activities and the Tampa International Airport. Be sure to watch the video and look at the 360 interior views!

2063 Warwick Drive, Oldsmar
109 Lakeside Drive, Oldsmar
$199,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome to this stunning, ground floor 2 bedroom to 2 bath condo in a guarded and gated community of East Lake Woodlands, where you can enjoy a maintenance-free Florida living at its best. Step inside and discover the seamless combination of quality updates with comfort. The spacious living and dining areas flow seamlessly together, creating an inviting, open atmosphere perfect for entertaining or simply relaxing at home. The well-appointed kitchen features a breakfast nook, convenient breakfast bar with a pass-through to the dining area, making both casual meals and gatherings a breeze. The desirable split-bedroom floor plan provides privacy, while the generously sized primary suite is a true retreat, featuring THREE walk-in closets! Additional highlights include plantation shutters throughout, living room fireplace, and an enclosed, all-weather Florida room overlooking a pond. Imagine starting your mornings with coffee while enjoying the serene water views or unwinding in the evening surrounded by nature. Enjoy the convenience of a lock-and-leave Florida lifestyle, with monthly condo fees covering basic cable, internet, water, sewer, and trash removal. Less time worrying about maintenance means more time enjoying everything Florida has to offer! Nestled within the well-established East Lake Woodlands community, residents enjoy the comfort of guarded entry. For those seeking an active, resort-inspired lifestyle, optional membership to Ardea Country Club offers access to golf, tennis, pickleball, fitness facilities, clubhouse amenities, and more. Location is another standout feature! Conveniently situated near shopping, restaurants, parks, entertainment, and everyday essentials, with easy access to Tampa International Airport and St. Pete-Clearwater International Airport. Whether you're looking for a full-time residence or a seasonal Florida getaway, this exceptional ground-floor condo checks all the boxes! Beautiful updates, spacious living, pond views, and a sought-after gated community make this an opportunity you won't want to miss. Come experience the charm, comfort, and convenience of East Lake Woodlands living!

109 Lakeside Drive, Oldsmar
131 Brent Circle, Oldsmar
$849,900
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
This rare, customized end unit townhome is located on Old Tampa Bay in Oldsmar in the sought after gated community of Seaside Estates. Enjoy breathtaking open water views from any of the floors largely due to the abundance of windows and 3 generous sized patios/decks. Relaxing will come naturally as you gaze out over the green space, seawall and open water. Home features 1834 sf and 3 bedrooms, 3 baths. There are 2 outside parking spaces within a few feet of the attractive entry to the unit. Upon entering the bottom floor you have a foyer and to the left an oversized 2+ car tandem parking garage with an abundance of storage and rear covered patio. Garage also has a vented portable air conditioner and a dehumidifier creating a perfect storage and work area. The ground entry foyer has stairs leading up to the main living area floor where you are greeted with great light from the multi windows and large deck/patio. It is truly a breathtaking view looking out on Old Tampa Bay. This floor features a living room, dining room, updated kitchen (2018/2019), one bedroom with a built-in murphy bed plus desk and a full bath. Ascending one more floor, there is the master suite with sliders leading to a spacious deck, a second en-suite bedroom with its private full bath. There is also a laundry area with double doors for easy access and stackable washer/dryer. Throughout the wooden floors are beautiful with some tile in the wet areas. Multiple outdoor spaces providing approximately 200sf of outdoor living on each floor and a screened patio on ground floor so you can enjoy the Florida lifestyle throughout this open unit. Don't let the multi-stories be an issue as this unit boasts an ELEVATOR installed 2025 to help you move yourself and your belongs easily throughout. As an added bonus, this unit comes with a DEEDED BOAT SLIP located behind the unit at the mouth of the channel. So whether you prefer fishing from the seawall, inshore fishing or shooting out in the Gulf for a little offshore fishing or just pleasure boating maybe to local restaurants/bars such as close by Jack Willie's, you're ready to go! While feeling very private, this unit offers it all . . . privacy yet close to shopping and restaurants for your daily needs.

131 Brent Circle, Oldsmar
116 Brent Circle, Oldsmar
$405,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Welcome to Seaside Estates! This is a 3 bedroom, 3 bathroom townhome on the canal with your own private dock. If you’ve been looking for a place to keep your jet ski or kayak right outside your door, this is it. The entry level gives you direct access to the garage, where sliders on the back open right out to the docks. Load up your gear and be on the water in minutes. The second floor features a large living room that opens onto a balcony overlooking the canal. This level also includes the kitchen, a full bathroom, and a bedroom, a great setup for guests or a home office. Head up to the third floor to find two more bedrooms, each with its own ensuite bathroom. The owner’s suite has a private balcony with views of the canal, the perfect spot for morning coffee or evening sunsets. Laundry is conveniently located on this level, right where you need it. This home is ready for a new owner to make it their own. With some fresh paint, new carpet, and your personal touches, you can build equity and create the waterfront retreat you’ve been dreaming of. Opportunities with private dock access like this don’t come along often. Call today to schedule your showing!

116 Brent Circle, Oldsmar
151 Lakeview Way Unit 151, Oldsmar
$189,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Virtually Staged. WATERFRONT, GROUND FLOOR, UPDATED and MOVE-IN READY! Enjoy one of the most peaceful, nature-filled views in the highly sought-after East Lake Woodlands community from this beautifully updated 2-bedroom, 2-bath condo with assigned COVERED PARKING. Step inside to a spacious, open layout with NO CARPET and plenty of natural light. The updated kitchen features NEW GRANITE COUNTERTOPS, NEW CABINETS, a pantry closet, generous storage, and a large breakfast bar overlooking the dining and living areas. The inviting living room features a cozy WOOD-BURNING FIREPLACE, perfect for those occasional cool Florida evenings. Sliding glass doors from BOTH the living room and primary suite open to the tiled lanai, creating a wonderful extension of the living space and the perfect place to enjoy your morning coffee while taking in the tranquil WATERFRONT VIEW and surrounding wildlife. The spacious primary suite features QUARTZ COUNTERTOPS, WALK-IN SHOWER, and a stylish NEW BARN DOOR. The guest bathroom includes a newer vanity, and both bathrooms feature NEW ELONGATED CHAIR-HEIGHT TOILETS installed in 2023. You'll also appreciate the abundance of closet and storage space throughout the home. Additional updates include a NEW A/C IN 2023, NEW BLINDS IN 2023, NEW CEILING FANS, laminate flooring in both bedrooms, and ceramic tile throughout the remainder of the condo, including the lanai. Assigned covered parking is included, along with plenty of additional guest parking. The community HEATED POOL is just a short walk away for year-round enjoyment. East Lake Woodlands offers a beautiful, gated country club setting surrounded by mature landscaping, lakes, and natural Florida scenery. Optional club memberships provide access to additional amenities that may include golf, tennis, fitness, dining, pools, and clubhouse facilities. Conveniently located near shopping, restaurants, parks, beaches, and Tampa International Airport. GROUND FLOOR + WATERFRONT VIEW + UPDATED INTERIOR + COVERED PARKING + NO CARPET = Florida living made easy!

151 Lakeview Way Unit 151, Oldsmar
1332 Preservation Way, Oldsmar
$1,700,000
4 Beds ⋅ 4 Baths ⋅ Preserve, The SubDv. ⋅ 34677 Zip Code
Pre-Construction. To be built. TO-BE-BUILT CUSTOM HOME- An exceptional opportunity to build your dream home in the prestigious East Lake Woodlands community. Located within The Preserve, this proposed custom residence is situated on a beautiful homesite in a double-gated, private golf community, offering an unparalleled combination of privacy, security, and an exceptional lifestyle. This proposed custom home offers approximately 3,530 square feet of heated living space and 4,465 square feet total under roof, featuring 4 bedrooms, 4 full bathrooms, a private den, and a 2-car garage. The thoughtfully designed floor plan showcases spacious living areas and a modern custom-home concept designed to complement this exceptional homesite. The property is offered as a to-be-built custom home package, including the lot. The floor plan, renderings, and images are provided as a representation of the proposed residence and are intended to showcase the potential of this custom-home opportunity. However you can choose the paint, finishes, cabinets and flooring. OR----- Create your own home, floorplan, size, dimensions and layout! Minimum square footage is 3500sf. Please note: This is a proposed home and has not yet been constructed. Floor plans, renderings, dimensions, finishes, features, and specifications are conceptual and subject to change. Final design, construction, selections, and approvals are subject to builder, buyer, architectural review, association requirements, and applicable governmental approvals. A rare opportunity to secure a beautiful homesite and create a brand-new custom residence in one of Oldsmar's most desirable communities.

1332 Preservation Way, Oldsmar
3010 Palm Key Avenue, Oldsmar
$388,500
2 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
Welcome to waterfront living at its best! Located on beautiful Old Tampa Bay, this exceptional community offers a relaxed Florida lifestyle with amenities designed for everyday enjoyment and entertaining. Gather with friends around the gas firepit, share a meal beneath the pavilion with two grills, or relax in the large heated infinity pool while taking in beautiful water views. Stay active in the fully equipped gymnasium, fish from the pier extending into the bay, or launch a kayak for an afternoon on the water. The electronically gated entrance provides added security. Ideally situated directly across from the pool, this residence truly stands out. Beautiful landscaping and lush greenery welcome you at the entrance, while thoughtful enhancements continue throughout, including a gleaming epoxy-finished garage floor and garden-like screened porch. The porch creates a wonderful outdoor retreat for morning coffee, relaxing evenings, or entertaining guests. Inside, beauty and functionality continue. The entire first floor features beautiful tile flooring for a polished appearance and easy maintenance. In 2024, all recessed lighting was upgraded to LED bulbs, with downstairs lights featuring dimmers and amber-light options for the perfect ambiance. Even the spacious walk-in pantry has automatic lighting that illuminates the generous storage space when the door opens. The open-concept main living area is perfect for entertaining and everyday life, offering space for a full dining table and casual dining at the granite breakfast bar. Numerous light-gray cabinets provide abundant storage, complemented by a convenient coffee bar and mini-mudroom near the garage entrance. The living area flows effortlessly through pocket sliders to the screened porch, creating a wonderful indoor-outdoor living experience. A conveniently located half bath completes the first floor, while Custom Nantucket remote-control shades provide privacy and light control. Upstairs, a generous flex room offers incredible versatility as a den, second family room, playroom, home office, or temporary third bedroom. The nearby laundry room adds convenience. The primary suite offers a peaceful retreat with an expansive granite double-sink vanity, abundant storage, glass-enclosed shower, beautiful natural light, decorative tray ceiling, and custom walk-in closet with built-in shelving. Custom Nantucket remote shades complete the space. The spacious second bedroom is equally inviting, with natural light, decorative tray ceiling, and exceptional storage. Two closets, including a very large walk-in, provide plenty of room. The second full bath features wood cabinetry, pull-out drawers, granite countertop, and glass-enclosed shower. Additional upgrades include a new electrical panel installed in 2024 and gutters added in 2021 along with the undercounter lighting and downstairs crown molding. The location offers convenient access to Tampa, area airports, major shopping, restaurants, beautiful beaches, and more. With its waterfront setting, resort-style amenities, thoughtful upgrades, flexible living spaces, and outstanding location, this home offers an exceptional opportunity to enjoy the Florida lifestyle.

3010 Palm Key Avenue, Oldsmar
4951 Augusta Avenue, Oldsmar
$574,900
3 Beds ⋅ 3 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to 4951 Augusta Avenue, a spacious two-story pool home situated on a desirable corner lot in the gated East Lake Woodlands community. Offering approximately 2,316 square feet, this well-maintained residence features 3 bedrooms, 2.5 bathrooms, a versatile upstairs loft, a formal living room, and a 2-car garage. A grand two-story entrance welcomes you into a bright interior with soaring vaulted ceilings and abundant natural light. The formal living and dining areas provide an elegant setting for entertaining, while the comfortable main living space offers plenty of room for everyday relaxation. Upstairs, the open loft can serve as a home office, media area, game room, or additional lounge space. Step outside to your private screened swimming pool and covered patio—an ideal setting for entertaining, outdoor dining, or relaxing while enjoying Florida’s year-round sunshine. The screened enclosure provides additional comfort, while the corner lot offers extra outdoor space and privacy. Ideally located near Tampa Road, East Lake Road, and McMullen Booth Road, the property offers convenient access to Oldsmar, Palm Harbor, Safety Harbor, Clearwater, Westchase, and Tampa. Shopping, restaurants, medical facilities, Tampa Bay Downs, Countryside Mall, parks, nature preserves, and recreational trails are all nearby. Gulf beaches, Honeymoon Island, Tarpon Springs, and Tampa International Airport are also within easy reach. East Lake Woodlands Country Club offers golf, tennis, pickleball, fitness, swimming, dining, and social activities through optional membership. Enjoy private pool living, flexible interior space, and a central Tampa Bay location within an established gated community.

4951 Augusta Avenue, Oldsmar
221 Caryl Way Unit 221, Oldsmar
$165,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
MOTIVATED SELLERS! OFFERING A 2/1 BUYDOWN! Experience the beauty of golf course living in the highly desirable East Lake Woodlands community of Oldsmar, Florida! Welcome to 221 Caryl Way #221, a beautifully updated 2-bedroom, 2-bath condominium offering picturesque views of the 18th fairway of the East Lake Woodlands South Course, modern conveniences, and an exceptional Florida lifestyle. Step inside to discover an inviting floor plan designed for comfortable everyday living and entertaining. The updated kitchen features elegant granite countertops, designer cabinetry, stainless steel appliances, a brand-new refrigerator, and a convenient breakfast bar that connects the kitchen to the living area. Whether preparing your favorite meal or hosting friends, this thoughtfully designed space combines style and functionality. The spacious primary bedroom provides a comfortable retreat with three closets offering exceptional storage. Two full bathrooms, updated toilets, hurricane windows, and an in-unit washer and dryer add to the home's everyday convenience and appeal. Imagine starting your morning with peaceful views of the 18th fairway, surrounded by the beautifully maintained golf course landscape. Just across the street, the community swimming pool and clubhouse provide convenient opportunities to relax, socialize, and enjoy the Florida sunshine. For those who appreciate an active country club lifestyle, nearby Ardea Country Club offers optional private memberships featuring two championship 18-hole golf courses, two heated swimming pools, tennis and pickleball courts, a fitness center, clubhouse, dining, and a variety of member social events. Club membership is separate and subject to availability and membership requirements. Located in the heart of Oldsmar, East Lake Woodlands offers convenient access to shopping, restaurants, parks, recreation, and destinations throughout Tampa Bay, combining a peaceful golf course setting with everyday convenience. Whether you're searching for a golf course condominium, a seasonal Florida retreat, or a low-maintenance year-round residence, this East Lake Woodlands condo checks the boxes. With 2 bedrooms, 2 bathrooms, an updated kitchen, granite countertops, hurricane windows, in-unit laundry, beautiful fairway views, and a community pool just steps away, this home offers an outstanding opportunity to enjoy the Florida lifestyle. Your golf course lifestyle awaits! Schedule your private showing of 221 Caryl Way #221 today and discover why East Lake Woodlands is such a special place to call home.

221 Caryl Way Unit 221, Oldsmar
129 Brent Circle, Oldsmar
$460,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
HUGE PRICE IMPROVEMENT - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situated in the exclusive gated community of SEASIDE ESTATES in picturesque and historic Oldsmar. Nestled within a Townhome Complex of 67 units, this particular unit stands out as truly unique. The magnificent sunsets are breathtaking. The kitchen has STONE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and offers ease with the CENTRAL VACUUM SYSTEM. Additional highlights include custom-built shelving in both His and Her Primary Closets. The primary suite, located on the third level, boasts a generously sized UPDATED BATHROOMS. The spacious floor plan ensures ample natural light and stunning water views. Enjoy the Florida lifestyle in this golf cart-friendly community, offering amenities such as a swimming pool, Jacuzzi and tennis/pickleball courts. The dock area provides good fishing opportunities, and the residence is only a few minutes away from waterfront public parks, shopping, restaurants, and various recreational facilities. The community hosts more than 20 events annually, with monthly dinners strategically planned around the scenic Tampa Bay. Minutes from downtown Oldsmar and Safety Harbor which offer a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, This complex is PET FRIENDLY. 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater and world-famous Clearwater Beach, 20 min to Caladesi State Park and the pristine Honeymoon Island.

129 Brent Circle, Oldsmar
1330 Preservation Way, Oldsmar
$2,300,000
7 Beds ⋅ 5 Baths ⋅ Preserve The SubDv. ⋅ 34677 Zip Code
Welcome to an exceptional 7-bedroom, 4½-bath estate nestled within the prestigious double-gated community of East Lake Woodlands in Oldsmar. Set on over half an acre and backing directly to a peaceful preserve, this remarkable property offers an unparalleled sense of privacy, tranquility, and security. Recently updated and beautifully refreshed, the home features a newly renovated kitchen, newly renovated bathrooms, newly renovated laundry room, newly refinished floors, and fresh interior paint throughout. The spacious and versatile floor plan provides abundant room for comfortable living and entertaining, with generously sized bedrooms and a dedicated office and fitness room with a built-in sauna, creating your own private space to work, exercise, and relax. Step outside to your private Florida retreat, complete with a sparkling pool and expansive deck, surrounded by lush greenery and the natural beauty of the preserve. The peaceful preserve backdrop creates a rare feeling of seclusion while providing a beautiful setting for morning coffee, outdoor dining, entertaining, or simply enjoying the Florida sunshine. Located within a premier golf community, East Lake Woodlands offers an exceptional lifestyle surrounded by mature landscaping and natural beauty, with championship golf, tennis, pickleball, fitness facilities, resort-style amenities, dining, and social activities. Conveniently located near local shops, restaurants, cafés, grocery stores, parks, and everyday conveniences, while offering easy access to some of the area's most beautiful Gulf Coast beaches, including Honeymoon Island, Clearwater Beach, and Caladesi Island. Tampa International Airport is also easily accessible for convenient travel. With seven bedrooms, 4½ bathrooms, over half an acre, preserve frontage, a private pool, dedicated office and gym, built-in sauna, newly renovated kitchen and laundry room, updated bathrooms, refinished floors, and fresh paint, this extraordinary estate offers the perfect combination of luxury, privacy, space, and Florida lifestyle.

1330 Preservation Way, Oldsmar
353 Bay Arbor Boulevard, Oldsmar
$550,000
3 Beds ⋅ 2 Baths ⋅ Bay Arbor SubDv. ⋅ 34677 Zip Code
MOVE-IN READY in the gated Bay Arbor community of Oldsmar! This beautifully updated 3-bedroom, 2-bath home is ready for its new owners. Major improvements have already been taken care of, including a brand-new roof, screened patio and fresh interior and exterior paint, allowing you to move in and enjoy from day one. The desirable split-bedroom floor plan offers privacy and an easy flow for everyday living. The open kitchen and family room combination creates a welcoming central gathering space, while the spacious primary suite offers a separate office or sitting area, providing the flexibility for a home office, reading room, or private retreat. The primary bath features dual vanities, a separate shower, and a relaxing Jacuzzi tub. Step outside to the screened-in patio and enjoy peaceful conservation views in a private backyard setting. With no rear neighbors, this is a wonderful place to unwind while enjoying the Florida outdoors. Additional features include an inside laundry room with washer and dryer included, a two-car garage, and plenty of storage. Located within the gated Bay Arbor community, residents enjoy access to a community pool and playground along with beautifully maintained neighborhood grounds. The Oldsmar location offers convenient access to shopping, restaurants, parks, recreation, Tampa International Airport, and major roadways, with easy access to both Pinellas and Hillsborough County. A well-maintained home, a desirable gated community, a peaceful conservation setting, and the big-ticket updates already completed—this one is truly ready for its next chapter.

353 Bay Arbor Boulevard, Oldsmar
Start Your Search

How much is your home worth?

Get instant property value now!