Location: Oldsmar , 34677
Do Not Show Listings
9009 PALM KEY AVE, OLDSMAR, FL 34677
$644,900197 Days on yellowkey MLS ID: TB8461356
REDUCED by $5,000 (0.8%) on 07/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2018Monthly Fee: $580 Tax: $6,740 (2025)Community: Bayside TerraceTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,740
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
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)
130 NANCY DR #37, OLDSMAR, FL 34677
$199,00061 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
Elementary School: Forest Lakes Elementary-PN
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)
2055 DIAMOND CT, OLDSMAR, FL 34677
$1,150,00034 Days on yellowkey MLS ID: TB8520799
0 Days Off yellowkey (back on 6/23/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3237 Built: 1996Monthly Fee: $142 Tax: $8,014 (2025)Community: Diamond CrestSpa: YesSingle Family
Taxes:$8,014
Elementary School: Cypress Woods Elementary-PN
Remarks: Under contract-accepting backup offers. Welcome to 2055 Diamond Court, an exceptional residence located in the highly sought after guard gated community of Eastlake Woodlands. Situated on a rare trifecta lot with views of the pond, conservation and the golf course. Updated well-appointed home with 3 spacious bedrooms and a dedicated office that could also be an exercise or nursery room. A circular drive leads to the portico entrance. The views immediately greet you upon entering. The generous formal living and dining areas, high ceilings, abundant natural light and multiple gathering spaces create a warm and inviting atmosphere. Entertain easily in the updated gourmet kitchen and expansive family room that overlook the views and pool area. The primary suite is a retreat with pool and spa access, ensuite bath and walk-in closet. Beautifully remodeled primary bath includes a walk in shower, double sinks with quartzite counters and a relaxing stand-alone tub. Additional bedrooms are spacious with entry to the second and third remodeled baths. Enjoy the outdoor view on the travertine pool deck. Take a dip in the solar heated pool or relax in the spa. The expanded pool deck allows for several dining arrangements on the patio. Updates include a 2018 tile roof, 2021 HVAC, exterior and interior paint, updated kitchen and all baths. Located in the subdivision of Diamond Crest, a small one street community inside Eastlake Woodlands. Residents enjoy a beautifully maintained setting with convenient access to shopping, dining, parks, highly rated schools, Tampa International Airport and the area’s award winning Gulf Coast beaches. Eastlake Woodlands is home to the prestigious Ardea Country Club with two championship golf courses, tennis, pickle ball, fitness center, restaurant and banquet room. There are various memberships to choose from to fit your lifestyle. This is a rare opportunity to enjoy Florida’s year round sunshine, private home oasis and a premier Oldsmar location. Please be sure to watch the video for more photos and drone photography.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)
Listing Agent: Debra Gross (727-463-2271)
108 WOODLANDS CT #108, OLDSMAR, FL 34677
$175,00043 Days on yellowkey MLS ID: TB8514193
REDUCED by $24,000 (12.1%) on 07/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1151 Built: 1981 Tax: $2,378 (2025)Community: East Lake Woodlands Condo Unit 7Spa: YesCondo
Taxes:$2,378
Elementary School: None
High School: None
Middle School: None
Remarks: This adorable 2nd floor, 2 bedroom, 2 bathroom condo in the guarded/gated community of East Lake Woodlands! An open and airy front balcony welcomes you in to the unit. NO REAR NEIGHBORS! Just views of the lovely back yard wooded area and daily deer sightings from your 2nd balcony which is private and screened-in! A big picture window, recessed lighting, solid wood cabinets and tiled backsplash accent the kitchen. The kitchen has a floor to ceiling pantry and is open to living / dining with an breakfast bar. An elegant, 2 tiered chandelier, crown molding and new modern ceiling fan grace the ceiling. Newer laminate flooring installed in the living /dining and both bedrooms. Step through the living room sliding doors and onto the screened-in balcony where the true Florida lifestyle begins. Roller shades on the balcony create privacy while still allowing the cool breezes to flow through. This unit features a split bedroom plan with NO CARPET! Master bedroom has its own bath en suite with separate shower/commode area, 3 walk in closets (YES! 3), tropical ceiling fan with palm leaf blades, double picture window with beautiful views of the wooded back yard! It is spacious enough for a king bedroom furniture set and also has a set of sliding doors out to the balcony! Guest bedroom features a large closet and an adjacent full bathroom with tub/shower in the hall. No lack of storage here with a coat closet in the main entry hall and a full wall to wall reach in closet in the guest hallway. A side by side washer and dyer are conveniently located in the balcony closet. Your assigned covered parking spot is right in front of the entrance (#108). Plenty of extra guests spots for a 2nd car too. Heated pool just steps away! Love to golf? East Lake Woodlands County Club will become your new favorite spot with (2) 18 hole championship courses, upscale restaurant, fitness center, clubhouse, tennis courts, 2 pools and a multimillion dollar renovation underway! Located just around the corner from Oldsmar sports complex on Tampa Rd with a playground, ball hockey rink, BMX supercross track and fields for baseball football and soccer. Adjacent to the complex is Woodlands Square Mall with an IMAX movie theater, gourmet restaurants and shopping. East Lake Rd houses 2 large shopping centers with Target, Walmart, and an assortment of fast food chains. Short drive to Countryside mall, Tampa Airport, and the sugar sands of the Gulf’s finest beaches. Bring your furry friends! Two cats or dogs allowed under 20 lbs each (or a total of 40 lbs between the 2). Low condos fees with water, sewer, trash and basic cable included. Make your appointment to see today!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Jo Walker (727-657-9898)
1815 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$427,50069 Days on yellowkey MLS ID: W7885693
REDUCED by $500 (0.1%) on 07/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1855 Built: 1972 Tax: $2,731 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$2,731
Remarks: This beautifully remodeled three-bedroom, two-bath home is perfectly located in Oldsmar at the top of Tampa Bay. Completely updated from top to bottom, it features a stunning new kitchen with stainless steel appliances, soft-close cabinetry, leather-finished quartz countertops, and a cozy breakfast nook. One of the standout features is how all three bedrooms are nicely separated for added privacy. The spacious master suite boasts a huge California-style walk-in closet, peaceful backyard views, and a gorgeous bathroom with a walk-in shower. The open-concept living space extends into a roomy bonus area at the back of the house, accented by tandem ceiling fans. From here, French doors lead to a fully fenced backyard, complete with a poured slab ready for a shed. A generous laundry room with a utility sink connects to the two-car garage, featuring a new hurricane-rated door and opener. Oldsmar offers unmatched access to the Pinellas Beaches, all that Tampa has to offer, plus its own great dining, excellent schools and shopping scene. Don’t miss the opportunity to check out this beautiful home!
Listing is courtesy of: SNAP REALTY LLC (727-457-5453)
Listing Agent: Dean Glicos (727-509-9296)
260 BALSAM DR, OLDSMAR, FL 34677
$249,900294 Days on yellowkey MLS ID: TB8433742
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1250 Built: 1981Monthly Fee: $440 Tax: $960 (2024)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$960
Tax Year: 2024
Remarks: SIGNIFICANT PRICE DECREASE!!! Owners are motivated!!! This desirable end-unit villa in exclusive East Lake Woodlands combines comfort, privacy, and an ideal layout for everyday living or entertaining. Featuring two spacious primary suites, each with its own ensuite bath and split floor plan design, the home provides excellent privacy for residents and guests alike. The open layout includes a welcoming family room, a dedicated dining room, and a bright eat-in kitchen with a generous pass-through bar—perfect for casual dining, entertaining, or extra storage. A charming front courtyard offers an inviting spot for morning coffee or al fresco meals, while the expansive lanai, complete with removable windows, provides a versatile additional living space to enjoy year-round. Thoughtful storage solutions are found throughout, with ample closet space to keep everything organized. Important updates include a roof replacement in 2021, an upgraded electrical panel in 2017 and a 2016 AC system. The HOA provides peace of mind with coverage that includes roof replacement, exterior painting, wood repairs, landscaping, lawn maintenance, irrigation, and fertilization. Located within the highly regarded East Lake Woodlands, a premier gated golf course community, residents have access to optional membership opportunities that feature golf, tennis, swimming, fitness, dining, and social events. With its combination of thoughtful design, modern updates, and resort-style community amenities, this villa offers the perfect place to call your year round home or winter residence. Don't delay.
Listing is courtesy of: MARC JOSEPH REALTY, INC (727-644-9333)
Listing Agent: Colleen Monagas (727-644-9333)
372 COBIA WAY, OLDSMAR, FL 34677
$170,00093 Days on yellowkey MLS ID: TB8499655
REDUCED by $24,995 (12.8%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 1984Monthly Fee: $60 Tax: $3,232 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,232
Remarks: Welcome to 372 Cobia Way — one of the best locations in Gull-Aire Village, sitting directly across from the community pool, spa, and clubhouse! This resident-owned, 55+ golf cart friendly community in the heart of Oldsmar offers the best of Florida retirement living at an unbeatable value. Step inside to a bright, open floor plan featuring dark hardwood-style flooring and bold coastal teal accents throughout. The spacious living and dining areas flow into a well-appointed kitchen with wood cabinetry, a center island with breakfast bar, and stainless steel appliances. The primary suite includes a private en-suite bath, with a second full bath rounding out the layout. Screened lanai, wide carport, inside laundry, and a utility shed out back — this one has it all. You own the land. No lot rent. Ever. Low HOA and an active social calendar to boot. Community amenities include a heated pool & spa, clubhouse, sauna, library, shuffleboard, and bocce ball. Walk across the street to AMC Theatres, Beall's, Marshalls, and a full lineup of restaurants. Minutes to Publix, Walmart, and Countryside Hospital. Just ~10 miles to Honeymoon Island and Caladesi State Park. NOT in a flood zone!
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Justin Cans (347-238-0790)
417 DOLPHIN DR S, OLDSMAR, FL 34677
$269,00083 Days on yellowkey MLS ID: TB8504194
2 Days Off yellowkey (back on 7/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1253 Built: 1985Monthly Fee: $70 Tax: $3,616 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,616
Remarks: Under contract-accepting backup offers. Welcome to this beautifully renovated home in the desirable 55+ Gull-Aire Village, where comfort, style, and convenience seamlessly come together. Step inside to discover luxury vinyl flooring throughout, a modern kitchen featuring elegant Shaker cabinetry, granite countertops, a convenient pot filler, premium stainless-steel appliances, smooth ceilings, and five-inch baseboards. The custom kitchen island comfortably seats three, perfect for casual dining or entertaining. The primary bathroom has been thoughtfully designed for both style and accessibility, boasting a fully updated, wheelchair-friendly walk-in shower. The guest bathroom is also refreshed, offering a versatile tub/shower combination. The spacious laundry room includes newly installed custom cabinetry and a sink, with the potential to serve as a second kitchen for those who enjoy cooking. Enjoy Florida living year-round in the expansive glass-enclosed, air-conditioned Florida room, complete with durable vinyl plank flooring. Upgrades include a new air conditioning system installed with permit in November 2018, a permitted TPO roof added in August 2012, and a whole-house Generac generator that guarantees uninterrupted power during any weather. Additional storage is available in the handy shed. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball courts, a heated pool, and spa. Residents can take part in regular activities like bingo, card games, and line dancing, fostering an active, social lifestyle. The golf cart-friendly streets make getting around the neighborhood both easy and fun. Enjoy affordable living with HOA fees of just $70 per month in this meticulously maintained community. Pet owners are welcome—one pet of any size is allowed, and a second pet may be permitted with an emotional support letter from a physician. Ownership includes the land, so there is no lot rent. Everyday conveniences are right across the street, with shopping options like AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store. Dining choices abound, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are about ten minutes away. Outdoor enthusiasts will love being just ten miles from the stunning beaches at Honeymoon Island and Caladesi State Park, plus direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
3087 DUANE AVE, OLDSMAR, FL 34677
$250,00013 Days on yellowkey MLS ID: TB8527948
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1969 Tax: $4,131 (2024)Community: West Oldsmar Sec 1Single Family
Taxes:$4,131
Remarks: Auction Property. *** Live Auction! *** THIS IS PART OF A PROPERTY SETTLEMENT. THE SELLER HAS COMMITTED TO A TIMELY, SMOOTH AND TRANSPARANT AUCTION SALE. THE AUCTION SALE IS HELD AT THE PROPERTY ON SATURDAY AUGUST 1 at 10am with PREVIEW FROM 9am ON SALE DAY. *** EVERYONE WELCOME TO BID *** Because this is an auction sale, the home may sell for less or more than the list price. REGISTER at the auction sale. Bring photo ID and a personal or business check (you'll need it if your the winning bidder) .......AUCTION TERMS AT BOTTOM OF THIS PAGE........... THIS HOME IS OWNED FREE AND CLEAR. CLEAN TITLE TRANSFERES TO NEW BUYER *** You can use cash or financing.*** Located in a highly sought-after West Oldsmar neighborhood, this move-in-ready home offers flexibility and privacy.One of the standout benefits is the private in-law suite, which the owners converted into a private Verified Listing on Airbnb. The owner reports successful bookings throughout the year, making it a great option for extended family, guests, a private office, or a potential short-term rental. Set on nearly one-third of an acre with NO HOA restrictions, the property offers ample space to enjoy, expand, or customize.. Additional updates include a durable metal roof, hurricane-rated windows, and elevated entryways. The owners have also made thoughtful drainage improvements, including a front culvert drain, French drains, and a sump pump system. Seller reports no known flooding of the home; buyers should verify all information to their satisfaction. Inside, the home features an open layout that connects the living, dining, and kitchen areas, creating a comfortable flow for everyday living and entertaining. The private in-law suite has its own entrance, giving the home added versatility for multi-generational living, guests, work-from-home needs, or income-producing possibilities. The fully fenced backyard is spacious and inviting, with mature landscaping, fruit trees, and a paved patio area ready for an outdoor kitchen, a fire pit, or a lounge area. A custom-built shed/workshop adds even more usable space for storage, tools, hobbies, or a creative studio. Conveniently located near Gulf Coast beaches, parks, shopping, restaurants, downtown Dunedin, Clearwater, and St. Petersburg, this home offers a peaceful residential setting while keeping you close to everything Tampa Bay has to offer............................................................ TERMS:....... At the end of the sale, the winning bidder will sign the contract for sale and purchase, place a 5% deposit (personal or business checks are accepted) with AMERICAN HERITAGE AUCTIONEERS to be held in escrow, balance is due within 45 days, Seller pays for Title Insurance Policy and Documentary Stamps. Clean Title is transferred free and clear of all debt. PAPPAS LAW and TITLE will close the transaction.
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Benjamin Pietras (727-207-3732)
3073 DUANE AVE, OLDSMAR, FL 34677
$410,000339 Days on yellowkey MLS ID: TB8417476
5 Days Off yellowkey (back on 7/13/2026)
REDUCED by $30,000 (6.8%) on 06/05/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2122 Built: 1973 Tax: $1,936 (2024)Community: West Oldsmar Sec 1Single Family
Taxes:$1,936
Remarks: Under contract-accepting backup offers. Located in a quiet and friendly Come and see this beautiful house with a lot of potential. No HOA ,It has a spacious master bedroom with an in-suite bathroom and a large walk-in closet. Outside, you’ll find a large detached porch with big storage, perfect for storing a golf cart, bikes, kayaks, or motorcycles—or transform it into two bedroom, gym, or office or a party place . The backyard is a standout, surrounded by trees that keep the home cooler and energy bills lower. It’s perfect for relaxing or entertaining. . Enjoy gorgeous sunsets or cast a line off the nearby pier at one of the area’s best parks. Buyer and/or buyers agent to verify all room sizes.
Listing is courtesy of: S P O R T REALTY GROUP INC. (813-452-8301)
Listing Agent: Madelin Martinez (813-359-7784)
120 EVELYN CT, OLDSMAR, FL 34677
$239,90088 Days on yellowkey MLS ID: TB8501596
REDUCED by $9,100 (3.7%) on 07/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1979Monthly Fee: $490 Tax: $5,156 (2025)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$5,156
Remarks: Welcome to 120 Evelyn Ct, Oldsmar, FL 34677, a beautifully maintained villa located within the highly desirable East Lake Woodlands community, one of the most sought-after neighborhoods in Pinellas County and the Tampa Bay area. This home offers a wonderful opportunity for buyers seeking low-maintenance living in a prime Oldsmar location. This immaculate villa has been very well maintained through the years and is ready for move-in, while also allowing the next owner the opportunity to update and personalize over time. The home features a thoughtfully designed floor plan with spacious living areas and generously sized bedrooms, creating a comfortable and functional living environment. The primary suite includes a walk-in closet and private ensuite bathroom, providing privacy and convenience. The additional bedroom is also well-sized, making the home ideal for guests, seasonal living, or a home office. One of the standout features of this property is the large sunroom/lanai, offering a bright and inviting space that can be enjoyed year-round. Whether you’re relaxing with your morning coffee or entertaining guests, this versatile area adds valuable living space and enhances the overall flow of the home. Important updates include an HVAC system installed in 2015, a new electrical panel installed in 2022, and a newer water heater, providing peace of mind for the next owner. The property also includes covered parking and ample storage space, adding convenience for everyday living. The home is fairly priced based on recent comparable sales within the East Lake Woodlands community, making it a strong opportunity in today’s Oldsmar real estate market. East Lake Woodlands is known for its beautiful surroundings, mature landscaping, and central location within Pinellas County. Residents enjoy easy access to shopping, restaurants, parks, golf courses, and everyday conveniences. The property is also conveniently located with an estimated 30-minute drive to Tampa International Airport, as well as a similar drive to many of Pinellas County’s award-winning Gulf Coast beaches. If you are searching for a villa in Oldsmar within East Lake Woodlands, 120 Evelyn Ct offers a combination of location, comfort, and value in one of the Tampa Bay area’s most desirable communities. Schedule your private showing today and discover everything this well-maintained Oldsmar villa in East Lake Woodlands has to offer.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Lance Willard Llc (727-487-1894)
101 BAYSIDE BLVD, OLDSMAR, FL 34677
$375,00014 Days on yellowkey MLS ID: TB8527353
0 Days Off yellowkey (back on 7/12/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1098 Built: 1984 Tax: $4,617 (2025)Community: Bayside Meadows-Phase ISpa: NoSingle Family
Taxes:$4,617
Remarks: Under contract-accepting backup offers. HOA-FREE & MOVE-IN READY IN FLOOD ZONE X! Welcome to this beautifully updated, concrete block gem in the Bayside Meadows neighborhood of Oldsmar. Offering the ultimate peace of mind, this 3-bedroom, 2-bathroom home features a NEW 2025 ROOF and NEW 2026 HURRICANE WINDOWS, plus it's high and dry with no flood insurance required. Step inside to an open-concept living space where vaulted ceilings create a bright, airy atmosphere. Every inch of this home has been refreshed, boasting luxury vinyl plank flooring throughout, modern remodeled bathrooms, and a pristine updated kitchen with stylish shaker cabinets and new stainless steel appliances. What truly sets this home apart are the massive, premium infrastructure upgrades completed in 2026. Enjoy ultimate energy efficiency, storm protection, security, and exceptional outside noise reduction with brand-new, double-hung vinyl argon low-E IMPACT WINDOWS throughout. Mechanical updates include a brand-new, high-efficiency Rheem 2.5-ton heat pump HVAC system and a new, hurricane-braced insulated garage door with a Genie smart opener. Outside, you’ll find a freshly painted exterior, a newly poured concrete driveway section, and a fully fenced backyard with a covered patio deck. Location is everything! Situated right at the front of the neighborhood, you are steps away from ultimate convenience: walk across the street to Starbucks, Panera, AMC Theatres, and outstanding local dining. Benefit from A-rated public schools and an unbeatable central location offering a quick commute to Tampa International Airport, Clearwater, Safety Harbor, Dunedin, and world-class Gulf beaches. Completely turnkey and worry-free. Schedule your showing today!
Listing Agent: James Wheeler, Pa (813-285-1229)
202 HEMINGWAY DR, OLDSMAR, FL 34677
$316,00052 Days on yellowkey MLS ID: TB8514350
INCREASED by $47,000 (17.5%) on 07/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1452 Built: 1997Monthly Fee: $240 Tax: $2,197 (2025)Community: Sun Ketch Twnhms At Cypress LakesSpa: NoTownhouse
Taxes:$2,197
Remarks: AS IS – Owner selling due to health concerns! This spacious 3-bedroom, 2.5 bath, townhome in the highly desirable community of Sun Ketch Townhomes of Cypress Lakes needs some cosmetic attention, but the structure and amenities are already there: vaulted ceilings, an inside laundry room, a kitchen pantry, a walk-in bathtub in the primary bathroom, and an enclosed porch, and much more. A new A/C unit was installed in October 2017. The HOA Fee is only $240 monthly. HOA Documents are available for review - contact the listing agent.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Ganier (727-403-5611)
416 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,000159 Days on yellowkey MLS ID: TB8475710
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1293 Built: 1959 Tax: $644 (2025)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$644
Remarks: Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting. The master suite has it's own bath and modern shower. It is a beauty. The secondary bath is very modern with decorator fixtures and lighted mirror, all done very tastefully. This shower has beautiful ceramic tile and modern features. There is spacious great room and separate dining room which is leading to the perfect entertaining back yard. There are 2 decks, brick pavers and it features a jacuzzi tub. You'll love the separate shed for storage and fenced in yard. There is plenty of room for your toys with gated entry to the back yard. No CDD or HOA fees here but there are several parks and a boat ramp in the neighborhood. Move in ready and a must see.
Listing is courtesy of: MURRAY BELL REAL ESTATE LLC (813-629-8202)
Listing Agent: Jenny Meers (813-748-8112)
126 CYPRESS CT #26, OLDSMAR, FL 34677
$189,90014 Days on yellowkey MLS ID: TB8524688
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,382 (2025)Community: East Lake Woodlands Cypress EstatesSpa: NoCondo
Taxes:$3,382
Remarks: MOVE-IN READY! This beautiful 2nd Floor unit is situated on a quiet and private street in the highly sought-after East Lake Woodlands Community, a Country Club Community. Flooring & counter tops/cabinets are 2020, HVAC 2018, Water heater 2008, and the Wash/dryer staying with unit. Also included is a $4,000 leveluk sd501 platinum kangen water machine. There is new wood plank tile on Balcony (with Laundry Closet) where you can sit and enjoy the beautiful views of your backyard. For additional Fee you can join the East Lake Woodlands Country Club which includes Two Golf Courses, Clubhouse, a Heated Pool, Tennis Courts and Fitness Center. This Condo allows for serene living without Sacrificing Convenience as it is mere minutes from Shopping and Fine Dining, approximately 20 Minutes from Tampa (and the airport), and less than 30 minutes from Clearwater Beach.
Listing is courtesy of: ARC REALTY GROUP (800-636-2080)
Listing Agent: Brittany Hasemeier (813-517-4759)
4856 WESTCHESTER CT, OLDSMAR, FL 34677
$579,00048 Days on yellowkey MLS ID: TB8515993
REDUCED by $10,000 (1.7%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2184 Built: 1996Monthly Fee: $295 Tax: $4,281 (2025)Community: KingsmillSingle Family
Taxes:$4,281
Remarks: Welcome to Kingsmill in the highly sought-after East Lake Woodlands community! This beautifully maintained waterfront home features 3 bedrooms, 2 bathrooms, and a 2-car garage, and has been lovingly cared for by its original owner. From the moment you arrive, you'll be impressed by the home's private cul-de-sac location and newly paved driveway. Step inside to discover luxury vinyl flooring that flows seamlessly throughout the main living areas and bedrooms. High ceilings and natural light create an open, airy atmosphere throughout the home. The spacious living and dining room combination is highlighted by a cozy fireplace, creating the perfect setting for both everyday living and entertaining. The kitchen features wood cabinetry, solid-surface countertops, a tile backsplash, brand new matching GE stainless steel appliances, and a breakfast nook overlooking the water. A full pocket sliding glass door opens to the lanai, allowing you to fully enjoy the tranquil lake views. The primary suite is a true retreat, offering water views and private access to the screened porch through sliding glass doors. The ensuite bathroom features dual vanities, a garden tub, a walk-in tiled shower, tile flooring, and two walk-in closets. The secondary bedrooms provide ample storage with built-in closets, while the guest bathroom includes tile flooring, a wood vanity with a solid-surface countertop, and a walk-in tiled shower. Additional features include an indoor laundry room with brand new washer and dryer included, a freshly painted garage floor, a 2021 roof, 2026 water heater, and 2017 HVAC system. Enjoy maintenance-free living with low monthly HOA fees that include lawn maintenance and trash service. Located within the gated East Lake Woodlands community, residents have the option to join Ardea Country Club, which offers exceptional amenities including two championship 18-hole golf courses, a fitness center, restaurant, swimming pools, tennis courts, racquet sports facilities, and more. Conveniently located near shopping, dining, airports, and some of Florida's most beautiful beaches, this home offers the perfect combination of comfort, convenience, and resort-style living. Don't miss this opportunity—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Chris Arata (727-415-7271)
110 LAKESIDE CT #110, OLDSMAR, FL 34677
$175,000133 Days on yellowkey MLS ID: TB8484399
REDUCED by $14,900 (7.8%) on 07/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981 Tax: $621 (2025)Community: East Lake Woodlands CondoCondo
Remarks: Nestled within the highly desirable East Lake Woodlands community of Oldsmar is this beautiful 1094 sq ft 2 bedroom 2 bath 2nd floor condominium. The kitchen has been updated with granite countertops and contemporary white cabinets that have been professionally resurfaced. There is also a laundry closet with a washer and dryer inside that is accessed from the lanai. This unit has closets galore! With plenty of storage space including three closets in the primary bedroom ensuite alone, you'll find there is ample storage for all your needs. As a bonus, the lanai/balcony has access not only from the amazing great room but from the primary bedroom as well. East Lake Woodlands is rich in tree-lined streets and nature trails and is a 24-hour gated community! Enjoy a convenient HEATED salt water pool just steps away from the unit. The modest $465 monthly condo association fee includes just about everything: water, sewer, trash, lawn care, internet and cable, insurance, the heated pool you can see from your window, pest control, the reserve fund and outdoor maintenance including the recently replaced roof. For an additional membership fee you can enjoy the East Lake Woodlands Country Club which offers two 18-hole golf courses, an olympic-sized swimming pool, tennis, a remodeled country club and more. You will also have a reserved covered parking space conveniently located right below the unit! Pets are welcome as are people and children of all ages. Your new home will be conveniently located to shopping, restaurants, excellent medical facilities, theaters, Tampa International Airport, the beautiful Pinellas beaches and all that the Tampa Bay area has to offer. Please note that the furnishings currently in the unit can remain at no extra cost should you want them. This beautiful home will not last long so schedule your showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Barry Rothstein (727-365-4725)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,00090 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 Agent: Jennifer Kashtan (813-310-7200)
1713 MAPLELEAF BLVD, OLDSMAR, FL 34677
$379,00025 Days on yellowkey MLS ID: TB8523949
1 Days Off yellowkey (back on 7/11/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1622 Built: 1981 Tax: $1,382 (2025)Community: Harbor Palms- Unit Eight ASpa: NoSingle Family
Taxes:$1,382
Remarks: HOME FEATURES SPACIOUS OPEN FLOOR PLAN WITH SPLIT-BEDROOMS. COMPLETELY REMODELED KITCHEN, 2BATHS AND HOME SITS HIGH AND DRY. THIS 4-BEDROOM HOME HAS A TWO-CAR GARAGE AND INSIDE LAUNDRY. THIS HOME HAS NEVER FLOODED OR SUSTAINED ANY HURRICANE DAMAGE. THE KITCHEN IS THE CENTER OF THE HOME WITH WARM WOOD CABINETRY AND GORGEOUS GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, BEVERAGE/WINE FRIDGE, FULL-SIZE FRENCH DOOR REFRIGERATOR, CONVECTION OVEN WITH AIR FRYER, GLASS TOP RANGE AND ISLAND RANGE HOOD PLUS DISHWASHER AND STORAGE GALORE. THE GREAT ROOM HAS A BOW WINDOW THAT LETS IN NATURAL LIGHT. DINING SPACE ALSO HAS A BOW WINDOW THAT TAKES IN VIEWS OF THE BACKYARD AND FIREPIT. PRIMARY BEDROOM HAS EN SUITE BATH AND WALK-IN CLOSET. THE HOME HAS TWO COVERED PORCHES. THE FRONT PORCH HAS CONCRETE PAVERS THAT LEAD TO THE FRONT DOOR AND THE BACK PORCH IS SCREEN ENCLOSED WITH TILED FLOORING AND ENOUGH SPACE TO ENTERAIN WITH CEILING FAN AND ADIRONDACK SEATING. THE BACKYARD ALSO HAS AN EXTRA-LARGE STORAGE SHED AND IS FENCED. THE ENTIRE HOUSE HAS NEW IMPACT RESISTANT DOUBLE HUNG WINDOWS. HARBOR PALMS IS CLOSE TO SHOPPING, BEACHES, PARKS AND TAMPA AIRPORT. SCHOOLS HAVE ABOVE AVERAGE STANDARDIZED TESTING SCORES ON EXCELLENT LIST (4 YRS). THE PROPERTY CAN BE SOLD FULLY FURNISHED ALONG WITH KITCHEN DISHES AND POTS AND PANS IF THE BUYER SO DESIRES.
Listing Agent: M Sam Mclaughlin (727-647-6767)
604 LIMETREE DR, OLDSMAR, FL 34677
$369,00092 Days on yellowkey MLS ID: O6401483
REDUCED by $6,000 (1.6%) on 06/27/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1430 Built: 1980 Tax: $3,108 (2025)Community: Harbor Palms Unit ElevenSingle Family
Taxes:$3,108
Remarks: This beautifully updated home in Oldsmar is a rare gem! Originally a 2-bedroom, 2-bath, the garage has been fully permitted and converted into a third bedroom and bath with its own shower. Both main bedrooms offer spacious walk-in closets and private exterior doors ideal for a mother-in-law suite or rental income. The home boasts laminate wood floors throughout, a modern kitchen with granite countertops, and brand-new stainless steel appliances. Relax on the screened porch or enjoy the large, shaded patio. With a big driveway and no HOA or CDD, you have total freedom. Plus, it’s in a fantastic location just minutes from St. Pete and Tampa, the airport, shopping malls, top schools, and some of the best beaches in the area.
Listing is courtesy of: JUPITER PROPERTIES, INC (386-547-6161)
Listing Agent: Sulamita Del Valle (813-510-9619)
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