Oldsmar Homes with Gated Amenities

Oldsmar Homes with Gated Amenities

Welcome to Oldsmar, a charming city located in Pinellas County, Florida. Known for its beautiful landscapes and vibrant community, Oldsmar offers a perfect blend of suburban tranquility and urban convenience.

For those seeking homes with gated amenities, Oldsmar has a range of options to choose from. Gated communities provide residents with an added sense of security and exclusivity, making them an attractive choice for many homebuyers. Whether you're looking for a single-family home, a townhouse, or a condo, you can find properties with gated amenities to suit your preferences in Oldsmar.

Living in a gated community in Oldsmar not only offers peace of mind but also provides access to additional perks such as community pools, fitness centers, and recreational facilities. Residents can enjoy a resort-style living experience right at their doorstep.

If you're looking to invest in a home with gated amenities in a picturesque city like Oldsmar, you'll find a variety of options to choose from that cater to your lifestyle and preferences.

Newest Oldsmar Homes with Gated Amenities

$719,000
4 Beds 2 Baths East Lake Woodlands SubDv. 34677 Zip Code
Tucked away in the highly desirable gated community of East Lake Woodlands, this one-of-a-kind 4-bedroom, 2-bath waterfront retreat offers a rare opportunity to experience the timeless beauty of Old Florida. With an extraordinary 180-degree view of lush natural surroundings and a tranquil waterway, this private setting feels like a world of its own—where trees, abundant wildlife, and peaceful water views create a backdrop that is both breathtaking and serene. A large circular driveway welcomes you to the home, where a new double-door entry opens to vaulted ceilings and an inviting, light-filled interior. The formal living room features French doors leading to the screened lanai, while the dining room is accented by a beautiful Tiffany-style light fixture. Throughout the home, tile flooring and roller shades provide a clean, timeless aesthetic. The updated kitchen features granite countertops and opens naturally to the family room, where one of two fireplaces creates a warm and inviting gathering space. The primary suite offers its own featured fireplace, creating a cozy retreat, along with an updated private bathroom featuring an oversized glass-enclosed shower and soaking tub. An updated guest bathroom provides additional modern convenience sandwiched between two of the additional bedrooms. Step outside and discover what truly sets this property apart. The expansive screened lanai surrounds a beautiful saltwater pool and spa, with a painted cool-deck surface and lush tropical landscaping creating your own private resort-style escape. Beyond the pool, a Trex dock and completely renovated seawall (2020) provide the perfect vantage point to take in the incredible natural setting and 180-degree views of Old Florida. Thoughtfully maintained and updated, the home features impact and double-pane windows with galvanized storm shutters, a hybrid water heater, water softener, new shingle roof (2024), gutters, French drains extending to the lake and exterior paint completed in August 2026. The wrought-iron fenced yard adds privacy and enhances the beautifully landscaped grounds. Located outside a flood zone and within a top-rated A-rated school zone, this exceptional home also offers the opportunity to become a social, golf, or tennis member at Ardea Country Club, adding an optional lifestyle component to an already remarkable property. Private waterfront, resort-style amenities, thoughtful updates, and an unmatched Old Florida setting—this is more than a home; it’s a rare opportunity to own your own piece of paradise in East Lake Woodlands.

80 Foxfire Lane, Oldsmar

$229,000
2 Beds 2 Baths East Lake Woodlands Cluster Homes SubDv. 34677 Zip Code
Virtually Staged. 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. 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. Gated EAST LAKE WOODLANDS GOLF COMMUNITY is considered a Bird Sanctuary with Sidewalks & Paths for Walking & Biking to see Nature & Wildlife. Fees to Join Social or Golf Course Membership at ARDEA COUNTY CLUB with its two Golf Courses, Pools, Tennis Courts, Exercise Room, & Restaurant. Close to John Chestnut park, Oldsmar Park and Safety Harbor Philippe Park. Craving some BEACH time - just a short drive away is Stunning Caladesi Island State Park in Dunedin and Famous Clearwater Beach. Easily accessible for your Travels:Tampa International & St. Petersburg/Clearwater Airports. With shopping options, Movie Theaters, Malls, Diverse Restaurants & Entertainment Venues just minutes away, this location is not only beautiful it is convenient!

20 Evelyn Court, Oldsmar

$830,700
4 Beds 3 Baths Cross Pointe SubDv. 34677 Zip Code
Welcome to an exceptional 2,736-square-foot luxury home nestled within Cross Pointe, a gated community inside the prestigious guard gated golf community of East Lake Woodlands . Offering 4 bedrooms, 3 baths, a spacious 2-car garage,with workbench area. and bonus space. This beautifully appointed residence blends elegant finishes, thoughtful design, and exceptional outdoor living. Pool access & views from almost every room. Desirable split-bedroom floor plan features soaring ceilings and travertine flooring complemented by engineered hardwood & tile floors. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring Bosch and Frigidaire appliances, (Range has induction cooktop & convection/air fry oven) quartz tops, crisp white cabinetry, and a striking navy island. Breakfast area overlooking pool. The family room offers a warm wood-burning fireplace (updated 2020) and a sophisticated navy wine bar, creating an inviting gathering space. Spacious primary suite includes a comfortable sitting area and sliders that open directly to the screened porch, offering beautiful views of the private pool and backyard . Walk-in closet with organizers. Primary bath has soaking tub, large marble shower, private water closet & dual sink vanities. 3 guest bedrooms, with one having an ensuite bath also providing convenient access to the pool area—perfect for effortless poolside living. Bonus/Flex room with its own A/C (2026) is perfect for an office, hobby room, studio, gym, etc. Outdoor living is truly exceptional. The screened rear porch features paver flooring and overlooks the Saltwater PebbleTec pool , complete with Caribbean blue tile, a charming, soothing waterfall and gazebo. Pool pump & new salt system (2025). An expanded paver patio (2025) extends into the private backyard, providing ample space for entertaining, relaxing, and enjoying the peaceful surroundings. Many updates include tile roof (2019), HVAC (2017), Paver patio (2022), Kitchen updated (2020) with professional kitchen cabinet refinishing (2026), Bosch refrigerator (2025), Frigidaire appliances (2026). All ceiling fans updated (2024 & 2025). Newly textured ceilings (2022), modern lighting. With its luxurious finishes, spacious layout, updated kitchen, resort-style pool, and prime location within two prestigious gated communities, this home offers an exceptional Florida lifestyle with privacy, comfort, and elegance at every turn. Centrally located to Tampa International and St . Pete/Clearwater Airport, award winning beaches, boating and fishing, professional sporting events, historic Dunedin and Safety Harbor, Pinellas and Duke Energy Bike Trails, restaurants, shopping, and hospitals. East Lake Woodlands is a golf community with an optional membership available to the nationally renowned ELW Country Club, featuring outstanding amenities including two championship golf courses, sixteen tennis courts, pickleball, fully-equipped fitness center, lap & freeform pools, splash pad, dining, full social calendar/club, and is also part of ClubCorp/Invited with reciprocal rights to 300+ clubs. Low HOA and NO flood insurance required. A fantastic value! Call today for your private tour!

1723 Captiva Drive, Oldsmar

$250,000
2 Beds 2 Baths St Andrews Condo SubDv. 34677 Zip Code
Discover this beautifully remodeled GROUND-FLOOR END UNIT in the highly sought-after Saint Andrews community of East Lake Woodlands. Located just steps from the community pool, one of the largest in the area, this condo offers resort-style living. East Lake Woodlands is home to top-rated schools and an optional Ardea Country Club membership, providing access to two championship golf courses, 12 tennis courts, a pickleball complex, a fitness center, and an on-site restaurant. Overlooking the 18th hole of the North Course, this move-in ready condo offers breathtaking golf course views and a beautifully updated interior. Recent upgrades include new shaker kitchen cabinets, granite countertops, luxury vinyl plank flooring in both bedrooms, fresh interior paint, and stylish light fixtures. The spacious kitchen features ample storage and a cozy breakfast nook, while the open living and dining area is filled with natural light from oversized sliding glass doors leading to a screened porch overlooking the course. The split-bedroom floor plan provides privacy, and the primary suite includes a walk-in closet, double vanity, soaking tub, and private porch access. Relax on the screened lanai and enjoy peaceful golf course views, beautiful sunsets, and Florida's natural beauty. With modern updates, an ideal layout, and an unbeatable location, this condo offers the perfect blend of comfort and convenience

121 Lindsay Lane Unit 31, Oldsmar

$530,000
3 Beds 3 Baths Seaside Estates SubDv. 34677 Zip Code
Endless sunsets create this picture-perfect location in Seaside Estates. Resting on the banks of Old Tampa Bay, where everyday living feels like a vacation. This townhome has 3 bedrooms, 3 bathrooms, and 1,834 square feet of thoughtfully designed living space. The main living level, high ceilings, skylights, and oversized windows frame breathtaking open-water views and unforgettable sunsets. A spacious bedroom with a full bath is also located on this level, ideal for guests or flexible living. The top floor is home to the owner’s retreat, complete with a private balcony, double walk-in closets, a garden tub, separate shower, and dual vanities. An additional bedroom with a full bath and a conveniently located laundry area complete the upper level. The first level features a tandem 3 car garage offering enough space to store your water toys and vehicles. There is newly installed epoxy flooring, extra storage under the stairs, and a covered patio perfect for a grill. A deeded boat slip with a new 7000lb. electric lift is right outside the unit. Just steps from the pool, spa, and tennis courts, this community invites an active waterfront lifestyle. Launch a kayak into nearby mangroves, stroll the expansive boardwalk while watching dolphins and manatees, or enjoy the heated pool, playground, picnic areas, and harbor views. With minimal pet restrictions and HOA fees that include roof, exterior paint, water, sewer, exterior insurance, trash and amenities, living here is truly effortless. Located in the heart of Oldsmar, you’re just steps from R.E. Olds Park, a 15-acre waterfront park offering sweeping views of Tampa Bay. From seasonal festivals and community events to a 400-foot fishing pier and playground, this vibrant park is truly an extension of your neighborhood. With Pinellas beaches, Tampa International Airport, and downtown Tampa all nearby, you’ll enjoy easy access to everything the Tampa Bay area has to offer.

158 Brent Circle, Oldsmar

$399,000
3 Beds 2 Baths Heatherwood Unit One Condo SubDv. 34677 Zip Code
Beautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car garage and an added BONUS space/office! Right as you enter, notice the entire entryway is newly UPDATED with a custom door, paint, sconce lighting and Stanton carpet up the stairwell. Prepared to be wowed in the living room by the elegant, NEW custom built entertainment center with an electric fireplace. Set your color of choice and it can heat up the room for chilly nights. With the natural light from the 3 skylights, luxury vinyl plank flooring, vaulted ceilings, 2 huge fans on remotes.. this is quite the spot for entertaining. Kitchen features newer leathered granite countertops, wood cabinetry with soft close doors, stainless steel appliances, breakfast bar and new custom drapes. Step outside to the fully screened lanai with adjustable sunshades. Cool off with a new variable speed fan while enjoying all the wildlife East Lake Woodlands as to offer. The owner's suite also has a sliding door to the lanai, 2 closets with ample space, double bathroom vanities, countertops, garden tub and floor-to-ceiling tiled, glass-enclosed shower. Two other bedrooms with large windows share an updated bathroom. Enjoy an upstairs inside laundry with storage space and a bonus room with a convenient wet bar area. This space can be a TV room, office, playroom, sitting room for morning coffee..the ideas are endless. Additional updates include NEW water heater, new epoxy garage floor, remote blinds, water softener and light fixtures. HOA fee includes internet, cable, water, sewer, trash, community pool, exterior maintenance, grounds and insurance. Furniture is also available for purchase. East Lake Woodlands is central to Florida's most famous beaches, shopping, Tampa airport, A-rated schools and numerous dining options. There also is an option to join the Ardea Country Club and have access to 2 championship golf courses, tennis courts, fitness center, clubhouse, dining, swimming pools and social events. Don't miss this opportunity!

208 Clays Trail Unit 208, Oldsmar

$425,000
3 Beds 2 Baths East Lake Woodlands Pinewinds SubDv. 34677 Zip Code
One look and you'll be sold! This beautifully maintained, move-in-ready villa offers the perfect combination of comfort, privacy, and convenience. Featuring three bedrooms, two bathrooms, and an attached two-car garage, this home is sure to check all the boxes. Step inside to a spacious Great Room with soaring cathedral ceilings and a cozy wood-burning fireplace, creating the perfect space for relaxing or entertaining. The home's thoughtful layout and meticulous upkeep make it truly move-in ready. One of this property's most outstanding features is its premium location on one of the most private lots in all of East Lake Woodlands. With no rear neighbors, you'll enjoy exceptional privacy while overlooking a tranquil pond and wooded preserve. Start your mornings with coffee or unwind in the evenings with a glass of wine on the private screened lanai as you take in the peaceful views. Located on a quiet cul-de-sac in the desirable Pinewinds community within the gated East Lake Woodlands neighborhood, this home offers both security and a relaxed lifestyle. Residents enjoy convenient access to shopping, dining, beautiful Gulf beaches, medical facilities, parks, Tampa International Airport, and St. Pete–Clearwater International Airport. The HOA handles exterior maintenance, lawn care, and the community pool, allowing you to enjoy a true low-maintenance, resort-style lifestyle year-round. Whether you're searching for a full-time residence, a seasonal retreat, or a vacation getaway, this exceptional villa is an outstanding opportunity. Priced to sell, this home won't stay on the market for long. Schedule your private showing today before it's gone!

80 Summerwinds Lane, Oldsmar

$279,900
2 Beds 2 Baths East Lake Woodlands Cluster Homes SubDv. 34677 Zip Code
Tucked within the gated community of East Lake Woodlands, this beautifully refreshed 2-Bedroom, 2-Bath End unit Villa offers the perfect blend of low-maintenance living and Florida lifestyle appeal. Boasting amazing walk-up curb appeal, this move-in ready home welcomes you in with fresh paint throughout and updated fixtures at every turn. Inside, the thoughtful split floor plan offers privacy and comfort, with a built-in office off the second bedroom—perfect for the work-from-home professional, or anyone who wants a dedicated space for a desk and computer without cluttering up a bedroom. The kitchen has been updated and highlights granite counter tops, a brand-new stainless steel refrigerator and microwave, ready for your everyday living, entertaining, or a 2nd home retreat. The updated primary bathroom adds a fresh, modern touch, while a new water heater, newer roof (2020), and newer HVAC system (approximately 6 years old) offer real peace of mind for years to come. As an end unit, this villa offers extra privacy and added outdoor space—ideal for tossing the ball around when the grandkids come by or hosting guests. Your dedicated spot includes covered parking with additional storage, and there's plenty of room for guest parking nearby. Take a stroll through the beautifully landscaped, gated community, or take advantage of the option to join Ardea Country Club for Social or Golf Membership, featuring two championship 18-hole golf courses, pools, tennis courts, an exercise room, and on-site dining. East Lake Woodlands is considered a bird sanctuary, with sidewalks and paths for walking and biking among nature and wildlife. Conveniently located in the heart of Oldsmar, you're close to John Chestnut Park, Oldsmar Park, and Safety Harbor's Philippe Park, with Caladesi Island State Park and Clearwater Beach just a short drive away. Tampa International and St. Pete/Clearwater Airports make travel easy, and shopping, dining, and entertainment are just minutes away. Don't miss this opportunity to experience low-maintenance Florida living at its finest—schedule your private showing today!

75 Poole Place, Oldsmar

$175,000
2 Beds 2 Baths East Lake Woodlands Condo Unit 7 SubDv. 34677 Zip Code
This adorable 2nd floor, 2 bedroom, 2 bathroom condo in the guarded/gated community of East Lake Woodlands! An open and airy front balcony welcomes you in to the unit. NO REAR NEIGHBORS! Just views of the lovely back yard wooded area and daily deer sightings from your 2nd balcony which is private and screened-in! A big picture window, recessed lighting, solid wood cabinets and tiled backsplash accent the kitchen. The kitchen has a floor to ceiling pantry and is open to living / dining with an breakfast bar. An elegant, 2 tiered chandelier, crown molding and new modern ceiling fan grace the ceiling. Newer laminate flooring installed in the living /dining and both bedrooms. Step through the living room sliding doors and onto the screened-in balcony where the true Florida lifestyle begins. Roller shades on the balcony create privacy while still allowing the cool breezes to flow through. This unit features a split bedroom plan with NO CARPET! Master bedroom has its own bath en suite with separate shower/commode area, 3 walk in closets (YES! 3), tropical ceiling fan with palm leaf blades, double picture window with beautiful views of the wooded back yard! It is spacious enough for a king bedroom furniture set and also has a set of sliding doors out to the balcony! Guest bedroom features a large closet and an adjacent full bathroom with tub/shower in the hall. No lack of storage here with a coat closet in the main entry hall and a full wall to wall reach in closet in the guest hallway. A side by side washer and dyer are conveniently located in the balcony closet. Your assigned covered parking spot is right in front of the entrance (#108). Plenty of extra guests spots for a 2nd car too. Heated pool just steps away! Love to golf? East Lake Woodlands County Club will become your new favorite spot with (2) 18 hole championship courses, upscale restaurant, fitness center, clubhouse, tennis courts, 2 pools and a multimillion dollar renovation underway! Located just around the corner from Oldsmar sports complex on Tampa Rd with a playground, ball hockey rink, BMX supercross track and fields for baseball football and soccer. Adjacent to the complex is Woodlands Square Mall with an IMAX movie theater, gourmet restaurants and shopping. East Lake Rd houses 2 large shopping centers with Target, Walmart, and an assortment of fast food chains. Short drive to Countryside mall, Tampa Airport, and the sugar sands of the Gulf’s finest beaches. Bring your furry friends! Two cats or dogs allowed under 20 lbs each (or a total of 40 lbs between the 2). Low condos fees with water, sewer, trash and basic cable included. Make your appointment to see today!

108 Woodlands Court Unit 108, Oldsmar

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