Location: Oldsmar
Do Not Show Listings
244 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$220,000103 Days on yellowkey MLS ID: TB8465176
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $3,637 (2024)Community: Countryside KeyTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,637
Elementary School: Curlew Creek Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. Brand new fresh carpets. The monthly HOA fees cover a wide range of services, including water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Enjoy the convenience of being just minutes from the shopping, dining, a movie theater, parks, bike trail and more.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Lin Huang (727-417-5186)
904 VINEYARD LN, OLDSMAR, FL 34677
$340,00065 Days on yellowkey MLS ID: TB8479523
0 Days Off yellowkey (back on 4/13/2026)
REDUCED by $10,000 (2.9%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1525 Built: 2017Monthly Fee: $418 Tax: $3,149 (2025)Community: Tuscany Woods PreserveTownhouse
Taxes:$3,149
Elementary School: Forest Lakes Elementary-PN
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Private Preserve Views | Move-In Ready | Optional Turnkey Furnished. Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the gated Tuscany Woods Preserve community. Built in 2017, this newer construction home offers a rare combination of privacy, low-maintenance living, and a peaceful natural setting. The open-concept layout is filled with natural light and designed for everyday comfort and easy entertaining. The kitchen features stone countertops, solid wood cabinetry, stainless steel appliances, and a seamless flow into the living and dining areas. Upstairs, the spacious primary suite offers a walk-in closet and a well-appointed bath with dual vanities and a glass-enclosed shower. Two additional bedrooms provide flexibility for guests, a home office, or additional living space. Step outside to one of the home’s standout features — a covered and screened lanai with an extended paver patio overlooking a private preserve. With no rear neighbors, this is the perfect place to relax and unwind. Additional highlights include a 1-car garage with built-in overhead storage, gated community access, and a convenient central location close to shopping, dining, and major roadways. Furniture is available separately, making this a potential turnkey opportunity for buyers seeking a fully furnished home.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (813-749-0875)
Listing Agent: Peter Gawienczuk (813-743-4178)
291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$258,000105 Days on yellowkey MLS ID: TB8463435
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $2,205 (2025)Community: Countryside KeyTownhouse
Taxes:$2,205
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to the highly sought-after gated community of Countryside Key, ideally located in the heart of Oldsmar! This well-maintained home offers wood laminate flooring, a convenient ground-level laundry closet, and a screened-in lanai with an additional storage closet—perfect for relaxed Florida living. The kitchen opens seamlessly to the dining and living areas, creating an inviting open-concept layout ideal for everyday living and entertaining. Upstairs, you’ll find a desirable split floor plan featuring vaulted ceilings and two spacious, carpeted bedroom suites, each with its own private bath. Residents of Countryside Key enjoy a wealth of amenities, including a secure gated entrance, community pool, tennis courts, and a car wash station. Boat and RV parking are also available. Low monthly HOA fees cover cable, internet, phone, water, sewer, trash, exterior building maintenance, and exterior insurance—offering both convenience and peace of mind. Recent updates include new shut-off valves and a 2024 water heater. Ideally situated near airports, dining, shopping, entertainment, sports venues, and Florida’s award-winning Gulf beaches. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
2208 SUNSET WIND LOOP, OLDSMAR, FL 34677
$365,000184 Days on yellowkey MLS ID: TB8441891
1 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1667 Built: 2019Monthly Fee: $545 Tax: $1,495 (2024)Community: Bayside TerraceTownhouse
Taxes:$1,495
Remarks: Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 bathroom townhome located in the heart of Oldsmar and is ready for a new owner. This spacious open concept has tile throughout the first floor. The stunning kitchen features white cabinets and granite countertops, a breakfast bar that seats 6 comfortably, pendant lighting, stainless appliances, and large pantry. The living room has sliders leading into the screened, paved, and covered patio. Upon entering the second floor, you will be greeted with a large loft area that can be used as an additional living room, library, or whatever your heart desires. The bedrooms are a split floorpan with the primary bedroom on the left while the remaining bedrooms and full bathroom on the right. The primary bedroom has 2 walk-in closets. The primary bathroom has dual sinks and a stand up shower. There is a laundry closet upstairs making it easy to do laundry. This unit also has a one car garage. The community features: a fitness room, pool with cabana, outdoor kitchen with grilling area, community dock, and is gated. Included in the HOA is exterior paint, roof, lawn care, water, were, and wifi/cable.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Yael Hatfield (813-264-7754)
112 BRENT CIR, OLDSMAR, FL 34677
$499,000114 Days on yellowkey MLS ID: TB8461018
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1834 Built: 2004Monthly Fee: $473 Tax: $4,946 (2025)Community: Seaside EstatesTownhouse
Taxes:$4,946
Elementary School: Oldsmar Elementary-PN
Remarks: PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the most updated waterfront townhome in the gated community of Seaside Estates. This beautifully maintained three-story home radiates pride of ownership and offers three bedrooms, three bathrooms, and over 1,800 square feet of thoughtfully designed living space. Premium features include IMPACT WINDOWS, IMPACT SLIDERS, and PLANTATION SHUTTERS, providing extra security, energy savings, and a whisper-quiet interior. Inside, this immaculate townhouse shines with high ceilings, skylights, an open-concept layout, luxury waterproof flooring, and modern updates in the kitchen and all three bathrooms. The inclusive HOA fee covers your roof (replaced in 2017), water, sewer, trash, and fire sprinklers, making this one of the most affordable and low-maintenance lifestyles available. The DEEDED SLIP is perfect for kayaks, jet skis, or a flats boat. Complete with a new AC (2023), 3-car garage, and resort-style pool/spa/tennis, every detail is covered. Located in the heart of Oldsmar, you’ll enjoy easy access to all the best of the Tampa Bay area, including sparkling Gulf Coast beaches, Tampa International Airport, Westshore, Clearwater, and Tampa/St Pete. You’re also just steps away from R.E. Olds Park, a 15-acre waterfront park with the city pier, amphitheater, playgrounds, trails, beach volleyball and more. Whether it’s your primary residence or Florida getaway, this waterfront gem delivers the lifestyle you’ve been waiting for. Schedule your showing today!
Listing Agent: James Wheeler, Pa (813-285-1229)
1001 STARBOARD CT, OLDSMAR, FL 34677
$534,90028 Days on yellowkey MLS ID: TB8492967
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1928 Built: 2019Monthly Fee: $580 Tax: $5,109 (2025)Community: Bayside TerraceTownhouse
Taxes:$5,109
Remarks: Under contract-accepting backup offers. WATERFRONT CORNER UNIT with very LOW, TRANSFERABLE Flood Policy! Don’t miss this once-in-a-lifetime opportunity to own the highly sought-after SANTA ROSA CORNER MODEL in the gated waterfront community of Bayside Terrace. This is the only model of its kind currently available, offering stunning water views of Tampa Bay, unmatched privacy, and an abundance of natural light throughout. This upgraded 3 bedroom, 2.5 bathroom, 2 car garage townhome has been meticulously maintained with attention to every detail. As a corner unit, it enjoys extra windows and sunlight, creating a bright and inviting atmosphere from the moment you walk in. Soaring 18 foot ceilings and an open floor plan showcase breathtaking water and sunset views from the entire main living area. The modern kitchen is both functional and elegant, featuring granite countertops, stainless steel appliances, under cabinet lighting, ample cabinetry, a large island, and a spacious walk-in pantry. Tile flooring spans the main living areas, while upgraded luxury vinyl plank flooring flows through the primary suite, stairs, and entire upstairs, combining style with easy maintenance. Additional upgrades include plantation shutters, sliding blinds, and a water filtration system. Step outside to your private screened lanai and enjoy spectacular sunsets over the bay, all while watching dolphins swim by. The first floor primary suite is a true retreat, offering coffered ceilings, serene water views, a spacious walk-in closet, and a conveniently located laundry area inside the master closet. The spa-like en suite includes dual sinks, a granite vanity, and a walk in shower. Upstairs, a large loft provides a flexible space for a game room, media room, home office, or family room, with partial water views. The two additional bedrooms are generously sized, each with walk-in closets, and share a beautifully updated full bathroom that is perfect for family or guests. The two car garage includes extra shelving and space for kayak storage. Hurricane shutters are included, and this home has never experienced storm surge or water damage from Hurricane Helene, offering rare peace of mind on the water. Bayside Terrace offers resort-style, maintenance-free living with a heated salt water infinity pool, fitness center, clubhouse, fire pit, BBQ area, and a waterfront dock with kayak and canoe launch. Ideally located near Tampa International and St Pete airports, award winning beaches, shopping, dining, and just minutes from Safety Harbor, Dunedin, and Honeymoon Island. Washer and dryer convey. This is a rare, one-of-a-kind opportunity, and the only Santa Rosa Corner Model currently available with the master room downstairs. Schedule your private showing today and secure your dream waterfront home before it’s gone.
Listing is courtesy of: TOM TUCKER REALTY (727-692-3997)
Listing Agent: Dave Doherty (727-639-2371)
209 HEMINGWAY DR, OLDSMAR, FL 34677
$294,90054 Days on yellowkey MLS ID: TB8483445
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1086 Built: 1997Monthly Fee: $240 Tax: $672 (2024)Community: Sun Ketch Twnhms At Cypress LakesTownhouse
Taxes:$672
Remarks: Stunning Sun Ketch Townhome | Bright, Airy & Move-In Ready! Welcome to your slice of paradise in the highly sought-after Sun Ketch community of Oldsmar! This meticulously maintained 2-bedroom, 2-bathroom townhome offers the perfect blend of style, comfort, and convenience. Step inside to find gorgeous, rich cherry floors that flow through the living spaces, adding warmth and a touch of luxury through out. Large sliders, skylights and a thoughtful layout ensure the entire home feels light-filled and spacious. It is exceptionally clean and move-in ready. This unit includes a one-car garage perfect for parking, extra storage, or a home hobby space. Outdoor Living: Enjoy the Florida sunshine at the beautiful community pool, just a short stroll from your front door. Located in the heart of Oldsmar, you’re minutes away from restaurants shopping, scenic waterfront parks, walking trails, 2 airports and easy commutes to both Tampa and the Gulf beaches. Live the easy life in a community known for its charm and quiet atmosphere.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (813-839-3800)
Listing Agent: Melissa Hinchliffe (813-928-0269)
108 BRENT CIR, OLDSMAR, FL 34677
$399,00049 Days on yellowkey MLS ID: TB8483935
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1834 Built: 2002Community: Seaside EstatesTownhouse
Taxes:
Tax Year:
Remarks: Welcome to coastal lifestyle living in one of Oldsmar’s most desirable gated waterfront communities called Seaside Estates. This beautifully maintained home offers the perfect blend of comfort, convenience, and outdoor living just minutes from Tampa Bay. Step inside to an open-concept floor plan filled with natural light, high ceilings, and spacious living areas designed for both everyday living and entertaining. Sliding glass doors create a seamless connection between indoor and outdoor spaces, while the private patio provides the perfect setting for relaxing evenings. The home features a spacious primary suite with ensuite bath, additional guest accommodations, and a flexible office or study space ideal for remote work or hobbies. The open kitchen flows naturally into the main living area, creating an inviting atmosphere for gatherings. Additional highlights include walk-in closets, a cozy fireplace, and an oversized tandem garage offering plenty of storage. Recent improvements include a new A/C system 2022 and water heater installed 2025, with roof updates completed in 2017, offering peace of mind for future homeowners. Residents enjoy exceptional community amenities including scenic waterfront boardwalks, fishing pier, kayak and small-boat access, and peaceful water views where dolphins and manatees are frequently seen. Walking trails, parks, playgrounds, and picnic areas create a relaxing park-like setting within the neighborhood. Conveniently located near Tampa International Airport, downtown Tampa, Ybor City, shopping, dining, and Gulf beaches, this home offers the perfect balance of tranquility and accessibility. Experience the best of Florida coastal living in Oldsmar.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Bernie Lutz (813-855-4982)
1505 SUNSET WIND LOOP, OLDSMAR, FL 34677
$390,00058 Days on yellowkey MLS ID: W7883526
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1667 Built: 2018Community: Bayside TerraceTownhouse
Remarks: 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.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Eric Jenkins, Pa (727-409-3484)
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