Oldsmar Homes with Gated Community - Guard Community Features

Oldsmar Homes with Gated Community - Guard Community Features

Welcome to Oldsmar, a vibrant city located in Pinellas County, Florida. Known for its beautiful landscapes, friendly community, and convenient location, Oldsmar offers a perfect blend of suburban charm and urban amenities.

Nestled in the heart of Pinellas County, Oldsmar provides its residents with easy access to the best of both worlds. With its proximity to Tampa Bay and the Gulf of Mexico, outdoor enthusiasts can enjoy a variety of water activities such as boating, fishing, and kayaking. The city is also home to several parks and nature preserves, including the popular R.E. Olds Park, where you can relax, have a picnic, or take a stroll along the waterfront.

One of the notable features of Oldsmar's real estate market is the availability of homes with gated and guard communities. If you value privacy, security, and exclusivity, these communities are an excellent choice. With their 24/7 security personnel and controlled access, you can have peace of mind knowing that your home and loved ones are well-protected.

Living in a gated community in Oldsmar also offers additional perks. Many of these communities boast impressive amenities such as swimming pools, tennis courts, fitness centers, and clubhouses. These facilities provide residents with opportunities to stay active, socialize, and build lasting relationships with their neighbors.

Whether you're looking for a cozy single-family home or a luxurious estate, Oldsmar's real estate market has plenty of options to suit your preferences. With its desirable location, beautiful homes, and the added security of gated communities, Oldsmar is an ideal place to call home.

Newest Oldsmar Homes with Gated Community - Guard Community Features

$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. 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 complete 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

$799,000
4 Beds 3 Baths Cross Pointe SubDv. 34677 Zip Code
Virtually Staged. 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!

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
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

$189,000
2 Beds 2 Baths East Lake Woodlands Condo SubDv. 34677 Zip Code
Welcome to this beautiful 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after East Lake Woodlands community. Built in 1979 with durable masonry construction and a slab foundation, this charming residence offers the perfect blend of comfort, character, and convenience. Enjoy peaceful pond views from the rear of the home while being surrounded by the outstanding amenities this master-planned community has to offer, including golf courses, nature trails, swimming pools, and a clubhouse. Ideally located between Hillsborough and Pinellas Counties, you'll have easy access to an incredible selection of shopping, dining, entertainment, and Gulf Coast attractions. Inside, timeless elegance shines through with beautiful oak flooring, a cozy wood-burning fireplace, and a convenient pass-through from the kitchen to the living area, creating an open and inviting space for everyday living or entertaining. The in-unit utility closet includes a washer and dryer for added convenience, while the generous closet space provides exceptional storage rarely found in condominium living. A covered parking space located directly in front of the unit makes unloading groceries and staying dry during Florida's afternoon showers a breeze. Whether you're looking for a year-round residence, a seasonal retreat, or an investment opportunity, this exceptional condo offers the best of maintenance-free living in one of the area's most desirable gated communities. Come experience the beauty and lifestyle of East Lake Woodlands and make 205 Martha Lane your new home!

205 Martha Lane Unit 205, 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

$1,124,900
4 Beds 3 Baths Greenhaven Unit Two SubDv. 34677 Zip Code
Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb appeal. As you approach the grand double-door entrance, soaring 12 foot ceilings immediately set the tone for what awaits inside. Step through the front doors and your eyes are instantly drawn to the breathtaking views of the sparkling pool and peaceful pond beyond. The home has been freshly painted inside and out and showcases new luxury waterproof vinyl plank flooring throughout, creating a seamless, modern aesthetic. Designed with both everyday living and entertaining in mind, the home features a desirable three way split floor plan, offering privacy for family members and guests alike. The spacious primary suite is a true retreat, complete with high ceilings, plantation shutters, and a spa-inspired ensuite bathroom. Relax in the freestanding soaking tub or unwind in the oversized walk-in shower featuring a rainfall showerhead and body jets. The luxurious bath also includes dual vanities, a dedicated makeup station, and an illuminated LED mirror. As you continue into the heart of the home, you'll discover a stunning open-concept kitchen and family room designed to impress. The fully remodeled kitchen features brand-new solid wood soft-close cabinetry, Taj Mahal quartz countertops, a cooktop with pot filler, new stainless steel appliances, and exceptional workspace for the home chef. Adjacent to the kitchen is a bright breakfast nook overlooking the pool, as well as a separate butler's pantry perfect for a coffee bar, beverage station, or additional storage. Entertaining is effortless thanks to the beautifully redesigned wet bar, featuring rich dark cabinetry, ambient lighting, a sink, and a built-in wine refrigerator. Just beyond, the expansive family room provides ample space for gatherings of any size. A beautifully renovated guest bathroom off the kitchen features designer tile, a modern vanity, and an LED mirror. Toward the rear of the home, you'll find two additional spacious bedrooms and another fully remodeled bathroom with dual sinks, LED mirrors, and convenient access to the pool. Step outside to your own private backyard oasis. The oversized screened lanai surrounds the sparkling pool and offers the perfect setting for year-round Florida living. The outdoor kitchen is equally impressive, showcasing stunning Brown Fantasy granite countertops, a new built-in grill, and a beverage refrigerator. The finishing touch? Your very own private putting green. Whether you're practicing your short game, entertaining guests, or simply enjoying the peaceful pond views, this backyard is designed to be enjoyed. Every detail of this remarkable home has been thoughtfully updated, creating a truly move-in-ready opportunity in one of the area's most desirable gated communities. Additionally residents have the opportunity to join the on-site Ardea Country Club, optional memberships provide access to championship golf, tennis, pickleball, a resort style lap pool, state of the art fitness center and dining. Minutes from top rated schools, Tampa International and St. Pete-Clearwater airports, award-winning Gulf beaches, professional sports team and more!

35 Greenhaven Trail, Oldsmar

$216,000
2 Beds 2 Baths East Lake Woodlands Condo SubDv. 34677 Zip Code
Welcome home to this beautifully updated second-floor condo located in the highly sought-after, gated community of East Lake Woodlands with picturesque golf course views. Known for its peaceful surroundings and resort-style living, this community offers both comfort and convenience in an ideal setting. You are greeted by a new storm door before stepping inside to discover a bright and airy interior filled with natural light. This move-in-ready residence has been thoughtfully upgraded with an amazing eat-in kitchen featuring new quartz countertops, a closet pantry, newer appliances (only two - four years old), and Wi-Fi-compatible dishwasher and range—perfect for everyday living and entertaining alike with a convenient pass-through window to the dining area. Fresh interior paint and new LVP and tile flooring flow seamlessly throughout the home, complemented by energy-efficient LED lighting, ceiling fans, and updated bathrooms for a clean, modern, and cohesive design. The home also features upgraded, HOA-approved Stainmaster LVP underlayment for the LVP flooring, providing enhanced comfort and sound reduction. The air conditioning system is equipped with a UV light for improved air purification and indoor air quality. The spacious primary bedroom offers three closets, including two walk-in closets, a separate dressing area, and an updated en-suite bathroom with a walk-in tiled shower and glass door. The guest bedroom features generous wall closets. A brand-new washer and dryer are scheduled to be installed in mid-August and are conveniently located in the hall closet near the guest quarters. Generous storage and ample closet space add to the home's functionality and overall comfort. Enjoy the added privacy of a second-floor location while taking advantage of the exceptional lifestyle within East Lake Woodlands. The community pool and Condo 2 Clubhouse are just across the parking lot! Pets are welcome, and the monthly maintenance fee provides outstanding value and ease of living. If you're ready to explore, the location is fantastic. Nearby, Ardea Country Club offers optional private memberships with two heated swimming pools, two 18-hole championship golf courses, tennis and pickleball courts, a fitness center, clubhouse, restaurants, and a full calendar of social activities. The condo is also conveniently located near Westfield Countryside Mall, shopping, restaurants, entertainment, the beautiful beaches of Honeymoon Island, and numerous parks and walking trails for a relaxed Florida lifestyle. You'll also enjoy easy access to the charming downtown districts of Tarpon Springs, Dunedin, and Safety Harbor for even more dining, shopping, and entertainment.

222 Caryl Way, 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

$874,874
4 Beds 4 Baths East Lake Woodlands SubDv. 34677 Zip Code
Welcome to this exceptional 4-bedroom, 4-bathroom pool home located on a corner lot within the gated golf community of East Lake Woodlands in Oldsmar. Offering an impressive 3,441 square feet of living space, this beautiful residence combines elegant interiors, flexible living spaces, and a resort-style outdoor setting. Major updates include a 2021 roof, HVAC systems replaced in 2022 and 2023, and a 2022 water heater, providing peace of mind for years to come. A spacious foyer welcomes you into the home, where soaring vaulted ceilings with stunning wood beams and a wood-burning fireplace create a warm and inviting focal point in the living room. Double sliding doors seamlessly connect the indoor living areas to the screened pool and expansive outdoor entertaining spaces, embracing Florida's sought-after indoor-outdoor lifestyle. The thoughtfully designed split floor plan offers privacy and functionality, including a private fourth bedroom with its own en-suite bathroom, perfect for guests or multi-generational living. The spacious bonus room with built-in shelving provides endless possibilities as a home gym, movie theater, studio, game room, or additional living area. The beautifully appointed kitchen is designed for both everyday living and entertaining, featuring quartzite countertops, stainless steel appliances, a double oven, abundant cabinetry, pantry organizers, and a walk-in pantry for exceptional storage. A charming breakfast nook overlooks the pool, while the formal dining room provides an elegant setting for special gatherings. Wood-look tile flooring extends throughout the main living areas, complemented by crown molding throughout the home. The oversized primary suite serves as a luxurious retreat, featuring two large walk-in closets with custom organizers and a spa-inspired en-suite bathroom complete with a soaking tub, walk-in shower, private water closet, and generous vanity space. The updated shared bathroom showcases a modern double-sink vanity with a marble top, an illuminated mirror, and a shower/tub combination. A spacious laundry room with additional cabinetry adds even more convenience. Step outside to your private oasis. The rebuilt pool features all-new equipment and a heater, allowing for year-round enjoyment. The screened lanai offers abundant space for entertaining, including a covered dining area and convenient pool bath with a shower. New tropical landscaping further enhances the home's curb appeal and atmosphere. Residents of East Lake Woodlands enjoy a prime location close to parks, shopping centers, numerous dining options, and highly rated schools. Optional memberships are available at Ardea Country Club, offering access to golf, tennis, fitness facilities, swimming, social events, and more. This remarkable home offers the perfect combination of luxury, space, and lifestyle in one of Oldsmar's most sought-after communities.

475 Holly Hill Road, Oldsmar

Start Your Search