Oldsmar Homes with Rain Gutters Exterior Features

Oldsmar Homes with Rain Gutters Exterior Features

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! This vibrant city, ideally located between Tampa and Clearwater, offers a unique blend of small-town charm and modern conveniences. With its picturesque parks, scenic waterfront views, and a variety of recreational activities, Oldsmar is the perfect place for families, young professionals, and retirees alike.

Oldsmar boasts a rich history and a strong sense of community, with annual events that bring residents together in celebration. Explore the bustling downtown area, where you’ll find an array of delightful shops, restaurants, and cafes, all infused with local flavor. Outdoor enthusiasts will appreciate the numerous parks and nature trails, as well as the proximity to beautiful Gulf Coast beaches.

When it comes to homeownership in Oldsmar, you’ll discover a diverse selection of properties that cater to various lifestyles and budgets. Many of these homes feature essential exterior amenities, such as rain gutters, designed to protect your investment and enhance your living experience. Rain gutters are not just practical; they add to the overall aesthetic of your home while ensuring proper drainage and preventing water damage.

Whether you’re seeking a cozy single-family home or a spacious townhome, Oldsmar’s real estate market has something for everyone. With its warm climate, friendly atmosphere, and well-maintained neighborhoods, it’s no wonder that Oldsmar is becoming a sought-after destination for homebuyers. Come and experience the charm of Oldsmar – your dream home awaits!

Newest Oldsmar Homes with Rain Gutters Exterior Features

$349,900
3 Beds ⋅ 1 Baths ⋅ Harbor Palms-Unit One SubDv. ⋅ 34677 Zip Code
A beautifully maintained home in the desirable Sheffield Village area of Oldsmar, this property offers comfort, convenience, and the welcoming charm the community is known for. Located on a quiet cul-de-sac, 415 Maplewood Cir features a bright, open layout with spacious living areas perfect for everyday living and entertaining. The home’s interior is filled with natural light, highlighted by well-kept finishes and a functional floor plan. Complete with granite countertops, the kitchen anchors the living space, offering plenty of storage and easy access to the dining and family areas. Generously sized bedrooms provide privacy and flexibility for guests, family, or a home office. Step outside to enjoy a peaceful backyard with room to relax, garden, or create your ideal outdoor space. Mature landscaping and the neighborhood’s tree-lined streets add to the home’s inviting appeal. Residents of this Oldsmar location enjoy quick access to parks, top-rated schools, shopping, dining, and major commuter routes, making it easy to reach Tampa, Clearwater, and the Gulf beaches. With its combination of location, comfort, and community charm, this Maplewood Circle home is an excellent opportunity in one of Oldsmar’s most established neighborhoods. This home was high and dry during recent storms. Come check this one out today.

415 Maplewood Circle, Oldsmar
$170,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
Welcome to 219 Palmetto Ct. in the highly sought after East Lake Woodlands community, Oldsmar. Gated community of East Lake Woodlands, this ground-floor corner condo offers easy, low-maintenance living surrounded by lush greenery and natural beauty. This affordable 2-bedroom, 2-bath home combines comfort, privacy, and convenience with a desirable split-bedroom layout, bright open living spaces, and serene views from nearly every room. Inside, the spacious great room opens to tranquil green space through two sets of sliding glass doors, creating an airy indoor-outdoor feel perfect for everyday living or entertaining. The open kitchen flows seamlessly into the dining and living areas, while recent updates—including fresh interior paint (2025), new carpet, tile flooring in the kitchen and living room, and a new AC and heating system installed in 2024 with a transferable 10-year warranty—make the home truly move-in ready. The primary suite features two walk-in closets plus additional linen storage, while the home also includes a washer and dryer, stove, and a dedicated storage/laundry room with hookups. Step outside to enjoy a screened lanai and private paver patio overlooking peaceful green space, with the community pool conveniently located just beyond the trees for both accessibility and privacy. Additional highlights include covered carport parking directly in front of the unit, ample guest parking, and a resident-only rear entrance offering quick access to shopping, dining, and everyday conveniences along East Lake Road and Tampa Road. Residents of East Lake Woodlands enjoy a beautifully maintained gated setting adjacent to the 8,700-acre Brooker Creek Preserve, known for its scenic natural landscapes, wildlife, lakes, and walking trails. Optional memberships are available at East Lake Woodlands Country Club, offering championship golf, tennis, pickleball, fitness facilities, dining, and a resort-style pool. Seller will pay for the FIRST 4 MONTHS, 50% of the monthly condo fees which provide 24/7 gated security, 24 hours guard, manager, all exterior maintenance, roof, building insurance, escrow reserves fund, water, sewer, trash, pest control, cable, grounds maintenance, and pool access—providing simple, predictable ownership whether you’re looking for a primary residence, seasonal getaway, or investment opportunity.

219 Palmetto Court Unit 219, Oldsmar
$259,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Experience the exceptional lifestyle offered by this immaculate 1989 Jacobsen home—a true gem that blends modern updates with timeless charm. Step inside to a bright, open floor plan featuring soaring cathedral ceilings and elegant luxury tile flooring throughout. The beautifully textured walls and Key West-style plantation shutters add a touch of sophistication, while the newly installed 50-gallon hot water heater ensures efficiency and comfort. The kitchen has been thoughtfully updated with stunning quartz countertops, providing both style and functionality, and the expansive indoor laundry room boasts a brand-new washer and dryer, abundant storage, and convenience for daily chores. Retreat to the spacious primary suite, complete with a generously sized walk-in closet. The remodeled primary bathroom highlights a contemporary walk-in shower and sleek quartz countertop, while the guest bath has been upgraded with a custom shower and vanity for added luxury. Enjoy easy maintenance and impressive curb appeal, thanks to Shark Coating on the porch, driveway, walkway, and main entry. The substantial utility room is ideal for a workshop or extra storage. At the heart of this vibrant community, the clubhouse invites residents to monthly events and offers a wealth of amenities—including a pool table, shuffleboard and bocce ball courts, a heated pool, and a relaxing spa. Engage in regular activities like bingo, card games, and line dancing, fostering a lively and social atmosphere. Navigate the golf cart-friendly streets with ease and enjoy affordable living, with HOA fees at just $70 per month in a meticulously maintained neighborhood. Pet lovers are welcome: one pet of any size is permitted, and a second may be allowed with an emotional support letter from a physician. Ownership includes the land—no lot rent required. Conveniences are right at your doorstep, with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store just across the street. Savor a variety of dining options, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve's Family Restaurant. Major retailers like Super Walmart and Publix, as well as Countryside Hospital, are only ten minutes away. Outdoor enthusiasts will appreciate being just ten miles from the breathtaking beaches at Honeymoon Island and Caladesi State Park, plus direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.

214 Dolphin Drive N, Oldsmar
$240,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Beautifully updated 2-bed, 2-bath home with brand-new luxury flooring in the highly sought-after Gull-Aire Village—complete with a FREE GOLF CART included with the sale. This property comes with the land, meaning absolutely NO LOT RENT, offering exceptional long-term value. Step inside to discover fresh designer paint, and tastefully renovated bathrooms that elevate the home’s modern, move-in-ready appeal. The screened-in front porch provides a peaceful spot to unwind and enjoy the Florida breeze. Gull-Aire Village is an active 55+ community known for its vibrant lifestyle, featuring a large, heated pool, spacious clubhouse, and a full calendar of social activities. The location is unbeatable—just moments from grocery stores, retail shopping, restaurants, entertainment, and everything Oldsmar has to enjoy. Move-in ready—enjoy your golf cart and start enjoying the Florida lifestyle. Please note: photos show the previous flooring; new laminate is being installed throughout.

116 Dolphin Drive S, Oldsmar
$299,900
5 Beds ⋅ 4 Baths ⋅ Oldsmar Revised Map SubDv. ⋅ 34677 Zip Code
Exceptional builder or investor opportunity in a prime Oldsmar location! Situated on an oversized 11,347 sq. ft. lot directly across from scenic R.E. Olds Park, this property offers partial water views of Tampa Bay, park views, and outstanding redevelopment or renovation potential. The existing structure includes a 3-bedroom, 2-bath upper level plus two 1-bedroom, 1-bath lower-level units, offering multiple possibilities for redevelopment or renovation (buyer to verify permitted use). Additional features include a 2-car carport and a concrete block storage building. Enjoy a golf cart-friendly community with walking trails, fishing pier, playgrounds, picnic shelters, and year-round events just across the street. Cash offers only. Property is being sold As Is with no repairs. Conveniently located with easy access to Tampa, St. Petersburg, Tampa International Airport, and Gulf beaches.

613 Chestnut Street, Oldsmar
$299,900
3 Beds ⋅ 2 Baths ⋅ Oldsmar Revised Map SubDv. ⋅ 34677 Zip Code
Investor special with exceptional upside! This 3-bedroom, 2-bath, 1-car garage home sits on a spacious quarter-acre corner lot directly across from scenic R.E. Olds Park, offering water views, walking trails, playgrounds, a fishing pier, picnic shelters, volleyball courts, seasonal events, and a dog park. The home features a split-bedroom floor plan with a primary suite that includes a walk-in closet, en-suite bath with a step-in shower, and sliding glass doors leading to a patio. The guest bath offers a tub/shower combination. The roof was replaced in 2016. Double-pane sliding glass doors open to two patios overlooking the park. No HOA or deed restrictions—bring your boat, RV, or golf cart! Great central location with convenient access to Tampa and St. Petersburg.

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

158 Brent Circle, Oldsmar
$665,000
3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code
RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "THIS IS A MAINTENANCE FREE COMMUNITY." WALK THRU DOUBLE GLASS ENTRY DOORS TO FOYER THAT OPENS TO LIVING ROOM. LIGHT AND BRIGHT EXPANDED FAMILY ROOM AND KITCHEN OFFERS QUIET VIEWS OF CONSERVATION AND GOLF COURSE AREA. NEWLY EXPANDED LANAI WITH PARORAMIC BIRDCAGE SCREENING. KITCHEN OVER LOOKS FAMILY ROOM HAS CENTER ISLAND AND WOOD CABINETRY, BUILT-IN PANTRY, GRANITE COUNTER TOPS AND ALL STAINLESS-STEEL APPLIANCES. SEPARATE DINING ROOM WITH EASY ACCESS FROM THE KITCHEN. MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND MASTER BATH WITH FREE STAND TUB, SEPARATE STALL SHOWER, PRIVATE TOILET CLOSET, DOUBLE SINK VANTY WITH GRANITE COUNTER AND CUSTOM TILE. OFFICE WITH DOUBLE DOOR ENTRY CAN ALSO BE USED AS THIRD BEDROOM WITH CLOSET. SECLUDED SECOND BEDROOM IS PERFECT FOR GUESTS WITH ADJOINING BATH. INSIDE LAUNDRY ROOM WITH UTILITY SINK AND EXTRA STORAGE. GARAGE HAS EXTRA STORAGE AND SPACE FOR TWO CARS. THIS SEPTACULAR HOME LOCATED ON A PRIVATE CUL-DE-SAC. FOR SOCIAL ENJOYMENT YOU CAN RELAX IN THE COMMUNITY POOL. CLUBHOUSE MEMBERSHIP IS ALSO AVAILABLE FOR TENNIS AND GOLF. CLOSE TO BEACHES, SHOPPING, HOSPITALS, AND AIRPORTS. THIS IS WAITING FOR YOU!

5250 Pinehurst Court, Oldsmar
$925,000
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
$429,500
3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
Imagine coming home to breathtaking waterfront surroundings, resort-style amenities, and maintenance-free living in one of Tampa Bay's most desirable gated communities. Welcome to Bayside Terrace, where this beautifully upgraded 3-bedroom, 2.5-bath townhome with a 1-car garage offers the perfect blend of luxury, convenience, and coastal lifestyle. Ideally situated just steps from the community pool and clubhouse, this move-in-ready residence features one of the community's most desirable locations with peaceful courtyard views and easy access to all the amenities. Designed for today's lifestyle, the open-concept floor plan showcases soaring ceilings, abundant natural light, and elegant wood-look tile flooring throughout the main living areas. The chef-inspired kitchen is the centerpiece of the home, featuring stunning quartz countertops, custom all-wood cabinetry with pull-out shelving, a large quartz preparation island, designer lighting, a walk-in pantry, stylish backsplash, and premium stainless steel appliances including a double oven range and French door refrigerator. Whether entertaining guests or enjoying quiet evenings at home, this space was designed to impress. The spacious great room flows seamlessly onto the covered and screened lanai, creating an inviting indoor-outdoor living experience overlooking a tranquil courtyard. It's the perfect setting for morning coffee, evening cocktails, or simply relaxing after a day on the water. Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully appointed frameless glass shower. Two additional bedrooms each feature walk-in closets, ceiling fans, and upgraded carpeting with premium padding for exceptional comfort. Living in Bayside Terrace means enjoying a true Florida waterfront lifestyle. Residents have exclusive access to a resort-style swimming pool, fitness center, clubhouse, fishing pier, kayak launch, and direct access to the beauty of Tampa Bay. Whether you enjoy kayaking, fishing, walking along the waterfront, or simply watching spectacular sunsets, every day feels like a vacation. Included with all of these amenities, the HOA offers exterior property insurance, high speed internet, cable tv, maintenance of exterior and pool, 24 virtual guard gate, common area taxes plus water, sewer and trash. Perfectly positioned between Hillsborough and Pinellas Counties, this exceptional location offers convenient access to Tampa International Airport, St. Pete-Clearwater International Airport, downtown Tampa, award-winning Gulf beaches, waterfront dining, shopping, and major employers. Whether you're searching for a waterfront townhome, a gated community with resort amenities, a low-maintenance primary residence, a second home, or a Florida retreat close to Tampa and the Gulf Coast, this exceptional property offers everything today's buyers are looking for. Schedule your private showing today and discover why Bayside Terrace continues to be one of Tampa Bay's most sought-after communities.

2410 Arch Avenue, Oldsmar
$525,000
3 Beds ⋅ 2 Baths ⋅ Tampashores Bay Sec SubDv. ⋅ 34677 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the heart of Oldsmar, offering 1,856 square feet of thoughtfully designed living space on an oversized 0.41-acre lot. Featuring a spacious floor plan with a Florida room and dedicated home office, this property provides the perfect blend of comfort and modern upgrades. This home has been extensively upgraded for peace of mind, including a new high-efficiency HVAC system (2023), new electric water heater, complete electrical rewire with updated panel, whole-house plumbing re-pipe, impact-rated exterior doors, LED lighting throughout, high-efficiency ceiling fans, and modern underground electrical service. Natural light fills the home through impact-rated Simonton double-hung windows, complemented by cellular window treatments and blackout blinds in the primary suite. Durable porcelain tile flooring extends throughout the home, creating a seamless and elegant look. The remodeled kitchen is designed for entertaining, showcasing quartz countertops, a stunning clay-fired farmhouse sink, a large,10 ft center island, solid-wood soft-close cabinetry, and modern stainless-steel appliances. The spacious primary suite offers a private retreat with walk-in shower and beautifully updated finishes. Both bathrooms have been tastefully remodeled with premium fixtures, including TOTO and KOHLER features, bidets, and marble countertops. Additional features include a butcher block laundry room workspace, spare garage rated refrigerator, a pull-down attic access with plywood flooring for extra storage, outdoor solar security lighting, front yard irrigation system utilizing reclaimed city water, and low utility costs through TECO services. Step outside to enjoy an expansive, fully fenced backyard with plenty of space for boat or RV parking and a large Tough Shed equipped with 220-volt electrical service, providing endless possibilities for storage, hobbies, or workshop space. Ideally located just minutes from the Oldsmar Trail, numerous parks including R.E. Olds Park and Mobbly Bayou Beach Park, shopping centers, and a variety of dining options, this exceptional home offers the perfect combination of location, space, and extensive upgrades. Schedule your private showing today!

601 Shore Drive E, Oldsmar
$449,000
3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit One SubDv. ⋅ 34677 Zip Code
**PRICE IMPROVEMENT** Your opportunity just got better.! This beautiful home is now offered at a NEW LOWER PRICE.! If you’ve been waiting for the right time to make a move. This Is It.!!! Welcome to one of Oldsmar's hidden gems! This beautifully maintained 3-bedroom, 2-bath pool home is nestled in the highly desirable Harbor Palms neighborhood, offering the perfect combination of location, comfort, and the Florida lifestyle. The bright split-floor plan features premium laminate and tile flooring, a spacious living room with French doors leading to your private backyard oasis, a formal dining room with a picture window, and a beautifully appointed kitchen with granite countertops, wood cabinetry, and stainless-steel appliances, to include a Point of use Reverse Osmosis Water Purification System. The interior laundry room includes the washer, dryer, and ample storage cabinets. The spacious primary suite offers dual walk-in closets and a beautifully updated en-suite bath with quartz countertops, soft-close cabinetry, and a custom-tiled walk-in shower. Step outside to the screened, covered lanai overlooking a sparkling pool with a tranquil waterfall. The pool is equipped with a child safety fence, which is included with the home. The oversized, fully fenced backyard offers plenty of room to entertain, relax, or enjoy Florida's year-round sunshine. Ideally located just a short walk or bike ride to the neighborhood's beloved Sheffield Park, featuring playgrounds. You'll also enjoy being just 25 minutes from Honeymoon Island and Tampa International and St. Pete-Clearwater airports, and only minutes from shopping, dining, and everyday conveniences. Opportunities like this in Oldsmar are rare—don't miss your chance to own this move-in-ready Florida retreat.

416 Maplewood Drive, Oldsmar
Start Your Search