Oldsmar Homes with Shingle Roof

Oldsmar Homes with Shingle Roof

Welcome to Oldsmar, Florida—a charming gem nestled in the heart of Pinellas County. With its picturesque landscapes and vibrant community spirit, Oldsmar offers a unique blend of suburban tranquility and easy access to the bustling energy of nearby cities. Situated just a stone's throw from the stunning Gulf Coast, residents enjoy a year-round temperate climate that beckons outdoor enthusiasts and families alike.

Oldsmar is known for its friendly neighborhoods, where tree-lined streets and well-kept parks create an inviting atmosphere. The city boasts a variety of recreational opportunities, from the scenic trails of the Oldsmar Trail to the serene waters of the nearby Tampa Bay. Whether you're enjoying a leisurely stroll, participating in community events, or indulging in local dining, Oldsmar has something for everyone.

When it comes to housing, Oldsmar features a diverse array of homes, many adorned with classic shingle roofs that add a touch of timeless elegance. These homes not only enhance the aesthetic appeal of the neighborhood but also provide durability and protection against Florida's weather. With options ranging from cozy single-family residences to spacious family homes, you're sure to find the perfect fit for your lifestyle.

Living in Oldsmar means embracing a community that values connection, recreation, and the joys of everyday life. Discover your dream home in this delightful city, where comfort meets convenience, and every day feels like a vacation. Explore the charm of Oldsmar and start your journey toward a vibrant new lifestyle in one of Florida's best-kept secrets!

Newest Oldsmar Homes with Shingle Roof

2 Beds ⋅ 2 Baths ⋅ TB8548305 MLS ⋅ 104 BLDG.

This condo had a fire. HOA has replaced and all is new. New sub-floor, walls, doors, windows, plumbing, electric, a/c unit, sliding glass doors. Unit needs needs finishing.

104 Cypress Lane Unit 104, Oldsmar

4 Beds ⋅ 2 Baths ⋅ A12088007 MLS

Completely renovated property, new roof 2026, new A/C 2026, new electricity system and water heater 2026, costume made chicken and bathrooms, 4 Bedrooms 2 Bathrooms plus den; 1,732 SqFt; Lot size 9,788 SqFt You deserve a quality home that you can shape to fit your personality. And here it is. Invite your family and friends for quality time in a home that reflects your spirit. The living space's stylish a blank canvas you can make your own. You’ll love the beautiful kitchen complete with premium cabinets, granite countertops and stainless-steel appliances. The cooking space is roomy and set up to accommodate a cook who knows their way around a kitchen. The backyard brings the whole house together. Keep the fun going in this wide-open fenced backyard that your furry friends will be more than happy to claim for themselves. Very motivated seller!!! Assistance with closing costs will be considered.

311 Country Club Drive, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8546989 MLS

Virtually Staged. Welcome home to Gull-Aire Village, a 55+ community that is Pet & Golf Cart friendly in the Heart of Oldsmar! Gull-Aire Village is a Land-Owned community, which means you OWN the Land & Home. This home is Priced to Sell for an easy transaction. It boasts a New Roof (11/24), Luxury Vinyl flooring throughout the living areas, laundry room is inside with Washer & Dryer included. The kitchen opens to the dining room for easy entertaining. The large living room offers comfort and opens to the enclosed Florida Room for a great flexible space offing additional living room space or privacy with the sliding glass doors. The primary bedroom features an En-Suite bathroom with walk in shower, the guest bedroom can double as an office and guest bathroom has a bathtub. The outside front area has a large covered carport for your car. There is also room under cover for a golf cart. You will appreciate the covered patio area that also includes an enclosed storage shed for garden tools or hobbies. The HOA fee covers the community amenities of a Heated Pool, Spa, Active Clubhouse with a varaity of events and activities, a Library, Pool Table, Shuffleboard courts and Bocce ball court. Just across the street are restaurants, shopping, and a movie theater. A walking/running trail is located adjacent to Canal Way, which takes you directly to Sheffield Park, which is a park with trails and a Dog Park. Gull-Aire Village is close to Safety Harbor, Dunedin and Honeymoon Island! Less than 30 minutes to Tampa International Airport. This home is a great value at this price and is a must see.

340 Canal Way, Oldsmar

3 Beds ⋅ 1 Baths ⋅ TB8540486 MLS

**Welcome to 310 Country Club Dr — Beautifully Renovated & Move-In Ready!** Discover a beautifully renovated Oldsmar home where modern style, quality finishes, and functionality come together. This 3-bedroom, 1-bath property features a **new roof, new A/C, hurricane impact windows, a fully remodeled kitchen and bathroom, upgraded flooring, and updated finishes throughout**. The stunning kitchen showcases **modern quartz countertops**, contemporary cabinetry, and a clean, refined design that flows beautifully into the living areas. The home features a stylish combination of **porcelain tile and laminate flooring**, providing both elegance and practicality. From the kitchen and bathroom to the flooring, major systems, windows, and exterior improvements, this home has been extensively renovated with attention to detail. **Permits for the completed improvements are up to date**, providing added confidence to the next owner. The location adds even more appeal. Just a short walk from a **nearby boat ramp**, this property provides convenient access for those who enjoy boating, jet skis, fishing, and the Florida waterfront lifestyle. **Golf is also nearby**, along with shopping, dining, recreation, and everything this home brings together. Whether you're looking for a **primary residence, vacation home, or investment opportunity**, this property provides an attractive combination of location, lifestyle, and extensive updates. Its proximity to the water and recreational amenities may also appeal to buyers exploring **short-term or vacation rental potential, subject to applicable local regulations and rental restrictions**. **Beautifully renovated, ideally located, and ready to enjoy — schedule your private showing today!**

310 Country Club Drive, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8545931 MLS

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

4 Beds ⋅ 2 Baths ⋅ TB8548017 MLS

Completely renovated property; You deserve a quality home that you can shape to fit your personality. And here it is. Invite your family and friends for quality time in a home that reflects your spirit. The living space's stylish a blank canvas you can make your own. You’ll love the beautiful kitchen complete with premium cabinets, granite countertops and stainless steel appliances. The cooking space is roomy and set up to accommodate a cook who knows their way around a kitchen. The backyard brings the whole house together. Keep the fun going in this wide-open fenced backyard that your furry friends will be more than happy to claim for themselves.

311 Country Club Drive, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8546601 MLS ⋅ 4 BLDG.

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

5 Beds ⋅ 3 Baths ⋅ O6440578 MLS

Charming older block home. 5 bedroom 3 bath ranch style home in Historic Part of Oldsmar. 300 yds from Tampa Bay and 2 blocks from an "A" rated Elementary School. Home has several upgrades but needs a little TLC. Home sits on 2 lots, and the vacant Lot 13 is available for separate purchase at $349k. You can purchase the house on Lot 12 only for $449k and a leaseback of Lot 13.

604 Chestnut Street, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8546900 MLS

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 ⋅ TB8544937 MLS

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 ⋅ TB8545646 MLS ⋅ 0000 BLDG.

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 ⋅ TB8545637 MLS

Virtually Staged. Beautifully updated and move-in ready, this 2-bedroom, 2-bath Oldsmar home offers the perfect combination of modern updates, outdoor living, and everyday convenience with NO HOA and NO CDD! Step inside to a bright, inviting floor plan featuring tile flooring throughout and an open living and dining area that creates an easy flow for both everyday living and entertaining. The updated kitchen is a true highlight, featuring quartz countertops, stylish backsplash, updated cabinetry, and new stainless steel appliances(2025). The spacious primary bedroom offers a comfortable retreat, while the second bedroom provides flexibility for guests, a home office, or additional living space. Both bathrooms complement the home's clean, updated feel. Open the sliding doors and step into your screened in lanai, an ideal spot for morning coffee, outdoor dining, or relaxing at the end of the day. Beyond the lanai, the fully fenced backyard provides privacy and plenty of space to enjoy the outdoors, entertain, garden, or let the pets play. The home sits on approximately 0.14 acres in a quiet, established neighborhood. The updates don't stop at the kitchen! Major improvements include: A/C (2025), flooring (2025), appliances (2025), French drain (2025), gutters (2025), water heater (2023), windows (2021), and roof (2020), giving the next owner peace of mind and allowing you to enjoy the home rather than worry about major projects. NO HOA - NO CDD - Numerous major updates - Fenced yard - Screened lanai and easy access to Tampa, St. Petersburg, Tampa International Airport, and some of the area's most popular Gulf Coast beaches. This is the kind of home that checks the boxes buyers are looking for: updated, comfortable, and ready to enjoy. Come see it for yourself!

1707 Hibiscus Circle N, Oldsmar

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