Oldsmar Homes with Deed Restrictions Community Extras

Oldsmar Homes with Deed Restrictions Community Extras

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! This vibrant city, known for its rich history and beautiful landscapes, offers a perfect blend of suburban charm and natural beauty. With its picturesque parks, scenic waterfront, and a strong sense of community, Oldsmar is an ideal place for families, retirees, and everyone in between.

Oldsmar is renowned for its welcoming atmosphere and active lifestyle. Residents enjoy a variety of recreational opportunities, including outdoor activities at the stunning Oldsmar City Park and the serene waterfront along Old Tampa Bay. With a thriving downtown area filled with unique shops, delicious dining options, and community events, there’s always something happening in this lively city.

For those seeking a home in Oldsmar, the community offers a selection of homes with deed restrictions, ensuring that the neighborhood maintains its charm and appeal. These deed-restricted communities provide a sense of security and commitment to quality living, making them an attractive option for prospective homeowners. Enjoy well-maintained properties, beautifully landscaped common areas, and a friendly environment where neighbors look out for one another.

In Oldsmar, you’ll find a variety of housing options that cater to diverse lifestyles and budgets. Whether you’re looking for a cozy single-family home or a spacious townhouse, there’s something for everyone in this delightful city. Embrace the Oldsmar lifestyle, where community spirit meets the beauty of Florida living – your dream home awaits!

Newest Oldsmar Homes with Deed Restrictions Community Extras

260 Balsam Drive, Oldsmar
$205,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome home to this beautiful 2-bedroom, 2-bathroom villa nestled within the highly desirable gated community of East Lake Woodlands! Offering an exceptional blend of comfort, style, and functionality, this inviting residence features a desirable split-bedroom floor plan designed to provide privacy for both owners and guests. Step inside to discover a spacious, light-filled living room, perfect for everyday living and entertaining. A dedicated dining area and charming wet bar create the ideal setting for hosting family and friends. The well-appointed kitchen features a full appliance package, abundant cabinetry, and generous counter space, providing both convenience and functionality. The spacious primary suite offers a peaceful retreat, complete with a walk-in closet and private en-suite bathroom featuring a large walk-in shower. The secondary bedroom is conveniently located near a full guest bathroom, providing comfort and privacy for visitors. An expansive additional family room offers versatile living space, ideal for a media room, home office, or relaxing entertainment area. Enjoy the best of Florida's indoor-outdoor lifestyle with two inviting outdoor spaces! Sliding glass doors lead to a private, fenced front courtyard, perfect for enjoying your morning coffee, outdoor dining, or simply unwinding in a tranquil setting. At the rear of the home, a generously sized enclosed porch provides additional space for relaxing or entertaining year-round. Located within the beautiful, gated East Lake Woodlands community, residents have the opportunity to enjoy an array of exceptional amenities through optional club membership, including championship golf, tennis, fitness facilities, dining, and a variety of social activities. Surrounded by lush landscaping and a peaceful atmosphere, this sought-after community offers a wonderful Florida lifestyle. Conveniently situated near shopping, restaurants, entertainment, medical facilities, and major roadways, this villa combines the tranquility of gated community living with easy access to everyday conveniences. Don't miss this wonderful opportunity to own a beautiful villa in one of the area's most desirable communities. Schedule your private showing today and experience all that East Lake Woodlands has to offer!

260 Balsam Drive, Oldsmar
209 Dolphin Drive, Oldsmar
$194,900
2 Beds ⋅ 2 Baths ⋅ Gull Aire Vlg SubDv. ⋅ 34677 Zip Code
In Gull Aire Village, Oldsmar’s 55+ community, you own the land under your home and pay just $70 a month in HOA fees. This 2-bedroom, 2-bath home is move-in ready. Fresh paint, wood-look floors, and ceiling fans run throughout. A tiled Florida room welcomes you inside, and the open living room centers on a cozy fireplace for the cooler evenings. The spacious kitchen has plenty of cabinet space, a breakfast bar for morning coffee, and stainless appliances, including the range, dishwasher, and microwave. Storm season is less stressful here, with hurricane shutters and a hurricane-rated sliding glass door that opens to ramp access. The AC has been regularly maintained, and the laundry area has new flooring. An enclosed workshop gives you room for projects and hobbies. Outside your door you’ll find an active clubhouse, library, billiards, shuffleboard, and a heated pool and spa. One pet of any size is welcome, and leasing is allowed. Restaurants, shopping, and entertainment are a stones throw from here and Gulf beaches and Tampa-area airports are a short drive away. Homes at this price with land ownership don’t last, so schedule your private showing today. Room sizes are approximate and should be verified.

209 Dolphin Drive, Oldsmar
380 Rosalind Lane, Oldsmar
$569,999
3 Beds ⋅ 3 Baths ⋅ Bay Arbor SubDv. ⋅ 34677 Zip Code
Virtually Staged. PRICED TO SELL!!! Make your appointment now as it will sell quickly at this price! Plus this house has 400 sq. ft. MORE than most homes on market in the neighborhood and there are no back yard neighbors! Enjoy the comfort and character of this beautifully maintained 3 bedroom, 2.5 bath home tucked away on a quiet cul-de-sac in the gated Bay Arbor community of Oldsmar. Set on a wooded lot with no rear neighbors, this inviting two-story home blends classic architectural details with modern updates and thoughtful touches throughout. Recent improvements include a NEW AC (2026), NEW ROOF (2022), NEW screen enclosure (2024) and Impact-Resistant Hurricane Windows (2022)! This house is ready to move in with all the major updates necessary for peace of mind!. Inside, high ceilings and an open upstairs overlook create an airy sense of space, while porcelain tile and wood flooring, decorative chandeliers, and a gorgeous dark-stained staircase add character and style. The main floor offers a combination living and dining room, along with a spacious kitchen, dinette, and family room combination designed for everyday living and entertaining. The updated kitchen features clean, crisp cabinetry in a functional U-shaped layout, quartz countertops, stainless steel appliances, and a convenient breakfast bar with additional seating. Just beyond, sliding glass doors connect the family room to the partially covered, screened patio, where decorative brick pavers create an inviting outdoor space to relax or gather with friends and family. Beyond the patio, a large vinyl-fenced backyard backs to a wooded setting, providing added privacy and a peaceful backdrop. Upstairs, a spacious bonus room or loft provides additional flexibility for a media room, home office, or second living area. The conveniently located laundry room and all three bedrooms are also on the second floor. The generously sized primary suite features a walk-in closet and an updated, spa-like ensuite bath complete with a dual-sink vanity, soaking tub, and separate shower. Two additional spacious bedrooms share a full guest bathroom and shower. Bay Arbor offers a desirable gated neighborhood setting with a community pool, playground, and recreational facilities, while the surrounding Oldsmar area provides plenty of opportunities to enjoy the outdoors. Nearby attractions include Mobbly Bayou Wilderness Preserve and Mobbly Beach Park, along with miles of walking and biking trails, waterfront recreation, and local dining and shopping. With its combination of thoughtful updates, versatile living spaces, private backyard setting, and convenient location, this home offers a wonderful opportunity to enjoy all that Oldsmar and the Tampa Bay area have to offer!

380 Rosalind Lane, Oldsmar
109 Lakeside Drive, Oldsmar
$199,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome to this stunning, ground floor 2 bedroom to 2 bath condo in a guarded and gated community of East Lake Woodlands, where you can enjoy a maintenance-free Florida living at its best. Step inside and discover the seamless combination of quality updates with comfort. The spacious living and dining areas flow seamlessly together, creating an inviting, open atmosphere perfect for entertaining or simply relaxing at home. The well-appointed kitchen features a breakfast nook, convenient breakfast bar with a pass-through to the dining area, making both casual meals and gatherings a breeze. The desirable split-bedroom floor plan provides privacy, while the generously sized primary suite is a true retreat, featuring THREE walk-in closets! Additional highlights include plantation shutters throughout, living room fireplace, and an enclosed, all-weather Florida room overlooking a pond. Imagine starting your mornings with coffee while enjoying the serene water views or unwinding in the evening surrounded by nature. Enjoy the convenience of a lock-and-leave Florida lifestyle, with monthly condo fees covering basic cable, internet, water, sewer, and trash removal. Less time worrying about maintenance means more time enjoying everything Florida has to offer! Nestled within the well-established East Lake Woodlands community, residents enjoy the comfort of guarded entry. For those seeking an active, resort-inspired lifestyle, optional membership to Ardea Country Club offers access to golf, tennis, pickleball, fitness facilities, clubhouse amenities, and more. Location is another standout feature! Conveniently situated near shopping, restaurants, parks, entertainment, and everyday essentials, with easy access to Tampa International Airport and St. Pete-Clearwater International Airport. Whether you're looking for a full-time residence or a seasonal Florida getaway, this exceptional ground-floor condo checks all the boxes! Beautiful updates, spacious living, pond views, and a sought-after gated community make this an opportunity you won't want to miss. Come experience the charm, comfort, and convenience of East Lake Woodlands living!

109 Lakeside Drive, Oldsmar
1334 Fallsmeade Court, Oldsmar
$899,000
3 Beds ⋅ 3 Baths ⋅ Aberdeen Unit Two SubDv. ⋅ 34677 Zip Code
Luxury, privacy and breathtaking water views come together exceptionally in this home located in the desirable subdivision of Aberdeen in the gated golf community of East Lake Woodlands. Nestled on a cul de sac and perfectly positioned to be set back and angled from other homes, this residence affords real privacy. An approximately 200-foot-deep lot with neighbors on only one side along with an extended driveway gives the feeling of your own resort-style retreat - and it's Zone X which does not require flood insurance. From its striking architecture and stone-accented columns, this stunning three-bedroom-plus-office, two-and-a-half-bath, three-car garage home offers an impressive blend of elegance and thoughtful design. Step inside through the elegant double-glass entry doors and travertine foyer and immediately enjoy serene views extending through the home to the pool and water beyond. Soaring ceilings, crown molding and beautiful hardwood flooring create a memorable impression. Located at the front of the home, the office or den exudes an elegant, comfortable style and is highly versatile with ample room for a home office, den, exercise room or other possibilities. Inviting describes the dining room with warm natural light, exquisite chandelier and open flow to the living room so perfect for gatherings. French doors from the living room, breakfast area and primary suite provide an effortless connection to the covered lanai and private backyard retreat. The well-appointed kitchen features custom wood cabinetry including built-in glass display cabinets with serving space, a center island with bar seating and copper vegetable sink plus gleaming granite countertops accented with beautiful sparkle. Open to the kitchen, the family room offers a custom-designed stone fireplace that adds warmth and ambiance. A custom-designed entertainment center is nestled in the corner and can be removed since the owners kept original additional windows in place. Two generously sized secondary bedrooms provide comfortable accommodations and have access to the full bath updated with wood cabinetry and stunning tile accents. Measuring approximately 29 feet long, the primary suite provides luxury complete with sitting area to feel truly pampered. Classic touches continue in the updated primary bath with expansive dual vanities, gorgeous tile selections and large soaking tub. Outside, the covered living area is ideal for relaxing, dining and enjoying the beautiful water views in complete privacy. A special waterfall highlights the pool and spa with Mexican tumbled marble, creating a calming atmosphere in the lushly landscaped backyard. Additional highlights include a tile roof installed in 2012 and sleek, special-order Clopay high-impact garage doors and propane gas for the fireplace, outdoor grill and water heater. As a second residence, this home has been gently lived in and well maintained. From the secluded setting to the elegant finishes and serene water views, this is a true sanctuary that must be seen to be fully appreciated. For additional fees, optional memberships are available to Ardea Country Club, featuring two golf courses, a fitness center, tennis and pickle ball and pools as well as dining and special events and activities. And enjoy a premier location providing convenient access to Tampa International Airport, award-winning Gulf beaches, medical facilities, fine dining, professional sporting events and all Tampa Bay area has to offer.

1334 Fallsmeade Court, Oldsmar
238 Pelican Drive N, Oldsmar
$196,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Virtually Staged. Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers spacious living, dining and kitchen areas, newer stainless-steel appliances, updated bathroom vanities, beautiful laminate flooring, updated subflooring throughout, fresh paint throughout, a newer vapor barrier, and an open-concept layout. The generously sized primary suite features a spacious walk-in closet, an en-suite bathroom, with a separate garden-like tub, a separate water closet with walk-in shower creating a comfortable space to unwind. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers an exceptional lifestyle with resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the added advantage of owning the land with an affordable monthly HOA fee of just $70. One pet of any size is welcomed and two boat and RV storage areas are available for a low monthly rental fee. You’ll love the unbeatable location is less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximately 2 miles away, St.Pete/Clearwater Int'l Airport is a quick 11-miles away and Tampa Int'l Airport is only a 15-mile drive. For those of you who enjoy the outdoors, the adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, offering another wonderful way to embrace Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil pond views, you’ll appreciate the welcoming atmosphere and vibrant lifestyle that make Gull-Aire Village such a special place to call home. Don’t miss this opportunity to enjoy affordable Florida living in a desirable, amenity-rich community. Schedule your private tour today! (Room dimensions are approximate and should be verified by the Buyer.)

238 Pelican Drive N, Oldsmar
105 Palmetto Court, Oldsmar
$165,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
Just what you have been waiting for....! FIRST floor, pet friendly (up to 40 pounds), condo located in Cypress Estates III of the popular gated community of East Lake Woodlands Country Club, a community that has been designed to enhance your lifestyle. Direct entrance takes you to open views of the dining and living room area out thru the sliding doors to your screened lanai overlooking a park like setting view. This home has been carefully maintained and has a split bedroom plan and the primary bedroom offers two closets, ensuite bath with updated sink vanity and newer tiled shower in the primary bath. Spacious guest bedroom with wall closet. The laundry closet is located off your lanai with washer/dryer. There is a community pool just down from the condo, one covered parking space and other available guest spaces. Optionally, you could join the Ardea (formerly the East Lake Woodlands) Country Club for use of their facilities that will include Clubhouse, two Championship 18 hole golf courses, additional heated pools, tennis courts, fitness center and Clubhouse restaurants and social gatherings. Minutes away from Countryside Mall and the sandy beaches of Honeymoon Island along with parks, restaurants and entertainment. This is a gated, golf cart friendly community (must be street legal), which is handy to run over to the nearby shopping plaza for some of your everyday needs. Location is everything! It is approximately 15 miles from Tampa Airport and less than 10 miles to the beach. For more information about the community and the area go to the East Lake Woodlands website.

105 Palmetto Court, Oldsmar
261 Woodlake Wynde Unit 261, Oldsmar
$199,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code
Welcome to this highly desirable ground-floor 2-bedroom 2-bathroom residence located in the gated community of East Lake Woodlands. This bright and inviting home offers an open, spacious layout designed for comfortable Florida living. Recent updates include beautifully updated bathrooms and flooring in 2025, a newer AC system installed in 2022, and fresh interior paint completed in 2026. The home also features two private lanais, providing the perfect spaces to relax and enjoy the Florida lifestyle. The spacious primary bedroom offers a walk-in closet, while generous closet and cabinet storage throughout the home provide plenty of room for everyday living. An in-unit washer and dryer add convenience and ease. The monthly HOA fee offers exceptional value, including water, sewer, trash, pest control, high-speed internet, cable, and access to numerous streaming apps, along with use of two community pools. For golf and country club enthusiasts, optional membership is available at Ardea Country Club, home to one of the area's premier golf courses. Enjoy the convenience of a low-maintenance lifestyle in one of the area's most desirable communities, where comfort, convenience, and resort-style amenities come together. This is Florida living at its finest!

261 Woodlake Wynde Unit 261, Oldsmar
131 Brent Circle, Oldsmar
$849,900
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
This rare, customized end unit townhome is located on Old Tampa Bay in Oldsmar in the sought after gated community of Seaside Estates. Enjoy breathtaking open water views from any of the floors largely due to the abundance of windows and 3 generous sized patios/decks. Relaxing will come naturally as you gaze out over the green space, seawall and open water. Home features 1834 sf and 3 bedrooms, 3 baths. There are 2 outside parking spaces within a few feet of the attractive entry to the unit. Upon entering the bottom floor you have a foyer and to the left an oversized 2+ car tandem parking garage with an abundance of storage and rear covered patio. Garage also has a vented portable air conditioner and a dehumidifier creating a perfect storage and work area. The ground entry foyer has stairs leading up to the main living area floor where you are greeted with great light from the multi windows and large deck/patio. It is truly a breathtaking view looking out on Old Tampa Bay. This floor features a living room, dining room, updated kitchen (2019), one bedroom with a built-in murphy bed plus desk and a full bath. Ascending one more floor, there is the master suite with sliders leading to a spacious deck, a second en-suite bedroom with its private full bath. There is also a laundry area with double doors for easy access and stackable washer/dryer. Throughout the wooden floors are beautiful with some tile in the wet areas. Multiple outdoor spaces including the ground floor patio plus oversized patios/decks as one on each floor really expand the living space so you can enjoy the Florida lifestyle throughout this open unit. Don't let the multi-stories be an issue as this unit boasts an ELEVATOR installed 2025 to help you move yourself and your belongs easily throughout. As an added bonus, this unit comes with a DEEDED BOAT SLIP located behind the unit at the mouth of the channel. So whether you prefer fishing from the seawall, inshore fishing or shooting out in the Gulf for a little offshore fishing or just pleasure boating maybe to local restaurants/bars such as close by Jack Willie's, you're ready to go! While feeling very private, this unit offers it all . . . privacy yet close to shopping and restaurants for your daily needs.

131 Brent Circle, Oldsmar
127 Camphor Drive Unit E, Oldsmar
$114,900
2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 34677 Zip Code
Welcome to The Gardens of Forest Lakes! This spacious FIRST-FLOOR, 2-BEDROOM, 2-BATH CONDO offers comfortable, low-maintenance Florida living with no stairs, TILE FLOORING THROUGHOUT and BEAUTIFUL POND VIEWS! Nestled in a peaceful setting surrounded by mature landscaping and lush greenery, this light and bright residence offers a wonderful combination of comfort, convenience and scenic surroundings. Step inside to a living and dining area with plenty of space to relax or entertain. Sliding glass doors lead to a covered patio overlooking the tranquil pond, creating the perfect spot to enjoy your morning coffee, watch the wildlife or simply unwind while taking in the peaceful water views. The kitchen offers ample cabinetry, generous counter space and a convenient breakfast/pass-through bar that opens to the main living area. The primary bedroom features a private ensuite bathroom and walk-in closet, while the second bedroom provides flexibility for guests, a home office or additional living space & adjacent guest bath. An interior laundry area adds everyday convenience. With tile flooring throughout and a functional floor plan, this condo provides a great opportunity to add your own personal touches while enjoying its desirable first-floor location and picturesque setting. Beyond the condo, residents can enjoy an impressive array of community amenities in a scenic lakefront setting. Forest Lakes offers a large community swimming pool and spa, tennis courts, basketball, racquetball/handball courts, playground, picnic and grilling areas, and a waterfront dock overlooking the lake. Mature trees, tropical landscaping and generous green spaces create an inviting atmosphere throughout the community. Conveniently located in the heart of Oldsmar, close to shopping, dining, parks, beautiful Gulf beaches and Tampa International Airport. Whether you're searching for a primary residence, seasonal getaway or investment opportunity, this first-floor condo with beautiful pond views offers an excellent opportunity to enjoy the Florida lifestyle. Schedule your private showing today!

127 Camphor Drive Unit E, Oldsmar
1633 Shady Oaks Drive, Oldsmar
$545,000
3 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 3 SubDv. ⋅ 34677 Zip Code
Pool, heated spa, and a 3-car garage in East Lake Oaks. This 3-bedroom, 2.5-bath Oldsmar home pairs a screened outdoor setup with solid updates: roof 2017, AC 2021, and vinyl fence 2021. The two-story layout opens with vaulted ceilings over a combined living and dining room. The kitchen features wood cabinetry, stainless steel appliances, and an eat-in area, and it opens to the family room for easy everyday flow. The remodeled primary bath includes dual sinks, a standalone tub, and a separate shower. Out back, the screened lanai offers covered seating, the heated spa, and the pool, all within a vinyl-fenced yard for added privacy. Community amenities include a pool, playground, and ponds. Harbor Palms Nature Park, Estuary Preserve, and Sheffield Park are nearby for bike trails, disc golf, and tennis. Centrally located near shopping, restaurants, and theaters, with easy drives to downtown Safety Harbor, downtown Dunedin, Tampa, the airports, and Clearwater Beach.

1633 Shady Oaks Drive, Oldsmar
129 Caryl Way Unit 129, Oldsmar
$129,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Short Sale. UNAPPROVED SHORT SALE – Renovation Opportunity in Highly Desirable East Lake Woodlands! Bring your vision and transform this 2-bedroom, 2-bathroom condo into your ideal Florida retreat! Located within the highly sought-after, guard-gated community of East Lake Woodlands in Oldsmar, this property presents an excellent opportunity for buyers looking to renovate and make it their own. Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this condo offers plenty of potential. Enjoy the beautiful surroundings of this established community, conveniently located near shopping, dining, entertainment, beaches, and everything the Tampa Bay area has to offer. The HOA fee includes cable TV, high-speed internet, water, sewer, trash collection, exterior maintenance, grounds maintenance, community pool, and reserves, providing added convenience and value. Property is being sold as an unapproved short sale, subject to lender approval. Bring your creativity and take advantage of this opportunity to own in one of Oldsmar's most desirable communities!

129 Caryl Way Unit 129, Oldsmar
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