Location: Oldsmar
Do Not Show Listings
382 ROSALIND LN, OLDSMAR, FL 34677
$822,000308 Days on yellowkey MLS ID: TB8408993
1 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3273 Built: 2001Monthly Fee: $100 Tax: $8,003 (2024)Community: Bay ArborSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,003
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. 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)
370 S WOODLANDS DR, OLDSMAR, FL 34677
$369,999428 Days on yellowkey MLS ID: TB8361268
REDUCED by $27,400 (6.9%) on 05/01/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 1979Monthly Fee: $340 Tax: $5,324 (2025)Community: East Lake Woodlands Patio HomesSpa: NoVilla
Taxes:$5,324
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Virtually Staged some photos. Price Reduction!! Attention all Golfers and Tennis players Dream in East Lake Woodlands that showcases 2 Championship 18 hold golf courses and 14 HAR-Tru tennis courts with no membership required!!.Newly remolded Patio Home with 2 bedroom 2 full bathroom with possible office/dining area in the Golf Course Community of East Lake Woodlands. This meticulously maintained 1500 sq. ft. open floor plan home features New Contemporary Cabinetry (2025), brand new quartz countertops (2025), brand new kitchen sink (2025), brand new garbage disposal (2025), brand new light fixtures including can lighting throughout (2025), and new stainless steel appliances including double oven. Both bathrooms have been remolded with new cabinets, new tile shower tile (2025), new vanities and sinks (2025). Imported Italian tile throughout the home. Wood plantation shutters through out, large crown and floor molding, California closets in master bedroom, 4 magnificent skylights that bring in natural light, LARGE electric retractable patio awning for private courtyard perfect for entertaining, 2 car oversized garage, new AC (2016), new TPO Roof (2016), new Hurricane Impact Triple Sliding Doors and ALL Windows (2020), new Hurricane Impact Garage Door (2015), new Ceramic Tile Floors (Wood Look)(2018), new Construction of Den/Study w/ Vaulted Wood Ceiling and Ceiling Fan (2018), new Brick Paver Walkway and Patio area (2018), new Water Heater (2018), new Water Softener (2016), new LARGE Driveway (2023), new Epoxy Garage Floor (2023), All new Interior Paint (2023), All new Exterior Lights (2023), A MUST SEE to truly appreciate this turnkey home! Home is located within approximately 15- 30 minutes to the beaches ( Honeymoon Island, Caladesi Island and Clearwater Beach). You can also drive to Walt Disney World, Epcot and Hollywood Studios in approximately 1 hour and 30 minutes depending on traffic. Call today to schedule your showing appointment!
Listing is courtesy of: 27NORTH REALTY (630-803-8506)
Listing Agent: Michele Davis (813-787-4413)
472 TROUT LN, OLDSMAR, FL 34677
$195,900416 Days on yellowkey MLS ID: TB8369073
REDUCED by $10,000 (4.9%) on 04/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1998Monthly Fee: $70 Tax: $3,420 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,420
Remarks: Gull-Aire Village. 55+ community. Welcome to this 1998 Jacobsen home, built to newer standards and offering the perfect blend of comfort and convenience. This spacious residence features a desirable split floor plan with three bedrooms, providing ample privacy for family or guests. The chef’s kitchen is a true highlight, boasting high-quality Kraft Maid Cabinetry with custom pull-outs for effortless organization and use. A convenient washer and dryer hookup is tucked away in a kitchen closet, maximizing space and functionality. Enjoy easy-care ceramic tile and laminate flooring throughout the home. The A/C and hot water heater were both replaced approximately five years ago, ensuring peace of mind and energy efficiency. Step into the enclosed, air-conditioned Florida room at the front of the house—perfect for relaxing year-round with its stylish tile flooring. There is also a screened porch on the side, ideal for enjoying Florida’s beautiful weather. Custom concrete curbs and pavers add curb appeal, while the generously sized utility room offers excellent storage—great for bikes or hobbies. The community is vibrant and welcoming, featuring a socially active clubhouse, library, pool table, shuffleboard, Bocce ball court, and a heated pool and spa. Monthly planned activities at the clubhouse include yoga, pool exercise, bingo, cards, and line dancing, so there is always something to do. The neighborhood is golf cart friendly for added convenience. HOA fees are just $70.00 per month. Gull-Aire Village is pet friendly—you can have one pet of any size. If you have two pets, one is permitted, and the second is allowed with an emotional support letter from your doctor. You own your land here, offering security and peace of mind. Location is unbeatable! Across the street, from the community you will find AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and the Dollar Store for all your shopping needs. Great dining options nearby include Shaker and Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve’s Family Restaurant. You are just minutes from Super Walmart, Publix, and Countryside Hospital. The stunning beaches of Honeymoon Island and Caladesi State Park are just ten miles away, perfect for weekend getaways. Outdoor enthusiasts will love the biking/walking trail along the canal, with two convenient access points from Gull-Aire. Room sizes are approximate; buyers should verify measurements. Do not miss the opportunity to own this home in a sought-after, amenity-rich community!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000205 Days on yellowkey MLS ID: TB8442794
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1539 Built: 1973 Tax: $4,086 (2024)Community: Harbor PalmsSingle Family
Taxes:$4,086
Elementary School: Oldsmar Elementary-PN
Remarks: Under contract-accepting backup offers. 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)
507 SHORE DR E, OLDSMAR, FL 34677
$239,00065 Days on yellowkey MLS ID: TB8488465
2 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1237 Built: 1972 Tax: $1,158 (2025)Community: Tampashores Bay SecSingle Family
Taxes:$1,158
Remarks: Under contract-accepting backup offers. Don’t miss this exceptional opportunity to build your dream home on a spacious homesite with beautiful views of Tampa Bay. Situated on a generous, nearly 1/3-acre lot measuring approximately 75 x 175, this property is being offered at land value—perfect for new construction. Located on a street experiencing exciting growth, with several newly built homes already completed and more underway, this is an ideal setting for your custom residence. The community offers an outstanding lifestyle with amenities including parks, playgrounds, a fishing pier, and a dog park. The property is also zoned for A-rated schools, adding to its long-term value and appeal. Conveniently located with easy access to Tampa International Airport, as well as a variety of restaurants, shopping, and entertainment options. Plus, you’re just a short drive from some of America’s most renowned beaches. Whether you’re a builder, investor, or future homeowner, this is a rare chance to secure a premium lot in a desirable waterfront area.
Listing is courtesy of: ENGEL & VOLKERS BELLEAIR (727-461-1000)
Listing Agent: Chris Stivers (727-542-5729)
172 LAKEVIEW WAY #172, OLDSMAR, FL 34677
$165,00043 Days on yellowkey MLS ID: TB8496591
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)
1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$379,900187 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
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)
1505 SUNSET WIND LOOP, OLDSMAR, FL 34677
$390,00082 Days on yellowkey MLS ID: W7883526
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1667 Built: 2018Monthly Fee: $580 Tax: $5,187 (2025)Community: Bayside TerraceTownhouse
Taxes:$5,187
Remarks: This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor, providing added privacy and a more open feel from the lanai. Grilling is allowed in the backyard area, giving you the ability to enjoy outdoor cooking and entertaining. The home has been meticulously kept and shows true pride of ownership. It also includes a private 1 car garage for secure parking and additional storage. Upon entering, you immediately notice the ultra-modern feel and the exceptionally well-maintained condition of the property. The spacious kitchen features an extra-large island that is so generously sized it feels like it has its own zip code, along with an under-mount sink, quartz countertops, stainless steel appliances, and a walk-in pantry. The main living area has tile flooring throughout, creating a clean and seamless look, and opens to a screened-in lanai with brick pavers for easy indoor and outdoor living. Upstairs, the upgraded Berber-carpeted staircase with elegant railing leads to a loft area and all bedrooms. The primary suite is generously sized and includes multiple walk-in closets and a beautifully designed en-suite bathroom. Bedrooms two and three each feature carpeting and their own walk-in closets, offering excellent storage and flexibility. The home also includes hurricane shutters stored in the garage, providing added storm protection and peace of mind. Bayside Terrace offers resort-style amenities including a waterfront infinity heated salt-water pool, a covered pavilion overlooking the water, a cabana, two BBQ grills, a gas fire pit, a fitness center, clubhouse, and a dock with kayak and canoe launch access. The gated entrance and deed restrictions add an extra layer of privacy and security, while the waterfront setting allows residents to enjoy Florida sunsets and an active coastal lifestyle. Please view two videos: Tour 1 & Tour 2.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Eric Jenkins, Pa (727-409-3484)
238 PELICAN DR N, OLDSMAR, FL 34677
$199,000432 Days on yellowkey MLS ID: TB8360914
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1983Monthly Fee: $70 Tax: $2,285 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,285
Remarks: This home is in highly desirable 55+ Gull-Aire Village! This beautifully updated Palm Harbor home boasts 1,286 square feet of comfortable living space with two generous bedrooms and two modern baths. The open floor plan is perfect for entertaining family and friends, while the freshly painted interior and brand-new luxury wide-width, high-traffic vinyl plank flooring with new baseboards add a touch of sophistication throughout. The hall bath features a stunning new white wood vanity with marble top, new brushed nickel faucets, a mirrored medicine cabinet, LED lighting, and elegant custom wainscoting. The main suite bath is equally impressive, offering double white wood vanities with marble tops, (2) mirrored medicine cabinets, LED lighting, and custom wainscoting for a spa-like retreat. Both bathrooms are equipped with new shut-off valves for peace of mind. The chef’s kitchen is outfitted with a brand-new range, stainless steel refrigerator, dishwasher, range hood, and bright LED lighting. You will appreciate the spacious pantry and convenient, inside washer/dryer hookup. Relax in the inviting living room with an electric fireplace or enjoy the sunshine year-round in the spacious Florida room with acrylic windows. Additional storage is provided by a utility room—perfect for bikes and lawn equipment. The home also features a newer vapor barrier and metal roof-over. Gull-Aire Village offers incredible amenities including a socially active clubhouse, library, pool table, shuffleboard, Bocce ball court, and a heated pool & spa. There are planned events at the clubhouse every month, plus regular activities such as yoga, bingo, cards, and line dancing. The community is golf cart friendly, and the HOA is just $70.00 per month. Pet lovers rejoice—one pet of any size is welcomed, and if you have two pets, the additional pet will need an emotional support letter from the Buyers doctor for approval. You own your own land! Conveniently located across the street from AMC Theatres, Beall’s, Marshalls, PetSmart, Five Below, and Dollar Store, with a variety of restaurants including Shaker and Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve’s Family Restaurant just steps away. You are only minutes from Super Walmart, Publix, and Mease Countryside Hospital. For nature lovers, the stunning beaches of Honeymoon Island and Caladesi State Parks are about ten miles away, and a scenic biking/walking trail along the canal offers two access points from Gull-Aire Village. Room sizes are approximate and should be verified by the Buyer. Do not miss your chance to own this move-in ready gem—schedule your showing today and experience all that Gull-Aire Village living has to offer!
140 BRENT CIR, OLDSMAR, FL 34677
$565,000204 Days on yellowkey MLS ID: O6357016
REDUCED by $35,000 (5.8%) on 04/11/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1791 Built: 2002Monthly Fee: $475 Tax: $3,527 (2024)Community: Seaside EstatesTownhouse
Taxes:$3,527
Remarks: Seller Motivated! Asking price is under last appraisal value. Come take a look at this beautiful 3 bedroom, 3 bath bay front townhome overlooking Old Tampa Bay and Safety Harbor. Seaside Estates is a gated community, located in the heart of Oldsmar, which offers may options for access to the water, as well as major thoroughfares. 3 Car tandem garage that walks out to a beautiful view, the common area and boat docks. This unit owns Slip 12, with a cover and brand new $17,000 boat lift. One of two grandfathered in with covered biminy top. Stainless Steel appliances, wood flooring, renovated spare bathrooms, and spacious balconies from the great room, and the primary bedroom as well. A wood burning fireplace is also located in the primary bedroom for those cosy nights overlooking the water. The spacious floor plan beautiful water views. Seaside estates is a golf cart-friendly community, offering amenities such tennis and pickelball courts, a swimming pool and Jacuzzi. There is a dock area that offers fishing opportunities and houses the particular residents that own boat docks. Located on a few minutes away from waterfront public parks, recreational facilities, and restaurants. 20 events annually are hosted by the community annually, with monthly dinners strategically planned around the scenic Tampa Bay. This neighborhood is just minutes from downtown Oldsmar and Safety Harbor which have a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, Seaside estates is also pet friendly. 20 min to Caladesi State Park and the pristine Honeymoon Island and 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater. Come take a look at this waterfront gem. Some of these photos have been virtually staged.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Nicci Meyer, Pa (407-913-1131)
271 HEMINGWAY DR, OLDSMAR, FL 34677
$380,000250 Days on yellowkey MLS ID: TB8426952
REDUCED by $5,000 (1.3%) on 04/28/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1452 Built: 1998Monthly Fee: $265 Tax: $1,157 (2024)Community: Sun Ketch Twnhms At Cypress LakesSpa: NoTownhouse
Taxes:$1,157
Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2.5-bath townhome with a private garage, perfectly set on a premier conservation lot, in the quaint Oldsmar community of Sun Ketch Townhomes of Cypress Lakes. Step inside to find brand-new luxury vinyl plank flooring and a bright, open layout. The spacious great room features sliding glass doors leading to a sunroom, expanding your living area while offering serene views of the conservation! The kitchen is both functional and stylish, with white cabinetry, solid-surface countertops, tile flooring, a breakfast bar and a closet pantry. For added convenience, the inside laundry room—complete with full-size Bosch washer and dryer—is located just off the kitchen. Upstairs, the primary suite impresses with vaulted ceilings, a walk-in closet and a private bath, while the additional bedrooms are well-sized for family, guests, or office space. Enjoy the saltwater, community pool, a low HOA fee of only $265 per month and the unbeatable location! Oldsmar is the gateway to Tampa, offering easy access to shopping, dining, parks, Tampa Skating Academy, and highly rated schools including Forest Lakes Elementary, Carwise Middle, and East Lake High. Plus, Tampa International Airport is less than 30 minutes away!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Marcy Daniels (727-560-8080)
4766 STONEVIEW CIR, OLDSMAR, FL 34677
$645,00057 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
Elementary School: Cypress Woods Elementary-PN
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.
Listing Agent: Vanessa Leonard (727-647-2706)
835 CHRISTINA CIR, OLDSMAR, FL 34677
$485,00078 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
$1,199,900130 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!
Listing Agent: Nancy Leslie (727-789-5555)
207 CYPRESS LN, OLDSMAR, FL 34677
$180,00046 Days on yellowkey MLS ID: TB8492844
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $2,309 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,309
Remarks: First-floor 2-bedroom, 2-bathroom condo located in the East Lake Woodlands community in Oldsmar. This pet-friendly unit offers a peaceful pond view and a comfortable, functional layout. The living room and kitchen feature updated luxury vinyl flooring, creating a clean and cohesive living space. The primary bedroom includes two walk-in closets, private access to the enclosed Florida room, and an updated en-suite bathroom. All windows have been upgraded for efficiency and durability, including hurricane impact windows throughout the main living areas and double-pane Low-E windows in the Florida room. The AC was replaced in 2023, and the washer and dryer are approximately 3 years old. The enclosed Florida room overlooks the pond and offers a comfortable space to relax and enjoy nature and the Florida weather. Just outside, the patio features updated pavers installed in 2023, adding to the outdoor usability and appeal. The HOA covers water, sewer, trash, exterior maintenance including the roof, and common areas, making upkeep simple. Residents also have access to a heated community pool. The unit includes an assigned covered parking space. Located near East Lake Woodlands Country Club, which offers optional memberships with access to golf courses, tennis courts, fitness facilities, dining, and social events. Conveniently located near shopping, dining, and major roadways, this condo offers low-maintenance living in a well-kept community.
Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)
Listing Agent: Scott Mayhew (617-631-4060)
402 SHORE DR W, OLDSMAR, FL 34677
$849,00067 Days on yellowkey MLS ID: TB8485835
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1711 Built: 1999 Tax: $3,890 (2025)Community: Oldsmar Rev MapSpa: YesSingle Family
Taxes:$3,890
Remarks: One or more photo(s) has been virtually staged. Gorgeous water views of Old Tampa Bay from this custom-built, original-owner home in a prime Oldsmar location, directly across from popular R.E. Olds Park with its amphitheater, fishing pier, playgrounds, sand volleyball and annual fireworks you can enjoy from your front porch. The resort-style backyard features a large inground pool with spa, kiddie pool, spillover fountain and fiberoptic lighting, all within a screened enclosure with covered area for dining and parties. A spacious concrete pad doubles as a basketball court and offers room to store a boat or add a shed, plus parking for 2 cars under carports and a deep driveway that has accommodated 10+ vehicles, with overflow available at the park. Upstairs, the main living level welcomes you through double hurricane-rated doors to beautiful Brazilian hand-scraped wood floors, abundant windows, and an eat-in kitchen with granite counters and arched opening to the living room, along with a formal dining room. An office or bedroom on this level opens via sliding glass doors to a balcony overlooking the pool, and a convenient half bath completes the floor. The bedroom level begins with a newer washer/dryer closet for easy access to all bedrooms. The primary suite offers stunning water views from sliders, the third-level deck and multiple windows, and its ensuite bath was updated in 2017 with new cabinetry, tile and quartz counters; the second full bath was also updated. Major updates include a 2016 roof and 2023 A/C, making this well-maintained home ideal for both everyday living and large gatherings.
Listing is courtesy of: HOMES BY SANDERS REALTY (727-409-6929)
Listing Agent: Mike Sanders (727-409-8000)
401 PARK BLVD, OLDSMAR, FL 34677
$1,150,000274 Days on yellowkey MLS ID: TB8420002
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3000 Built: 2025 Tax: $2,064 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$2,064
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Experience the perfect blend of luxury and location at 401 Park Blvd, Oldsmar. This brand-new 2025 custom home combines hurricane-resilient construction with modern elegance—all just minutes from Tampa’s vibrant downtown, world-class beaches, and waterfront parks. Set on a quiet street in the beautiful historic district, this home rises at a 12’ elevation with solid concrete block construction on both floors, full impact-rated windows & doors, and spray foam insulation for energy efficiency and peace of mind. Inside, soaring 10’ ceilings and expansive living spaces flow into a chef’s kitchen with Bosch appliances, quartz waterfall island, and butler’s pantry—designed for everyday comfort and stylish entertaining. The main home offers 4 bedrooms, 3.5 baths, 3-car garage and over 3,000 sq ft of living space, complemented by a detached 1 bed / 1 bath garage apartment (780 sq ft) with private AC and water heater—ideal for multi-generational living, guests, or rental income. Step outside to enjoy covered porches, an upstairs deck, a paver driveway, irrigation system, and lush landscaping with privacy fencing. From your front door, you can bike to R.E. Olds Park, waterfront trails, and community events, or drive just 20 minutes to Downtown Tampa, Tampa International Airport, or the amazing beaches of Clearwater and Honeymoon Island. Oldsmar’s central location puts you at the crossroads of Pinellas and Hillsborough, offering a lifestyle that’s both connected and serene. This is more than a home—it’s a rare opportunity to own new construction in a hidden-gem location, built for luxury, resilience, and convenience.
Listing is courtesy of: DANVA URBAN REAL ESTATE LLC (786-322-9729)
Listing Agent: Jessica Scialletti (754-217-9348)
83 PELICAN DR N, OLDSMAR, FL 34677
$205,000128 Days on yellowkey MLS ID: TB8465003
REDUCED by $5,000 (2.4%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1985Monthly Fee: $70 Tax: $3,045 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,045
Remarks: Discover exceptional value in Gull-Aire Village, a vibrant 55+ community, with this meticulously maintained home ready for its next owner. Move right in! this sale includes all furnishings and contents, including a 60-inch TV, for a seamless transition. Enjoy peace of mind with a host of recent upgrades: In March of 2024 a brand-new shingle roof, 11 new hurricane windows, and 11 new solar panels for energy efficiency were installed. Additional improvements include a new carport roof in 2025, a hot water heater installed in February 2026, updated flooring in the back bedroom (July 2025), and a modern A/C unit (September 2020). A vapor barrier was replaced in 2010.Convenience abounds with inside laundry and a relaxing screened porch. There is a utility room for storage or bikes. Gull Aire Village offers outstanding amenities, including a lively clubhouse, library, pool table, shuffleboard courts, bocce ball court, and a large, heated pool and spa. Residents enjoy a rich calendar of planned activities and the freedom of a golf cart-friendly neighborhood. The affordable HOA fee is just $70 per month. Pet lovers are welcome. One pet of any size is permitted, and a second pet is allowed with an Emotional Support letter from your primary physician. Best of all, you own the land. This ideal location places you across the street from popular destinations like AMC Theatres, Beall's, Marshall's, Pet Smart, Dollar Store, Ulta Beauty, and an array of dining options including Craft Street Kitchen, Country Pizza Italian Grill, Shaker and Peel, Chipotle, Mandolas, and Eve's Family Restaurant. Essential services such as Super Walmart, Publix, and Countryside Hospital are just a 15-minute drive away, while the stunning beaches of Honeymoon Island and Caladesi State Parks are approximately ten miles from your doorstep. All room measurements are approximate and should be verified by the buyer. Do not wait!
113 NINA WAY #113, OLDSMAR, FL 34677
$199,900423 Days on yellowkey MLS ID: TB8366634
REDUCED by $25,100 (11.2%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1979 Tax: $2,895 (2024)Community: East Lake Woodlands CondoSpa: NoCondo
Taxes:$2,895
Remarks: Here is your opportunity to purchase a great condo in the popular East lake Woodlands development. This beautiful 2 bedroom, 2 full bath condo has plentiful closet space, the primary bedroom has 3! Unit has its own washer and dryer located in the enclosed porch just off the living room. All furniture is included! Both bathrooms have been remodeled along with the kitchen. The kitchen has quartz countertops, new cabinets and stainless appliances. You also get one covered parking spot under the carport. Plenty of guest parking. Walking distance to the pool. Close to schools, shopping, dining and the movie theaters. New acrylic windows and new screens will be installed on the porch by the end of May.
Listing is courtesy of: BRICK HOUSE REALTY SERVICES (727-804-4992)
Listing Agent: Joe Courey (727-804-4992)
4007 PALM KEY AVE, OLDSMAR, FL 34677
$629,000228 Days on yellowkey MLS ID: TB8435073
REDUCED by $10,000 (1.6%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2019Monthly Fee: $580 Tax: $7,398 (2024)Community: Bayside TerraceTownhouse
Taxes:$7,398
Remarks: Walk in the front door and look straight out to the water. Head out to the screened-in back porch to hang out and enjoy the views, from dolphins and mother duck with her ducklings, to the pink & orange glowing sunsets. This unit comes with floodplain X zoning tied to the title, which means you’re grandfathered in, and the cheap flood insurance is transferable to you (less than $800/yr.). Soaring ceilings, open floor plan, hard floors throughout, and a finished garage with a high-end epoxy floor that makes it feel like you’re parking in a showroom. Built in 2019, it looks and feels fresh and new. 1st floor bedroom with water views (great for guests!). Large media room upstairs with numerous possibilities. It could be a game room. It could be a gym or just a TV area. 3 bedrooms upstairs, including the master. The master bath overlooks the water with an oversized tub, a walk-in shower, dual vanities, and a custom walk-in closet. DirectTV, Frontier internet, water, recycling, and trash (2x/week) are included in the monthly HOA fee. The unit is far enough away from the gate, where you won't hear the road noise of 580. Bayside Terrace offers an array of amenities, including an infinity-edge swimming pool, BBQ area, a gym, a fire-pit, and a community dock with kayak, paddleboard, and canoe launch. This exceptional townhome provides the perfect blend of luxury, comfort, and Florida's natural beauty
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Jacob Gross (727-303-2063)
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