Oldsmar Homes with Gated Community - Guard Community Features

Oldsmar Homes with Gated Community - Guard Community Features

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County, where charm meets convenience. This vibrant city boasts a perfect blend of natural beauty and modern amenities, making it an ideal place for families, retirees, and everyone in between. With its picturesque parks, scenic waterfront views, and a bustling downtown area, Oldsmar offers a laid-back lifestyle just minutes away from the stunning Gulf Coast beaches.

One of the standout features of Oldsmar is its exceptional gated communities, which provide residents with an added layer of security and peace of mind. These guard-gated neighborhoods are designed for those who appreciate privacy and exclusivity, offering a tranquil retreat from the hustle and bustle of everyday life. Imagine living in a beautifully landscaped community where friendly neighbors greet you as you stroll along tree-lined streets, and children play safely in designated areas.

Homes within these gated communities reflect a range of architectural styles, catering to diverse tastes and preferences. From luxurious single-family homes to elegant townhouses, each property is thoughtfully designed with modern amenities and high-end finishes. Residents can enjoy access to exclusive community features such as sparkling swimming pools, fitness centers, and recreational facilities, fostering a sense of camaraderie and an active lifestyle.

In Oldsmar, you’ll find more than just a home; you’ll discover a welcoming community that values safety, comfort, and a vibrant way of life. Experience the charm of Oldsmar and explore the outstanding gated communities that make this city a truly special place to call home.

Newest Oldsmar Homes with Gated Community - Guard Community Features

$210,000
2 Beds 2 Baths East Lake Woodlands Condo SubDv. 34677 Zip Code
Relax and enjoy effortless Florida living with the Much-Coveted Combination of a FIRST FLOOR, MOVE-IN READY, MAINTENANCE FREE 2-Bedroom, 2-Bath Condo in the GATED GOLF COMMUNITY OF EAST LAKE WOODLANDS. Beautiful Engineered Hardwood Flooring graces the living area with Tile Floors in the Entry, Kitchen and Baths creating a warm, low-maintenance interior, while Plantation Shutters throughout add timeless style and privacy. The Updated Kitchen features Stainless Steel Appliances, Generous Pantry Storage, Eat- In Area and an open view into the Spacious Great Room, where the living and dining areas blend seamlessly for everyday comfort and easy entertaining. Step onto the great Patio complete with Pavers and unwind beside a Calming Water View also enjoyed from the Primary Bedroom. The Primary Suite offers 3 Closets plus an Updated Private Bath with Beautifully Appointed Shower Tile. A Generously-Sized 2nd Bedroom and Full Guest Bath provide welcoming space for visitors, a home office or seasonal living. Convenience continues with an Assigned Covered Carport Space directly in front of the unit and a Sparkling Community Pool just steps away. Enjoy Maintenance-Free Living with Building Exterior and Grounds Maintenance included in the condo fee, along with Pool Maintenance, Cable TV, Internet, Trash and even Water! Updates include Engineered Hardwood Flooring in 2024, a 2-Ton Trane A/C Unit installed in 2020, New Refrigerator in 2024, New Microwave in 2021 and Water Heater in 2018. Furniture is negotiable, making this an easy move and an ideal choice for a year-round residence, seasonal retreat or Florida vacation home. Optional memberships for additional fees are available for a wide array of amenities with Ardea Country Club including 2 Golf Courses, Tennis and Pickle Ball, Fitness Center and Classes, Heated Lap Pool and Free Form Pool, Dining and Social events. All this in a Premier Location convenient to Tampa International Airport, Medical Facilities, A-Rated Schools, Award-Winning Beaches as well as Professional Sporting Events, Concerts and more in the Tampa Bay area. Schedule your private showing and discover the comfort, water views and gated-community lifestyle of East Lake Woodlands!

221 Nina Way Unit 61, Oldsmar

$224,000
2 Beds 2 Baths East Lake Woodlands Condo SubDv. 34677 Zip Code
Welcome to carefree Florida living in this beautifully updated second-floor, two-bedroom, two-bath condo nestled within the sought-after East Lake Woodlands community! The HOA fee includes an impressive array of amenities and services, including cable TV, internet, community pool access and maintenance, reserves, exterior and grounds maintenance, sewer, water, and trash. With so much included, your only utility expense is electricity—giving you more time to simply relax and enjoy your Florida lifestyle. Step inside and immediately appreciate the welcoming, light-filled interior and luxury vinyl wood-look flooring. The updated kitchen features granite countertops, tile backsplash, a pantry closet, updated hardware, and a double stainless-steel sink overlooking the breakfast bar. Open to the living and dining areas, the kitchen creates a comfortable flow for everyday living and entertaining, with room for a small dining table if desired. The spacious living and dining area is enhanced by a beautiful shiplap-style wood ceiling and warm wood-look flooring, creating an inviting atmosphere with plenty of character. All windows and sliding glass doors throughout the condo have been updated to hurricane-impact glass, providing added protection and peace of mind. The beautiful sliding glass doors open to your private, screened-in lanai—a wonderful extension of your living space and the perfect spot to enjoy your morning coffee, curl up with a good book, or dine al fresco. A charming nook on the lanai provides an ideal reading retreat, while a table and chairs would transform the space into your own private outdoor oasis. The lanai also offers private sliding-door access to the primary suite. Your primary suite is generously sized and offers exceptional storage, with three walk-in closets. The en-suite bathroom features a updated dual-sink vanity with additional storage and a convenient step-in shower with glass enclosure. The second bedroom is located toward the front of the condo and is bright, comfortable, and nicely sized, with two generous wall closets. A second full bathroom with a tub/shower combination is conveniently located off the hallway. The spacious laundry closet is located inside the unit - a rare feature in this community! Perhaps one of the most appealing features of this home is its peaceful setting. The condo backs to a private, tree-filled area with no immediate rear neighbors, creating a tranquil, park-like backdrop that you can enjoy from your screened lanai. Located just off Tampa Road, East Lake Woodlands offers a convenient central location with easy access to Tampa, Tampa International Airport, restaurants, shopping, golf, and Florida's beautiful beaches. You'll also enjoy convenient access to U.S. Highway 19 and St. Petersburg. With numerous updated done, this spacious, private, and wonderfully maintained condo offers the perfect combination of comfort, convenience, and carefree Florida living. Come see it for yourself and discover how easy Florida living can be!

128 Nancy Drive, Oldsmar

$324,900
4 Beds 2 Baths East Lake Woodlands Cluster Homes SubDv. 34677 Zip Code
Beautifully remolded villa in gated East Lake Woodlands is turnkey and move in ready. Recent updates include newly redesigned open concept kitchen with shaker style cabinets, soft close doors and drawers, under cabinet lighting, polished marble backsplash and beautiful Quartz countertops. All new stainless steel appliances including refrigerator, range, dishwasher, microwave and disposer. Master bath shower and floor features new elegant porcelain tile, new fixtures, lighting, mirrors and dual sink vanity with Quartz top. Second bath also updated with new tub, tile, fixtures, lighting, mirrors and vanity with Quartz top. All new doors, lighting, fixtures and beautiful Luxury Vinyl Plank flooring throughout with 5.5-inch baseboards. Home has all new recessed lighting fixtures as well as fresh interior paint in neutral colors. HVAV system and Electrical panel recently updated as well. All windows and sliders were updated in 2018 and are Impact rated. Shingle roof replaced in 2019. Unit offers a private fenced patio off one of the bedrooms with a pleasant nature view. Two convenient storage/utility rooms - one next to the carport out front and another on the back screen porch that overlooks a pond. East Lake Woodlands offers a gated setting, mature landscaping, scenic golf course surroundings, and optional country club memberships with golf, tennis, pickleball, swimming, fitness, dining, and social amenities available. 24hr manned guard gate along with 2 championship 18-hole golf courses. Conveniently located near shopping, restaurants, parks, beaches, airports. Porch carpet to be replaced with commercial grade earth tone color.

110 Evelyn Court, Oldsmar

$230,000
2 Beds 2 Baths East Lake Woodlands Condo SubDv. 34677 Zip Code
Stunning 2BR/2BA Condo with Conditioned Lanai in East Lake Woodlands! Welcome home to maintenance-free Florida living at its absolute finest! Nestled within the highly sought-after, guard-gated golf community of East Lake Woodlands in Oldsmar, this beautiful 2-bedroom, 2-bathroom condo seamlessly combines modern upgrades with peak comfort. Step inside to a spacious, open floor plan that makes entertaining effortless. The kitchen features a convenient breakfast counter perfect for your morning coffee, elevated by a brand-new sink, new faucet, garbage disposal, dishwasher & refrigerator. Ceiling fans are strategically placed throughout the main living areas, both bedrooms and the Lanai to keep the home breezy and energy-efficient year-round. Premium Upgrades & Storage Galore. Rest easy knowing the heavy lifting has already been done for you! This condo boasts brand-new insulated windows for excellent climate control, and a water heater less than 3 years old. Storage is never an issue here, as the floor plan includes numerous spacious closets throughout the home to keep your living space organized and clutter-free. All-Weather Florida Lanai, one of the crown jewels of this property is the completely glassed-in, fully conditioned lanai. This bonus room serves as a versatile four-season sanctuary—perfect for a cozy sunroom, a vibrant home office, or a peaceful reading nook, completely shielded from the elements. Convenient Maintenance-Free Amenities your monthly association fee covers almost everything, offering ultimate lock-and-leave convenience. Included in your HOA: Basic cable TV & internet Water, sewer, and garbage removal. One assigned, covered parking spot to protect your vehicle, one designated guest parking spot right nearby. The Location Living inside the secure gates of East Lake Woodlands puts you just minutes from premium shopping, dining, and top-tier golf courses. Enjoy effortless commutes across the Tampa Bay area while returning home to a quiet, park-like neighborhood retreat. Schedule your private showing today and step into your dream Florida lifestyle!

105 Lakeside Court Unit ELW VI UNIT 5, Oldsmar

$385,000
4 Beds 2 Baths East Lake Woodlands Cluster Homes SubDv. 34677 Zip Code
Welcome to 150 Poole Place, a spacious 4-bedroom, 2-bath villa offering approximately 1,550 square feet of flexible living space in the gated community of East Lake Woodlands. Ideally positioned along the 15th hole of the South Course, this immaculate home offers beautiful golf course views and a peaceful setting that can be enjoyed from multiple areas of the property. Inside, the split-bedroom floor plan provides privacy and versatility, with four bedrooms that can easily accommodate family, guests, a home office, or hobby space. The living room features a decorative electric fireplace that adds character and ambiance, while the kitchen offers generous cabinetry, ample counter space, and all appliances included. An enclosed Florida room expands the living area and creates a comfortable space to relax while overlooking the golf course. French doors, tile flooring throughout, plantation shutters, interior laundry, and ample storage add to the home’s functionality and appeal. Outdoor living continues with patio areas that offer the perfect place for morning coffee, entertaining, or simply enjoying the scenic surroundings. A new water softener system was installed in July 2026. The monthly HOA fee of $490.08 includes internet, cable, building maintenance, roof, and lawn care, providing a convenient low-maintenance lifestyle. East Lake Woodlands is known for its gated setting, mature landscaping, scenic golf course surroundings, and optional country club lifestyle. Golf, tennis, pickleball, swimming, fitness, dining, and social amenities are available through separate club membership. Conveniently located near shopping, restaurants, parks, beaches, airports, and all that the Tampa Bay area has to offer, 150 Poole Place combines space, flexibility, and a desirable golf course setting in one of Oldsmar’s most established communities.

150 Poole Place, Oldsmar

$599,000
4 Beds 2 Baths East Lake Woodlands SubDv. 34677 Zip Code
A True Find for exceptional living in the highly desirable Gated Golf Community of East Lake Woodlands! Perfectly positioned on a Private Golf Course Lot overlooking the 7th fairway of the South Course, this spacious 4-Bedroom, 2-Bath home with a Sparkling Pool and Spa offers more than 2,200 square feet of comfortable living, beautiful views and outstanding value in one of North Pinellas County’s premier communities – plus Top-Rated Schools. Designed for indoor-outdoor living, the large living room and dining room combination features Glass Sliders that frame views of the Gorgeous Pool and Spa, Covered Lanai with Pavers and Lush Golf Course backdrop. This lot provides privacy and creates a peaceful retreat ideal for relaxing, entertaining and enjoying the best of East Lake Woodlands. The Well-Equipped Kitchen includes an inviting Eat-in Area, Ample Storage and Pass-Thru Window to the outdoor patio. Updates include Stainless Steel Appliances with LG Refrigerator (2022), LG Dishwasher (2022), LG Microwave (2024) and the bonus of a Euhomy Wine Cooler (2024). Additional major updates include a New Shingle Roof (2023) and Flat Roof (2023), Water Heater (2024), A/C Unit (2019) and Pool Sweep (2022). So many possibilities to meet your needs with this Flexible Floor Plan! The 4th bedroom offers plenty of options as a Home Office, Den, Guest Room, Hobby Space or Media Room and the 3rd bedroom comes complete with a murphy bed. Generously sized bedrooms provide comfortable accommodation with the Primary Suite measuring 23 ft. long and featuring a dedicated Extra Space ideal for lounging, reading, exercising or working from home, plus 2 Walk-In Closets and a Spacious Bath with Large Walk-In Shower, Dual Sinks and abundant Vanity Counter space. East Lake Woodlands offers a much sought-after setting tucked away and surrounded by beautiful landscaping, golf course scenery along with convenient access to everyday amenities. For additional fees, optional memberships are available to Ardea Country Club, featuring two Golf Courses, a Fitness Center, Tennis, Pickle Ball, Heated Lap Pool, Freeform Pool and Poolside Café as well as Dining and a full host of Special Events and Activities. Enjoy a Premier Location currently zoned for top rated East Lake High School, Joseph L. Carwise Middle School and Forest Lakes Elementary. Plus this East Lake Woodlands address provides convenient access to Tampa International Airport, award-winning Gulf Beaches, Parks, Medical Facilities, Shopping, Fine Dining, Professional Sporting Events and all that the Tampa Bay area has to offer - while providing the privacy and serenity of a gated golf course setting. Overall, an amazing opportunity to own a 4-Bedroom Retreat with Beautiful Pool and Spa and Sweeping Golf Course Views with the peace of mind of a Newer Shingle and Flat Roof and many other updates and the chance to make this home your own!

550 Palmdale Drive, Oldsmar

$775,000
4 Beds 3 Baths Cross Pointe SubDv. 34677 Zip Code
Virtually Staged. NEW PRICE! A must-see former model home in the gated Cross Pointe neighborhood of East Lake Woodlands, a premier country club community with abundant green space & optional membership amenities. This 4-bedroom, 3-bath home offers a private backyard retreat with a beautiful Pebble Tec pool & new pool cage screening, creating a perfect setting for relaxing or entertaining outdoors. The covered patio just outside the sliding doors of the house has hookups for TV & space for your table & chairs for outdoor dining. The popular three-way split floor plan provides excellent gathering spaces, including formal living room & dining rooms plus an open kitchen, dinette & family room. The family room is the heart of the home, featuring a warm wood-burning fireplace flanked by built-in bookshelves. The kitchen offers granite countertops, generous amounts of raised panel cabinetry, a large island-style sink area with seating, ample workspace, a closet pantry, a built-in desk & a breakfast area overlooking the pool & patio. A private guest bedroom sits at the rear of the home directly across from the pool bath, making it ideal for visitors or a home office. Two more spacious bedrooms are found on the opposite side of the family room. The primary suite is set apart on the other side of the home & features plenty of space, a walk-in closet, & a lovely rose toned bath with dual sinks, a soaking tub, a separate shower & a private water closet. Optional membership is available at Ardea Country Club which unlocks an impressive array of amenities, including golf, tennis, pickleball, an Olympic sized pool + a second smaller pool, splash area, a cafe & a restaurant, a fitness center, & year-round social events. Contact Ardea Country Club for details. Move in with confidence thanks to major updates including a new roof in 2026, a 50 gallon water heater 2021, a Square D electrical panel, & HVAC 2016, AND NOT IN A FLOOD ZONE! This exceptional property offers peace & tranquility while keeping you close to the world class beaches of Pinellas County. You will love living here! Yes there are updates needed but the bones are good and we are priced under homes nearby!! Make this your home and you will not be sorry!

1730 Captiva Drive, Oldsmar

$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

$830,700
4 Beds 3 Baths Cross Pointe SubDv. 34677 Zip Code
Virtually Staged. 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), Water Heater (9/2026), 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

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