Location: Oldsmar
Do Not Show Listings
395 WINGATE CIR, OLDSMAR, FL 34677
$575,000162 Days on yellowkey MLS ID: TB8450027
REDUCED by $15,000 (2.5%) on 04/29/2026
Bed: 5 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2827 Built: 2001Monthly Fee: $100 Tax: $9,963 (2025)Community: Bay ArborSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,963
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Lowest Listed Price Per Square Foot for this community. Picture Perfect Bay Arbor, a gated community. (Approved plans to extend fence in backyard) The School District zoned for this home has two A and one B+ rated schools and zoned for Palm Harbor University IB program. Just a mile walk or golf card ride through the community to just outside the gates brings you to the local First Watch, Beef O' Bradys, Aveda, Tijuanna Flats, and Hot Tuna Sushi. The communities natural surroundings, abundant with community green-space, wildlife, and a community Pool & Playground. A 3 car garage, paver driveway & paver path to the front porch greets you out front. The foyer immediately opens up to high ceilings, filled with natural light. The laundry room and the flex room/5th bedroom, media room, office, and/or den are available on the first level. A Breakfast Bar, generous amounts of counter space, and stainless steel appliances for the kitchen. The Breakfast Nook has a large pantry space and overlooks the fenced backyard. The Primary Bedroom and Bedrooms 2-4 are an easy trip up with the two-side staircase. The Primary Bedroom fits a King Size Bed, 2 Walk-in Closets, Glass shower, Garden Tub, and Dual Vanities. You will appreciate the 240sq.ft. rear screened patio leading to your shady, vinyl fenced yard. Your peace of mind knowing the Roof was installed in 2022 and the dual zone A/C system is 2018 and 2012. Convenient to the Tampa airport, Mobbly Bayou Beach Park, Honeymoon Island, UTBP Nature Center, AMC Woodlands Square 20, Tampa Bay Downs. Come enjoy the true Florida Lifestyle!
Listing is courtesy of: STOFEL & ASSOCIATES REALTY (727-350-0373)
Listing Agent: Joey Torres (727-415-7017)
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$634,00013 Days on yellowkey MLS ID: TB8496854
REDUCED by $15,000 (2.3%) on 04/27/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2084 Built: 1998Monthly Fee: $140 Tax: $4,902 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Taxes:$4,902
Elementary School: None
High School: None
Middle School: None
Remarks: REDUCED - SELLER MOTIVATED ... Plus -Enjoy peace of mind with a seller-provided 1-year Home Warranty. OVERSIDED - FULLY FENCED CORNER LOT in highly desirable area/community of Oldsmar - Preserve At Cypress Lake. 4 Bedrooms, 2 Full Bathrooms, no carpeting, only wide-plank flooring & ceramic tile throughout. Separate Living/Dining Room area (currently being used for home Theatre/Office set up). Enjoy another separate Gathering Room. Large Eat-In Kitchen has Breakfast Bar opening to Gathering Room - perfect for entertaining or everyday living. Stainless Steel Appliances, Granite Counters, Pantry, Roll-Out Cabinetry. Connects to inside Laundry Room includes Washer/Dryer. Primary Bedroom large enough for King size Bedding, large Walk-In Closet. Private Ensuite full Bathroom with separate Shower, Garden Tub and Dual Sinks. Other 3 Bedrooms are adequately sized and share another full Bathroom. Closets are equipped with custom closet systems. Plantation Shutters on formal Living Room, Dining Room and Kitchen windows. The outdoors will not disappoint. Screened Lanai features amazing Pool for all your recreation, relaxation & oversized extra Patio space - all under the screened area. Enjoy additional entertaining or everyday living space with grassed area in back yard and another large Paver Patio - perfect for Grilling, Fire Pit, taking in the sun or sitting under an umbrella. Roof installed in 2017. New Hot Water Heater in 2025. Location is SUPBERB ... close to Forest Lakes Elementary, YMCA, Cypress Forest Recreation Center/Waterpark-Spray Park Splash Pad. Enjoy the nearby Nature Trail, Restaurants, Stores, Oldsmar Flea Market, BMX Complex, Oldsmar Hockey Complex, Ball Parks, convenient to Airport, directly down Tampa Road to all the happenings in Dunedin Main Street, Honeymoon Island and all the other Beaches in the area. Enjoy the holiday festivities this community has sponsored - riding on a horse drawn wagon to view neighborhood houses that have decorated. OLDSMAR & Preserve At Cypress Lakes is the place to be !!!
Listing is courtesy of: FLORIDA HOME REALTY GROUP, LLC (813-523-2280)
Listing Agent: Phyllis Clark (813-523-2280)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,0007 Days on yellowkey MLS ID: TB8501214
REDUCED by $20,000 (5.4%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2015Monthly Fee: $285 Tax: $3,417 (2025)Community: Hayes Park VillageSingle Family
Taxes:$3,417
Remarks: NEW PRICE! Location, location, location is the key to finding the perfect home - and this one delivers on every level. If you have been searching for a place that blends character, convenience, and community, look no further. This charming 3-bedroom home sits in the picturesque neighborhood of Hayes Park Village, a community that feels like a slice of the French Quarter right here in Florida. Nestled in the heart of the City of Oldsmar, this home offers the best of old-world-charm with modern comfort. Oldsmar is a great City known for having more parks per sq. mile than any other city in the state along with excellent schools and an abundance of activities for all ages. Also, the home of Tampa Bay Downs and Tampa Bay Skating Academy. It is a place where community pride runs deep and quality of life comes naturally. The homes inviting wrap-around porch sets the tone from the moment you arrive. Enjoy your morning coffee as you look out to the neighborhood courtyard complete with a welcoming fire pit, creating the perfect setting for neighborhood gatherings. Inside the home, gleaming hardwood floors flow through an open concept living space that feels both spacious and cozy. The kitchen is beautifully appointed with granite countertops and 36" cabinets and a center island that anchors the room- ideal for cooking, entertaining or simply enjoying daily life. A convenient first floor powder room adds practicality for guest and family alike. The master suite opens to a second floor balcony that overlooks the lake and Richard B. Rogers Park. The Master bedroom also features a tray ceiling with crown molding and an upgraded bathroom with frameless glass shower enclosure and a walk-in closet. Two additional ample sized bedrooms and a guest bath complete the upstairs. THIS HOME HAS BEEN WELL MAINTAINED; ROOF IS JUST OVER A YEAR OLD AND THE AC IS JULY OF 2025, WATER HEATER REPLACED IN 2024. The PERFECT LOCATION connects TAMPA to PINELLAS COUNTY. Close commute to Tampa International Airport and International Mall. Within minutes of Clearwater and downtown Safety Harbor, Approximately 30 minutes to the Gulf Coast Beaches.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jennifer Kashtan (813-310-7200)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$329,00079 Days on yellowkey MLS ID: TB8475078
REDUCED by $10,000 (2.9%) on 04/15/2026
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
Elementary School: Oldsmar Elementary-PN
Remarks: Yes! These are the real pictures of what this home REALLY looks like! No virtual staging here - these photos are of the REAL DEAL found inside this move-in ready, renovated mid-century modern home located in the heart of Oldsmar. Stop searching and start packing because this rare architectural gem is PRICED UNDER APPRAISAL. Why pay waterfront prices, when this home sits yards away from boat ramp access to Moobly Bay & Safety Harbor. With NO HOA, park your toys with ease - boats, RVs, trailers, golf carts and work trucks. 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 air 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. Bring your offers!
Listing is courtesy of: SELLSTATE COASTAL REALTY (813-940-0101)
Listing Agent: Faith Walston (813-303-1239)
1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$379,900165 Days on yellowkey MLS ID: TB8447176
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 1973 Tax: $1,160 (2024)Community: Harbor Palms-Unit TwoSpa: NoSingle Family
Taxes:$1,160
Tax Year: 2024
Remarks: Under contract-accepting backup offers. GREAT BUY ON THIS WONDERFUL 3 BEDROOM POOL HOME LOCATED IN THE DESIRABLE HARBOR PALMS SUBDIVISION. THE HOME FEATURES AN EXCELLENT SPLIT-BEDROOM FLOOR PLAN, A SPACIOUS LIVING ROOM, A COMFORTABLE FAMILY ROOM, AND GENEROUSLY SIZED BEDROOMS. ENJOY A SCREENED-IN POOL AND AN OVERSIZED ONE-CAR GARAGE. RECENT UPDATES INCLUDE A NEW A/C (2022), NEW ELECTRICAL PANEL (2023), AND A ROOF INSTALLED IN 2012. WITH INTERIOR UPDATES, THIS ADORABLE, COZY HOME CAN BECOME EXACTLY WHAT YOU’RE LOOKING FOR. NO FLOOD DAMAGE FROM RECENT STORMS. GREAT OLDSMAR LOCATION CLOSE TO MAJOR SHOPPING, GROCERY STORES, AREA BEACHES, PARKS, AND MORE!
Listing is courtesy of: SELECT PROPERTIES INC (727-934-4099)
Listing Agent: Frank Acerra (727-410-9849)
1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$849,00098 Days on yellowkey MLS ID: TB8467569
3 Days Off yellowkey (back on 4/29/2026)
REDUCED by $30,000 (3.4%) on 04/07/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2650 Built: 1992Monthly Fee: $207 Tax: $11,111 (2024)Community: Greenhaven Unit ThreeSpa: YesSingle Family
Taxes:$11,111
Remarks: Under contract-accepting backup offers. Welcome home to a rare blend of privacy, space, and resort-style living in this stunning four-bedroom, two-and-a-half-bath residence, nestled on two secluded acres within the exclusive 22-home enclave of Greenhaven II, a sought after gated community in Oldsmar. This exceptional property offers the tranquility of a private retreat while remaining close to Tampa International Airport, top dining and shopping destinations, professional sports and concert venues, and world-class Gulf beaches. From the moment you arrive, you’ll feel how special this home truly is. Inside, abundant natural light pours through large windows, illuminating tile flooring throughout and an open, airy layout designed for both everyday comfort and effortless entertaining. The open-concept kitchen and family room serve as the heart of the home—perfect for morning coffee, lively gatherings, and relaxed evenings—while separate living and dining spaces provide added flexibility for hosting or quiet moments. Step outside and embrace the best of Florida indoor-outdoor living. A heated pool and spa offer year-round enjoyment, whether you’re entertaining on the weekends, unwinding after a long day, or simply soaking in the peaceful surroundings of your expansive, private lot. The primary suite is a serene retreat featuring his-and-hers closets, while thoughtful updates—including a 2018 roof and a 2020 HVAC system—add confidence and peace of mind. Optional membership at the on-site ARDEA Country Club unlocks an impressive array of amenities, including golf, tennis, pickleball, a lap pool, fitness center, restaurant, and a full calendar of social, holiday, and private events for family and guests. Homes offering this level of privacy, acreage, and exclusivity within a gated setting are truly rare. This isn’t just a place to live—it’s a place to slow down, entertain, and fully enjoy the Florida lifestyle. Schedule your private showing today!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Ian Deran (813-508-7118)
311 VISTA CRUISER LN, OLDSMAR, FL 34677
$350,000158 Days on yellowkey MLS ID: TB8450597
REDUCED by $5,000 (1.4%) on 04/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1547 Built: 2015Monthly Fee: $248 Tax: $3,551 (2024)Community: Hayes Park VillageSingle Family
Taxes:$3,551
Remarks: What else could you want ... This charming 3-bedroom, 2.5-bath home offers the perfect blend of style, comfort, and peace of mind. Outfitted with hurricane shutters, impact windows, and a hurricane-rated garage door, the home ensures lasting security while sitting just moments from parks and walking trails. A brick-paved walkway and covered front porch create a warm welcome, leading into an inviting open-concept living, dining, and kitchen space adorned with elegant diagonal tile flooring, crown molding, and wide baseboards. The kitchen shines with 42" ebony cabinets, rounded granite countertops, a stylish tile backsplash, a spacious island perfect for casual dining, and a generous walk-in pantry. Your half bath is conveniently located off the hallway that also leads to your oversized 2-car garage. Upstairs, the primary suite feels like a private retreat, offering tray ceilings, a walk-in closet, and an en suite bath featuring an oversized step-in shower, private water closet, and dual-sink vanity. Step through your private door to a covered balcony—an ideal spot for morning coffee or evening breezes. Two additional bedrooms share a charming Jack-and-Jill bath, while the upstairs laundry room with shelving adds everyday practicality. The abundant guest parking make hosting effortless, and the community fire pit invites cozy gatherings and neighborhood connection. Enjoy yard maintenance and water included in your HOA, city-style living in an exceptional location just minutes from top-rated schools, parks, a spray park off Pine, beautiful beaches, Tampa International Airport, and a wide array of dining and shopping—including Walmart and Starbucks just a stone’s throw away. All furniture is negotiable, making this a beautifully simple, move-in-ready opportunity. Come check it out You will also enjoy Oldsmar living offering so much - tons of eateries, parks, zip line fun, pickleball courts, walking trails and so much more!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
4953 POINTE CIR, OLDSMAR, FL 34677
$885,0004 Days on yellowkey MLS ID: TB8502016
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2513 Built: 1997Monthly Fee: $142 Tax: $11,677 (2025)Community: Cross PointeSpa: YesSingle Family
Taxes:$11,677
Elementary School: Cypress Woods Elementary-PN
Remarks: This newly renovated 4 bedroom 3 bath home is nestled in a quiet, cozy part of the elite Cross Pointe neighborhood located in the highly sought after Eastlake Woodlands development. From the moment you walk through the door, you’ll notice the attention to detail and inviting atmosphere that make this home truly special. Natural light, functional spaces, and stylish touches create a setting that’s both elegant and comfortable. Enjoy the amenities of Ardea Golf, Tennis, and Social club. This gem will not last long - schedule a viewing today.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
1654 BAYHILL DR, OLDSMAR, FL 34677
$570,000198 Days on yellowkey MLS ID: TB8438417
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2320 Built: 1995Monthly Fee: $177 Tax: $5,855 (2024)Community: CreeksideSingle Family
Taxes:$5,855
Remarks: "SELLER OFFERING $6000 TOWARDS CLOSING COSTS" THIS HOME SITS IN THE QUAINT SECLUDED CREEKSIDE COMMUNITY INSIDE THE GATES OF EASTLAKE WOODLANDS, LARGE FAMILY HOME OF 4 BEDROOMS, 2 AND HALF BATHS, 2 CAR GARAGE WITH POOL, YOUR OPEN CONCEPT OF DINING AND LIVING ROOM GREAT FOR THE FAMILY TO GATHER, KITCHEN WITH GRANITE COUNTER TOPS AND UPDATED BACKSPLASH, APPLIANCES TO INCLUDE DISHWASHER OCTOBER 2025, FAMILY ROOM WITH SLIDING GLASS DOORS GOING TO YOUR PERSONAL PARADISE TO ENJOY YOUR SCREENED ENCLOSED PAVED PATIO INGROUND POOL OUT DOORS ANOTHER GREAT ENTERTAINMENT SPACE, THEN OUTSIDE TO SWING AND ENJOY THE WILD LIFE AND DEER AND THE PRIVATE AND QUIET BROOKER CREEK PRESERVE AREA, THEN YOUR BEAUTIFUL STAIRCASE TO YOUR PRIMARY BEDROOM RETREAT WITH LARGE EN-SUITE BATHROOM, INSIDE LAUNDRY ROOM, AC SYSTEM INSTALLED 2021, ROOF 2018. DON'T MISS OUT ON THIS RARE OPPORTUNITY TO OWN THIS MUCH SQUARE FOOTAGE FOR SUCH A GREAT COMMUNITY. POSSIBILITIES ARE ENDLESS!!
Listing is courtesy of: ECKERT REALTY & PROPERTY MGMT (727-240-0668)
Listing Agent: Karen Hutson (727-240-0668)
433 TANGERINE DR, OLDSMAR, FL 34677
$419,900249 Days on yellowkey MLS ID: TB8421066
6 Days Off yellowkey (back on 3/3/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1498 Built: 1980 Tax: $2,758 (2024)Community: Harbor Palms Unit 11Spa: YesSingle Family
Taxes:$2,758
Remarks: Under contract-accepting backup offers. Charming single-story home located in the heart of Oldsmar, offering comfort and convenience. This property features a spacious open floor plan with abundant natural light throughout the living and dining areas. The kitchen is well-appointed with ample cabinet space and overlooks the main living area, perfect for everyday living and entertaining. The bedrooms are generously sized, and the primary suite includes a private bath. Outside, enjoy a large yard with mature landscaping that provides both privacy and outdoor enjoyment. Ideally situated near top-rated schools, parks, shopping, dining, and with easy access to Tampa, Clearwater, and the Gulf beaches.
Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)
Listing Agent: Esther Fleitas Padron (813-817-8803)
504 FEDERAL ST, OLDSMAR, FL 34677
$1,180,000207 Days on yellowkey MLS ID: TB8427180
REDUCED by $90,000 (7.1%) on 04/25/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2961 Built: 2026 Tax: $1,498 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$1,498
Remarks: This stunning new three-story residence by Danva Construction perfectly blends modern luxury with resilient, high-end design. Located at 504 Federal Street in the desirable waterfront community of Oldsmar, this home is built for peace of mind with a solid concrete block structure, pilings, impact-resistant windows, and a durable TPO roof, all backed by a comprehensive builder warranty. The exterior is finished in Sherwin Williams Chantilly Lace, creating a clean, modern curb appeal enhanced by professional landscaping and a signature magnolia tree. Inside, the open-concept layout features soaring ceilings, porcelain tile flooring, and a gourmet kitchen that serves as a true showpiece. The kitchen is complete with a waterfall island, designer backsplash, and premium Bosch 800-series appliances. The luxurious primary suite offers a spa-inspired retreat with a freestanding soaking tub and porcelain tiled walls. Indoor-outdoor living shines with a second-floor porcelain tile balcony and a covered lanai. Note that some images are virtually staged to show the home's potential. Perfectly positioned just one block from Tampa Bay and five minutes to Mobbly Bayou Beach Park, this home offers a lifestyle of privacy and convenience. Oldsmar is a charming waterfront community known for its parks and trails, with effortless access to Tampa International Airport (under 20 mins), Downtown Tampa (30 mins), and the world-famous beaches of Clearwater. The location is a true paradise for outdoor enthusiasts and urban commuters alike. You are steps away from the Upper Tampa Bay Trail, offering miles of scenic cycling and jogging paths. Just minutes away, the historic downtown Oldsmar district provides an array of boutique dining, local craft breweries, and community events like the annual Oldsmar Days. For shopping, the International Plaza and Bay Street are a short drive away, offering world-class retail experiences. Nature lovers will appreciate being adjacent to the Mobbly Bayou Wilderness Preserve, featuring over 400 acres of kayaking, hiking, and even a zip-line adventure park. Golfers can enjoy proximity to several championship courses including the nearby East Lake Woodlands Country Club. Whether you are catching a flight for business or spending a Saturday at Honeymoon Island State Park, this central location puts the very best of the Florida Gulf Coast right at your doorstep. This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location.This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location. All financing information is for illustrative purposes only and not a commitment to extend credit.
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Virginia Torres Bond (813-352-2933)
4766 STONEVIEW CIR, OLDSMAR, FL 34677
$645,00035 Days on yellowkey MLS ID: TB8487161
4 Days Off yellowkey (back on 4/27/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2114 Built: 1993Monthly Fee: $108 Tax: $3,755 (2025)Community: StonebriarSingle Family
Taxes:$3,755
Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly desirable Stonebriar enclave of East Lake Woodlands—where timeless design meets effortless Florida living. This impeccably maintained four-bedroom, two-bath pool home showcases true pride of ownership and offers a seamless blend of comfort, functionality, and style. From the moment you arrive, the home’s pristine condition and inviting curb appeal set the tone. Step through the front door and be immediately captivated by a stunning sightline that draws your eye through the living space to the screened lanai and sparkling pool beyond—an ideal introduction to the indoor-outdoor lifestyle that defines this residence. To the right, the formal dining room offers generous proportions, perfect for hosting gatherings both intimate and grand. Straight ahead, the formal living room provides direct access to the lanai, creating a fluid transition for entertaining and allowing you to fully embrace Florida’s beautiful weather year-round. Privately positioned to the left of the entry, the primary suite is a serene retreat featuring its own access to the lanai. The en suite bath is thoughtfully appointed with a deep soaking tub, step-in shower, and a spacious walk-in closet—delivering both comfort and convenience. At the heart of the home, the updated kitchen is a standout, boasting white shaker cabinetry, stone countertops, and an elegant tile backsplash. A breakfast bar and optional nook space add flexibility, while the open layout flows effortlessly into the family room, complete with a cozy wood-burning fireplace—perfect for relaxed evenings at home. The split-bedroom floor plan enhances privacy, with three additional generously sized bedrooms located toward the rear of the home, each offering ample closet space. The secondary bath features a tub/shower combination and provides direct access to the laundry room and lanai, functioning perfectly as a pool bath. Step outside to your private oasis—an expansive screened lanai featuring a solar heated saltwater pool, ideal for year-round enjoyment. The covered area offers the perfect setting for outdoor dining and lounging, and select patio furnishings are available for purchase, making this space move-in ready for immediate enjoyment. A spacious backyard completes the outdoor experience. With its thoughtful layout, stylish updates, and inviting indoor-outdoor flow, this home is truly ready for its next chapter. Roof 2013, HVAC 2024, Hurricane rated impact windows throughout, new gutters and pool cage rescreening. Don’t miss the opportunity to experience everything this exceptional property has to offer—schedule your private showing today.
165 MOBBLY BAY DR, OLDSMAR, FL 34677
$1,219,900219 Days on yellowkey MLS ID: TB8430614
REDUCED by $20,000 (1.6%) on 04/21/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3945 Built: 2012Monthly Fee: $183 Tax: $8,887 (2024)Community: Estuary Of Mobbly BaySpa: YesSingle Family
Taxes:$8,887
Remarks: Wow!! Picture perfect model home located in the exclusive gated community of ‘Estuary of Mobbly Bay’. This home boasts 5 large bedrooms, plus a den/office, plus an upstairs bonus room, 4 full baths and a 3-car garage... Nearly 4,000 sq.ft. of grandeur! The moment you walk through the commanding solid wood front door you are greeted to excellence!!! A true “family home” with separate formal living and dining areas. The kitchen and family room are perfectly positioned as an entertainer’s dream! The kitchen includes a cook top, wall oven/microwave, granite counters and a designer tile back splash. The desirable double island layout allows for a substantial breakfast bar in addition to an eat-in area. And this wide-open space overlooks the huge family room accented by magnificent French doors and views of a beautiful outdoor living space! Of course, the splendor extends outside!! There is a large pavered lanai & beautifully designed pool, with a ‘sun shelf’ and raised hot tub!! The remainder of the main living level claims 4 of the 5 bedrooms. All generously sized with large windows revealing a light & bright setting. The primary retreat is fit for royalty and has upgrades galore! Crown molding, ensuite w center set soaking tub and a massive double-entry ‘walk in’ shower! All bathrooms are elegantly designed and completed with striking finishes! A bonus living space and the 5th bedroom with an additional full bath are found upstairs. Absolutely perfect for a nanny or in-law quarters or a fitting design for a large family! Infinite upgrades! Pride of ownership and exquisite taste prevail in this stunning home near to shopping, restaurants, Tampa International Airport and the famed Gulf beaches!! This one has it all! A true must see!!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nancy Leslie (727-789-5555)
1404 EAST LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$1,225,00016 Days on yellowkey MLS ID: TB8496474
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 4312 Built: 1990Monthly Fee: $207 Tax: $8,294 (2025)Community: Greenhaven Unit ThreeSpa: NoSingle Family
Taxes:$8,294
Remarks: Located in the highly desirable gated community of East Lake Woodlands, this spacious 4 bedroom, 3 bathroom home offers a versatile layout with 2 bonus rooms and a dedicated office. One of the bonus rooms is located upstairs, providing added flexibility for multi-use living. Pool table will convey with the sale. The home features a solar-heated in-ground pool with a large pool deck, fully enclosed by a screened lanai, creating the perfect space for year-round Florida living and entertaining. The inviting living room includes a fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with abundant wood cabinetry, generous storage, and a center island ideal for cooking and gathering. The split-bedroom floor plan provides privacy, with the primary suite featuring sliding glass doors to the pool, a walk-in closet, and an en-suite bath with dual vanities, a bathtub, and a separate shower. Additional highlights include a 2-car garage, a laundry room, and exceptional interior space throughout. A unique third garage bay has been converted into an interior room, offering even more flexible living options. Residents of East Lake Woodlands enjoy resort-style amenities including a clubhouse, golf courses, country club, heated pools, tennis and pickleball courts, fitness center, dining options, and scenic walking and biking paths within a secure gated community. Conveniently located in Oldsmar, this home provides easy access to Gulf beaches, Tampa International Airport, top-rated schools, dining, and shopping, offering the best of the Tampa Bay lifestyle.
Listing is courtesy of: CONCI, REALTORS (727-405-0005)
Listing Agent: Cyndi Olmstead (727-203-4967)
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$535,000116 Days on yellowkey MLS ID: TB8460875
REDUCED by $14,000 (2.6%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$4,041
Remarks: One or more photo(s) has been virtually staged. 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)
1758 OAK POND CT, OLDSMAR, FL 34677
$650,000205 Days on yellowkey MLS ID: TB8435691
Bed: 6 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2867 Built: 2001Monthly Fee: $12 Tax: $4,032 (2024)Community: Eastlake Oaks Ph 4Single Family
Taxes:$4,032
Remarks: **REDUCED** Price Drop to sell!! Welcome to this spacious 6-bedroom, 3-bathroom home with cathedral ceilings throughout nestled in the beautiful community of Eastlake Oaks. The grand staircase welcomes you into this meticulously kept one owner home. The first floor houses the first bedroom or office and bathroom plumbed for a third piece. The large family room large kitchen combo makes it easy to entertain and host your holiday gatherings and special occasions. The spacious lanai and backyard complete your outdoor Florida living. Five additional bedrooms, including the primary suite await you on the second floor along with an upstairs laundry room. The roof is 5 years young with a newer hot water heater and newer A/C. The garage is air conditioned separately as an added bonus. This home is conveniently located near shops, restaurants and entertainment. It is a short 20-minute drive to Tampa International Airport. With the quaint cities of Dunedin and Safey Harbor nearby. Come take a look and put your personal touch to call this property your new home!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Cecilia Rubio (727-204-0464)
835 CHRISTINA CIR, OLDSMAR, FL 34677
$485,00056 Days on yellowkey MLS ID: TB8483303
0 Days Off yellowkey (back on 4/26/2026)
REDUCED by $14,999 (3.0%) on 04/11/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1692 Built: 1994Monthly Fee: $68 Tax: $2,569 (2025)Community: Bays EndSpa: NoSingle Family
Taxes:$2,569
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 2-bath pool home in the highly sought-after Bays End community of Oldsmar, a private neighborhood of just 53 homes where properties rarely come available. Perfectly positioned with only one neighboring home, this property offers exceptional privacy along with stunning water views and breathtaking sunset skies from your own backyard. Inside, the home features soaring ceilings, spacious bedrooms, and a bright open layout that creates an inviting atmosphere for both everyday living and entertaining. The home has been thoughtfully upgraded with numerous major improvements, providing peace of mind for years to come. Recent upgrades include Category 5 double-insulated impact windows and sliding doors (2024), all new kitchen appliances (2024), a new hot water heater (2024), and a beautifully remodeled guest bathroom (2025). The HVAC system underwent a full rebuild in 2019 including condenser, compressor, ductwork, registers, and intake grates, ensuring efficient cooling throughout the home. Step outside to your private screened pool area, where the pool was remarcited in 2023 along with a new filter and motor, creating the perfect space to relax while enjoying peaceful water views and colorful Gulf Coast sunsets. Additional improvements include a new architectural shingle roof (2018) and new garage door (2020). This home is also equipped with solar panels installed in 2019–2020 through Sunrun, significantly reducing monthly electric costs. The system includes an LG Brightbox battery backup capable of powering six 120-volt outlets, currently supporting the refrigerator, microwave, office outlets, and living room outlets, with the ability to reassign circuits through Sunrun. Homes in Bays End are rarely available, and this one offers an incredible combination of privacy, water views, energy efficiency, major upgrades, and a fantastic Oldsmar location close to parks, shopping, dining, and Tampa Bay’s best amenities. Don’t miss the opportunity to own a pool home with water views in one of Oldsmar’s premier neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)
Listing Agent: Jonathan Hernandez (727-417-1122)
110 DEERPATH DR, OLDSMAR, FL 34677
$1,199,900108 Days on yellowkey MLS ID: TB8462357
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4246 Built: 1991Monthly Fee: $263 Tax: $10,446 (2024)Community: Deerpath Unit OneSpa: YesSingle Family
Taxes:$10,446
Remarks: Simply sensational in prestigious Deerpath of East Lake Woodlands!! Enter through double leaded glass entry doors to this spectacular, sprawling executive residence! 4,246 sq. ft. of exceptionally well-planned design and custom built to precise detail. Soaring ceilings with four bedrooms, plus a study that could be a 5th bedroom and 3.5 baths… elegantly designed! Privacy prevails on this gorgeous, wooded home site surrounded by lush landscaping. Enter the grand foyer and take in the refined view of three sets of French doors with lovely transom windows looking out on the lanai and pool area. The formal living and dining areas highlight the gorgeous architecture of the home and the sunken living room is beautifully designed with plant shelves and lighted niches! The 5th bedroom is currently used as an office. It has its own set of French doors and boasts custom built-in desk and shelving with granite counters and desktop. A convenient half bath completes the entry area and leads to the magnificent kitchen! Wow! An entertainer’s dream! Ingenious design with prep space and cabinetry galore! Designer quartz counters are stunning! Large center island as well as a breakfast bar and butler’s pantry with beverage fridge in addition to a generous sized eat-in breakfast room. Stainless appliances include a 4-door refrigerator. Huge walk-in pantry! Lovely bead board accents with chair railing, gorgeous pendant lighting…designer lighting throughout the home! The kitchen overlooks the large family room centered by a travertine faced wood burning fireplace and walk-in bar with sink. The primary retreat is nothing short of fabulous! Large sitting area, romantic 2-way wood burning fireplace and totally updated spa-like ensuite bath with massive counter space, separate sink areas, whirlpool tub, walk in shower with designer tile work, water closet, Venetian finish on walls and a massive walk-in closet. Secondary bedrooms are vast and have large wall closets or walk-in closet space! The shared bath space is creatively redesigned with fashionable updates and substantial counter space accented by double sinks with splendid oiled bronze hardware. And the additional full bath/pool bath boasts the most recent upgrades with the same designer granite counters and a beautifully tiled, glass enclosed walk-in shower. All bathrooms are stylishly upgraded. Entertaining and family space is extended outdoors to the grand lanai and pool area! Gorgeous pool with spillover spa and vaulted screen enclosure looks out on a lushly landscaped and private wooded paradise! The convenient pool bath has been recently, renovated with designer touches. And a poolside kitchen area with sink completes the setting and allows for ultimate entertaining! Truly a must see. Endless upgrades and details! All found within the gates of the fabulous East Lake Woodlands Country Club community… A+ rated schools, close to everything, medical, shopping, parks, restaurants, TIA and gorgeous Gulf beaches! An extraordinary find!
304 PATTY DR, OLDSMAR, FL 34677
$397,0006 Days on yellowkey MLS ID: TB8500425
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $3,150 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$3,150
Remarks: Incredible Opportunity in Oldsmar! Potential for Water Views and Coastal Lifestyle Discover the perfect canvas for your next dream home or investment project in this single-family property located in the coveted Oldsmar Country Club Estates subdivision. Situated on a generous lot of approximately 1/4 acre (10,054 square feet), this residence offers an unbeatable location just across the street from the Oldsmar boat ramp and the beautiful Mobbly Bayou. 3 bedrooms and 2 full bathrooms spread over 1,344 square feet of living space. It has a large family/multipurpose room of 450 sq. ft. and plenty of storage space. The house has newer windows and a recent metal roof. The current structure allows for renovation or upward construction to capture spectacular water views from a second level. Enjoy the true Florida lifestyle with immediate access to launch your kayak or boat. The property is highly walkable to several waterfront parks, including R.E. Olds Park, Bicentennial Park, and Veterans Memorial Park, where you will find dog areas, pickleball courts, and playgrounds. There is no HOA or CDD, offering maximum flexibility for the owner. Located in Pinellas County, with easy access to local amenities in Oldsmar and major routes to Tampa and Clearwater.
Listing is courtesy of: SELLING USA, LLC (813-723-0086)
Listing Agent: Eleydi Alvarez Lopez, Llc (813-585-2717)
1795 BAYHILL DR, OLDSMAR, FL 34677
$539,90018 Days on yellowkey MLS ID: TB8476650
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 1994Monthly Fee: $199 Tax: $8,406 (2025)Community: CreeksideSingle Family
Taxes:$8,406
Remarks: This unique home exudes character and is located on a peaceful conservation lot with no rear neighbors situated within the secure, gated community of East Lake Woodlands! The minute you step inside this charming home, you'll be captivated with impressive design features such as stone accents, glass block, mirrored walls and doors that display vibrant color prints contributing to the home’s style and appeal! The impressive living area has a stone-face fireplace and attractive laminate flooring. The kitchen with solid surface counters, stainless steel appliances, a wine refrigerator, stackable washer/dryer and closet pantry offers an abundance of cabinets and counterspace, complemented by plant shelves for additional decor! The home has a split bedroom layout for maximum privacy. The primary bedroom offers an ensuite bath with soaking tub, double vanities, a step in shower with artistic tile and relaxing shower jet system. A versatile bonus room with French Doors at the front of the home, provides endless possibilities, whether you require a guest room, office, playroom, reading nook, den or exercise room. Both bedrooms and the bonus room are outfitted with striking wall-mounted wood closet organizer systems. Sliding doors from the living room open fully to a screened porch, which leads to a pavered patio offering serene views of nature – a perfect place to unwind and enjoy the outdoors! Your new home is equipped with a Tesla home battery system powered by solar panels and includes 3 powerwalls, all paid off! Additional features include a water filtration system, sprinkler system and impact-resistant windows and sliding doors for peace of mind and energy efficiency. The craftsman of the home will appreciate the garage with its working table, storage cabinets, an auto-rewind air hose reel, an overhead drop cord with electrical outlet and convenient sink. The roof was installed in 2016, AC in 2012 and water heater in 2014. Enjoy low HOA fees, NO CDD fees and non-Flood Zone X. Living in East Lake Woodlands provides a casual way of living surrounded by natural beauty, wildlife, walking paths, conservation areas, ponds and lakes. The Ardea Country Club offers residents membership options for their resort style amenities which include two 18 hole championship golf courses, driving range, tennis and pickleball courts, lap and freeform pools, clubhouse, dining, fitness center, children's clubs and social activities. This premier location is close to major medical facilities, entertainment venues, a wide array of restaurants, malls, parks, marinas, sporting events and concerts. There’s easy access to Honeymoon Island, Clearwater Beach and both Tampa International Airport and St. Pete/Clearwater Airport are just a 35 minute drive away. This home is truly a must see for those looking for privacy, modern conveniences and a relaxing lifestyle!
Listing Agent: Rose Brown (727-403-0180)
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