Oldsmar Homes with Gated Community - No Guard Community Features

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

Virtually Staged. Welcome to effortless Florida living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo, ideally situated within the gated community of East Lake Woodlands. Offering a spacious great-room floor plan and a recently remodeled interior, this charming residence combines comfort, convenience, and a relaxed resort-style lifestyle. The inviting kitchen has been upgraded with tile countertops and a contemporary backsplash, creating a stylish and functional space for everyday living and entertaining. The main living areas and bedrooms feature comfortable carpeting, while both bathrooms offer neutral finishes and appointments, providing a versatile backdrop for your personal decorating style. The generously sized primary bedroom offers an abundance of space and features two walk-in closets for exceptional storage. Sliding glass doors provide easy access to the private screened-in porch, where you can unwind with your morning coffee or enjoy a peaceful evening while taking in relaxing views of the expansive green space. The porch also provides convenient access to the laundry closet. Recent improvements include a new hot water heater installed in 2026, offering added peace of mind for the new owner. The condo also includes covered carport parking conveniently located next to the mailbox, making everyday living even more convenient. Residents of this quiet, well-maintained gated community have access to a beautiful community pool, providing the perfect setting for cooling off, relaxing, or entertaining guests. For those seeking an even more elevated country-club lifestyle, residents have the option to join Ardea Country Club for an additional fee. Membership opportunities include access to an impressive array of amenities, including: Two championship 18-hole golf courses, Pickleball and tennis courts, Olympic-style lap pool, Fitness center, On-site restaurant A variety of social activities and events Beyond the community, the location offers exceptional convenience. Enjoy easy access to airports, medical facilities, shopping, restaurants, beautiful Gulf beaches, and a wide variety of entertainment and recreation, all just a short drive away. Whether you're looking for a full-time residence, a seasonal retreat, or a low-maintenance Florida getaway, this lovely East Lake Woodlands condo offers comfort, convenience, and carefree living in a peaceful country-club setting.

110 Lakeside Court Unit 110, Oldsmar

$1,700,000

4 Beds ⋅ 4 Baths ⋅ Preserve, The SubDv. ⋅ 34677 Zip Code

Pre-Construction. To be built. TO-BE-BUILT CUSTOM HOME- An exceptional opportunity to build your dream home in the prestigious East Lake Woodlands community. Located within The Preserve, this proposed custom residence is situated on a beautiful homesite in a double-gated, private golf community, offering an unparalleled combination of privacy, security, and an exceptional lifestyle. This proposed custom home offers approximately 3,530 square feet of heated living space and 4,465 square feet total under roof, featuring 4 bedrooms, 4 full bathrooms, a private den, and a 2-car garage. The thoughtfully designed floor plan showcases spacious living areas and a modern custom-home concept designed to complement this exceptional homesite. The property is offered as a to-be-built custom home package, including the lot. The floor plan, renderings, and images are provided as a representation of the proposed residence and are intended to showcase the potential of this custom-home opportunity. However you can choose the paint, finishes, cabinets and flooring. OR----- Create your own home, floorplan, size, dimensions and layout! Minimum square footage is 3500sf. Please note: This is a proposed home and has not yet been constructed. Floor plans, renderings, dimensions, finishes, features, and specifications are conceptual and subject to change. Final design, construction, selections, and approvals are subject to builder, buyer, architectural review, association requirements, and applicable governmental approvals. A rare opportunity to secure a beautiful homesite and create a brand-new custom residence in one of Oldsmar's most desirable communities.

1332 Preservation Way, Oldsmar

$584,900

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

$379,900

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

$389,900

2 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

Virtually Staged. WELCOME TO WATERFRONT LIVING IN BAYSIDE TERRACE! Built in 2019, this spacious 2-bedroom, 2.5-bath townhome with an oversized loft offers 1,888 SF of beautifully designed living space in a gated community along Tampa Bay. The open-concept main level is designed for everyday living and entertaining, featuring real wood cabinetry, quartz countertops, included appliances and a large walk-in pantry. Storage is abundant throughout the home, with generous closets and thoughtfully designed storage space rarely found in townhome living. The dining and living areas flow effortlessly to a private screened porch, perfect for enjoying Florida living year-round. A ONE-YEAR-OLD A/C adds comfort and peace of mind! Upstairs, both oversized bedrooms feature private en-suite baths and excellent closet space, while the exceptionally spacious loft offers even more flexibility for a home office, media room, gym, playroom or second living area. The lifestyle continues outside your front door! Bayside Terrace offers resort-style amenities directly on Tampa Bay. Relax by the waterfront pool and enjoy spectacular west-facing sunsets from the cabanas, fish from the private community dock, or launch your kayak or paddleboard directly onto the bay. The community is gated with 24-hour virtual guard service, and pets are welcome! HOA fees include water, sewer, trash, basic cable, community amenities, maintenance, escrow reserves and 24-hour guard service. Leasing is permitted after two years of ownership. Centrally located in Oldsmar, with convenient access to Tampa, Clearwater, Westchase, Palm Harbor and Safety Harbor, plus nearby shopping, dining, parks, golf, recreation, Tampa International Airport and the Gulf beaches. Spacious. Storage-packed. Gated. Waterfront. Resort-style living. Come experience everything 2404 Arch Ave has to offer!

2404 Arch Ave, Oldsmar

$2,300,000

7 Beds ⋅ 5 Baths ⋅ Preserve The SubDv. ⋅ 34677 Zip Code

Welcome to an exceptional 7-bedroom, 4½-bath estate nestled within the prestigious double-gated community of East Lake Woodlands in Oldsmar. Set on over half an acre and backing directly to a peaceful preserve, this remarkable property offers an unparalleled sense of privacy, tranquility, and security. Recently updated and beautifully refreshed, the home features a newly renovated kitchen, newly renovated bathrooms, newly renovated laundry room, newly refinished floors, and fresh interior paint throughout. The spacious and versatile floor plan provides abundant room for comfortable living and entertaining, with generously sized bedrooms and a dedicated office and fitness room with a built-in sauna, creating your own private space to work, exercise, and relax. Step outside to your private Florida retreat, complete with a sparkling pool and expansive deck, surrounded by lush greenery and the natural beauty of the preserve. The peaceful preserve backdrop creates a rare feeling of seclusion while providing a beautiful setting for morning coffee, outdoor dining, entertaining, or simply enjoying the Florida sunshine. Located within a premier golf community, East Lake Woodlands offers an exceptional lifestyle surrounded by mature landscaping and natural beauty, with championship golf, tennis, pickleball, fitness facilities, resort-style amenities, dining, and social activities. Conveniently located near local shops, restaurants, cafés, grocery stores, parks, and everyday conveniences, while offering easy access to some of the area's most beautiful Gulf Coast beaches, including Honeymoon Island, Clearwater Beach, and Caladesi Island. Tampa International Airport is also easily accessible for convenient travel. With seven bedrooms, 4½ bathrooms, over half an acre, preserve frontage, a private pool, dedicated office and gym, built-in sauna, newly renovated kitchen and laundry room, updated bathrooms, refinished floors, and fresh paint, this extraordinary estate offers the perfect combination of luxury, privacy, space, and Florida lifestyle.

1330 Preservation Way, Oldsmar

$565,000

3 Beds ⋅ 2 Baths ⋅ Bay Arbor SubDv. ⋅ 34677 Zip Code

MOVE-IN READY in the gated Bay Arbor community of Oldsmar! This beautifully updated 3-bedroom, 2-bath home is ready for its new owners. Major improvements have already been taken care of, including a brand-new roof, screened patio and fresh interior and exterior paint, allowing you to move in and enjoy from day one. The desirable split-bedroom floor plan offers privacy and an easy flow for everyday living. The open kitchen and family room combination creates a welcoming central gathering space, while the spacious primary suite offers a separate office or sitting area, providing the flexibility for a home office, reading room, or private retreat. The primary bath features dual vanities, a separate shower, and a relaxing Jacuzzi tub. Step outside to the screened-in patio and enjoy peaceful conservation views in a private backyard setting. With no rear neighbors, this is a wonderful place to unwind while enjoying the Florida outdoors. Additional features include an inside laundry room with washer and dryer included, a two-car garage, and plenty of storage. Located within the gated Bay Arbor community, residents enjoy access to a community pool and playground along with beautifully maintained neighborhood grounds. The Oldsmar location offers convenient access to shopping, restaurants, parks, recreation, Tampa International Airport, and major roadways, with easy access to both Pinellas and Hillsborough County. A well-maintained home, a desirable gated community, a peaceful conservation setting, and the big-ticket updates already completed—this one is truly ready for its next chapter.

353 Bay Arbor Boulevard, Oldsmar

$275,000

2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code

Virtually Staged. Welcome home to this beautiful END UNIT & FULLY UPDATED 2BR/1.5BA townhome in the gated Countryside Key community, offering the rare benefit of an extra-large side yard for addl. outdoor space & privacy. Even better, assoc. fees INCLUDE water, trash, cable & internet! With extensive improvements, an enclosed patio, reserved parking directly in front, & an outstanding Pinellas County location (NON-FLOOD ZONE), this home is truly move-in ready. Step inside to an inviting open first floor designed for comfortable everyday living & entertaining. The kitchen features quartz countertops, custom cabinetry installed in '22, including larger cabinets providing excellent storage. The owners thoughtfully removed the upper cabinetry around the sink & counter area, creating a more open feel and better connection between the kitchen & adjoining living space. Updated appliances, lighting & ceiling fans complement the space, while no popcorn ceilings on either the first or second floor give the home a clean, updated look. Fresh interior paint was completed in August '26. Just beyond the main living area, the enclosed patio creates additional flexible space to relax, entertain, work from home, or just enjoy throughout the year. As an end unit, this home also possesses an extra-large side yard, providing additional outdoor space & separation rarely found with townhome living. Upstairs, the spacious primary suite features large dual closets, built-in bookshelves (providing both character & functional storage), while the generous windows bring an abundance of natural light into the space. Relax in the large private upgraded bathroom to complete the suite! The home has also benefited from an impressive list of improvements. HVAC, water heater & appliances were replaced in '22, along with new attic insulation in '22, washer & dryer in '24, & new light fixtures & ceiling fans. A new impact-rated rear door window was added in '22 for enhanced security, & exterior doorknobs, deadbolts & keys were also replaced. More recently, the home received new exterior paint in '26 & new interior paint in '26. Enjoy the everyday convenience of reserved parking directly in front of the unit's door, along with ample guest parking throughout the gated community & specifically near this unit! Countryside Key also offers a community pool overlooking the pond, tennis courts, & a designated storage area for camper vehicles, boats, trailers, &/or commercial vehicles (subject to association requirements - see HOA). This INCREDIBLE LOCATION is conveniently positioned near the Hillsborough County line & just minutes from the charm, restaurants, waterfront parks & activities of Safety Harbor. You're also only 8.7 miles from beautiful Honeymoon Island State Park and its Gulf beaches, with convenient access to Tampa International Airport, shopping, dining, entertainment and major roadways connecting you throughout the Tampa Bay area (all points). This Countryside Key townhome offers an exceptional combination of privacy, convenience, value & move-in-ready living.

279 Countryside Key Boulevard, Oldsmar

$489,000

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

** Seller is willing to work with buyers on owner financing options, or a substantial buy-down on buyer's interest rate** Welcome to refined coastal living in this beautifully appointed 3-bedroom, 2.5-bath townhome located within a highly desirable waterfront community in Oldsmar. Offering a blend of contemporary design, quality construction, and low-maintenance living, this home is ideal for those seeking comfort, style, and convenience. This home, built in 2018, feels like brand new construction. Even though the home is only 8 years old, it shows like new construction, as it has only been lived in a short period of time over the past 8 yrs. Enter the home through the leaded glass front door and you’ll appreciate the bright, open-concept layout. Wood-look ceramic tile flooring extends throughout the entire home without transitions. The spacious living and dining areas are filled with natural light and flow seamlessly into the well-designed kitchen. The kitchen features contemporary cabinetry, premium quartz countertops, stainless steel appliances, and generous workspace for preparing meals and gathering with family and friends. Modern finishes, and carefully selected details create a polished and cohesive look throughout the home. Upstairs, the spacious primary suite offers a comfortable private retreat with a well-appointed en-suite bathroom and generous walk-in closet space. Two additional bedrooms provide flexibility for guests, family members, or a dedicated home office. A large loft creates valuable additional living space and is perfect for a media room, family room, play area, or home office. The 2nd floor also has a huge laundry room convenient to all bedrooms. Your garage is finished with an epoxy paint on the surface making for a very attractive and functional space. One of the home’s most appealing features is the private backyard setting with no direct rear neighbors. The covered rear porch provides a peaceful place to relax, entertain, or enjoy the outdoors while overlooking a more open and secluded backdrop. Home is being sold with washer & dryer, water softener and the water heater was replaced under a year ago. Energy-efficient windows and doors help enhance year-round comfort, while modern construction standards provide added peace of mind. Residents enjoy access to an impressive selection of community amenities, including a clubhouse, fitness center, resort-style pool, gated entry, sidewalks, and a community fishing pier. Conveniently located near parks, walking trails, shopping, dining, and entertainment, the community also offers easy access to Tampa, St. Petersburg, Clearwater, and the area’s beautiful Gulf beaches. Whether you’re searching for a primary residence or a low-maintenance Florida retreat, this exceptional home delivers stylish finishes, backyard privacy, generous living space, and an outstanding Tampa Bay location.

1103 Mango Court, Oldsmar

$168,000

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. Low maintenance living because the fee $568/month include water, sewer, trash, internet and cable. For utilities pay only electric. 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, one half 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

$799,000

4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code

Virtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within Cross Pointe, a gated community inside the prestigious guard gated golf community of East Lake Woodlands . Offering 4 bedrooms, 3 baths, a spacious 2-car garage,with workbench area. and bonus space. This beautifully appointed residence blends elegant finishes, thoughtful design, and exceptional outdoor living. Pool access & views from almost every room. Desirable split-bedroom floor plan features soaring ceilings and travertine flooring complemented by engineered hardwood & tile floors. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring Bosch and Frigidaire appliances, (Range has induction cooktop & convection/air fry oven) quartz tops, crisp white cabinetry, and a striking navy island. Breakfast area overlooking pool. The family room offers a warm wood-burning fireplace (updated 2020) and a sophisticated navy wine bar, creating an inviting gathering space. Spacious primary suite includes a comfortable sitting area and sliders that open directly to the screened porch, offering beautiful views of the private pool and backyard . Walk-in closet with organizers. Primary bath has soaking tub, large marble shower, private water closet & dual sink vanities. 3 guest bedrooms, with one having an ensuite bath also providing convenient access to the pool area—perfect for effortless poolside living. Bonus/Flex room with its own A/C (2026) is perfect for an office, hobby room, studio, gym, etc. Outdoor living is truly exceptional. The screened rear porch features paver flooring and overlooks the Saltwater PebbleTec pool , complete with Caribbean blue tile, a charming, soothing waterfall and gazebo. Pool pump & new salt system (2025). An expanded paver patio (2025) extends into the private backyard, providing ample space for entertaining, relaxing, and enjoying the peaceful surroundings. Many updates include tile roof (2019), HVAC (2017), Water Heater (9/2026), Paver patio (2022), Kitchen updated (2020) with professional kitchen cabinet refinishing (2026), Bosch refrigerator (2025), Frigidaire appliances (2026). All ceiling fans updated (2024 & 2025). Newly textured ceilings (2022), modern lighting. With its luxurious finishes, spacious layout, updated kitchen, resort-style pool, and prime location within two prestigious gated communities, this home offers an exceptional Florida lifestyle with privacy, comfort, and elegance at every turn. Centrally located to Tampa International and St . Pete/Clearwater Airport, award winning beaches, boating and fishing, professional sporting events, historic Dunedin and Safety Harbor, Pinellas and Duke Energy Bike Trails, restaurants, shopping, and hospitals. East Lake Woodlands is a golf community with an optional membership available to the nationally renowned ELW Country Club, featuring outstanding amenities including two championship golf courses, sixteen tennis courts, pickleball, fully-equipped fitness center, lap & freeform pools, splash pad, dining, full social calendar/club, and is also part of ClubCorp/Invited with reciprocal rights to 300+ clubs. Low HOA and NO flood insurance required. A fantastic value! Call today for your private tour!

1723 Captiva Drive, Oldsmar

$229,500

2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code

Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar

Oldsmar Homes with Gated Community - No Guard Community Features

Newest Oldsmar Homes with Gated Community - No Guard Community Features