Oldsmar Homes with Attached Property Description

Welcome to Oldsmar, a charming city located in Pinellas County, Florida. Known for its picturesque scenery, vibrant community, and convenient location, Oldsmar offers a perfect blend of suburban tranquility and urban amenities.

If you're looking for homes with attached properties in Oldsmar, you're in for a treat. True to its reputation for beautiful architecture and thoughtful design, Oldsmar boasts a variety of homes with attached properties that cater to different preferences and lifestyles. Whether you're seeking a cozy townhouse or a spacious duplex, you'll find a range of options to choose from in this lovely city.

Living in a home with an attached property in Oldsmar means enjoying the convenience of having additional space for your needs, whether it's for storage, entertaining guests, or simply relaxing in your own outdoor oasis. With well-maintained properties and a strong sense of community, Oldsmar is the ideal place to put down roots and create lasting memories.

Experience the best of Florida living in Oldsmar, where homes with attached properties offer comfort, style, and functionality in one delightful package. Come and discover your dream home in this welcoming city that truly has it all.

Newest Oldsmar Homes with Attached Property Description

$200,000

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code ⋅ TB8523772 MLS ⋅ Active Status

PRICE REDUCED!! Call to schedule your private showing of this beautifully furnished 2-bedroom, 2-bath upstairs condominium in the highly desirable gated community of East Lake Woodlands. Perfectly positioned in a quiet setting, this light-filled home welcomes you with soaring vaulted ceilings and an abundance of natural light streaming through the upper windows, creating a bright and spacious atmosphere you'll love coming home to. Designed for comfortable Florida living, this fully furnished condo is move-in ready. Snowbirds and seasonal residents can simply bring their clothes and groceries—everything else is already here, making your Florida getaway effortless. Enjoy refreshing breezes from two private screened patios. Sip your morning coffee as the sun rises or relax in the evening with your favorite beverage while taking in the peaceful surroundings. The screened balcony is accessible from both the spacious living room and the primary bedroom, creating a seamless indoor-outdoor lifestyle. The split-bedroom floor plan offers privacy for both owners and guests. The generous primary suite features a large walk-in closet and a private en-suite bathroom, while the guest bedroom is thoughtfully separated by the guest bath and closets, making it ideal for family and visitors. A convenient laundry closet with a washer and dryer is located on the screened kitchen patio and is easily accessible from both the kitchen and the guest bedroom. East Lake Woodlands is a beautifully maintained 24-hour guard-gated golf community where residents enjoy secure access with resident vehicle passes and a peaceful country club atmosphere. Optional memberships offer golf, tennis, fitness, dining, and social activities. Located at the corner of Tampa Road and East Lake Road, you'll be just minutes from grocery stores, shopping, restaurants, medical facilities, and entertainment, with beautiful Gulf beaches and Tampa International Airport only a short drive away. Whether you're looking for a seasonal retreat or a full-time Florida residence, this exceptional condo offers comfort, convenience, and the carefree lifestyle you've been dreaming about.

124 Woodlake Wynde, Oldsmar

$175,000

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code ⋅ TB8515822 MLS ⋅ Active Status

Welcome to Gull-Aire Village, one of Pinellas County's most desirable and active 55+ communities! Don't miss this opportunity to own a home in the highly sought-after Gull-Aire Village, where you own the land and enjoy an incredibly affordable HOA fee of just $70 per month. Whether you're looking for a full-time residence, seasonal retreat, or future investment property, this community offers exceptional flexibility with the ability to rent your home after only one year of ownership. Gull-Aire Village is known for its vibrant atmosphere, active social calendar, and unbeatable location. Residents enjoy the convenience of being within walking distance to shopping, entertainment, and dining, including AMC Theatres, Bealls, Marshalls, Earth Fare, PetSmart, and Dollar Tree. Nearby restaurants include Shaker & Peel, Craft Street Kitchen, and Eve's Family Restaurant. Additional conveniences such as Westfield Countryside Mall, Walmart, Publix, and Countryside Hospital are just minutes away. Plus, you'll be approximately 20 minutes from the award-winning beaches and natural beauty of Honeymoon Island and Caladesi Island State Park. Pet friendly with one pet allowed of any size. Experience affordable Florida living in a welcoming community that truly has it all. Schedule your private showing today! Cash only for the ease of the seller.

410 Dolphin Drive S, 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

$650,000

4 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8496402 MLS ⋅ Active Status ⋅ 138 BLDG.

Welcome to 138 Brent Circle in desirable gated Seaside Estates—an exceptional opportunity to own the largest corner townhome in this sought-after waterfront community in Oldsmar. Perfectly positioned to capture panoramic views of Tampa Bay, this residence offers a rare combination of space, scenery, and coastal lifestyle, complete with a private boat slip for easy access to the water. This spacious 4-bedroom, 3-bath home features a thoughtfully designed layout with abundant natural light and comfortable living areas ideal for both everyday living and entertaining. The inviting living room is anchored by a cozy fireplace, creating a warm focal point while showcasing the stunning water views beyond. A second fireplace in the primary bedroom adds an extra layer of comfort and charm, creating a relaxing private retreat. The kitchen offers ample cabinetry and workspace, seamlessly connecting to the dining and living areas for a functional, open feel. Each bedroom provides flexibility for a variety of living arrangements, while the three full bathrooms add convenience and comfort. An oversized garage delivers generous storage and parking space—an added benefit rarely found in townhome living. As a corner unit, the home enjoys enhanced privacy and additional natural light. Step outside and take in the tranquil waterfront setting, where you can relax, entertain, or set out for a day on Tampa Bay directly from your own boat slip. Conveniently located near parks, shopping, dining, and major roadways, this property offers the perfect blend of peaceful coastal living and everyday accessibility. Don’t miss your chance to own a premier waterfront residence in Seaside Estates—schedule your private showing today.

138 Brent Circle, Oldsmar

$189,900

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8485863 MLS ⋅ Active Status ⋅ East Lakes BLDG.

Welcome home to peaceful, easy living in the heart of East Lake Woodlands. This beautifully updated 2-bedroom, 2-bathroom condo features brand-new waterproof laminate flooring throughout the main living areas for a modern, low-maintenance feel, with cozy carpet exclusively in the bedrooms. Enjoy ultimate peace of mind with a newer HVAC system (only 15 months old). The spacious primary suite serves as a true retreat, highlighted by an impressive three walk-in closets, providing exceptional storage rarely found in condo living. Residents can enjoy tranquil surroundings and unwind at the community pool, creating a relaxed Florida lifestyle. Conveniently located in Oldsmar, this home offers easy access to shopping, dining, beautiful Gulf beaches, and Tampa International Airport, making commuting and travel effortless.

303 Martha Lane Unit 303, Oldsmar

$380,000

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code ⋅ W7883526 MLS ⋅ Active Status ⋅ Na BLDG.

This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor, providing added privacy and a more open feel from the lanai. Grilling is allowed in the backyard area, giving you the ability to enjoy outdoor cooking and entertaining. The home has been meticulously kept and shows true pride of ownership. It also includes a private 1 car garage for secure parking and additional storage. Upon entering, you immediately notice the ultra-modern feel and the exceptionally well-maintained condition of the property. The spacious kitchen features an extra-large island that is so generously sized it feels like it has its own zip code, along with an under-mount sink, quartz countertops, stainless steel appliances, and a walk-in pantry. The main living area has tile flooring throughout, creating a clean and seamless look, and opens to a screened-in lanai with brick pavers for easy indoor and outdoor living. Upstairs, the upgraded Berber-carpeted staircase with elegant railing leads to a loft area and all bedrooms. The primary suite is generously sized and includes multiple walk-in closets and a beautifully designed en-suite bathroom. Bedrooms two and three each feature carpeting and their own walk-in closets, offering excellent storage and flexibility. The home also includes hurricane shutters stored in the garage, providing added storm protection and peace of mind. Bayside Terrace offers resort-style amenities including a waterfront infinity heated salt-water pool, a covered pavilion overlooking the water, a cabana, two BBQ grills, a gas fire pit, a fitness center, clubhouse, and a dock with kayak and canoe launch access. The gated entrance and deed restrictions add an extra layer of privacy and security, while the waterfront setting allows residents to enjoy Florida sunsets and an active coastal lifestyle. Please view two videos: Tour 1 & Tour 2.

1505 Sunset Wind Loop, Oldsmar

$239,000

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8480878 MLS ⋅ Active Status

Located in East Lake Woodlands this quiet private second-story unit offers serene views overlooking the golf course and has a bright welcoming interior. Thoughtfully remodeled throughout, the home features abundant cabinet space, newer appliances, and major system upgrades including air conditioner and furnace. The unit has been tastefully finished with beautiful Florida-style decor, creating a light and relaxed atmosphere, perfect for full-time living or a seasonal retreat. Enjoy privacy, natural light and tranquil surroundings. Pool recently renovated and heated. Furnishings included if desired. Room measurements are estimated. Buyer agent and buyer to verify

104 E Cypress Court Unit 104, Oldsmar

$374,000

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8476573 MLS ⋅ Active Status ⋅ Seaside Estates BLDG.

PRICE IMPROVEMENT – NOW $25,000 LESS! Motivated seller has made a significant $25,000 price reduction, making this beautifully maintained home an exceptional value. Don't miss your opportunity to own this move-in-ready property at its new attractive price! Welcome to this stunning gated luxury townhome in the highly sought-after waterfront community of Seaside Estates! This beautifully maintained residence offers an exceptional blend of comfort, style, and coastal living. The open-concept main level features gorgeous bamboo hardwood flooring, a cozy fireplace, and a private balcony with scenic views, while the expanded kitchen (extended by 3 feet in 2021) provides extra functional space for everyday living and entertaining. This spacious floor plan includes 3 full baths and a flexible main-level third bedroom perfect for a home office, study, or guest retreat. The impressive primary suite features a private balcony, soaring ceilings, dual walk-in closets, and a spa-like bath, while bedroom two offers an ensuite bath and tranquil water views of Tampa Bay. The oversized 2–3 car tandem garage offers abundant storage and sliding doors to a ground-level patio with access to the dog walking trail. Residents enjoy a resort-style pool and spa, tennis courts, scenic boardwalk, and a community day dock with direct Tampa Bay access for kayaking or small boats, all just minutes to top dining, shopping, beaches, Tampa International Airport, and only a short walk to R.E. Olds Waterfront Park. Extensive updates include bamboo flooring (2021), kitchen expansion (2021), updated light fixtures and interior paint (2021), roof (2017), A/C (2013), water heater (2019), new toilets (2025), new faucets (2026), new washer (2025), blinds including electric living room blinds (2016), balcony floors painted (2025), balcony railing painted (2024), and quality appliances including GE washer (2024), GE cooktop (2021), LG refrigerator (2021), Bosch microwave drawer (2021), Blomberg dishwasher with panel (2021), and Hauslane range hood (2021). Immaculate and move-in ready — schedule your private showing today!

106 Brent Circle, Oldsmar

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,