Oldsmar Homes with Community Mailbox Community Features

Oldsmar Homes with Community Mailbox Community Features

Welcome to Oldsmar, a charming city located in Pinellas County, Florida. Known for its small-town charm and friendly community, Oldsmar offers a unique blend of suburban tranquility and urban convenience.

One of the standout features of homes in Oldsmar is the Community Mailbox Community. This feature not only adds to the aesthetic appeal of the neighborhood but also fosters a sense of community among residents. Imagine strolling down the tree-lined streets to pick up your mail, greeting your neighbors along the way – it's the epitome of neighborhood living.

In Oldsmar, you'll find a range of homes with Community Mailbox Community features, from cozy townhouses to spacious single-family homes. Whether you're a first-time homebuyer or looking to upgrade to your dream home, Oldsmar has something for everyone.

Beyond the Community Mailbox Community feature, Oldsmar boasts a variety of amenities and attractions. Explore the quaint downtown area with its local shops and restaurants, or spend a day outdoors at one of the city's parks or nature preserves. With easy access to nearby beaches and major cities like Tampa, Oldsmar offers the perfect balance of relaxation and excitement.

Come discover the beauty and warmth of Oldsmar – where Community Mailbox Community living meets Florida's laid-back lifestyle.

Newest Oldsmar Homes with Community Mailbox Community Features

$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8533834 MLS ⋅ Active Status ⋅ 4 BLDG.
Maintenance free condo living within the prestigious gates of East Lake Woodlands! Pride of ownership abounds in this well maintained first floor unit offering just under 1,100 sq ft of fine Florida living with 2 bedrooms, 2 bathrooms and a convenient covered carport. Open concept floor plan with a great room that combines living and dining spaces ideal for family gatherings and entertaining. Living and entertaining space is extended outside with sliding glass doors leading to a lanai looking out on the community’s well-manicured green spaces. A serene setting for morning coffee or afternoon cocktails. The lanai also houses a convenient storage closet. The spacious kitchen includes an eat-in area and features tile flooring. The appliances include a ceran top range, built-in microwave, refrigerator (5 yrs old) and dishwasher. Privacy prevails with an ideal split bedroom layout. The primary bedroom is located just off the living room and offers generous storage boasting 2 walk-in closets and an additional wall closet and the room offers a sliding glass door to the lanai. The ensuite features a single vanity with dressing area and a walk-in shower. The secondary bedroom is located on the opposite side of the home and features laminate flooring, a wall closet & ceiling fan. The hall bathroom is designed with a single vanity and a tub/shower combination. The hallway laundry closet is perfectly situated for ideal convenience, and the seller is generously including the washer and dryer. Additional features include AC 2022, WH 2022. The HOA includes exterior and grounds maintenance, community pool, water, sewer, trash, cable, internet. This condo is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a convenient location… carefree Florida living!

129 Nancy Drive, Oldsmar
$530,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code ⋅ OM728969 MLS ⋅ Active Status ⋅ 158 BLDG.
Endless sunsets create this picture perfect location in Seaside Estates, situated on 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. Upstairs on 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 suite 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
$289,900
2 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8525574 MLS ⋅ Active Status ⋅ 2 BLDG.
Maintenance free condo living in the sought after community of “Heatherwood” within the gates of prestigious East Lake Woodlands! This lovely first floor, fully remodeled end unit offers you over 1,200 sq ft of fine Florida living. Boasting 2 bedrooms, 2 bathrooms and 1 car garage, this modern open concept floor plan is ideal for family gatherings and entertaining. Lavish comfort from floor to ceiling as you enter to luxury vinyl flooring and soaring ceilings in the spacious great room with an abundance of natural light in your living and dining areas. Gorgeous, updated kitchen overlooks the great room with a convenient breakfast bar, white soft close cabinetry including cabinet pantry, granite countertop, dual undermount stainless steel sink and SS appliances including a ceran top range (2025), built-in microwave, dishwasher (2025) and 3 door refrigerator (2025). Extend your living and entertaining outdoors through the sliding glass doors to the screened lanai area with generous outdoor seating space for family enjoyment. The luxury vinyl flooring continues throughout the ideal split bedroom layout. Privacy prevails! The primary bedroom is located off of the great room and offers an elegant double door entry. The ensuite features white, soft close cabinetry, dual vanities with granite countertops, undermount sinks, linen and wall closets, a full walk-in shower with designer tile accents, ledge seat and glass door. The secondary bedroom is located on the opposite side of the home and features a wall closet & ceiling fan. The updated hall bathroom is designed with a single vanity, granite counter with undermount sink, and a tub/shower combination. A perfectly situated hallway laundry closet leads to the garage. Additional features include AC 2020, WH 2024. The HOA includes exterior maintenance and grounds, community pool, water, sewer, trash, cable, internet and exterior insurance. This premium homesite is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a prime, convenient location… carefree Florida living!

215 Clays Trail, Oldsmar
$179,950
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands SubDv. ⋅ 34677 Zip Code ⋅ TB8521469 MLS ⋅ Active Status ⋅ 01 BLDG.
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 ⋅ TB8504789 MLS ⋅ Active Status ⋅ Seaside Estates BLDG.
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 ⋅ W7885525 MLS ⋅ Active Status ⋅ V BLDG.
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
$275,000
2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8506563 MLS ⋅ Active Status ⋅ 10-60 BLDG.
Buyer financing fell through, now is your opportunity, don't wait to come and see this gorgeous condo! Welcome home to 10 Shamrock Way in sunny Oldsmar, nestled within the highly sought-after East Lake Woodlands community. This beautifully updated, FIRST FLOOR 2-bedroom, 2-bath, 1420sqft condo offers the perfect blend of comfort, privacy, and effortless Florida living. There is a private screened front porch with paver flooring that sets the tone, an inviting space for morning coffee, or quiet reflection as the day begins. Inside, soaring ceilings, natural light, and an open, airy layout create a sense of calm and spaciousness. Every window frames peaceful wooded conservation views, offering a rare level of privacy and a daily connection to nature. The updated kitchen is both stylish and functional, featuring generous cabinetry, added storage, recessed lighting, and a breakfast bar that opens seamlessly to the main living space, perfect for gathering and entertaining. Tile flooring flows through the main areas, while luxury vinyl plank flooring adds warmth to the bedrooms. Ceiling fans throughout and in-unit laundry add to the home’s everyday ease. The primary suite feels like a retreat, complete with two closets, one a walk-in with flexible use and a spacious en-suite bath with dual sinks, a tub, and separate shower. A split-bedroom layout offers comfort and privacy for guests or extended stays. Out back, the screened porch invites you to unwind and take in the quiet beauty of the surrounding conservation. With no stairs and easy ground-floor access, everyday living feels simple and relaxed. Enjoy a maintenance-free lifestyle with a community pool, covered parking, and an HOA that covers cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Just minutes from Tampa International Airport, beautiful Gulf beaches, shopping, and dining and within walking distance to Ardea at East Lake Woodlands Country Club with optional golf membership. Whether you’re looking for a full-time residence or a seasonal escape, this home offers a lifestyle that feels easy, peaceful, and truly inviting.

10 Shamrock Way Unit 10, Oldsmar
$260,000
3 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code ⋅ TB8507054 MLS ⋅ Active Status
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. Currently occupied by excellent tenants. For buyers looking to make this home their own, a lease termination may be negotiated.

260 Michaels Circle, Oldsmar
$149,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8502597 MLS ⋅ Active Status ⋅ 130 BLDG.
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
$350,000
3 Beds ⋅ 3 Baths ⋅ Hayes Park Village SubDv. ⋅ 34677 Zip Code ⋅ TB8501214 MLS ⋅ Active Status
NEW PRICE! Location, location, location is the key to finding the perfect home - and this one delivers on every level. If you have been searching for a place that blends character, convenience, and community, look no further. This charming 3-bedroom home with an attached garage, sits in the picturesque neighborhood of Hayes Park Village, a community that feels like a slice of the French Quarter right here in Florida. Nestled in the heart of the City of Oldsmar, this home offers the best of old-world-charm with modern comfort. Oldsmar is a great City known for having more parks per sq. mile than any other city in the state along with excellent schools and an abundance of activities for all ages. Also, the home of Tampa Bay Downs and Tampa Bay Skating Academy. It is a place where community pride runs deep and quality of life comes naturally. The homes inviting wrap-around porch sets the tone from the moment you arrive. Enjoy your morning coffee as you look out to the neighborhood courtyard complete with a welcoming fire pit, creating the perfect setting for neighborhood gatherings. Inside the home, gleaming hardwood floors flow through an open concept living space that feels both spacious and cozy. The kitchen is beautifully appointed with granite countertops and 36" cabinets and a center island that anchors the room- ideal for cooking, entertaining or simply enjoying daily life. A convenient first floor powder room adds practicality for guest and family alike. The master suite opens to a second floor balcony that overlooks the lake and Richard B. Rogers Park. The Master bedroom also features a tray ceiling with crown molding and an upgraded bathroom with frameless glass shower enclosure and a walk-in closet. Two additional ample sized bedrooms and a guest bath complete the upstairs. THIS HOME HAS BEEN WELL MAINTAINED; ROOF IS JUST OVER A YEAR OLD AND THE AC IS JULY OF 2025, WATER HEATER REPLACED IN 2024. The PERFECT LOCATION connects TAMPA to PINELLAS COUNTY. Close commute to Tampa International Airport and International Mall. Within minutes of Clearwater and downtown Safety Harbor, Approximately 30 minutes to the Gulf Coast Beaches.

208 Cutlass Way, Oldsmar
$169,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8494664 MLS ⋅ Active Status ⋅ 112 BLDG.
Welcome to 112 Cypress Ln in the highly sought-after East Lake Woodlands / Cypress Estates community in Oldsmar. This charming 2-bedroom, 2-bath condo offers comfortable Florida living in a peaceful, gated setting with access to a community pool and beautifully maintained grounds. The home features a functional split floor plan, in-unit laundry, and a private screened patio — perfect for enjoying your morning coffee or unwinding in the evenings. Residents of East Lake Woodlands enjoy access to a range of community amenities, including a clubhouse, golf course, tennis courts, and multiple pool areas, creating a resort-style living experience right in your neighborhood. Ideally located just minutes from shopping, dining, entertainment, and major roadways, this property provides easy access to Clearwater, Tampa, St. Petersburg, and the Gulf Coast beaches. Oldsmar is known for its parks, community events, and convenient lifestyle, making this an excellent option for full-time residents or seasonal living. Property is also available for lease or lease option.

112 Cypress Court Unit 112, Oldsmar
$188,000
2 Beds ⋅ 2 Baths ⋅ Meadows Condo At East Lake Woodlands SubDv. ⋅ 34677 Zip Code ⋅ A4686982 MLS ⋅ Active Status ⋅ Meadows/204 BLDG.
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
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