Location: Oldsmar , 34677
Do Not Show Listings
1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$380,00025 Days on yellowkey MLS ID: TB8488580
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1973 Tax: $1,036 (2025)Community: Harbor Palms-Unit TwoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,036
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, while the bedrooms are generously sized for comfort and flexibility. Conveniently located near parks, shopping, dining, and major roadways, this home provides easy access to Tampa, Clearwater, and surrounding areas. Don’t miss this opportunity to own a well-maintained home in a desirable location!
Listing is courtesy of: OUT FAST REALTY & INVESTMENTS (800-688-3278)
Listing Agent: Julio Vasquez (727-404-8889)
120 BRENT CIR, OLDSMAR, FL 34677
$520,00023 Days on yellowkey MLS ID: TB8484780
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1834 Built: 2004Monthly Fee: $473 Tax: $8,930 (2025)Community: Seaside EstatesTownhouse
Taxes:$8,930
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days on the water at a moment's notice. Inside, the home unfolds into an open, light-filled floor plan enhanced by soaring high ceilings and expansive windows that invite natural light throughout the day. The seemless flow between living, dining, and kitchen spaces creates an ideal setting for both RELAXED everyday LIVING and entertaining. Water views provide a constantly changing backdrop, adding a sense of CALM and CONNECTION to the outdoors. The generous layout offers flexibility for hosting family and guests, while the airy ceiling heights add architectural drama and a sense of openness rarely found in townhome living. Whether you're enjoying quiet mornings with coffee by the water or gathering with friends after a day on the boat, this home adapts effortlessly to your lifestyle. Outdoor living is just as compelling, with immediate access to the waterfront and your own boat slips just steps away - perfect for boating, paddleboarding, or sunset cruises. This is a home that blends convenience and luxury, offering the maintenance ease of a townhome with the experience of a private gated waterfront retreat. Ideally suited as a primary residence or a refined second home, this property delivers the best of waterfront living - space, light, and direct access to the water- all in one elegant package.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Darren Booth (813-310-0196)
509 LAKEVIEW DR, OLDSMAR, FL 34677
$499,90026 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
Elementary School: Forest Lakes Elementary-PN
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
$559,900173 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
Tax Year: 2024
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)
475 WOODS LANDING TRL, OLDSMAR, FL 34677
$255,00099 Days on yellowkey MLS ID: A4676723
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1200 Built: 1984Monthly Fee: $591 Tax: $4,082 (2024)Community: East Lake Woodlands Woods Landing TwnhmsTownhouse
Taxes:$4,082
Remarks: Welcome home to this beautifully updated Townhouse in the sought after East Lake Woodlands Gated Community. The views from the enclosed Florida room offering wooded pond view, wildlife and complete serenity. This home features 2 bedroom, 2.5 baths, private driveway with car port and storage shed, updated kitchen with granite countertops and stainless steel appliances. In the kitchen is a sliding door opening up to your private patio with jacuzzi hot tub and access to shed, a perfect spot to enjoy morning coffee or BBQing. Vinyl flooring throughout the first floor for a gorgeous seamless flow offering large living room/dining area combo. All New hurricane proof windows upstairs as well as the slider in the kitchen and in the updated 1/2 bath. Upstairs you will find the Primary suite which has a walk in closet and updated ensuite bath, the guest room also offers an additional walk in closet as well as it's own private bathroom. The laundry closet is conveniently located upstairs between the 2 bedrooms. There is a community pool in the neighborhood, heated and ready to use year round. For an extra fee you can join the Ardea Country Club, which has two – 18-hole golf courses, restaurants, bar, fitness center, tennis courts, pickleball courts, Olympic size pool, splash pads, ping pong and more. Centrally located to shopping, restaurants, airport, excellent schools and Florida’s award-winning Gulf Beaches. All of these features makes East Lake Woodlands the perfect place to call home.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Loren Roye (516-446-3614)
134 CYPRESS CT #134, OLDSMAR, FL 34677
$155,00033 Days on yellowkey MLS ID: TB8484548
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,044 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,044
Remarks: One or more photo(s) has been virtually staged. Welcome to easy Florida living in the peaceful Cypress Estates III neighborhood, located in the highly sought-after East Lake Woodlands gated golfing community. This light-filled two-bedroom, two-bath condo offers low-maintenance living with Condo fees that cover water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and the community pool. Your second-floor unit is just a short stroll from your assigned parking space, making everyday living convenient and accessible. Step inside and you’re greeted by an open and inviting living, dining, and kitchen area designed for both comfort and entertaining. Natural light flows throughout the space, highlighting the updated flooring that extends across the entire home. Sliding glass doors lead you out to a screened-in lanai, the perfect place to start your morning with coffee or unwind in the evening while enjoying tranquil conservation views nearby. The lanai also features a convenient laundry closet along with additional storage space. Tucked toward the rear of the home, the spacious primary suite provides a peaceful retreat. It features two generous walk-in closets, private sliding door access to the lanai, an oversized linen closet with extra storage, and an en-suite bathroom complete with a step-in shower. Back near the main living area, the kitchen offers ample cabinetry, a range, refrigerator, and dishwasher, a pantry closet with shelving to keep everything organized, and space for a table. Just around the corner, the hallway includes a linen closet, along with a second full bathroom featuring a tub and shower combination located conveniently across from the second bedroom. The second bedroom is well-sized and includes an oversized wall closet providing excellent storage. Quietly situated within this desirable community, this bright and welcoming condo offers comfort, convenience, and a lifestyle that’s hard to beat. With updated flooring already in place, all that’s left to do is move in and make it your own. Cypress Estates has a community pool that is only a short distance from your new home. Located in close proximity to shopping and restaurants, with easy access to Tampa and the beaches, this home is ready for its new owner! Come see this property today and experience the charm of East Lake Woodlands.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
380 WELLINGTON AVE, OLDSMAR, FL 34677
$1,155,000368 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 is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: James Wheeler, Pa (813-285-1229)
388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$246,00053 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)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$339,00062 Days on yellowkey MLS ID: TB8475078
REDUCED by $10,000 (2.9%) on 03/31/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $562 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$562
Remarks: Priced below appraisal. Move-in ready. Renovated mid-century modern in the heart of Oldsmar. Stop searching and start packing because this rare architectural gem is yards away from the Oldsmar boat ramp. With NO HOA, park your toys with ease - boats, RVs, trailers, golf carts and work trucks. Priced below appraisal for an immediate sale. Opportunities to own a move-in ready Mid-Century Modern masterpiece rarely arise. This is your chance to secure instant equity in this 3 bedroom, 2 bathroom property that seamlessly blends iconic design with today's high-end, low-maintenance lifestyle. This residence is a masterclass in quintessential mid-century style, defined by soaring exposed beams, expansive windows that flood the home with natural light, and terrazzo flooring. The split-floor plan offers three spacious bedrooms and two stylishly updated bathrooms. Bedrooms are large enough to fit two full-size beds, with plenty of room to walk-around. Stylish updated bathrooms bring the color of the outdoors into this modern design. At the heart of the home, the recently renovated kitchen features sleek modern finishes, 42-inch upper cabinets, quartz countertops, stainless steel appliances, and high-end cabinetry, making it as functional as it is beautiful. The potential for forced appreciation here is unmatched. A massive, versatile bonus room provides the perfect footprint for a dedicated home office, secondary living area, or quick conversion into an attached apartment or mother-in-law suite for multi-generational living or rental income. Furthermore, the expansive carport offers a ready-made foundation to create a fourth bedroom or enclosed family room, potentially adding over 400 square feet of conditioned living space to your investment. Outside, the fully fenced backyard serves as a private oasis for entertaining or pets. All major systems have been updated, providing complete peace of mind. This property has also performed well as a short-term rental, making it an ideal choice for savvy investors or snowbirds seeking flexible income. The lifestyle offered here is second to none, located just yards from the Oldsmar Boat Ramp with direct access to Tampa Bay for world-class fishing and water sports. Enjoy a bike-friendly community with rapid access to RE Olds Park, the Oldsmar Trail, and the historic horse track. You are steps away from pickleball, tennis, and the vibrant events that make this neighborhood one of the most beloved in the region. This is a rare opportunity to own architectural history with significant modern updates without the premium waterfront price tag. Because this home is priced to move immediately, it will not last. Schedule your private showing today before this below-appraisal deal disappears.
Listing is courtesy of: SELLSTATE COASTAL REALTY (813-940-0101)
Listing Agent: Faith Walston (813-303-1239)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000166 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
$180,00017 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)
408 LAKEVIEW DR, OLDSMAR, FL 34677
$499,90053 Days on yellowkey MLS ID: TB8478309
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1598 Built: 1983Monthly Fee: $35 Tax: $3,714 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$3,714
Remarks: Price Reduced - This lakefront, pool home overlooks stunning sunsets and a wooded conservation area. The entire back of the house is screen enclosed, giving you plenty of space to relax or entertain while enjoying the wildlife, sunsets and sparkling lake. The beautiful pool and attached hot tub are heated for year round enjoyment. Inside are lake views in almost every room! The home has 76' water frontage but has had NO flooding and is in a NON FLOOD Zone. It features a driveway that can easily park 6 cars, rare in this neighborhood, and a 2 car garage. Also inside this split bedroom floor plan are one of a kind marble floors, newer windows, HVAC and roof and a large walk-in shower and bench seat in the primary bathroom and a jetted tub/shower in the guest bath. Located in the Forest Lakes community with only $35 monthly HOA dues, offering pool, tennis/pickleball, basketball and racquetball courts, playground and dock. The city of Oldsmar is an easy commute to Tampa and Clearwater, Honeymoon Island, Clearwater Beach and to both the Tampa and St. Petersburg Airports. Oldsmar also boasts many beautiful parks and events for the whole family and is in highly sought after school zones.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
303 MARTHA LN #303, OLDSMAR, FL 34677
$189,90031 Days on yellowkey MLS ID: TB8485863
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1979 Tax: $613 (2025)Community: East Lake Woodlands CondoCondo
Taxes:$613
Remarks: Welcome home to peaceful, easy living in the heart of East Lake Woodlands. This well-maintained 2-bedroom, 2-bathroom condo offers a comfortable and functional layout ideal for everyday living or seasonal enjoyment. The spacious primary suite serves as a true retreat, highlighted by an impressive three walk-in closets, providing exceptional storage rarely found in condo living. Residents can enjoy tranquil surroundings and unwind at the community pool, creating a relaxed Florida lifestyle. Conveniently located in Oldsmar, this home offers easy access to shopping, dining, beautiful Gulf beaches, and Tampa International Airport, making commuting and travel effortless.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Shayna Teator (813-459-2207)
3073 DUANE AVE, OLDSMAR, FL 34677
$459,000239 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
$822,000269 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
$550,00028 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
$395,00076 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
$549,00099 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
$1,389,000169 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)
201 DUNKIRK RD, OLDSMAR, FL 34677
$399,00031 Days on yellowkey MLS ID: TB8486754
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1760 Built: 1959 Tax: $3,373 (2025)Community: Oldsmar Country Club Estates Sec 1 RepSingle Family
Taxes:$3,373
Remarks: Welcome to this beautifully updated Oldsmar property. 3 bedrooms and 2 bathrooms to accommodate the entire family or have your private office space. The kitchen is the center of this house, with plenty counter space and cabinets. Beautiful glass door cabinets buffet area for entertaining your guess while you prepare your meals. The master bedroom is a true retreat, with a soaking tub, separate shower and double sink, without forgetting about your walking closet, which is beautifully hidden with a modern barn door. This property is centrally located with quick access to TPA, boating ramp and walking distance to Richard Rogers Park (basketball, playground), Sheffield Park (dog park, disc golf, trails), and R.E. Olds Park (waterfront, fishing pier, kayak. If you also would like to take advantage of the huge backyard which can easily accommodate an income producing Tiny home and so much more. Do Not lose the opportunity to purchase this home......
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Gersie Schweizer (813-300-5339)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.