Location: Oldsmar, 34677
Do Not Show Listings
219 CYPRESS CT #219, OLDSMAR, FL 34677
$185,000106 Days on yellowkey MLS ID: TB8460111
1 Days Off yellowkey (back on 4/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $586 Tax: $2,893 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,893
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. Welcome to East Lake Woodlands – Cypress Estates, a gated golf course community offering maintenance-free Florida living. This updated ground-floor corner unit is move-in ready and perfectly positioned at the end of a quiet street for added privacy. This 2-bedroom, 2-bath condo features an open, airy floor plan with high ceilings and abundant natural light. Enjoy peaceful views from your screened-in porch overlooking a tranquil pond, ideal for relaxing and enjoying Florida wildlife. The spacious kitchen is designed for both function and style, featuring solid wood cabinetry, granite countertops, pantry, lazy Susan, recessed lighting, and ceiling fan. The primary suite offers two walk-in closets and a private en-suite bath with a walk-in shower and granite vanity. The guest bedroom includes brand-new luxury vinyl plank flooring (2025) and a large built-in closet. The second bath features a tub/shower combo, granite counters, and updated lighting. Recent Updates Include: ?? Electric Panel (2020) ?? HVAC (2021) ?? New Water Heater & Dishwasher ?? Updated Lighting & Bathrooms ?? LVP Flooring (2025 – Guest Bedroom) Additional features include assigned covered parking and access to a solar-heated community pool. The monthly HOA covers water, sewer, trash, cable, and internet, providing exceptional value. Located in the heart of Palm Harbor, just minutes from top-rated schools, shopping, dining, golf, and Gulf beaches, with easy access to Tampa International Airport, Downtown Dunedin, Honeymoon Island, and Clearwater Beach. Ideal for full-time residents, seasonal living, or investment—schedule your private showing today!
Listing is courtesy of: ORANGE GROVE PROPERTY SOLUTIONS (727-336-3202)
Listing Agent: Tara Cook (727-336-3202)
1705 IRONWOOD CT E, OLDSMAR, FL 34677
$330,00035 Days on yellowkey MLS ID: TB8486052
REDUCED by $5,000 (1.5%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1973 Tax: $1,600 (2025)Community: Harbor Palms-Unit SixSingle Family
Taxes:$1,600
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautifully renovated 2-bedroom, 2-bathroom home—perfect for first-time buyers or those looking to downsize without sacrificing comfort. The stunning kitchen, remodeled last year, features elegant quartz countertops and new stainless steel appliances, creating a modern and inviting space for cooking and entertaining. Just off the kitchen, you'll find a very spacious area that can easily serve as a family room, home office, or versatile flex space to suit your lifestyle. Step outside to enjoy the large backyard—perfect for relaxing, gardening, or hosting gatherings. Situated on a quiet street, this cozy yet stylish home is truly move-in ready. According to the owners, the A/C was replaced in August 2018 and the roof was replaced in June 2025, providing added peace of mind for the new owner. Don’t miss this opportunity to own a beautifully updated home with modern finishes and plenty of space to enjoy.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Aned Pantoja (813-264-7754)
470 HICKORYNUT AVE, OLDSMAR, FL 34677
$795,00037 Days on yellowkey MLS ID: TB8485715
REDUCED by $20,000 (2.5%) on 04/02/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2922 Built: 1987Monthly Fee: $110 Tax: $10,515 (2025)Community: East Lake WoodlandsSingle Family
Taxes:$10,515
Remarks: One or more photo(s) has been virtually staged. Located inside the highly desirable gated community of East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views. Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home features expansive living areas including a formal living and dining room and a large family room with fireplace. New Luxury Vinyl Plank flooring installed in 2026 runs throughout the main living areas, creating a modern and cohesive look, while new carpet installed in 2026 adds comfort to the guest bedrooms. The updated kitchen features granite countertops and stainless-steel appliances, flowing seamlessly into the main living space and breakfast area—perfect for gatherings and everyday living. The spacious primary suite offers direct access to the pool area along with a private bath and generous closet space. Enjoy Florida living at its best with a screened pool and lanai overlooking a tranquil pond, providing both privacy and relaxing water views. The home also features fresh exterior paint completed in 2026 and a 3-car garage, all situated on a generous homesite within this established golf-course community. Residents of East Lake Woodlands have the option to join the Ardea Country Club, a recently renovated club offering two championship golf courses, tennis and pickleball courts, fitness facilities, resort-style pool, and multiple dining venues. The club provides a vibrant social calendar and family-friendly amenities, creating a true country club lifestyle right inside the community. Located just minutes from shopping, dining, top-rated schools, and major commuter routes, this home offers convenient access to Tampa International Airport, Gulf beaches, and the best of the Tampa Bay area. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.
Listing is courtesy of: PARADISE LIFE REALTY (727-698-2996)
Listing Agent: Lou Tutko (727-698-2996)
2044 SHEFFIELD CT, OLDSMAR, FL 34677
$190,000497 Days on yellowkey MLS ID: TB8327277
4 Days Off yellowkey (back on 11/10/2025)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1986Monthly Fee: $110 Tax: $1,603 (2023)Community: Sheffield Village At Bayside MeadowsVilla
Taxes:$1,603
Elementary School: Oldsmar Elementary-PN
High School: Countryside High-PN
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Short Sale. High and dry with NEW ROOF and NEW HVAC!! Welcome to this charming 2-bedroom, 2-bathroom single-family villa, offering a perfect blend of comfort and style. As you enter, you'll be greeted by volume ceilings that create an open, airy atmosphere throughout the home. The spacious kitchen features beautiful granite countertops and wood cabinets, providing both elegance and functionality. Stainless steel appliances complete the modern kitchen, making it ideal for cooking and entertaining. Relax or entertain in your private enclosed patio or enjoy your own private yard, fully enclosed by a vinyl fence for added privacy and security. This home also boasts a new roof and a new HVAC system, ensuring peace of mind for years to come. Located just a short walk from the community pool, this villa is in a highly desirable school district, making it a fantastic option for families. Best of all, the HOA fees are only $110/month, offering incredible value for the community. Don’t miss the opportunity to make this wonderful home yours!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Christopher Grasso (727-379-2376)
204 WINDWARD PL #36, OLDSMAR, FL 34677
$195,00016 Days on yellowkey MLS ID: A4686982
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984 Tax: $3,166 (2025)Community: Meadows Condo At East Lake WoodlandsCondo
Taxes:$3,166
Remarks: Welcome to 204 Windward Place #36, a well-maintained and move-in-ready condo located in the desirable East Lake Woodlands community in Oldsmar, Florida. This residence offers a comfortable layout with abundant natural light and a private outdoor space ideal for relaxing or enjoying morning coffee. The interior has been thoughtfully maintained, providing a clean and inviting living environment suitable for a primary residence, seasonal use, or investment. Assigned parking is included, along with convenient guest parking. East Lake Woodlands is a gated community offering a secure and established setting with mature landscaping and scenic surroundings. Optional membership opportunities are available at the nearby Ardea Country Club, which features golf, tennis, fitness, pool, and dining amenities. Conveniently located near Tampa, Clearwater, and St. Petersburg, this property provides easy access to Gulf beaches, shopping, dining, medical facilities, and Tampa International Airport. This property presents an excellent opportunity for buyers seeking low-maintenance living in a well-located Pinellas County community. Schedule your private showing today.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Robert Dinan (941-993-7455)
4007 PALM KEY AVE, OLDSMAR, FL 34677
$639,000192 Days on yellowkey MLS ID: TB8435073
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2019Monthly Fee: $580 Tax: $7,398 (2024)Community: Bayside TerraceTownhouse
Taxes:$7,398
Tax Year: 2024
Remarks: Walk in the front door and look straight out to the water. Head out to the screened-in back porch to hang out and enjoy the views, from dolphins and mother duck with her ducklings, to the pink & orange glowing sunsets. This unit comes with floodplain X zoning tied to the title, which means you’re grandfathered in, and the cheap flood insurance is transferable to you (less than $800/yr.). Soaring ceilings, open floor plan, hard floors throughout, and a finished garage with a high-end epoxy floor that makes it feel like you’re parking in a showroom. Built in 2019, it looks and feels fresh and new. 1st floor bedroom with water views (great for guests!). Large media room upstairs with numerous possibilities. It could be a game room. It could be a gym or just a TV area. 3 bedrooms upstairs, including the master. The master bath overlooks the water with an oversized tub, a walk-in shower, dual vanities, and a custom walk-in closet. DirectTV, Frontier internet, water, recycling, and trash (2x/week) are included in the monthly HOA fee. The unit is far enough away from the gate, where you won't hear the road noise of 580. Bayside Terrace offers an array of amenities, including an infinity-edge swimming pool, BBQ area, a gym, a fire-pit, and a community dock with kayak, paddleboard, and canoe launch. This exceptional townhome provides the perfect blend of luxury, comfort, and Florida's natural beauty
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Jacob Gross (727-303-2063)
1704 HIBISCUS CIR N, OLDSMAR, FL 34677
$389,00059 Days on yellowkey MLS ID: TB8476647
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1430 Built: 1981 Tax: $6,573 (2025)Community: Harbor Palms Unit 6 ASingle Family
Taxes:$6,573
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET!!! Seller offering $5,000 credit to buyer - make it yours!!!! Welcome to this inviting Florida home designed for comfortable living and effortless outdoor enjoyment. The highlight of the property is the private, screened-in pool and expansive patio, surrounded by mature tropical landscaping that creates a peaceful setting ideal for relaxing or entertaining year-round. Inside, the home offers a functional, open layout with seamless indoor–outdoor flow from the main living areas to the pool and patio. Tile flooring throughout the main living spaces provides durability and easy maintenance, well suited for Florida living. The updated kitchen is well-appointed with ample cabinetry, generous counter space, stainless steel appliances (including a double oven range) and granite countertops, with an open connection to the dining and living areas making everyday living and entertaining easy and comfortable. The primary suite features a spa-inspired bathroom complete with a freestanding clawfoot tub and separate shower, creating a calm retreat at the end of the day. The garage has been converted to provide additional flexible space with storage, suitable for a third bedroom, home office, or bonus room. A dedicated laundry room adds everyday convenience. Additional features include owned solar panels, newer windows, and sliding glass doors. This home combines privacy, functionality, and true Florida outdoor living - a great opportunity for buyers seeking space, comfort, and a backyard designed to be enjoyed.
Listing is courtesy of: REALTY ONE GROUP BEYOND (727-900-7174)
Listing Agent: Chris Ziebell (727-900-7174)
509 LAKEVIEW DR, OLDSMAR, FL 34677
$499,90029 Days on yellowkey MLS ID: TB8487858
5 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1710 Built: 1984Monthly Fee: $35 Tax: $1,737 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$1,737
Remarks: Under contract-accepting backup offers. Location! Location! Location! This lovely home sits on a gorgeous conservation lot and offers tranquil stunning views in the desirable community of Forest Lakes… Move-in ready offering over 1,700 sq.ft. of fine Florida living featuring 3 bedrooms in a popular split bedroom layout, 2 baths and a 2 car garage. Covered front entry leads to Elegant single leaded glass door to the spacious living room featuring wood flooring and Bay window with plantation shutters providing tons of natural sun light. The formal dining room also features wood flooring, designer light fixture and French doors that lead to your outdoor paradise. The fabulous remodeled kitchen (2016) boasts porcelain tile flooring, granite countertops, soft close wood cabinetry with 2 lazy suzannes and under cabinetry lighting, designer tile backsplash, elegant hardware, wood accented raised ceiling, breakfast bar with lower cabinetry, pendant lighting, full wall pantry, stainless steel appliances including ceran top range and dishwasher (3/2026), built-in microwave (2025), and 4-door refrigerator (2023). Family room located just off the kitchen also has French doors leading to the outdoor paradise. Large primary bedroom boasts laminate flooring and features a walk-in closet with custom closet cabinetry and an impressive updated ensuite bath (2021) with stunning gorgeous granite countertops, dual undermount sinks, tumble marble backsplash, full walk-in shower through the block and glass door. The secondary bedrooms are located on the other side of the home with convenient hall bathroom serving them both boasting tub/shower Jacuzzi bathtub, single decorative vanity with tumble marble backsplash, and wainscoting wall accents. Extend your living and entertaining outdoors through either set of French doors to your serene oasis with roomy screen enclosed lanai which leads to a secondary outdoor entertaining deck with tranquil fountain and stunning conservation views!!! Fully fenced, Florida living at its best… enjoy a morning cup of coffee or afternoon cocktail watching the wildlife including turkeys and deer. Simply magnificent…Important updates include Roof 2025, Flat Roof 1/2026, AC 2025, Water Heater 2023, Washer 2026, Electrical panel 2024 including 30 amp hookup ideal for a generator, Hurricane impact garage door, garage door opener 2023, double paned windows 2016, Exterior Gutters 4/2025, and ceilings textured 2016. Forest Lakes Community offers fabulous amenities including, pool, playground and picnic area, basketball, racquet-ball, tennis and pickle ball courts. The ideal Oldsmar location is convenient for access to shopping, restaurants, airports and of course the famed Gulf beaches and Dunedin’s Honeymoon Island! A great place to call home!!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nancy Leslie (727-789-5555)
1637 GRAY BARK DR, OLDSMAR, FL 34677
$559,900176 Days on yellowkey MLS ID: TB8440841
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2146 Built: 1998Monthly Fee: $9 Tax: $5,256 (2024)Community: Eastlake Oaks Ph 2Single Family
Taxes:$5,256
Remarks: 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)
380 WELLINGTON AVE, OLDSMAR, FL 34677
$1,155,000371 Days on yellowkey MLS ID: TB8373443
Bed: 4 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3420 Built: 1992 Tax: $6,112 (2024)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$6,112
Remarks: PRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key West style pool home on an oversized conservation lot in highly desirable Oldsmar. Located on a cul de sac with no through traffic on nearly an acre of land, with lush tropical landscaping backing up to forested conservation for added privacy. At the main entry is an inviting wraparound porch. Step inside the welcoming foyer to a soaring vaulted ceiling in the great room, which also features a wood burning fireplace and two sets of French doors leading to screened back porches and beyond to a huge rear deck that spans the length of the house and overlooks the large free form pool and spa. The primary suite has two walk-in closets and a remodeled bathroom (2023) with two vanities, a whirlpool tub, tiled walk-in shower, and water closet. The remodeled gourmet kitchen (2022) features stainless steel appliances, Viking dual fuel range with pot filler and vent hood, quartz counters, plentiful cabinetry, and a large island with wine fridge and copper top (durable and naturally anti-microbial/anti-bacterial). Off the kitchen is a half bathroom, a laundry room with utility sink and extra pantry storage, and a wet bar/coffee nook with even more pantry storage. Upstairs are two spacious bedrooms, a loft/office area, and updated hall bathroom (2023). At the top of the house is a railed rooftop platform offering stunning views out to Tampa Bay. The ground floor features covered parking for at least 4 vehicles, spacious storage/workshop areas, and a garage apartment/in-law suite with a bedroom, living/game room, kitchenette, and full bathroom. The circular driveway, side driveway, and large parking pad provide abundant parking for guests, boats, RV, etc. No HOA or CDD. Oldsmar is a waterfront golf cart community known for wonderful parks, quality of life, A rated schools, and convenient access to Tampa International Airport, Gulf beaches, shopping, dining, and more. Schedule your private showing today! As an added bonus, the seller has an assumable government loan at just 2.75%! Call agent for details.
Listing Agent: James Wheeler, Pa (813-285-1229)
388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$246,00056 Days on yellowkey MLS ID: TB8478422
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1105 Built: 1997Monthly Fee: $433 Tax: $1,771 (2025)Community: Countryside KeyTownhouse
Taxes:$1,771
Elementary School: Curlew Creek Elementary-PN
Remarks: 2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-bathroom townhome located in the highly sought-after Oldsmar, FL community. This delightful two-story residence boasts an open-concept first floor with a spacious kitchen, ample cabinetry, a generous pantry, and a convenient laundry/utility closet with a full-size washer and dryer. The living and dining areas flow seamlessly, enhanced by a kitchen bar and a convenient first-floor half bath. Upstairs, you'll find two generously sized bedrooms, each featuring vaulted ceilings that create an airy ambiance. Step outside to your enclosed screened patio, a serene retreat perfect for unwinding and enjoying the Florida weather year-round. This pet-friendly community offers a wealth of amenities including a secure gate, sparkling pool, tennis courts, sidewalks, and a car-wash station, with recreational storage for your RV, boat, or trailer available for a nominal fee. You'll have an assigned parking spot right at your doorstep with ample guest parking. Monthly HOA fees cover water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Located in an area known for its highly-regarded school districts, buyers are encouraged to verify current school assignments and ratings. Situated near Tampa International Airport, St. Petersburg, and the area's stunning beaches, this gorgeous property offers an exceptional opportunity to create your dream home in a prime location. Don't miss out on this fantastic opportunity! Notable Features & Upgrades: HVAC-2025; Interior Paint-2025; Carpet-2017; Primary Bathroom Renovation-2016; Granite Countertops & Cabinets (Kitchen & Primary Bath)-2013; Upgraded Fixtures & Handles, Lights, Ceiling Fans.
Listing is courtesy of: TROPIC SHORES REALTY (800-775-1302)
Listing Agent: Kevin Baker (352-777-1507)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000169 Days on yellowkey MLS ID: TB8442794
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1475 Built: 1973 Tax: $4,086 (2024)Community: Harbor PalmsSingle Family
Taxes:$4,086
Remarks: Welcome to this beautifully remodeled home filled with natural light and modern charm. The open-concept floor plan features a spacious living area with brand new windows throughout the house, the new designed kitchen offers new cabinetry beautiful countertops, new stainless-steel appliances, and a breakfast bar the flows seamlessly into the dining and living spaces, interior laundry room with new cabinets and new washer & dryer. New central air condition and ductwork, new ceiling lights and fans, new flooring throughout the house. The primary bedroom includes a large closet and a stylish new bathroom with a glass - enclosed shower-tub combo, modern finishes. Two additional bedrooms provide versatility for guess, a home office, and the second new full bath is bright and modern. All interior doors are new so it is the front door and garage door, new interior and exterior paint, new wood fence, new landscape. this home is a perfect blend of comfort and value.
Listing Agent: Mena Reyes (727-789-5555)
115 WINDWARD PL #15, OLDSMAR, FL 34677
$180,00020 Days on yellowkey MLS ID: TB8490824
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984Monthly Fee: $431 Tax: $2,768 (2025)Community: Meadows Condo At East Lake WoodlandsCondo
Taxes:$2,768
Remarks: LOCATION, LOCATION, LOCATION! Close to entertainment, shopping, restaurants, airports, and world-famous beaches, this beautiful ground floor, end unit condo is waiting for you! Located in the highly desirable, gated community Meadows of Eastlake Woodlands, this home has it all! Gorgeous granite countertops highlight the kitchen as does the impressive cabinet space and closet pantry. The inviting open living space makes time together comfortable, yet the split bedroom floor plan offers privacy when needed. The primary bedroom is generous and offers two walk-in closets, an ensuite bath with step-in shower, and patio access. HVAC 2021. The HOA fees include water, sewer, trash, cable, community pool, exterior maintenance including the roof, and grounds maintenance. There is a community golf course that owners may access for an additional fee.
Listing is courtesy of: FLORIDA PREMIERE REALTY (727-437-0261)
Listing Agent: Millie Jackson (828-337-9468)
3073 DUANE AVE, OLDSMAR, FL 34677
$459,000242 Days on yellowkey MLS ID: TB8417476
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: 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. Seller will pay a coverage flood insurance for the first year.
Listing is courtesy of: S P O R T REALTY GROUP INC. (813-452-8301)
Listing Agent: Madelin Martinez (813-359-7784)
382 ROSALIND LN, OLDSMAR, FL 34677
$822,000272 Days on yellowkey MLS ID: TB8408993
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3273 Built: 2001Monthly Fee: $100 Tax: $8,003 (2024)Community: Bay ArborSingle Family
Taxes:$8,003
Remarks: NEW YEAR; NEW PRICE! Welcome to 382 Rosalind Ln., an extraordinary home in the exclusive gated community of Bay Arbor in Oldsmar. This thoughtfully upgraded and impeccably maintained residence offers over 4,000 square feet of elegant living space, combining luxury, privacy, and smart-home functionality. Situated on a quiet cul-de-sac and backed by a peaceful conservation lot, the home features soaring ceilings, abundant natural light, Italian marble-look tile, a formal living and dining room, a spacious office, and a beautifully updated full bath. The open-concept main living area opens to a stunning screened-in patio with a heated spa, pool, waterfall, and wooded views — ideal for relaxation and entertaining. The chef’s kitchen boasts cherry cabinetry, granite countertops, stainless steel appliances, purified water, wine storage, a breakfast bar, and an eat-in nook. Upstairs you'll find four spacious bedrooms and a soundproofed 18' x 20' media room, easily converted into a second primary suite or flex space. The luxurious primary suite includes two walk-in closets, a spa-style bathroom with soaking tub and walk-in shower. The fully fenced backyard oasis includes a new outdoor luxury kitchen, pet turf, and smart-controlled pool and spa with a waterfall and fountain feature. Additional upgrades include new pool equipment, attic insulation, UV air purification, custom shutters, new water heater, full security system, vinyl fencing, lightning and surge protection, new AC unit upstairs, and more. Just 20 minutes from Tampa International Airport and close to top beaches, this rare gem delivers the ultimate in Florida luxury living.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Stephanie Eisenbach (813-468-0230)
1764 OAK POND CT, OLDSMAR, FL 34677
$550,00031 Days on yellowkey MLS ID: TB8487110
0 Days Off yellowkey (back on 3/29/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2000 Built: 2000Monthly Fee: $13 Tax: $7,494 (2025)Community: Eastlake Oaks Ph 4Single Family
Taxes:$7,494
Remarks: STUNNING HOME!!! This recently renovated home is situated in the beautiful East Lake Oaks Community. As you step inside, you will be greeted with an inviting and functional living space that contains 3 bedrooms, 2 FULL bathrooms and a Flex room that can be used as an Office, Home gym or Dining Room. The open floor plan features vaulted ceilings (w/ crown molding in the living room as well as the owner's room), luxury porcelain tile and luxury, waterproof laminate flooring throughout the home. There is plenty of natural light that flows through the windows, that also feature wooden, plantation shutters. Off the entry hallway is a formal living room with the versatile flex room separated by nested doors. The heart of the home features an open kitchen and family room, that is perfect for conversing and lounging. This opens to the pool area through beautiful French doors. The owner's suite serves as a spacious retreat, that features a recently renovated bathroom with a double vanity, full size soaking tub, private toilet room and walk in closet. Down a separate hallway, this split floor plan features two additional bed rooms and full bathroom. Outside enjoy the fully screened in pool and lanai area that is great for entertaining or relaxing. It is an absolute oasis during those hot summers here in Florida. There is also complete privacy with the fully fenced in backyard; that is great for pets or littles ones to play. The garage also features an artistic, epoxy flooring that has recently been done as well. The East Lake Oaks community offers a beautiful community park/ playground and community pool. Oldsmar is the standout location that puts you nearby plenty of nature trails, walking paths and quick access to waterfront locations. Sheffield park, which is a short walk away features a playground, disc golf course, basketball court and field that is used for all sports. You will have fast access to Safety Harbor, Clearwater, Tampa and St Petersburg. Not to mention, you will also be close to fine dining, great beaches, have a great school system, nearby Hospital and the Tampa Airport. YOU DO NOT WANT TO MISS THIS HOME. IT WILL NOT LAST.
Listing Agent: Martha Legoas (727-744-7310)
1821 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$395,00079 Days on yellowkey MLS ID: TB8469044
2 Days Off yellowkey (back on 2/23/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2034 Built: 1972 Tax: $1,582 (2024)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$1,582
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated three-bedroom, two-bath home offering comfort, style, and an inviting outdoor retreat. Impact windows throughout provide peace of mind and energy efficiency, while luxury vinyl plank flooring adds durability and a modern touch. HVAC NEW 2022. The remodeled kitchen (2021) is a true standout, featuring a quartz island, farmhouse sink, high-efficiency vent, thoughtfully designed drawer organizers, abundant storage, and a Whirlpool refrigerator and freezer—perfect for both everyday living and entertaining. The spacious family room is filled with natural light and showcases skylights along with a storm-impact sliding door that opens to the backyard. In addition, this home is equipped with solar tubes providing extra energy efficiency and natural lighting. Step outside to your private oasis complete with a paved patio, fully fenced in back yard, refreshing pool, canopies for shaded lounging, multiple sheds for extra storage, and convenient outdoor outlets. In the front of the home, you are welcomed by a lush garden featuring a mango tree, pineapple plant, and avocado plant. Ideally located in Oldsmar just off Tampa Road, this home offers quick access to shopping, dining, parks, and major roadways, making commuting to Tampa, Clearwater, and surrounding areas a breeze. Enjoy nearby trails, waterfront parks, and everyday conveniences while living in an established neighborhood with NO HOA or CDD. This sought-after location provides a perfect balance of accessibility, outdoor lifestyle, and flexibility. No flood damage from recent storms. PRICED TO SELL!!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Lauren Levine (860-916-0473)
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$549,000102 Days on yellowkey MLS ID: TB8460875
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$4,041
Remarks: Enjoy a Relaxing Lifestyle in the desirable Gated, Golf Community of East Lake Woodlands and the convenience of Less Maintenance responsibilities! This home provides Privacy and Stunning Water Views with a Large, Covered Screened Lanai to enjoy that morning cup of coffee or evening glass of wine. Plus it’s situated in the preferred Zone X so no flood insurance is required. An added bonus is the Cul de Sac location and longer driveway for more parking for family and guests. Volume Ceilings, Crown Molding and an Open Concept highlight a versatile floor plan featuring 2 Bedrooms plus an Office or Den - complete with Custom Paneling, Spacious Desk and Bookcase and even the Luxury of a Wood Burning Fireplace! Open to the generous 28’ x 18’ Great Room, the bright Kitchen features an Eat-In Breakfast Area, Bay Windows with Plantation Shutters, Double Ovens, French Door Fridge and plenty of storage. The Primary Suite features 2 Walk-In Closets complete with Custom Built-in Shelving and Pull-Down Clothing Racks and a Large Bath with Dual Vanities, Large Soaking Tub and Separate Shower. Relax since the reasonable HOA fee includes Lawn Maintenance with Mowing, Fertilizing and Mulching, Cable TV and Internet, Trash and Recycling Collection, a Sparkling Community Pool and Spa for Cross Creek residents, Escrow Reserves, Pressure Cleaning of Roofs and Exterior Painting every 7 years. Home Updates include New Water Heater in Dec. 2025, New Tile Roof in 2019, A/C Unit New in 2018. Washer and Dryer included in the sale plus Manual and Remote-Controlled Exterior Hurricane Shutters and a Generac Generator. This long-time owner had no issues with the 2024 Hurricanes. Enjoy that Gorgeous View and put your touches on this home since this amazing price takes updating into account. All this in a Great Location convenient to Tampa International Airport, beautiful Beaches, Medical Facilities, Professional Sporting Events and Fine Dining. A variety of memberships to Ardea Country Club are available for additional fees and include access to 2 Golf Courses, a Fitness Center, Heated Lap Pool and Freeform Pool, Pickle Ball and Tennis plus Dining and a host of Activities and Events!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,389,000172 Days on yellowkey MLS ID: TB8440175
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3850 Built: 1998Monthly Fee: $142 Tax: $9,378 (2024)Community: Diamond CrestSingle Family
Taxes:$9,378
Elementary School: Cypress Woods Elementary-PN
Remarks: Welcome to 2151 Diamond Court ~ Where luxury meets everyday comfort and style. This beautifully updated residence in the exclusive, gated community of Diamond Crest at East Lake Woodlands offers stunning water and conservation views and a thoughtfully designed 3-way split floor plan with a dedicated front office. From the moment you step inside, you’ll notice the meticulous attention to detail. The spacious, newly renovated, gourmet kitchen features custom cabinetry, quartz countertops, Café Platinum Collection appliances (including double wall ovens with air fryer and 36” induction cook-top), and a show-stopping triple frosted glass pantry door. The kitchen opens seamlessly to the expansive great room where a 60”, three-sided glass linear fireplace and floor-to-ceiling picture window frame the serene natural backdrop. Nearly every major improvement has already been completed for peace of mind — including a new tile roof, PGT Low-E impact windows, luxury plank flooring throughout, and a panoramic-view screened lanai enclosure that beautifully extends your indoor living outdoors. Enjoy unobstructed views of lush conservation and tranquil water, making this home perfect for both relaxing and entertaining. The primary suite is generously sized with large windows that bring the outdoors in, while each guest wing offers privacy and comfort. All bathrooms have been tastefully remodeled, and remote-operated window treatments and ceiling fans add to the home’s thoughtful conveniences. Outside your front door, discover the newly re-imagined Ardea Country Club, offering championship golf, state-of-the-art racquet facilities, expanded dining, resort-style amenities, and engaging spaces for all ages. Membership is optional — simply visit the clubhouse for details. Location is unbeatable — tucked in a quiet, private setting yet just 20–25 minutes to Tampa International Airport, award-winning Gulf beaches, and the vibrant dining and shopping of both Tampa and Clearwater. This home truly has it all — luxury, convenience, and a view you’ll never tire of. Come experience it in person.
Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)
Listing Agent: Michelle Johncola (727-515-2415)
209 HEMINGWAY DR, OLDSMAR, FL 34677
$294,90042 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)
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