Oldsmar Homes with Community Mailbox Community Features

Oldsmar Homes with Community Mailbox Community Features

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County. With its charming blend of small-town warmth and modern conveniences, Oldsmar offers residents a unique lifestyle enriched by nature, community spirit, and vibrant local culture. Just a stone's throw from the stunning Gulf Coast beaches, this picturesque city is perfect for those seeking a serene yet active lifestyle.

Oldsmar is well-known for its lush parks, scenic waterfront, and a plethora of recreational activities. Whether you enjoy hiking, biking, or simply soaking in the sun, the city's numerous parks and nature trails are sure to delight. The Oldsmar City Hall, with its beautiful architecture and community events, is a centerpiece of local life, showcasing the city's commitment to fostering a strong sense of community.

When it comes to housing, Oldsmar boasts a variety of options to suit every lifestyle. One of the standout features of many homes in this area is the Community Mailbox, which fosters a sense of camaraderie among neighbors. Imagine the convenience of gathering your mail while engaging in friendly conversations with fellow residents. This feature not only enhances the community feel but also encourages social interactions, making it easy to forge lasting friendships.

With its ideal location, welcoming atmosphere, and diverse housing options, Oldsmar is more than just a place to live—it's a community where you can thrive. Explore the charm of Oldsmar today and discover why so many are proud to call this beautiful city home!

Newest Oldsmar Homes with Community Mailbox Community Features

$399,000
2 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
Welcome to waterfront living at its best! Located on beautiful Old Tampa Bay, this exceptional community offers a relaxed Florida lifestyle with amenities designed for everyday enjoyment and entertaining. Gather with friends around the gas firepit, share a meal beneath the pavilion with two grills, or relax in the large heated infinity pool while taking in beautiful water views. Stay active in the fully equipped gymnasium, fish from the pier extending into the bay, or launch a kayak for an afternoon on the water. The electronically gated entrance provides added security. Ideally situated directly across from the pool, this residence truly stands out. Beautiful landscaping and lush greenery welcome you at the entrance, while thoughtful enhancements continue throughout, including a gleaming epoxy-finished garage floor and garden-like screened porch. The porch creates a wonderful outdoor retreat for morning coffee, relaxing evenings, or entertaining guests. Inside, beauty and functionality continue. The entire first floor features beautiful tile flooring for a polished appearance and easy maintenance. In 2024, all recessed lighting was upgraded to LED bulbs, with downstairs lights featuring dimmers and amber-light options for the perfect ambiance. Even the spacious walk-in pantry has automatic lighting that illuminates the generous storage space when the door opens. The open-concept main living area is perfect for entertaining and everyday life, offering space for a full dining table and casual dining at the granite breakfast bar. Numerous light-gray cabinets provide abundant storage, complemented by a convenient coffee bar and mini-mudroom near the garage entrance. The living area flows effortlessly through pocket sliders to the screened porch, creating a wonderful indoor-outdoor living experience. A conveniently located half bath completes the first floor, while Custom Nantucket remote-control shades provide privacy and light control. Upstairs, a generous flex room offers incredible versatility as a den, second family room, playroom, home office, or temporary third bedroom. The nearby laundry room adds convenience. The primary suite offers a peaceful retreat with an expansive granite double-sink vanity, abundant storage, glass-enclosed shower, beautiful natural light, decorative tray ceiling, and custom walk-in closet with built-in shelving. Custom Nantucket remote shades complete the space. The spacious second bedroom is equally inviting, with natural light, decorative tray ceiling, and exceptional storage. Two closets, including a very large walk-in, provide plenty of room. The second full bath features wood cabinetry, pull-out drawers, granite countertop, and glass-enclosed shower. Additional upgrades include a new electrical panel installed in 2024 and gutters added in 2021 along with the undercounter lighting and downstairs crown molding. The location offers convenient access to Tampa, area airports, major shopping, restaurants, beautiful beaches, and more. With its waterfront setting, resort-style amenities, thoughtful upgrades, flexible living spaces, and outstanding location, this home offers an exceptional opportunity to enjoy the Florida lifestyle.

3010 Palm Key Avenue, 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
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
$510,000
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
$179,950
2 Beds ⋅ 2 Baths ⋅ Meadows Of East Lake Woodlands SubDv. ⋅ 34677 Zip Code
Welcome to 106 Windward Place, a two bedroom two bathroom condominium located in the Meadows at East Lake Woodlands. One of Oldsmar‘s most sought after gated communities. This is a bank owned (REO) property, an excellent opportunity for homeowners, investors, or buyers looking to customize a home of their own taste. The functional floor plan features a spacious, living and dining area, split bedroom, layout, and a private setting within the community. The Meadows offers beautifully maintained grounds, mature landscaping, and a peaceful residential atmosphere. Residents enjoy convenient access to shopping, dining, golf, parks, Tampa International Airport and the Beautiful Gulf beaches. Whether you are searching for a primary residence, seasonal getaway or investment property 106 Windward Place offers outstanding value and the chance to own within the desirable East Lake Woodlands community. Property is being sold as is.

106 Windward Place, Oldsmar
$525,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days on the water at a moment's notice. Inside, the home unfolds into an open, light-filled floor plan enhanced by soaring high ceilings and expansive windows that invite natural light throughout the day. The seemless flow between living, dining, and kitchen spaces creates an ideal setting for both RELAXED everyday LIVING and entertaining. Water views provide a constantly changing backdrop, adding a sense of CALM and CONNECTION to the outdoors. The generous layout offers flexibility for hosting family and guests, while the airy ceiling heights add architectural drama and a sense of openness rarely found in townhome living. Whether you're enjoying quiet mornings with coffee by the water or gathering with friends after a day on the boat, this home adapts effortlessly to your lifestyle. Outdoor living is just as compelling, with immediate access to the waterfront and your own boat slips just steps away - perfect for boating, paddleboarding, or sunset cruises. This is a home that blends convenience and luxury, offering the maintenance ease of a townhome with the experience of a private gated waterfront retreat. Ideally suited as a primary residence or a refined second home, this property delivers the best of waterfront living - space, light, and direct access to the water- all in one elegant package.

119 Brent Circle, Oldsmar
$224,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Beautiful First floor Condo in highly sought community of East Lake Woodlands. 2 BR, 2 BA, 1,094 sq/ft living, offering an unmatched maintenance free lifestyle in one of the Tampa Bay areas finest Communities. Enjoy serene pond views of pond with different species of birds from the Great room, Owners suite and screened covered porch. Updated, re-modeled, immaculately clean and move-in ready. Newer Luxury Vinyl Plank flooring - covering entry, Kitchen, great room/dining and both bedrooms. Kitchen features granite countertops and stainless appliances. Well maintained. Electric panels were retrofitted and updated in 2022. A/C is 6 years old. Maintenance free living with internet, cable, trash, water/sewer and exterior maintenance all covered with HOA fee. Included, Comnunity Pool is a short walk away. East Lake Woodlands is a popular golf course community that offers optional golf course, fitness and social club memberships. Gated and secured with 2 guarded entrances. East Lake Woodlands is central and convenient to many shopping options and healthcare. A short drive to Lake Tarpon, John Chestnut park, area beaches and Tampa International airport. A highly valued lifestyle and amenities all waiting for you!

107 Lakeview Place Unit 7, Oldsmar
$260,000
3 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Back on the market. Fresh and ready to go! Spacious 3-bedroom, 2-bath villa offering 1,385 square feet of comfortable living in desirable East Lake Woodlands. This home features ceramic tile throughout the main living areas and cozy carpet in the bedrooms. The bright living room is lined with sliding glass doors that open to a screened lanai spanning the full length of the villa—perfect for enjoying indoor/outdoor Florida living. The primary bedroom and third bedroom both feature private patio door access to the screened lanai, while ceiling fans in the bedrooms add extra comfort. Enjoy additional outdoor space with a fenced front patio, plus extra storage located on the screened lanai. Your covered carport includes an additional storage unit and comes with one assigned parking space.

260 Michaels Circle, Oldsmar
$149,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to this two-bedroom, two-bath condominium in Oldsmar, offering 1,054 square feet and a flexible opportunity for investors, first-time buyers or seasonal residents. This residence is vacant and ready for immediate occupancy or renovation. The interior reflects the original condition, presenting a value-add opportunity for customization. The primary bedroom includes a walk-in closet, and the layout supports functional living and dining spaces. Recent updates include an air-conditioning system installed in 2025, along with a washer, dryer and refrigerator replaced in 2024. This property is well-suited for buyers seeking to personalize a residence or secure an investment with long-term potential. Conveniently near shopping, dining and commuter routes, supporting full-time and seasonal living.

130 Cypress Lane Unit 130, Oldsmar
$188,000
2 Beds ⋅ 2 Baths ⋅ Meadows Condo At East Lake Woodlands SubDv. ⋅ 34677 Zip Code
Welcome to 204 Windward Place #36, a move-in-ready condominium located in the gated community of East Lake Woodlands, one of Oldsmar's most established residential communities. Offering low-maintenance living in the heart of Tampa Bay, this well-maintained residence combines comfort, convenience, and easy access to everything Florida's Gulf Coast has to offer. Designed with functionality and everyday living in mind, the thoughtfully planned floor plan features bright, inviting living spaces filled with natural light. The open living and dining areas provide flexibility for entertaining, relaxing, or working from home, while the private outdoor living space offers the perfect setting for morning coffee, evening sunsets, or enjoying Florida's year-round tropical climate. Whether you are searching for a primary residence, seasonal retreat, vacation home, or investment property, this move-in-ready condominium offers exceptional versatility and a low-maintenance lifestyle. Assigned parking and convenient guest parking add to the home's everyday convenience. East Lake Woodlands is a gated community known for its mature landscaping, peaceful surroundings, scenic walking areas, and established neighborhood appeal. Residents have the opportunity to join the nearby Ardea Country Club, where optional memberships provide access to championship golf, tennis, pickleball, a resort-style swimming pool, fitness center, dining, and an active social calendar. Ideally located in Oldsmar, this home is just minutes from Tampa, Clearwater, Dunedin, Safety Harbor, Palm Harbor, and St. Petersburg. Enjoy convenient access to award-winning Gulf beaches, Tampa International Airport, shopping, restaurants, parks, medical facilities, entertainment, and major commuter routes, making it easy to experience everything the Tampa Bay area has to offer. Combining an outstanding location, gated community living, and low-maintenance ownership, this East Lake Woodlands residence presents an exceptional opportunity to enjoy the Florida lifestyle in one of Pinellas County's most desirable communities.

204 Windward Place Unit 36, Oldsmar
$189,000
2 Beds ⋅ 3 Baths ⋅ Emerald Bay SubDv. ⋅ 34677 Zip Code
Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 Bathroom Townhome in Oldsmar, AC 7/23, newer luxury vinyl flooring and newer paint.

62 Emerald Bay Drive, Oldsmar
$185,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
**COME ON IN - MAKE YOURSELF AT HOME ** THE PRICE IS RIGHT!! ** Motivated Seller ** This 2 Bed 2 Bath GROUND FLOOR unit has been totally REMODELLED to an exceptionally high standard!! New Floors, New Bathrooms, New Windows, MOVE IN READY!! And what's more?? NOT OVERLOOKED at the rear!!! Enjoy your morning coffee or evening drink on the front enclosed patio or watch the wildlife from the rear patio .. you have a choice!! Within easy walking distance to the pool for relaxation and social. East Lake Woodlands is a fantastic golfing community and is not 5 minutes away from the Boot Ranch range of supermarkets, stores, banks, eateries and more!! THIS CAN BE ALL YOURS!! ** All Information Is Deemed Accurate - Buyer To Verify **

117 E Cypress Court Unit 117, Oldsmar
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