Location: Oldsmar
Do Not Show Listings
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,112
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
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
Tax Year: 2025
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 is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
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
Elementary School: Forest Lakes Elementary-PN
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
Elementary School: None
High School: None
Middle School: None
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)
908 VINEYARD LN, OLDSMAR, FL 34677
$385,00041 Days on yellowkey MLS ID: TB8481839
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1773 Built: 2017Monthly Fee: $418 Tax: $4,090 (2025)Community: Tuscany Woods PreserveTownhouse
Taxes:$4,090
Remarks: $14,000 PRICE REDUCTION! Welcome to elevated living in the heart of Oldsmar! This beautifully maintained 3-bedroom, 2.5-bath townhome by Taylor Morrison blends modern style, thoughtful upgrades, and a peaceful natural setting — all within a gated community. Step inside to a bright, open layout perfect for everyday living and entertaining. The stunning kitchen is a true centerpiece, featuring stainless steel appliances, granite countertops, 42-inch cabinets, and abundant storage, all flowing seamlessly into the spacious living and dining areas. Upstairs, brand-new carpet (Feb 2026) on the stairs and upper level adds warmth and a fresh, move-in-ready feel. This home is loaded with valuable upgrades, including a reverse osmosis system with electrolytes and a whole-home water softener, elevating your everyday comfort. Pride of ownership shines throughout in its pristine condition and meticulous care. Out back, enjoy rare privacy as the home backs to a tranquil conservation area — no rear neighbors, just peaceful nature views. The screened-in lanai is the perfect retreat for morning coffee or unwinding in the evening breeze. Location truly sets this home apart. Situated directly across from Cypress Forest Spray Park and Recreation Center and just minutes from parks, waterfront trails, shopping, dining, and easy access to Tampa and Clearwater, you get the best of convenience and serenity. Move-in ready, beautifully upgraded, and perfectly located — this is Oldsmar living at its finest. AC (2017); water heater (2025); reverse osmosis system with electrolytes and whole-home water softener (2024); new carpet (Feb 2026); NO flood insurance required; conservation view; gated
Listing Agent: Keegan Siegfried (813-670-7226)
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)
2270 CHRISTY LN, OLDSMAR, FL 34677
$1,250,00055 Days on yellowkey MLS ID: TB8477474
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3993 Built: 1996Monthly Fee: $181 Tax: $11,849 (2025)Community: Turtle Creek Unit-ThreeSingle Family
Taxes:$11,849
Remarks: Welcome to luxury living in the desirable Gated, Golf Community of East Lake Woodlands! This stunning home in Turtle Creek has a Premium Conservation Setting and features 4 Bedrooms plus Office/Den and Bonus Room, 4.5 Baths all on One-Story with the exception of the bonus room. Perfectly nestled on a picturesque Cul-de-Sac, tranquility and privacy are yours. Enjoy the best of both worlds with a serene, fenced back yard that’s easy to maintain while having the privacy of Deep Conservation beyond on this Expansive 1.95-acre lot. Plus this home is located in the preferred Zone X so No flood insurance is required! The wide Side Load Garage measuring 28’ x 22’ and large Pavered Driveway provide generous parking and set the tone for a stately entrance accented with Travertine along front and side. Step inside to Open Living Room and Dining Room elegance with Soaring Volume Ceilings, Stunning Crown Molding and Dramatic Windows that create an inviting ambiance. Flexibility abounds with this Floor Plan with the Office/Den and Bonus Room providing plenty of options to best fit your family’s needs now and in the future. And the Three-way Split bedroom layout gives everyone their own space. Need a 5th Bedroom? No problem, the front Office/Den is generously sized and features a closet plus gorgeous windows. The Open Concept continues to the Kitchen and Family Room ideal for entertaining small or large gatherings of family and friends. Stainless Steel Appliances including Oversized Fridge, Gas Range and loads of Storage highlight this kitchen in addition to its large Center Island with Prep Sink, Walk-In Pantry and Breakfast Bar for lots of seating. Retreat to the luxurious Primary Suite which occupies the entire right wing of the home and includes an Additional Sitting Area complete with Cozy Gas Fireplace and a Spa-like Primary Bathroom with long Dual Vanity, Deep Soaking Tub and all Neutral Creamy Tones - your personal oasis. This home also boasts a convenient shared bathroom for bedrooms 2 and 3 plus another separate 4th bedroom and bath. Outdoor Living and all that privacy is accentuated with the Gorgeous Pool and Spa with Electric and Gas Heaters respectively, impressive Covered and Screened Lanai and Extensive Pavers which carry through to the side walkway spanning the length of the home. Upgrades include Tankless Water heater installed in 2026, New Trane A/C for main portion of the house in 2021, Bosch Dishwasher in 2025, Electric Pool Heater in 2021, Reverse Osmosis System, Tile Roof in 2013, Aluminum Fencing and Mini-Split A/C in Garage. Plus 2023 Samsung Washer and Dryer are included in the sale. Relax and take advantage of Optional Memberships to Ardea Country Club including Resort-Style Amenities such as 2 Golf Courses, Fitness Center, Heated Lap Pool and Freeform Pool, Poolside Café, Pickleball and Tennis, Dining and a host of Events. Located conveniently to Tampa International Airport, Top-rated schools, Beautiful Beaches, Medical Facilities, Parks and Outstanding Dining, this exceptional home offers the perfect blend of Luxury, Convenience and Lifestyle. Don’t miss your opportunity to own this East Lake Woodlands gem!
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)
209 HEMINGWAY DR, OLDSMAR, FL 34677
$294,90039 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)
107 MARY DR #107, OLDSMAR, FL 34677
$189,00095 Days on yellowkey MLS ID: TB8462887
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981 Tax: $3,445 (2025)Community: East Lake Woodlands CondoCondo
Taxes:$3,445
Remarks: One or more photo(s) has been virtually staged. Move-In Ready Ground Floor Condo in Gated East Lake Woodlands Community! Step into this beautiful updated ground floor condo, where comfort meets convenience in a secure gated environment. The kitchen and bathrooms were thoughtfully renovated in 2017, and brand-new luxury vinyl plank flooring flows seamlessly throughout the living, dining, hall, and both bedrooms—no carpet to worry about! The master suite is impressively spacious, featuring three closets, including two walk-ins, providing ample storage. The abundant windows and sliding doors fill the living spaces with natural Florida sunlight, creating a warm and inviting atmosphere. Unwind in the screened lanai, complete with tranquil views of the green space behind and adjacent picturesque pond, perfect for relaxation or entertaining. Additional storage and a laundry closet are conveniently located in the lanai as well. Enjoy maintenance-free living with a monthly fee that covers building exterior, insurance, roof, grounds maintenance, community pool, basic cable, water/sewer, trash removal, and secure gated entry points, allowing you more time to enjoy your home! Residents of East Lake Woodlands can take advantage of exceptional lifestyle amenities available through membership at the newly remodeled Ardea Country Club. Indulge in championship golf, tennis, pickleball, a swimming pool, fitness center, and much more—all just minutes from top-rated schools, shopping, dining, award-winning beaches, and Tampa International Airport. Don't miss out on this wonderful opportunity to live in a vibrant community—schedule your showing today! Room sizes are approximate.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)
Listing Agent: Rachel Friesema (727-481-4757)
278 PELICAN DR N, OLDSMAR, FL 34677
$179,999131 Days on yellowkey MLS ID: TB8453637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1985Monthly Fee: $60 Tax: $2,239 (2024)Community: Gull-Aire VillageManufactured Home
Taxes:$2,239
Remarks: Don't miss this desirable and very active community of Gull-Aire Village! This is one of the most highly sought-after 55+ communities in Pinellas County. With HOA fees at only $60/mo and the ability to rent out your home after only 1 year of ownership, the possibilities are endless. This home includes a rare LARGE GARAGE! You own your own land. The owner has just replaced the range and refrigerator! One pet-any size. You can walk to AMC Theatres, Beall's, Marshalls, Earth Fare, Pet Smart and Dollar Store. Restaurants nearby include Shaker and Peel, Craft Street Kitchen, and Eve's Family Restaurant. Just minutes to Westfield Mall, Walmart, Publix, and Countryside Hospital. About 20 minutes to the beautiful beaches of Honeymoon Island and Caladesi State Parks. Schedule your private showing today!
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-466-0800)
Listing Agent: Jon Dant (727-504-6727)
1730 OAK POND CT, OLDSMAR, FL 34677
$584,00060 Days on yellowkey MLS ID: TB8476142
1 Days Off yellowkey (back on 3/29/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1918 Built: 1998Monthly Fee: $13 Tax: $7,594 (2025)Community: Eastlake OaksSingle Family
Taxes:$7,594
Remarks: Under contract-accepting backup offers. Price Improvement.! Tucked inside the desirable Eastlake Oaks neighborhood, this 3-bedroom, 2.5-bath residence with a 3-car garage offers 1,918 square feet of well-designed living space and the kind of backyard retreat Florida buyers are searching for. Set on an oversized 11,000+ sq ft lot with water views and no neighbors on three sides, this Eastlake Oaks property delivers a rare combination of privacy and space. From the moment you step inside, dramatic vaulted ceilings create a grand first impression. The layout offers both defined spaces and natural flow — with formal living and dining areas at the front of the home and an inviting family gathering space toward the rear. The kitchen is designed for connection and function, featuring stainless steel appliances, a gas range connection for cooking enthusiasts, and a breakfast bar that opens to the main living area. A gas fireplace anchors the space, adding warmth and character. Glass sliders lead to a spacious screened pool enclosure (over 600 sq ft), providing the perfect balance of sunshine and shade. Upstairs, the primary suite includes a private bath with soaking tub, separate shower, and enclosed water closet. Two additional bedrooms share a Jack-and-Jill bath, and the laundry closet is conveniently located upstairs where it belongs. This home has never had any water intrusion. Major updates include: • Roof (2017) • A/C (2017) • Gas water heater (2020) Positioned just minutes from schools, shopping, dining, parks, and Tampa Road conveniences — and approximately 20–30 minutes to Gulf beaches or Downtown Tampa — this location makes commuting and coastal living effortless. A well-maintained home, a spacious lot, and a pool made for Florida afternoons — all in one of Oldsmar’s most convenient communities.
Listing Agent: Kirsten Kelley (727-439-7545)
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