Oldsmar Homes with Sidewalks Community Features

Oldsmar Homes with Sidewalks Community Features

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County. This vibrant city is perfectly positioned between the bustling urban life of Tampa and the serene coastal beauty of the Gulf of Mexico. With its rich history, Oldsmar offers a charming blend of small-town warmth and modern amenities, making it an ideal place to call home.

Oldsmar is renowned for its beautiful parks, scenic waterfronts, and a strong sense of community. Residents enjoy a variety of recreational activities, from hiking and biking to fishing and boating along the picturesque Old Tampa Bay. The city boasts a lively downtown area filled with unique shops, delightful eateries, and community events that foster a close-knit atmosphere.

One of the standout features of Oldsmar is its commitment to creating a pedestrian-friendly environment. Many neighborhoods, including those in the Homes with Sidewalks community, are designed with walkability in mind. Picture yourself strolling along tree-lined sidewalks, engaging with friendly neighbors, and enjoying the fresh Florida air. This community feature not only promotes a healthy lifestyle but also enhances the overall sense of belonging.

Whether you’re a first-time homebuyer or looking to downsize, Oldsmar’s diverse real estate options cater to all preferences and budgets. From cozy single-family homes to charming townhouses, you’ll find a place that feels just right. Experience the allure of Oldsmar – where community spirit meets the beauty of Florida living. Embrace a lifestyle filled with outdoor adventures, friendly neighbors, and the perfect balance of tranquility and convenience. Welcome home!

Newest Oldsmar Homes with Sidewalks Community Features

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village Ph 2b SubDv. ⋅ 34677 Zip Code

Lovely Waterfront Single Family Home in Gull-Aire Village—never flooded, came through Hurricane Helene completely dry. Current appraisal is in the attachments. 534 Canal Way features a slab foundation, block and stucco construction on a continuous footing. Built in 2001, it offers 1,873 heated sq. ft., 2,441 sq. ft. under roof, and an attached 483 sq. ft. two-car garage. It includes two bedrooms, two full baths, granite kitchen countertops, and built-in bookshelves in the master bedroom. Upgrades include a new A/C system (2026), replacement windows and doors (2020), a $20k Generac standby generator with 300 Gallon propane tank (2020), and a porch added in December 2020. The roof was installed in 2014. There are too many extras to list. The backyard is a true highlight, featuring a lawn that slopes directly down to the water with no seawall, making it easy to launch a kayak, canoe, or small jon boat. With no seawall to maintain or replace, upkeep is minimal. Please note: there is no dock or boat lift, making this ideal for paddlers and small craft. The home is adapted for easy living, complete with a powered chair lift from the driveway to the front door, step railings, assisted lifting rails in the bedroom, and a Kohler walk-in tub in the second bathroom. Gull-Aire Village is a deed-restricted 55+ community where you own the land, with an HOA fee of just $70/month. Amenities include a clubhouse, large heated pool, spa, sauna, library, enclosed shuffleboard, bocce, picnic area, art gallery, and resident-run activity groups. Oldsmar has designated this a golf cart-friendly community. One pet per home is permitted, and association approval is required prior to closing. Conveniently located under a mile from Woodlands Square (Bealls, Marshalls, Ulta, PetSmart, AMC Theatres, Craft Street Kitchen, Shaker and Peel, and Eve's Family Restaurant). Publix, Target, Walmart Neighborhood Market, and Mease Countryside Hospital are within two miles. A walking/biking trail along Canal Way leads to Sheffield Park. Honeymoon Island is approximately 9 miles away, and Tampa International Airport is about 15 miles out. Room dimensions are approximate and should be verified by buyer.

534 Canal Way, Oldsmar

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

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

3 Beds ⋅ 3 Baths ⋅ Bay Arbor Unit 1a SubDv. ⋅ 34677 Zip Code

WELCOME HOME TO BAY ARBOR! This stunning 3-bedroom, 2.5-bathroom pool home offers the perfect combination of style, privacy, space, and location in one of Oldsmar’s most desirable gated communities. Situated on a peaceful, wooded lot with NO REAR NEIGHBORS, this move-in-ready home delivers the private backyard retreat buyers dream about while still being just minutes from everything Oldsmar has to offer! From the moment you arrive, the impressive curb appeal sets the tone with lush landscaping, a pavered driveway, and a beautiful paver walkway leading to the front door. Step inside and immediately appreciate the soaring two-story ceilings, abundant natural light, and spacious open layout. The Great Room, Dining Room, and Kitchen flow seamlessly together, creating an inviting space that is equally perfect for everyday living or entertaining. The beautifully remodeled kitchen (2022) is the heart of the home and features quartz countertops, stainless steel appliances, decorative backsplash, abundant cabinetry, generous counter space, and a charming eat-in area. Just beyond the kitchen, the formal dining area provides the perfect setting for family dinners and special gatherings. The highly desirable FIRST-FLOOR PRIMARY SUITE offers exceptional privacy and convenience, complete with a spacious walk-in closet and a fully remodeled ensuite bathroom (2022). The spa-like bath features dual vanities, a garden tub, and an oversized step-in shower with stunning decorative tile, five shower sprayers, and a built-in Bluetooth speaker. Upstairs, you'll find two additional bedrooms and a guest bathroom. Need a home office, playroom, or flex space? The possibilities are endless. And then there's the BACKYARD OASIS! Step through the converted porch area, an ideal spot for a small home office, reading nook, or relaxation space—and head outside to your private resort-style retreat. The expansive pavered pool deck, PebbleTec saltwater pool, and spillover spa create an incredible outdoor living experience. With brand-new pool equipment (2024) and Pentair automation with Touch system, enjoying your pool has never been easier. The screened-in patio provides the perfect setting for morning coffee, weekend barbecues, or relaxing evenings while overlooking the tranquil wooded backdrop. The upgrades continue throughout the home, including a NEW ROOF (2019), interior and exterior paint (2021), new garage doors and opener (2023), and epoxy-coated garage floors (2024). Located within the gated Bay Arbor community, this home offers an unbeatable Oldsmar lifestyle with easy access to highly regarded schools, shopping, restaurants, parks, trails, and RE Olds Park. Enjoy the best of peaceful suburban living without sacrificing convenience, with Tampa, Clearwater, and the Gulf beaches all within easy reach. Homes offering this combination of a first-floor primary suite, remodeled interiors, private wooded setting, and resort-style pool are hard to find. Don't miss your opportunity to make Bay Arbor your new neighborhood! Schedule your private showing today!

212 Arbor Woods Circle, Oldsmar

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. Water Heater 2018. 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

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

THE KITCHEN SETS THIS ONE APART. Step into a brighter, more open 3-bedroom, 3-bathroom townhome with over 1,800 square feet in the gated waterfront community of Seaside Estates. Bamboo flooring, a fireplace, high ceilings, and a private balcony create a light-filled, open-concept main level. The kitchen was extended 3 feet and the original dropped ceiling was removed, so the space feels tall and open to the living room -- a difference most of the 67 units in this community still don’t have. Quartz counters, new white cabinetry, stainless appliances, and a built-in pantry finish the update. A flexible bedroom on this level works as an office or guest suite. Upstairs, the primary suite offers soaring vaulted ceilings, dual walk-in closets, skylights, its own balcony, and a spacious ensuite, with laundry and a third bedroom with an ensuite bath on the same level. The oversized tandem garage adds storage and sliding-door access to a patio and green space. This building sits closer to the tennis court and main entrance, and farther from the pool noise. Residents share a resort-style pool/spa, tennis, boardwalk, and a floating dock for kayaks and paddleboards, with slips and boat lifts typically available to rent. Inclusive HOA fees cover the roof (2017), water, sewer, trash, and interior fire sprinklers. Just steps from R.E. Olds Park, a 15-acre waterfront park with the city pier, playgrounds, trails, beach volleyball and more, plus convenient access to Gulf Coast beaches, Tampa International Airport, Clearwater, and Tampa/St. Pete. Schedule your showing today!

106 Brent Circle, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome to easy Florida living in Gull-Aire Village! This beautifully maintained 2-bedroom, 2-bathroom manufactured home is located in the desirable 55+ Gull-Aire community of Oldsmar, where you own the land and enjoy an affordable HOA of just $70/month. Offered fully furnished and completely turn-key, this home is ready for you to move right in and start enjoying the Florida lifestyle—and the GOLF CART IS INCLUDED! The home features many updates, such as... a 2017 roof, newer A/C, water heater, and more… all providing peace of mind for its next owner. In addition to the comfortable interior living space, you'll love the bonus SCREENED-IN PORCH, perfect for relaxing with your morning coffee or enjoying Florida evenings. A convenient shed/laundry combination provides additional storage and functionality, while the carport offers covered parking. Gull-Aire Village offers a welcoming, active lifestyle with a calendar of planned activities, community events, and social gatherings. The neighborhood is GOLF-CART FRIENDLY, making it easy to get around and take advantage of everything the community has to enjoy. Location is another major highlight! You'll be directly across the street from a variety of shopping, entertainment, and dining options, including AMC Theatres, Bealls, Marshalls, Dollar Tree, and restaurants such as Craft Street Kitchen, Country Pizza Italian Grill and Shaker and Peel. When it's time for a day at the beach, Honeymoon Island is just a short 15 minute drive away. Whether you're looking for a full-time Florida residence, a seasonal retreat, or a low-maintenance place to enjoy retirement, this turn-key Gull-Aire Village home WITH FURNISHINGS AND GOLF-CART INCLUDED IN THE SALE... offers an exceptional opportunity to enjoy the best of the Florida lifestyle!

56 Pelican Drive S, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome to 428 Pelican Drive South in Gull-Aire Village, a welcoming 55+ golf cart friendly community in Oldsmar where you can enjoy the Florida lifestyle with room to spread out. This spacious 2-bedroom, 2-bathroom home offers large rooms, an indoor laundry area, and a desirable location toward the back of the community. Whether you’re looking for a full-time Florida residence, a seasonal retreat, or a comfortable place to enjoy your next chapter, this home offers the space and flexibility to make it your own. The generous room sizes provide plenty of opportunity for comfortable living, entertaining, hobbies, or welcoming visiting family and friends. The indoor laundry adds everyday convenience, while the peaceful setting toward the back of the community offers a welcome sense of privacy. It’s a wonderful opportunity to enjoy the ease of community living without giving up the space you desire. Located in Oldsmar, Gull-Aire Village offers the appeal of a Florida community with convenient access to shopping, dining, parks, and the many attractions of the Tampa Bay area. Come discover the possibilities at 428 Pelican Drive South and imagine making this spacious home your own. Gull Aire Village is an active community with an amazing line up of social events, community pool, clubhouse, and lots to do!

428 Pelican Drive S, Oldsmar

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

2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code

RARE FIRST-FLOOR, FULLY REMODELED 2 BED / 2 BATH CONDO IN OLDSMAR, PRICED TO STAND OUT. No stairs and no renovation project waiting for you. This move-in-ready 915 sq. ft. condo has been thoughtfully updated throughout with wood-look flooring, fresh neutral finishes and a bright, open living and dining area that opens directly to a private covered patio. The updated kitchen features shaker-style cabinetry with plenty of storage, quartz countertops, stainless steel appliances, modern hardware and a decorative tile backsplash. The spacious primary suite includes a large walk-in closet and updated ensuite bath with a tiled walk-in shower. The second bedroom is generously sized with excellent closet space, and the second full bath has also been updated with modern tile and a tub/shower combination. An interior laundry area with stacked washer and dryer adds another convenience rarely found at this price point. Gardens of Forest Lakes offers community amenities including a pool, tennis and basketball courts, playground, park and fishing dock, with convenient access to shopping, dining, parks, Tampa, Clearwater, Gulf beaches and Tampa International Airport. First floor, fully updated, two full baths, interior laundry and competitively priced within the community. This one is ready for its next owner.

133 Sabal Court Unit F, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code

Welcome to this charming FIRST FLOOR condo in the wonderful East Lake Woodlands community, a golf community with guarded gate entry. Featuring serene pond views from the screened lanai. This spacious 2 bedroom, 2 bath condo offers comfort, convenience and the option to purchase fully furnished. Step into the first floor entry to a light and bright kitchen that has been recently updated, with new quartz counters and cabinets with new dishwasher, and newer refrigerator. There is a small area in the kitchen for a nice breakfast. Then walk into the open dining and living room with wood flooring and a fireplace. AC is only 1 year new! The primary bedroom is HUGE with 3 walk-in closets for ample storage. The primary bath has been remodeled with a new vanity with double sinks, mirrors and lights. The new pocket door to the shower area has a lighted, full-length mirror attached. Both bathrooms have new chair height toilets. The 2nd bedroom is large enough for 2 beds with plenty of closet space. The guest bathroom has also been remodeled with a new vanity, sink, mirror and lights. There is a good sized screened lanai that has a closeted washer and dryer, which are included. There is a nice view of the pond and the pool is just down the street from your front door! East Lake Woodlands has miles of sidewalks, a golf course and the Ardea Country Club.

105 Lakeview Way Unit 105, Oldsmar

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

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