Location: Oldsmar , 34677
Do Not Show Listings
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$430,00042 Days on yellowkey MLS ID: TB8502786
REDUCED by $19,000 (4.2%) on 05/25/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1841 Built: 1940 Tax: $4,298 (2025)Community: Oldsmar Rev MapSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,298
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Fully renovated and move-in ready, this 3-bedroom, 2-bath home features 1,841 square feet of updated living space in a desirable area of Oldsmar. Recent improvements include a brand-new roof, new windows, fresh paint, brand-new appliances, and a fully refurbished HVAC system, creating a true turnkey opportunity. Inside, the home offers a spacious living area filled with natural light, a covered front porch, and an upstairs bonus room that can function well as a home office, playroom, guest area, kids room, or other flexible living space. The upstairs bonus room was not included in the total bedroom count. Situated on a double lot, the property includes ample outdoor space with room for a shed, carport, or future improvements. Conveniently located near parks, schools, shopping, dining, and other local amenities, this home brings together style, comfort, and convenience in one well-updated property. A clean 4-point inspection, wind mitigation report, WDO report, and recent appraisal are available. The recent appraisal came in at $475,000.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Bradley Dreher (863-346-0500)
228 TARPON LN, OLDSMAR, FL 34677
$269,00033 Days on yellowkey MLS ID: TB8506652
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1686 Built: 1991Monthly Fee: $70 Tax: $2,143 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,143
Remarks: Discover this 1,686 sq ft, 1991 Jacobsen retirement home, featuring a new roof (2025), new A/C (2024), new water heater (2026) and a new Rainsoft water softener in 2020. The layout offers both comfort and flexibility for relaxing or entertaining. Step into the oversized living room featuring soaring cathedral ceilings and an abundance of windows that fill the space with natural light, creating a welcoming atmosphere. The chef’s kitchen is a standout, with ample cabinetry for storage, a convenient pantry, and generous countertops perfect for meal preparation. A separate dining room makes everyday meals and entertaining easy and elegant. The expansive family room, measuring 27x15, is ideal for a large screen TV and gathering with friends and family. Retreat to the updated primary suite, which boasts new, modern bath cabinet with double sinks for added style and functionality. The indoor laundry room is equipped with custom built-in cabinets, a desk, and countertop space—perfect for folding clothes or tackling craft projects. The 11x11 Florida room sits behind the carport with acrylic windows. The utility room can be used for a workshop or bike storage. The vibrant clubhouse serves as the lively centerpiece of the community, offering a welcoming space for residents to connect and unwind. Enjoy a wide range of amenities, including a pool table, shuffleboard, bocce ball court, and a luxurious heated pool and spa. Monthly events and regular activities such as bingo, card games, and line dancing create endless opportunities for fun and socializing, ensuring you stay active and engaged. Navigating the neighborhood is easy and enjoyable thanks to golf cart-friendly streets. With HOA fees at just $70 per month, you will appreciate affordable, worry-free living in a meticulously maintained environment. This pet-friendly community welcomes one pet of any size, and a second pet is allowed with an emotional support letter from your doctor. Ownership includes the land—no lot rent—giving you peace of mind and long-term value. Everyday conveniences are right at your doorstep, with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store just across the street. Savor the variety of dining options nearby, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers like Super Walmart and Publix, as well as Countryside Hospital, are only about 10 minutes away. For outdoor enthusiasts, the breathtaking beaches of Honeymoon Island and Caladesi State Park are approximately ten miles from home, offering the perfect escape for sun and sand. A scenic biking and walking trail along the canal provide easy access from within the community, inviting you to enjoy nature at your own pace. This remarkable home combines comfort, practicality, and style, making it a wonderful place for your next chapter. Room sizes are approximate.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
129 CAMPHOR CIR #C, OLDSMAR, FL 34677
$180,000120 Days on yellowkey MLS ID: TB8474438
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986 Tax: $170 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$170
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Welcome to The Gardens of Forest Lakes, one of Oldsmar’s well-kept secret communities. This 2 bedroom 2 bathroom condo is a true move-in ready home. The features and amenities are apparent upon entering this well-decorated unit. The newer luxury vinyl flooring set the stage for a great showing. The living room/dining room combination offers an open & spacious area you can call home. The kitchen was updated to include custom wood cabinets with hydraulic drawers; led area lighting; newer appliances including a brand new refrigerator & a double oven; brand new hot water heater (5/26); deep double steel sink; tile backsplash; granite-looking Formica countertops; Both bathrooms were updated to include wood-like tile; the guest bathroom offers a deep soaker tub; Enjoy the beautiful pond view from both bedrooms and the private balcony; An inside laundry room with a newer washer/dryer combo for your convenience; The master bedroom offers a walk-in closet; The balcony has a storage room for your extra stuff; The community has a recreation center that includes a swimming pool, tennis & racquetball courts, a playground and a fishing pier. Close to shopping, dining, entertainment and more. Schedule your private showing today. You’ll be glad you did.
Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)
Listing Agent: Garrett Grimes (727-403-8723)
130 NANCY DR #66, OLDSMAR, FL 34677
$199,00018 Days on yellowkey MLS ID: W7886022
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1096 Built: 1979Monthly Fee: $560 Tax: $621 (2025)Community: East Lake WoodlandsCondo
Taxes:$621
Remarks: "RESORT STYLE LIVING" in East Lake Woodlands! This beautifully maintained 2-bedroom,2-bath condominium offers approximately 1,151 sq ft of comfortable living space in one of Oldsmar’s most desirable gated communities. Major updates provide peace of mind, including flooring, A/C system, hot water heater, dishwasher, washer and dryer, and bedroom carpeting all approximately 3 years old, plus a refrigerator replaced in 2025. The open living and dining areas create an inviting space for entertaining, Move-in ready, thoughtfully designed and updated this home features a spacious layout, abundant natural light, and a screened lanai—perfect for enjoying Florida’s year-round lifestyle. Enjoy the convenience of covered parking and maintenance-free living. Residents enjoy access to a community pool, pool club house, beautifully maintained grounds, and optional country club amenities including golf, tennis, fitness, and social activities. Ideally located near shopping, dining, parks, beaches, Tampa International Airport, and top Pinellas destinations, this condo offers the perfect blend of convenience, value, and resort-style living. Whether you’re looking for a full-time residence, seasonal retreat, or investment opportunity, this East Lake Woodlands gem is one you won’t want to miss!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (727-845-4321)
Listing Agent: Steve Dematos (727-457-2795)
40 SYLVIA PL, OLDSMAR, FL 34677
$289,00079 Days on yellowkey MLS ID: TB8487410
0 Days Off yellowkey (back on 5/23/2026)
REDUCED by $5,900 (2.0%) on 05/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1385 Built: 1978Monthly Fee: $450 Tax: $5,439 (2025)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$5,439
Remarks: Under contract-accepting backup offers. NEW PRICE!! Welcome to this exceptional 3-bedroom villa located in the fabulous East Lake Woodlands community. This villa is move-in ready and offers a split bedroom floor plan, making it ideal for comfort and convenience. Enjoy a relaxing water view from the rear of the home, perfect for peaceful contemplation. The open floor plan features wood-look tile throughout the living spaces, creating a warm and inviting atmosphere. The island bar with seating is designed for entertaining guests. The updated kitchen is both cozy and functional, equipped with cherry wood cabinets, granite countertops, and high-end Frigidaire Gallery appliances. The master bedroom boasts a large walk-in closet and a sliding door that leads to the screened patio, allowing you to enjoy water views when you wake up. The en-suite master bath has been tastefully updated with a spacious vanity area featuring double sinks, quartz countertops, newer fixtures, mirrors, and a medicine chest. The separate shower and toilet area have also been refreshed for your comfort. Your guest bedrooms are perfectly suited for visitors. Bedroom 2 has a sliding patio door that opens onto the rear screened lanai, while bedroom 3, located at the front, is ideal for use as an office or for any additional needs. The hall guest bath has been thoughtfully updated with a newer vanity featuring a solid surface top, updated fixtures, and a shower/tub combination. This villa offers ample outdoor space, including a front open patio that is perfect for BBQs and a rear screened lanai for relaxing without the annoyance of insects. There is also a large storage area/closet at the end of the lanai for your extra belongings. The home includes a deeded one-car carport with its own storage closet, as well as open parking available in the cul-de-sac for guests. Enjoy peace of mind with recent updates, including a roof installed in 2025, HVAC system from 2021, water heater from 2022, and an updated electrical panel. These improvements should ensure there are no insurance issues based on 4-point inspections. Optional membership is available at the Ardea Country Club, which offers two championship 18-hole golf courses, a large clubhouse, tennis and pickleball courts, two pools with a splash play area, putting greens, a restaurant and snack bar near the pool, and a fitness center. Contact Ardea for additional information. This community is served by top-rated schools and offers convenient access to all surrounding areas. What's not to like here? Make your deal today! some furniture may be available, let us know if interested. All measurements are believed to correct and buyer is encouraged to verify through inspections or other methods. Seller not responsible for any inaccuracies and home sold strictly as is.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Cathy Mccarthy (727-452-9339)
340 CANAL WAY, OLDSMAR, FL 34677
$168,00075 Days on yellowkey MLS ID: TB8491525
REDUCED by $8,000 (4.5%) on 05/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1993Monthly Fee: $50 Tax: $2,288 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,288
Remarks: Welcome to easy Florida living in the sought-after 55+ community of Gull-Aire Village in Oldsmar. This well-maintained 2BR/2BA home offers a comfortable, open layout with updated flooring, a spacious living area, and a split-bedroom floor plan that gives both you and your guests privacy. The kitchen and bathrooms are clean and functional with room to make it your own, making this a great opportunity to move right in and update over time to your style. Enjoy the benefits of a covered carport, extra storage, and low-maintenance living in a community where neighbors know each other and there’s always something to do. Gull-Aire Village is a resident-owned 55+ community featuring a clubhouse, heated pool and spa, fitness center, shuffleboard courts, and a full calendar of social activities. Conveniently located near shopping, dining, Gulf beaches, Tampa International Airport, and major highways—everything you need is close by. Land-owned with no lot rent—perfect for a full-time residence or a seasonal Florida escape.
Listing is courtesy of: ACROPOLIS REALTY GROUP LLC (315-396-0493)
Listing Agent: Sal Degaetano (315-396-0493)
291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$225,000147 Days on yellowkey MLS ID: TB8463435
REDUCED by $15,000 (6.3%) on 05/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $2,205 (2025)Community: Countryside KeyTownhouse
Taxes:$2,205
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)
1637 GRAY BARK DR, OLDSMAR, FL 34677
$559,900230 Days on yellowkey MLS ID: TB8440841
1 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2146 Built: 1998Monthly Fee: $9 Tax: $5,256 (2024)Community: Eastlake Oaks Ph 2Spa: YesSingle Family
Taxes:$5,256
Elementary School: Oldsmar Elementary-PN
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Beautifully maintained 4-bedroom, 3-bath, 2-story home with over 2,100 square feet of living space and a 2-car garage. The home features wood flooring throughout, tall ceilings, and a comfortable, open layout. The kitchen and bathrooms have been fully updated with modern finishes, quality cabinetry, and solid-surface countertops. Recent improvements include a roof replacement in 2022. The living area offers a wood-burning fireplace, and updated lighting and fixtures enhance the home’s appeal. AC system 2014. Enjoy the screened pool and covered veranda with NO REAR NEIGHBORS, offering added privacy and a relaxing outdoor setting. This property combines thoughtful updates with a functional floor plan in a desirable location. Make your showing appointment today!
Listing is courtesy of: LISA HALL REALTY, INC (727-742-5830)
Listing Agent: Lisa Hall (727-742-5830)
208 HEMINGWAY DR, OLDSMAR, FL 34677
$305,00076 Days on yellowkey MLS ID: TB8490712
REDUCED by $9,900 (3.1%) on 05/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1207 Built: 1997Monthly Fee: $265 Tax: $4,507 (2025)Community: Sun Ketch Twnhms At Cypress LakesVilla
Taxes:$4,507
Remarks: Under contract-accepting backup offers. This beautifully maintained end-unit villa offers the perfect combination of comfort, privacy, and modern upgrades along with water views from most rooms. Step inside to high-volume ceilings that create a bright and spacious atmosphere throughout. The home features all-new luxury flooring, giving every room a sleek and cohesive look. The thoughtful layout includes a separate living and dining area, ideal for both everyday living and entertaining guests. From here, step out onto your private screened lanai with an epoxy floor, overlooking a serene pond—a perfect spot for morning coffee or relaxing evenings. The back yard is fenced for extra privacy. The split-bedroom floorplan has a spacious primary suite boasting a large walk-in closet and an en suite bathroom with a walk-in shower and dual sink vanity. The open, tiled kitchen is a chef’s delight, offering ample counter space and a convenient breakfast bar. Additional highlights include a 2-car garage with extra driveway space, French drains, rain gutters, and the added privacy of an end unit. Conveniently located near shopping, airports, schools, beaches, and the community pool, this villa truly combines style, convenience, and tranquility. Your new home awaits—move in and enjoy the perfect blend of comfort and elegance!
Listing is courtesy of: RE/MAX MARKETING SPECIALISTS (727-853-7801)
Listing Agent: Lisa Heberlein Pa (727-432-8769)
107 LAKEVIEW PL #7, OLDSMAR, FL 34677
$224,90019 Days on yellowkey MLS ID: W7885525
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980Monthly Fee: $663 Tax: $2,780 (2025)Community: East Lake Woodlands CondoCondo
Taxes:$2,780
Remarks: 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!
Listing is courtesy of: SAMUELSEN BUILDERS REALTY LLC (727-243-4464)
Listing Agent: Michael Ryan (727-243-4464)
2313 SUNSET WIND LOOP, OLDSMAR, FL 34677
$425,000150 Days on yellowkey MLS ID: TB8461950
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $15,000 (3.4%) on 05/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2230 Built: 2019Monthly Fee: $580 Tax: $7,434 (2025)Community: Bayside TerraceTownhouse
Taxes:$7,434
Remarks: Under contract-accepting backup offers. Experience coastal luxury and step into a lifestyle of refinement in this stunning 3-bedroom, 2.5-bath, 2 car garage townhome, nestled within the impressive gated waterfront enclave of Bayside Terrace! Curb appeal draws you into an open-concept layout designed for seamless entertaining with 10’ ceilings and beautiful tile flooring. The gourmet kitchen is a showstopper, featuring tons of cabinets, endless gorgeous granite counters, top of the line appliances and a large center island. A butler’s pantry and a huge walk in pantry complete the kitchen. Enjoy casual meals at the breakfast bar and formal meals in the dining room, which is open to the living room. The great room is just perfect for entertaining large or small gatherings and is open to the screened lanai, where you can enjoy your morning coffee or a cocktail after dinner. Upstairs, you’ll find three well-appointed bedrooms, two full bathrooms, and a versatile loft area perfect for a home office, fitness space, or secondary living room. Plantation shutters grace the upper level, and ceiling fans are installed in every room. The primary suite features elegant tray ceilings and expansive his-and-hers walk-in closets, while the en suite bathroom offers dual vanities and a spacious walk-in shower. The guest bedrooms each include walk-in closets, and the guest bath is finished with granite countertops. An upstairs laundry room makes laundry day a breeze and adds everyday convenience. The desirable two-car garage includes durable epoxy flooring and custom built-in shelving. Low monthly maintenance fees cover cable and high-speed internet in addition to water, sewer and trash for added ease of living. Ideally located, Bayside Terrace offers quick access to Tampa, major highways, top-rated schools, dining, and shopping—along with spectacular sunrise and sunset views over the water. Flood insurance is required and can be assumable from the current owners at an affordable price. Experience true resort-style living with premier amenities including a clubhouse, a breathtaking saltwater infinity pool overlooking Tampa Bay, a gas fire pit, fully equipped fitness center, fishing pier, and kayak launch—all just steps from your door! Don’t miss the opportunity to enjoy waterfront resort living every day—schedule your private showing today!
Listing Agent: Nicole Harmon (727-385-1357)
1384 FORESTEDGE BLVD, OLDSMAR, FL 34677
$699,00076 Days on yellowkey MLS ID: TB8490510
REDUCED by $21,000 (2.9%) on 05/21/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2814 Built: 1991Monthly Fee: $243 Tax: $13,366 (2025)Community: Aberdeen Unit TwoSpa: NoSingle Family
Taxes:$13,366
Remarks: Under contract-accepting backup offers. Welcome to refined Florida living in the highly sought-after gated community of Aberdeen within East Lake Woodlands. This exceptional Arthur Rutenberg-built residence offers over 2,814 square feet of thoughtfully designed living space, perfectly positioned on an oversized lot with a private screened pool with lovely water feature. This freshly painted 4-bedroom, 2.5-bath split floor plan is designed for both comfort and sophistication. The expansive primary suite is a true retreat, featuring a spa-inspired bath with a freestanding clawfoot tub, separate shower, water closet, dual vanities, and walk-in closet, along with sliding glass doors leading directly to the pool. The pool bath features a jacuzzi tub and updated finishes. Enter through elegant double front doors into a light-filled interior with soaring ceilings and abundant natural light. The home offers a seamless blend of formal and casual living, including a formal living room with sliders to the pool, a dedicated dining space, and a spacious family room with wood burning fireplace that opens to the kitchen. The refreshed kitchen features an open layout, breakfast nook, with sliders leading to pool/patio making it an easy flow for entertaining. The large laundry room features a wash sink and an ample space for storage. Step outside to your screen-enclosed pool and covered patio, the perfect setting for year-round entertaining, relaxing, and enjoying Florida’s indoor-outdoor lifestyle. Additional highlights include a 3-car garage, new water softener system, 2013 Barrel Tile Roof. HVAC 2019 Located in Flood Zone X500 for added peace of mind, this home is surrounded by top-rated schools and unmatched convenience. Enjoy having an active lifestyle being close to Lake Tarpon, the Gulf beaches, Tampa International Airport, and outdoor destinations like John Chestnut Park, the Pinellas Trail, and the YMCA. Residents also have access to the newly renovated Ardea Country Club, offering two championship 18-hole golf courses, tennis and pickleball courts, fitness center, resort-style pool, and dining, available through optional membership. Don’t miss the rare opportunity to own a magnificent home in one of East Lake’s most desirable gated enclaves.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Kerri Rodriguez (727-385-8823)
705 SHORE DR E, OLDSMAR, FL 34677
$158,990170 Days on yellowkey MLS ID: TB8458306
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2155 Built: 1974 Tax: $5,427 (2025)Community: Tampashores Bay SecSingle Family
Taxes:$5,427
Remarks: Short Sale. Short Sale - Listed price has not been negotiated or approved by the current lender. There is a possibility the list price will not be the accepted contract price. Enter at your own risk. Mold and water damage throughout the property from hurricane flooding. The roof needs to be replaced. The pool caved in from flooding. Walls, and appliances need to be replaced. The only good thing about the home is that two new A/C units have been installed, since the flooding occurred. The home needs a complete rehab. We will be looking for highest and best offers once the property is listed for 10 days.
Listing is courtesy of: GREAT AMERICAN REALTY (813-961-9661)
Listing Agent: Michele Martinez (813-961-9661)
9009 PALM KEY AVE, OLDSMAR, FL 34677
$654,900154 Days on yellowkey MLS ID: TB8461356
REDUCED by $10,000 (1.5%) on 05/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2018Monthly Fee: $580 Tax: $6,740 (2025)Community: Bayside TerraceTownhouse
Taxes:$6,740
Remarks: Searching for a low-maintenance waterfront escape in Tampa Bay? Whether you’re looking for a full-time residence, seasonal escape, or the perfect “Lock Up & Go” second home, this property offers the ideal blend of low-maintenance living and resort-style amenities. An added bonus — the flood insurance is ASSUMABLE to new buyers at currently only $1,101 annually. The HOA includes cable, internet, water, trash, roof and grounds maintenance, and gated access, leaving electricity as the only additional utility needed. This rare oversized waterfront unit stands out as one of the few in the community with expanded water views from the main living areas, creating a brighter, more open feel throughout the home. Enjoy stunning bay and conservation views from the kitchen, dining, living room, and even the primary suite upstairs. High ceilings and an open-concept layout make the home feel spacious and inviting, while the upgraded kitchen was designed with entertaining in mind. Features include an extended island, side coffee/bar station with glass-front cabinetry, spacious walk-in pantry, and over $57,000 in builder upgrades throughout the home. Upstairs, the waterfront owner’s suite feels like a private retreat with beautiful water views, dual vanities, soaking tub, separate shower, and an oversized walk-in closet. Two additional bedrooms plus a generous bonus room provide flexible space for a media room, game room, second living area, or hosting guests. The oversized upstairs laundry room located just off the primary suite adds everyday convenience. Downstairs, the current office can easily be converted back into a fourth bedroom if desired. Step outside to your screened lanai and enjoy peaceful mornings or sunset evenings overlooking the water. Bayside Terrace offers RESORT-STYLE amenities including an infinity pool overlooking Old Tampa Bay, waterfront fire pit, fitness center, outdoor grills, kayak launch and storage, and a waterfront pier perfect for fishing or relaxing by the water. LOCATION, LOCATION, LOCATION — conveniently located just minutes to downtown Oldsmar, approximately 10 minutes to Safety Harbor, 20 minutes to Dunedin and Honeymoon Island, 25 minutes to Tampa International Airport, and 30 minutes to Clearwater Beach. This is waterfront living designed for both everyday enjoyment and effortless second-home ownership. You truly have to see it in person.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Nisa Gonzalez Smook (813-400-3680)
140 ASHLEY LN, OLDSMAR, FL 34677
$309,90039 Days on yellowkey MLS ID: TB8504188
1 Days Off yellowkey (back on 5/22/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1981Monthly Fee: $440 Tax: $1,408 (2025)Community: East Lake Woodlands Cluster HomesSpa: NoSingle Family
Taxes:$1,408
Remarks: Under contract-accepting backup offers. Positioned below two recent appraisals, presenting a compelling opportunity for buyers seeking immediate value. Located within a gated golf course community in North Pinellas County (club and golf memberships optional), this light and bright 4-bedroom, 2-bath villa offers a flexible split-bedroom floor plan and inviting indoor-outdoor living. The great room is the focal point, featuring updated sliding glass doors that frame tranquil pond and fairway views of the 13th hole on the South Course, along with recently installed recessed lighting and wood-look plank tile flooring that enhance both ambiance and overall brightness—creating a warm, open, and inviting living space. New plantation shutters throughout the home add a refined, cohesive look while enhancing light control and privacy. The enclosed lanai extends the living area and opens to an additional patio and deck, ideal for relaxing or entertaining while enjoying the scenic setting. The rear deck is further enhanced by a retractable awning, providing flexible shade and added comfort for outdoor living year-round. The updated kitchen includes wood cabinetry, solid surface countertops, abundant drawer storage, a closet pantry, coordinating wood-look tile flooring, and double sinks. A casual breakfast area offers direct access to a private rear patio, perfect for grilling. Interior laundry closet conveniently located just off the kitchen. The primary suite offers ample closet storage with dual sliding-door closets, along with a large vanity area and separate water closet with a glass-enclosed shower. Both bathrooms feature expansive counter space with room to accommodate dual vanities, offering flexibility for future customization. Three additional bedrooms are well-sized and thoughtfully positioned for privacy, with one offering access to a private side patio—ideal for guests, a home office, or flex space. Well-maintained and move-in ready, this villa delivers a low-maintenance lifestyle with water and golf course views in one of the area’s most desirable communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (727-472-1144)
Listing Agent: Rick Scherer (813-230-5472)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,00047 Days on yellowkey MLS ID: TB8501214
REDUCED by $20,000 (5.4%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2015Monthly Fee: $285 Tax: $3,417 (2025)Community: Hayes Park VillageSingle Family
Taxes:$3,417
Remarks: 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 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.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jennifer Kashtan (813-310-7200)
506 SHORE DR E, OLDSMAR, FL 34677
$900,00023 Days on yellowkey MLS ID: TB8509618
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1313 Built: 1955 Tax: $9,895 (2025)Community: Tampashores Bay SecSingle Family
Taxes:$9,895
Remarks: Exceptional waterfront opportunity on one of Oldsmar’s most desirable streets. Situated on a 75x205 (.33 acre) waterfront homesite overlooking beautiful Old Tampa Bay, this property presents a rare opportunity to create a custom luxury estate in an area experiencing significant redevelopment and impressive new construction. Currently utilized as a vacation rental, the home offers income producing potential while future plans take shape, though the true value lies in the land and its exceptional waterfront setting. For water enthusiasts, the lifestyle possibilities are endless. Launch a kayak or paddleboard from your backyard, enjoy boating and jet skiing on the Bay, or simply unwind while taking in panoramic water views and breathtaking sunset skies. With no HOA or deed restrictions, there is added flexibility and ample room for boat and RV parking. Ideally located approximately 20 minutes from Tampa International Airport and about 25 minutes to the Gulf beaches, the property is also just down the street from RE Olds Park and offers convenient access to pickleball, Mobbly Beach, Veterans Memorial Park, scenic biking and walking trails, dining, shopping, and everyday conveniences. Offering a unique blend of waterfront serenity and exceptional accessibility, this is a rare opportunity to create a one of a kind coastal retreat where the lifestyle is just as remarkable as the setting.
Listing is courtesy of: WESTWARD REAL ESTATE (813-285-4456)
Listing Agent: John Pestalozzi Jr Llc (813-285-4456)
219 PALMETTO CT, OLDSMAR, FL 34677
$182,000149 Days on yellowkey MLS ID: TB8463698
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,045 (2024)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,045
Remarks: Tucked into the peaceful, gated community of East Lake Woodlands, this ground-floor corner condo offers easy, low-maintenance living surrounded by lush greenery and natural beauty. 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. Monthly condo fees include exterior maintenance, roof, building insurance, water, sewer, trash, cable, grounds maintenance, and pool access—providing simple, predictable ownership whether you’re looking for a primary residence, seasonal getaway, or investment opportunity. (One or more photos have been virtually staged.)
Listing is courtesy of: KINEST REALTY (727-212-0021)
Listing Agent: Stephanie Person (727-212-0021)
1534 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$1,249,00024 Days on yellowkey MLS ID: TB8509589
1 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3402 Built: 1994Monthly Fee: $200 Tax: $7,125 (2024)Community: Greenhaven Unit-FourSingle Family
Taxes:$7,125
Remarks: Under contract-accepting backup offers. Welcome to this fully remodeled 4 bedroom (4th bedroom can double as office), 4 full bath, 3 car garage POOL HOME located in the amazing Greenhaven IV subdivision of E Lake Woodlands! This home has just undergone a full high end luxury remodel on the inside and out and features an amazing open concept floor plan that flows effortlessly and a professional interior design aesthetic with only one goal: to WOW you! In the heart of the home the kitchen features upscale quartz countertops, modern stainless steel appliances, wood soft close cabinets, an island so big it might as well be called a continent and more storage than you'll know what to do with. In the downstairs primary bedroom and bath, you'll find one of the grandest primary ensuites in all of central Florida. Featuring a massive wet room with a fully glass enclosed dual shower and tub setup you will enjoy spa like luxury everyday! The home additionally features a full laundry downstairs, full guest bathroom, dining and sitting areas as you walk in, an office/4th bedroom with glass light french doors, as well as a dedicated breakfast nook overlooking the pool. Upstairs you'll find 2 additional bedrooms, a bonus sitting area, SECONDARY LAUNDRY closet, as well as a full tub bath! On the outside, the goodies don't stop featuring a full circular 3 car driveway, fresh landscaping, full irrigation, pavered pool area that was fully resanded and sealed in 2026, a DEDICATED FULL pool bath, pool closet, vinyl fencing for privacy, and the crown jewel: a FULL outdoor kitchen and island for all the entertaining you could want. The TILE ROOF is from 2020, AC is from 2020 and has been fully serviced for your peace of mind. Water heater is 2018 also and there is a smart thermostat system so each area of the house can have their own AC setting! Located in the heart of Oldsmar, you're close to great schools, shopping centers, dining and central of everything. This home has it all come see it today!
Listing is courtesy of: KELLY RIGHT REAL ESTATE (813-321-2282)
Listing Agent: Louis Graniero (813-957-7160)
141 LAKEVIEW WAY #141, OLDSMAR, FL 34677
$169,00096 Days on yellowkey MLS ID: TB8483907
REDUCED by $4,900 (2.8%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980 Tax: $3,466 (2025)Community: East Lake WoodlandsSpa: NoCondo
Taxes:$3,466
Remarks: PRICE REDUCED! Why Rent when you can buy? Enjoy peaceful Florida living in this charming condo located in a quiet gated community in desirable East Lake Woodlands. This well-maintained residence offers a comfortable layout with abundant natural light and relaxing views of the lake, creating a serene setting to come home to each day. The living and dining areas flow seamlessly, providing an inviting space for both everyday living and entertaining. Large windows help bring the outdoors in while highlighting the tranquil lake view. The kitchen is conveniently located and designed for functionality and ease. Residents of this gated community enjoy access to a sparkling community pool, perfect for relaxing or cooling off on warm Florida days. The peaceful surroundings combined with scenic water views make this property especially appealing. Conveniently located near shopping, dining, parks, and major roadways, the home offers easy access to nearby destinations including Tampa, Clearwater, and St. Petersburg. A wonderful opportunity to enjoy low-maintenance living with beautiful lake views in one of Oldsmar’s most desirable gated communities, and with a freshly painted front door AND $8,000 in new HVAC.
Listing Agent: Douglas Brown (614-306-4665)
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