Location: Oldsmar
Do Not Show Listings
137 BRENT CIR, OLDSMAR, FL 34677
$774,90072 Days on yellowkey MLS ID: O6394251
REDUCED by $24,100 (3.0%) on 05/13/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2309 Built: 2002Monthly Fee: $473 Tax: $5,236 (2025)Community: Seaside EstatesTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,236
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: None
Remarks: Set within a gated, waterfront community in Oldsmar, this expansive townhouse at 137 Brent Circle offers a rare combination of space, thoughtful upgrades, and true Florida coastal living, complete with your own private, recently upgraded boat slip just steps out the back door. Featuring 3 bedrooms, 2 bathrooms, and approximately 2,300 square feet, this is one of the largest units in the neighborhood, ideally positioned at the end of a cul-de-sac for added privacy. The layout is both functional and versatile, offering expansive living areas, a large dining room, and flexible spaces perfect for a rec room, home office, or art studio, all enhanced by abundant natural light and gorgeous water views throughout. What truly sets this home apart is its direct connection to Upper Tampa Bay, where dolphins, manatees, and native wildlife are often seen. Enjoy ridiculously beautiful water views from dual balconies, perfectly positioned for both sunrise and sunset, because here, the lifestyle is just as important as the home itself. The kitchen has been professionally remodeled and architecturally designed, with renovations thoughtfully planned by an architect and interior designer, serving as a stunning focal point of the home. Additional interior upgrades include luxury flooring throughout, fresh interior paint, custom stair railing, and beautiful ceiling fans that elevate both style and comfort. The primary suite features a dramatic bath with travertine tile and oversized closets, while a generous laundry room adds everyday convenience. Practical upgrades provide peace of mind, including a new air conditioning system exceeding current codes and hurricane shutters on every window. The home also features a 3-car tandem garage, offering ample space for vehicles, storage, or recreational gear, with the option to add an elevator in the future if desired. Step outside to enjoy freshly painted balconies and a newly updated screened enclosure, creating the perfect setting to relax, entertain, and take in the views, because yes, wine really does taste better out here. The community enhances the lifestyle even further with a pool and hot tub, kayak launch, lighted boardwalk, and an active social committee. Located just minutes from the Safety Harbor boat launch, as well as a variety of restaurants, bars, parks, and entertainment, this home offers both tranquility and convenience. Oldsmar itself is known for its abundance of parks and natural beauty, making it a hidden gem along the Gulf Coast. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
219 BAY ARBOR BLVD, OLDSMAR, FL 34677
$550,00051 Days on yellowkey MLS ID: TB8498550
REDUCED by $10,000 (1.8%) on 06/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 2000Monthly Fee: $100 Tax: $7,973 (2025)Community: Bay Arbor Unit 1ASingle Family
Taxes:$7,973
Elementary School: Forest Lakes Elementary-PN
Middle School: Carwise Middle-PN
Remarks: Mrs. Clean lived here!! This beautiful home is ready for its new owners! Vaulted ceilings and an open floorplan welcome you as you step inside. The Living Room is HUGE, a wonderful place for family gatherings and entertaining for holidays and parties. The large Kitchen opens up to the Living Room for an expansion on entertaining space, featuring solid wood cabinets, matching Stainless Steel Frigidaire Appliances, and a large Breakfast Nook. The Formal Dining Room is set right across from the Kitchen, and is the perfect space for formal gatherings and family dinners. It even has a 4.5' x 2.5' nook that would house a China Cabinet or dry bar if desired. This home offers a split plan, providing maximum privacy to the Master Suite, as well as to the "Guest Wing" and other guest bedrooms. The Master Bedroom features a walk-in closet, access to the back patio, and a large en-suite Bathroom with dual vanities, a jetted tub and a standing shower. The "Guest Wing" or "Home Office Wing" is a wonderful layout to suit any needs. It has a bathroom located right off of the Bedroom, and is set apart from the rest of the bedrooms for added privacy. The other 2 Bedrooms are Jack-and-Jill style, both accessing the 3rd Full Bathroom. Large sliders in the Living Room open up to the peaceful back patio, laced in Slate Tile and fully covered. This space is a sanctuary, overlooking a small pond and greenery instead of facing a rear neighbor. The sun rises in the front of this home, so it is easy to enjoy your morning coffee at sun-up, as well as enjoy the sunsets thanks to the shade provided by the natural greenery. The Roof and Water Heater are NEW 2022, and the A/C was replaced in 2021! LOW HOA FEES only $100/month. This community is gated, with a playground and a community pool, as well as sidewalks for your morning jogs or evening walks! What's not to love?? Move right in and make this home your own!! Only a 30-minute drive to Tampa Int'l Airport, a 25-minute drive to Honeymoon Island, and just minutes from shopping, dining, and all you need to live your Florida dream to its fullest! Located in X Zone! That's right, NO FLOOD ZONE!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Jessica Jurek (727-487-4957)
138 BRENT CIR, OLDSMAR, FL 34677
$725,00052 Days on yellowkey MLS ID: TB8496402
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2258 Built: 2002Monthly Fee: $475 Tax: $9,980 (2025)Community: Seaside EstatesSpa: YesTownhouse
Taxes:$9,980
Remarks: Welcome to 138 Brent Circle in desirable gated Seaside Estates—an exceptional opportunity to own the largest corner townhome in this sought-after waterfront community in Oldsmar. Perfectly positioned to capture panoramic views of Tampa Bay, this residence offers a rare combination of space, scenery, and coastal lifestyle, complete with a private boat slip for easy access to the water. This spacious 4-bedroom, 3-bath home features a thoughtfully designed layout with abundant natural light and comfortable living areas ideal for both everyday living and entertaining. The inviting living room is anchored by a cozy fireplace, creating a warm focal point while showcasing the stunning water views beyond. A second fireplace in the primary bedroom adds an extra layer of comfort and charm, creating a relaxing private retreat. The kitchen offers ample cabinetry and workspace, seamlessly connecting to the dining and living areas for a functional, open feel. Each bedroom provides flexibility for a variety of living arrangements, while the three full bathrooms add convenience and comfort. An oversized garage delivers generous storage and parking space—an added benefit rarely found in townhome living. As a corner unit, the home enjoys enhanced privacy and additional natural light. Step outside and take in the tranquil waterfront setting, where you can relax, entertain, or set out for a day on Tampa Bay directly from your own boat slip. Conveniently located near parks, shopping, dining, and major roadways, this property offers the perfect blend of peaceful coastal living and everyday accessibility. Don’t miss your chance to own a premier waterfront residence in Seaside Estates—schedule your private showing today.
Listing Agent: Kathy Grams (727-259-9247)
165 MOBBLY BAY DR, OLDSMAR, FL 34677
$1,149,900256 Days on yellowkey MLS ID: TB8430614
REDUCED by $70,000 (5.7%) on 05/04/2026
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
Tax Year: 2024
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)
384 WINGATE CIR, OLDSMAR, FL 34677
$599,0005 Days on yellowkey MLS ID: TB8515031
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2428 Built: 2001Monthly Fee: $100 Tax: $8,778 (2025)Community: Bay ArborSpa: NoSingle Family
Taxes:$8,778
Remarks: Nestled on a quiet street in the desirable gated community of Bay Arbor, this lovely two-story home offers 3 bedrooms, 2.5 bathrooms, two spacious bonus/great rooms, a 2-car garage, and a spectacular custom pebble tech pool with a stunning stone waterfall, pool pump 2025 and new pool filter 2025. The back yard is completely fenced and backs up to a peaceful conservation. As you enter, you'll be welcomed by charming Florida saltillo ceramic tile flooring that adds warmth and old-world Florida character throughout the main living areas. The spacious eat-in kitchen features granite countertops, abundant cabinetry with convenient roll-out trays, a huge pantry, stainless steel appliances, newer dishwasher 2022, refrigerator 2024, and lovely French doors leading directly to the beautiful screened pool area—perfect for indoor-outdoor living and entertaining with no rear neighbor’s. The first floor offers a formal living and dining room, a large family room, and a convenient powder room. Upstairs, you'll find an enormous bonus/great room that can easily serve as a media room, game room, home office, gym, or potential fourth bedroom. The oversized primary suite features a large walk-in closet and a private ensuite bath complete with a walk-in shower, garden tub, private water closet, and linen closet. Two additional bedrooms offer generous closet space and share a full hall bath with a tub/shower combination. Newer Roof (2020), Water Heater (2021), newer HVAC System (2024). In addition the house comes with hurricane shutters which are stored in the garage. Bay Arbor residents enjoy access to a community pool, playground, and beautifully maintained common areas. Conveniently located near top-rated schools, shopping, restaurants, hospitals, churches, golf courses, and Florida's award-winning beaches. Easy access to Tampa, Clearwater, St. Petersburg,and New Port Richey makes commuting a breeze. This is Florida living at its finest! Come Live the dream in Tampa Bay, Call me today!
Listing is courtesy of: RE/MAX MARKETING SPECIALISTS (727-853-7801)
Listing Agent: Denise Denver Samsonenko (727-452-8608)
417 DOLPHIN DR S, OLDSMAR, FL 34677
$269,00037 Days on yellowkey MLS ID: TB8504194
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1253 Built: 1985Monthly Fee: $70 Tax: $3,616 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,616
Elementary School: None
High School: None
Remarks: Welcome to this beautifully renovated home in the desirable 55+ Gull-Aire Village where comfort, style, and convenience seamlessly come together. Step inside to discover luxury vinyl flooring throughout, a modern kitchen featuring elegant shaker cabinetry, granite countertops, a convenient pot filler, premium stainless-steel appliances, smooth ceilings, and five-inch baseboards. The custom kitchen island comfortably seats three, perfect for casual dining or entertaining. The primary bathroom has been thoughtfully designed for both style and accessibility, boasting a fully updated, wheelchair-friendly walk-in shower. The guest bathroom is also refreshed, offering a versatile tub/shower combination. The spacious laundry room includes newly installed custom cabinetry and a sink, with the potential to serve as a second kitchen for those who enjoy cooking. Enjoy Florida living year-round in the expansive glass-enclosed, air-conditioned Florida room, complete with durable vinyl plank flooring. Upgrades include a new air conditioning system installed with permit in November 2018, a permitted TPO roof added in August 2012, and a whole-house Generac generator that guarantees uninterrupted power during any weather. Additional storage is available in the handy shed. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball courts, a heated pool, and spa. Residents can take part in regular activities like bingo, card games, and line dancing, fostering an active, social lifestyle. The golf cart-friendly streets make getting around the neighborhood both easy and fun. Enjoy affordable living with HOA fees of just $70 per month in this meticulously maintained community. Pet owners are welcome—one pet of any size is allowed, and a second pet may be permitted with an emotional support letter from a physician. Ownership includes the land, so there is no lot rent. Everyday conveniences are right across the street, with options like AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store. Dining choices abound including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are about ten minutes away. Outdoor enthusiasts will love being just ten miles from the stunning beaches at Honeymoon Island and Caladesi State Park, plus direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
2272 WARWICK DR, OLDSMAR, FL 34677
$699,90040 Days on yellowkey MLS ID: TB8502055
REDUCED by $25,100 (3.5%) on 06/02/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2512 Built: 1995Monthly Fee: $133 Tax: $3,084 (2025)Community: Warwick HillsSpa: NoSingle Family
Taxes:$3,084
Elementary School: Cypress Woods Elementary-PN
Remarks: Welcome to 2272 Warwick Drive—where timeless elegance meets effortless Florida living. This well-maintained one-story home offers four spacious bedrooms, three full baths, a sparkling screened-in pool and a three-car garage. From the moment you arrive, stately columns and a grand double-door entry set the tone for what’s inside—soaring volume ceilings and an open, light-filled layout designed for both comfortable living and stylish entertaining. The living room is a true focal point, featuring a custom-built wall unit that adds both character and functionality. Peace of mind comes easy with a long list of recent updates, including a new HVAC system, water heater, and pool pump (2025), plus a resurfaced pool (2022) and new pool screens (2024). The beautifully updated eat-in kitchen is the heart of the home, featuring attractive maple cabinetry, granite countertops, a large center island and white appliances—including a new refrigerator (2026) and microwave (2025). Retreat to the oversized primary suite with its own sitting area—your private sanctuary—complete with a remodeled bath showcasing granite counters and refreshed cabinetry. Step outside and unwind in your private backyard oasis, where the pavered patio and screened pool overlooks the berm with no rear neighbors. Located in the exclusive Warwick Hills enclave within East Lake Woodlands, a 24/7 gated, resort-style community spanning 2,200 acres. Membership options available at the newly renovated Ardea Country Club. Indulge in championship golf, premier racquet facilities, a resort-style pool, fitness center, dining, and more. All of this, plus top-rated A schools and an unbeatable Oldsmar location just minutes to shopping, dining, parks, the Pinellas Trail, and Tampa International Airport—makes this home truly exceptional.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Marcy Daniels (727-560-8080)
304 WOODLAKE WYNDE #304, OLDSMAR, FL 34677
$164,90038 Days on yellowkey MLS ID: TB8498051
REDUCED by $5,000 (2.9%) on 05/29/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 674 Built: 1985Monthly Fee: $418 Tax: $2,403 (2025)Community: East Lake Woodlands Woodlake RunCondo
Taxes:$2,403
Remarks: Wake up to paradise every day!!! If you’re looking for a fabulous waterfront location and a beautiful condominium, this scenic Lakefront residence in Woodlake Run at East Lake Woodlands is the perfect fit. Set within a gated, very well-maintained community, the condo offers outstanding curb appeal, tranquil water views, mature landscaping, and a peaceful natural setting that defines one of Pinellas County’s most desirable areas Just steps from the front door, the heated pool provides year-round enjoyment and adds to the effortless lifestyle this property delivers. Inside, the comfortable living area features soaring ceilings and opens to a screened-in lanai overlooking the lake, The adorable kitchen includes shaker-style wood cabinetry and granite countertops, with the dining area conveniently positioned just off the kitchen for easy everyday living and entertaining. The spacious primary bedroom showcases gorgeous water views, brand-new 2026 carpet, and a generously sized walk-in closet. Major improvements include a 2023 A/C system, a brand-new 2026 water heater, a 2023 electrical panel, and a full-size washer and dryer. The owner is leaving everything with the unit, including a beautiful leather sofa, leather accent chair, king-size bedroom set, Smart TV, linens, kitchen utensils, décor, artwork, and all household items, making this a true turnkey opportunity. The maintenance-free lifestyle is impressively comprehensive and very reasonable, covering the heated pool, exterior maintenance, roof, internet, cable, water, sewer, pest control, waste services, grounds maintenance, and gated entry, with electric averaging under $100 per month. East Lake Woodlands is known for its scenic surroundings, two golf courses, and optional country club, tennis, and swimming amenities. The location is ideal, close to shopping, dining, and outdoor recreation, approximately fifteen minutes to Honeymoon Island State Park for stunning beaches and Gulf sunsets, and about thirty minutes to Tampa International Airport for convenient travel. The property is also located in a no-flood zone. Whether you’re seeking a primary residence, seasonal retreat, or investment property, this waterfront condo offers outstanding value in a highly sought-after community.
Listing is courtesy of: SELECT PROPERTIES INC (727-934-4099)
Listing Agent: Frank Acerra (727-410-9849)
412 SHORE DR E, OLDSMAR, FL 34677
$2,700,0005 Days on yellowkey MLS ID: TB8512698
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4454 Built: 1968 Tax: $15,354 (2025)Community: Country Club Add To Oldsmar RevSpa: YesSingle Family
Taxes:$15,354
Middle School: Oak Grove Middle-PN
Remarks: Unique opportunity to own a one-of-a-kind, beautiful property on Safety Harbour Bay with Direct access to Tampa Bay. Renovation by Herman Builders. The stunning modern completely updated home features: contemporary, Open and spacious Gourmet Chef's Kitchen High-end chef-quality appliances, with double ovens, fireplace Oversized Island loads of cabinets, storage , the home has natural stone floors throughout. Full water views across the entire back of the home large glass doors leading out to your beautiful contemporary pool. Boat Docs for keeping your boat and easy access to Tampa Bay for the deep water fishing. The home features mother-in-law's quarters separate from the main home. With kitchenette, and private entrance . On the main floor, there are also three Guest or family bedrooms a bonus space, laundry room , lots of storage. The Private owner's suite features a large spa bathroom fabulous walk-in closets with grand views of Safety Harbor bay. Conveniently located near airport and downtown with the best schools in Tampa.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (813-839-3800)
Listing Agent: Cynthia Kaszirer (813-743-2847)
586 KINGSMILL CT, OLDSMAR, FL 34677
$615,0003 Days on yellowkey MLS ID: TB8512390
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2452 Built: 1998Monthly Fee: $298 Tax: $10,436 (2025)Community: KingsmillSpa: YesSingle Family
Taxes:$10,436
Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting single-family home in the sought-after Kingsmill neighborhood of East Lake Woodlands—a premier gated community celebrated for its security, lush Florida landscapes, and vibrant lifestyle. Offering 2,453 square feet of living space, this beautifully updated residence features a grand total of three bedrooms, two full bathrooms, and a modernized half bath. Inside, the interior features soaring cathedral ceilings, fresh flooring, and brand-new carpeting. The main level hosts a formal dining room and an open kitchen that flows effortlessly into a spacious great room, complete with a cozy gas-burning fireplace. The primary suite is conveniently situated on the main floor, boasting a stunning, fully remodeled bathroom. Upstairs, discover the remaining bedrooms—including a flexible third bedroom created by walling in the former loft space, making it ideal for a quiet home office or guest room—alongside another full bath. Outside, the large backyard overlooks a peaceful pond and features an inground pool and spa under a brand-new screen enclosure, complemented by a built-in outdoor kitchen setup. Living here means embracing the East Lake Woodlands lifestyle. Residents can enjoy miles of scenic nature and biking trails, while a variety of optional club memberships unlock access to championship golf courses, a premier tennis and pickleball complex, resort-style swimming pools, and a private clubhouse with fine dining and social events. Located in the heart of Oldsmar, this property is also just minutes from excellent shopping, dining, highly rated schools, and pristine Gulf Coast beaches. Don’t miss the opportunity to make this Kingsmill gem your own. Schedule a private tour today to experience this beautiful pond-front retreat firsthand!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Susanne Jones (727-455-0769)
611 TANGERINE DR, OLDSMAR, FL 34677
$355,0009 Days on yellowkey MLS ID: TB8513141
REDUCED by $10,000 (2.7%) on 06/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1980 Tax: $1,040 (2025)Community: Harbor Palms Unit ElevenSingle Family
Taxes:$1,040
Remarks: Welcome to 611 Tangerine Drive a well-maintained 3-bedroom, 2-bathroom home located in one of Oldsmar’s most desirable and centrally located communities. Featuring a highly sought-after split floor plan, spacious living areas, and major system upgrades already completed, this home offers the perfect combination of comfort, functionality, and opportunity for a new owner to make the space their own over time. Inside, you’ll find tile flooring throughout the entire main living space, creating a clean, cohesive, and low-maintenance living environment. The split layout provides excellent separation between the primary suite and guest bedrooms, offering both privacy and flexibility for families, guests, or work-from-home living. The spacious primary suite features dual closets along with a beautifully updated master bathroom that adds a more modern touch to the home. The kitchen is equipped with stainless steel appliances and offers excellent functionality with ample cabinet and storage space, while still leaving room for future personalization and design possibilities to match your own style and vision. Several major improvements have already been completed for long-term peace of mind, including full-home repiping, a whole-house water softener and filtration system, and a durable Solar Shield metal roof designed for longevity, efficiency, and reduced maintenance for many years to come. The home has also never FLOODED! This provides additional confidence for future ownership. Outside, the screened-in porch creates the perfect place to relax and enjoy Florida’s year-round weather, while the newer fencing surrounds the backyard and offers both privacy and space for entertaining, pets, or outdoor enjoyment. A spacious two-car garage and abundant storage throughout the home further enhance everyday convenience. Located in the heart of Oldsmar, this property offers outstanding access to everything that makes the Tampa Bay area so desirable. Tampa International Airport, Clearwater Beach, Safety Harbor, Dunedin, and downtown Tampa are all within a convenient drive. Oldsmar is known for its excellent school district, strong community atmosphere, waterfront parks, scenic trails, playgrounds, nature preserves, and outdoor recreation. With its ideal location, major mechanical upgrades, flexible layout, and endless potential to further enhance and customize over time, 611 Tangerine Drive presents an exceptional opportunity in one of northern Pinellas County’s most sought-after communities.
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Sid Vehabovic (727-657-4349)
4761 STONEBRIAR DR, OLDSMAR, FL 34677
$785,00010 Days on yellowkey MLS ID: TB8509685
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2652 Built: 1993Monthly Fee: $117 Tax: $5,832 (2025)Community: StonebriarSingle Family
Taxes:$5,832
Remarks: Back on the Market.....PASSED 4point and Wind Mitigation. This is Florida luxury living at its finest in one of the area’s most desirable gated communities. Exclusive executive home located in the highly sought-after Stonebriar community within East Lake Woodlands, a desirable gated golf club community. Zoned for top-rated schools and ideally situated less than 30 minutes from Tampa International Airport and the area’s premier Gulf beaches. This exceptional 4-bedroom luxury residence offers the perfect blend of elegance, comfort, and privacy. Boasting 2,652 square feet of living space with soaring ceilings and abundant natural light, this beautifully updated home features a spacious oversized primary suite complete with a private sitting area overlooking the expansive screened pool, recently resurfaced for years of enjoyment. The gourmet kitchen is designed for both entertaining and everyday living. Newer appliances, newer pool pavers, Plantation shutters added throughout. Roof 2016, Water heater 2019, re screened porch 2017, fresh exterior pain 2019. The private conservation lot provides a tranquil setting ideal for relaxing or entertaining poolside. Room dimensions are approximate. All info is deemed to be reliable but not guaranteed. If there is an HOA, please confirm all information with the HOA directly.
Listing is courtesy of: PRIME INT'L REAL ESTATE GROUP (877-727-5259)
Listing Agent: Nichole Gaytan (305-323-8108)
627 TIMBER BAY CIR W, OLDSMAR, FL 34677
$310,0009 Days on yellowkey MLS ID: TB8513485
1 Days Off yellowkey (back on 6/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 1984 Tax: $645 (2025)Community: Shoreview Ph 2Single Family
Taxes:$645
Remarks: Under contract-accepting backup offers. Pond View!!! Charming 3 bed / 2 bath ranch-style home (1,274 sq ft) in a peaceful, family-friendly neighborhood. Built in 1984, this light-filled residence offers a comfortable, single-level floor plan ideal for everyday living and easy entertaining. Enjoy serene pond views from the private backyard — a perfect quiet oasis for morning coffee or safe outdoor play. The home includes a two-car garage, ample parking, and a low-maintenance lot. Well-suited for families, commuters, or anyone seeking a relaxed Tampa Bay suburb lifestyle with quick access to shopping, schools, parks, and major roads. Move-in ready with great bones. With a little vision this property is a great sweet equity opportunity. Schedule a showing today to experience the setting and location in person.
Listing is courtesy of: MILLENNIAL REALTY & PROPERTY MGMT. (813-217-5691)
Listing Agent: Christopher Nelson (813-313-6338)
2031 DOVER CT, OLDSMAR, FL 34677
$265,00047 Days on yellowkey MLS ID: TB8500444
REDUCED by $15,000 (5.4%) on 05/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1215 Built: 1982Monthly Fee: $160 Tax: $4,212 (2025)Community: Bayside Meadows Ph IiVilla
Taxes:$4,212
Remarks: Short Sale. Welcome to your peaceful retreat! This beautifully updated 2-bedroom, 2-bathroom, 1-car garage villa combines comfort, charm, and convenience in a quiet, sidewalk-lined neighborhood ideal for leisurely strolls and a true sense of community. Step inside to a spacious living area, featuring a large primary suite with a walk-in closet and private en suite bathroom. Enjoy Florida living with two large lanais, perfect for relaxing or entertaining. As an end unit tucked into a private cul-de-sac, this home boasts the largest yard in the community—a rare and valuable feature. Updates include new HVAC, fenced in backyard, luxury vinyl plank through out, fresh paint, water heater 2 years old, and roof is just 4 years old. Take advantage of the inviting community pool, or enjoy a short walk to Sheffield Park just 0.4 miles away. You'll love the unbeatable location—just minutes from Publix grocery (1.8 miles), shopping, dining, and Starbucks (1 mile), and a quick drive to the beach (9 miles) and Tampa International Airport (13 miles). With low HOA fees and easy access to everything you need, this villa is perfect as a full-time residence or a seasonal getaway. Don't miss your chance to enjoy effortless living in a prime location!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jay Umboh (813-539-3105)
1758 OAK POND CT, OLDSMAR, FL 34677
$585,00024 Days on yellowkey MLS ID: TB8507682
Bed: 6 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2867 Built: 2001Monthly Fee: $13 Tax: $4,224 (2025)Community: Eastlake Oaks Ph 4Single Family
Taxes:$4,224
Remarks: One or more photo(s) has been virtually staged. ROOM TO ROAM!!! From the moment you arrive at 1758 Oak Pond, the 6 bedroom 3 bath home’s beautifully maintained exterior and impressive curb appeal set the tone for the exceptional living experience within. A spacious two-car garage and elegant front entry welcome you inside, where a dramatic two-story foyer creates an immediate sense of grandeur and sophistication. Natural light pours through the space, highlighting the home’s soaring ceilings and thoughtfully designed layout. To the left of the entry, formal living and dining spaces offer the perfect setting for entertaining guests or hosting intimate gatherings. An architectural archway gracefully connects the dining room to the expansive kitchen, where abundant cabinetry, a built-in pantry, and the possibility of a dedicated breakfast area provide both style and functionality. Overlooking the inviting family room, this open-concept design allows for effortless everyday living and entertaining alike. Sliding glass doors lead to the oversized screened lanai, seamlessly blending indoor and outdoor living. Tucked discreetly beneath the staircase, an additional storage pantry offers exceptional convenience, while a nearby full powder bath and linen closet further enhance the home’s practical elegance. The adjacent first-floor bedroom provides flexibility for guests, multi-generational living, or a private home office. The expansive screened lanai stretches the full length of the residence and overlooks a private backyard retreat, creating the perfect atmosphere for relaxing evenings or weekend gatherings. Upstairs, the primary suite serves as a private sanctuary, featuring generous proportions, abundant natural light, and an en suite bath complete with a dual-sink vanity, tub, walk-in shower, private water closet, and multiple storage options including both a spacious closet and linen closet. The second floor also features a conveniently located laundry room with additional storage, four spacious secondary bedrooms, along with a full guest bath with tub/shower combination. Throughout the home, engineered hardwood flooring enhances the main living areas, complemented by tile flooring in all bathrooms. Recent updates include a newer HVAC system and hot water heater, offering peace of mind for years to come. The separately air-conditioned garage is an added luxury rarely found at this price point. This exceptional residence combines comfort, elegance, and functionality in one remarkable package. Ideally located with convenient access to Tampa, world-renowned Gulf beaches, premier shopping, dining, and entertainment, this home presents an incredible opportunity to enjoy the very best of Florida living. Come experience the lifestyle that awaits at 1758 Oak Pond and begin creating memories that will last a lifetime. No flooding in recent storms - flood $1010 a year and transferrable.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
1654 BAYHILL DR, OLDSMAR, FL 34677
$570,000235 Days on yellowkey MLS ID: TB8438417
0 Days Off yellowkey (back on 5/18/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2320 Built: 1995Monthly Fee: $199 Tax: $5,855 (2024)Community: CreeksideSingle Family
Taxes:$5,855
Remarks: Under contract-accepting backup offers. "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)
706 SWEETBRIAR DR, OLDSMAR, FL 34677
$440,00010 Days on yellowkey MLS ID: TB8513297
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1688 Built: 1987Monthly Fee: $35 Tax: $2,383 (2025)Community: Manors Of Forest Lakes The Ph 2Spa: NoSingle Family
Taxes:$2,383
Remarks: Under contract-accepting backup offers. Amazing opportunity to own this well-maintained 3 bedroom, 2 bathroom home in the desirable Forest Lakes community of Oldsmar, Florida! Major bonus - a brand NEW ROOF with warranty will be installed prior to closing, and the new homeowner will have the opportunity to choose the roof color! Situated on a beautiful CONSERVATION homesite, this home offers privacy and peaceful views from the oversized covered and screened outdoor living space , perfect for relaxing or entertaining year-round. The thoughtfully designed floor plan features a private primary suite located separately from the secondary bedrooms for added comfort and functionality. Enjoy multiple living areas including a spacious main living room, a formal dining area, and an additional flex/living space just off the kitchen, providing plenty of room for everyday living and gatherings. The backyard offers both privacy and space to enjoy the outdoors while taking in the serene conservation backdrop. Other NOTABLE FEATURES include IMPACT WINDOWS, IRRIGATION SYSTEM, and GUTTERS with gutter guards (majority of home). Residents of Forest Lakes enjoy fantastic amenities including pool, playground, splash pad, tennis courts, basketball courts, walking trails and access to the Oldsmar Trails and recreation center. With convenient access to shopping, dining, top-rated schools, Tampa International Airport, and the beautiful Gulf beaches this home will surely check all the boxes. Schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (813-907-8200)
Listing Agent: Carrie Frederickson (727-277-1901)
3073 DUANE AVE, OLDSMAR, FL 34677
$410,000293 Days on yellowkey MLS ID: TB8417476
REDUCED by $30,000 (6.8%) on 06/05/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2122 Built: 1973 Tax: $1,936 (2024)Community: West Oldsmar Sec 1Single Family
Taxes:$1,936
Remarks: Located in a quiet and friendly Come and see this beautiful house with a lot of potential. No HOA ,It has a spacious master bedroom with an in-suite bathroom and a large walk-in closet. Outside, you’ll find a large detached porch with big storage, perfect for storing a golf cart, bikes, kayaks, or motorcycles—or transform it into two bedroom, gym, or office or a party place . The backyard is a standout, surrounded by trees that keep the home cooler and energy bills lower. It’s perfect for relaxing or entertaining. . Enjoy gorgeous sunsets or cast a line off the nearby pier at one of the area’s best parks. Buyer and/or buyers agent to verify all room sizes.
Listing is courtesy of: S P O R T REALTY GROUP INC. (813-452-8301)
Listing Agent: Madelin Martinez (813-359-7784)
124 CYPRESS LN #124, OLDSMAR, FL 34677
$158,5003 Days on yellowkey MLS ID: TB8514283
0 Days Off yellowkey (back on 6/5/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,010 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,010
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to Cypress Estates, nestled within the sought-after East Lake Woodlands community of charming Oldsmar! This stunning second-floor 2-bedroom, 2-bathroom condo features an updated kitchen and a newly renovated primary bath, offering the perfect canvas for you to personalize and call home. Designed with an open-concept Florida lifestyle in mind, this 1,054-square-foot residence showcases wood-like porcelain tile flooring throughout the main living and dining areas, a split-bedroom floor plan, and a private owner's suite tucked at the rear of the condo. The generously sized owner's suite boasts two walk-in closets, a linen closet, and direct sliding glass door access to the screened balcony - your own peaceful retreat. The second bedroom, conveniently situated at the front of the condo, offers a comfortable layout with a standard closet. The open kitchen flows seamlessly into the main living area, making it an entertainer's dream. Step out onto the screened balcony to unwind and soak in the lush outdoor views, where Florida's wildlife makes for a delightful backdrop. Rest easy knowing you're in a 24/7 manned gated community, complete with one covered designated parking space and ample guest parking. Take a dip in the community pool just steps from your door, or explore an optional private membership to the East Lake Woodlands Country Club for access to the golf course, clubhouse, additional pool, fitness center, and tennis facilities. This pet-friendly community truly delivers maintenance-free living ...the monthly condo fee covers a 24-hour security guard, cable TV, community pool, building insurance, building and grounds maintenance, sewer, trash, water, and pest control. Ideally situated close to an abundance of dining, shopping, the AMC movie theater, Publix, Neighborhood Walmart, Target, and area hospitals, with Tampa International Airport just 25 minutes away. Don't miss this opportunity - call today to schedule your private showing!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Marianne Knowles (813-720-9201)
172 LAKEVIEW WAY #172, OLDSMAR, FL 34677
$150,00058 Days on yellowkey MLS ID: TB8496591
REDUCED by $15,000 (9.1%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980 Tax: $3,644 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$3,644
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2 bedroom, 2 bathroom second-floor condo located in the highly desirable gated community of East Lake Woodlands. This immaculate home features upgraded luxury vinyl plank flooring throughout and offers a serene, peaceful pond view perfect for relaxing mornings or evenings. Residents enjoy access to an exceptional lifestyle with two championship 18-hole golf courses, 14 Har-Tru tennis courts, and a stunning country club. Ideally situated near world-class beaches, scenic nature parks and preserves, and with convenient access to shopping and dining, this home is the perfect opportunity to embrace the best of the Florida lifestyle.
Listing is courtesy of: CENTURY 21 INTEGRA (800-593-7653)
Listing Agent: Becki Server (727-835-9696)
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