Location: East Lake Woodlands, Oldsmar
Do Not Show Listings
109 NANCY DR, OLDSMAR, FL 34677
$1,75025 Days on yellowkey MLS ID: TB8507657
REDUCED by $50 (2.8%) on 06/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1979Community: East Lake Woodlands CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Welcome to this beautifully maintained 2 bedroom, 2 bathroom first-floor condo located in the highly desirable gated community of East Lake Woodlands. This immaculate home features upgraded laminate flooring throughout and offers a serene view perfect for relaxing mornings or evenings. Residents may 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. Schedule your showing today!
Listing is courtesy of: CENTURY 21 INTEGRA (800-593-7653)
Listing Agent: Becki Server (727-835-9696)
300 CYPRESS CREEK CIR, OLDSMAR, FL 34677
$4,2005 Days on yellowkey MLS ID: TB8513245
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2730 Built: 1977Community: East Lake WoodlandsSpa: NoSingle Family
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Located in the desirable gated golf-course community of East Lake Woodlands, this lovely two-story pool home sits on a corner lot on a small canal. Thoughtfully designed for spacious, comfortable living and entertaining, it offers four bedrooms (including a large primary bedroom upstairs) plus a downstairs flex or office space, 3.5 baths, and a spacious two-car side-entry garage. The main level features generous living spaces including a large back sunroom, dining area, family room and a flexible den/bonus room, all finished with low-maintenance luxury vinyl, while upstairs the very large bedrooms showcase rosewood hardwood flooring and ample closet storage. The screened porch includes a covered lanai, paver deck and a pebble-tech swimming pool—perfect for relaxing or hosting guests. Additional conveniences include a large utility room with washer and dryer included and a sizeable downstairs storage closet/pantry. As a resident of East Lake Woodlands you’ll have access to optional Country Club memberships with championship golf courses, tennis courts, pools, a fitness center and elegant dining and event facilities. Situated in a prime Pinellas County location near top-rated schools, Gulf beaches, the airport, parks and shopping, this spacious, well-appointed home in a secure golf-course community is an exceptional rental opportunity for those seeking resort-style living. Don't wait - This is a rare opportunity as rentals don't come up very often in this desireable area!
Listing is courtesy of: FLORIDA EXECUTIVE REALTY (813-327-7807)
Listing Agent: Gina Miles (813-892-5686)
132 E CYPRESS CT, OLDSMAR, FL 34677
$1,8007 Days on yellowkey MLS ID: TB8514035
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Community: East Lake Woodlands Cypress Estates IiSpa: NoCondo
Remarks: Welcome home to this beautifully maintained 2-bedroom, 2-bath upstairs condo in the desirable gated golf community of East Lake Woodlands. Enjoy peaceful mornings and relaxing evenings on your private screened balcony overlooking a tranquil view. Convenience begins with your reserved parking space right out front, along with plenty of guest parking for visitors. Residents enjoy access to a sparkling community pool and the pristine surroundings that make East Lake Woodlands such a sought-after place to call home. So close to shopping and fine dining. Inside, you'll find a bright and inviting floor plan featuring stainless steel appliances, granite countertops, and an abundance of cabinetry for storage. The air conditioning system and water heater have both been updated within the last few years, providing added peace of mind. Water, Sewer, Trash, Cable and Internet INCLUDED. The thoughtfully designed split-bedroom layout offers maximum privacy, with the bedrooms separated by bathrooms and closet space. Freshly painted and move-in ready, this beautiful condo is waiting for you to start enjoying the East Lake Woodlands lifestyle. Schedule your showing today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)
Listing Agent: Fonda Dillard (813-514-5222)
112 CYPRESS CT #112, OLDSMAR, FL 34677
$1,75010 Days on yellowkey MLS ID: TB8506877
REDUCED by $50 (2.8%) on 05/30/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Community: East Lake Woodlands Cypress EstatesCondo
Remarks: Located at 112 Cypress Ln, Oldsmar, FL 34677, this charming 2-bedroom, 2-bath condo in the desirable East Lake Woodlands / Cypress Estates community offers comfortable, Florida living in a peaceful, gated setting with community pool access and well-maintained grounds. The home features a split floor plan, in-unit laundry, and a private screened patio — perfect for morning coffee or relaxing evenings. Residents enjoy the convenience of a secure neighborhood while being just minutes from shopping, dining, entertainment, and major roadways connecting you to Clearwater, Tampa, St. Petersburg, and beautiful Gulf Coast beaches. Oldsmar itself is a vibrant Pinellas County city with great schools, parks, and community events, providing both convenience and lifestyle appeal for full-time residents or seasonal guests alike. Move in requires first month, last month and $2000 deposit. Total amount required to move in for qualified tenants is $5600. No Application Fees! Drive by and Call us for Approval!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Wil Sanders (813-380-6048)
336 WOODLAKE WYNDE, OLDSMAR, FL 34677
$2,00014 Days on yellowkey MLS ID: TB8511765
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 924 Built: 1985Community: East Lake Woodlands Woodlake RunSpa: NoCondo
Remarks: Call to see and Enjoy your Florida getaway in this beautifully furnished 2 bedroom, 2 bath upstairs rental featuring a fantastic lake view and peaceful surroundings. Relax with your morning coffee or unwind in the evening on the private screened-in patio overlooking the water. Another screened patio off the guest room for more fresh air. Ceiling fans throughout the home help keep everything cool and comfortable year-round. This fully furnished rental includes everything you need for a carefree stay just bring your clothes, food, and a happy disposition. The spacious primary bedroom features a KING-size bed with calming lake views, while the guest bedroom offers two twin beds and is thoughtfully separated for added privacy. Conveniently located near wonderful shopping, dining, and entertainment, this property places you right in the heart of Florida living. Only 25 minutes to Tampa International Airport and approximately 20 minutes to beautiful Honeymoon Island. Enjoy nearby Dunedin and Oldsmar with their charming downtown areas, waterfront parks, festivals, restaurants, and endless activities. Call today for availability and enjoy your sunny Florida escape. Sorry No Pets. Available monthly till November and slightly higher for Dec to end of Feb.
103 PALMETTO CT #103, OLDSMAR, FL 34677
$1,80013 Days on yellowkey MLS ID: W7886064
Remarks: This is Florida living at its finest! This quiet community of Cypress Estates is nestled in the East Lake Woodlands neighborhood with great amenities like walking trails, wooded areas, and a pool to enjoy. If you are looking for security, location, value, and great style, with a no-maintenance lifestyle, look no further! This community has 6 private gates to go in and out from different locations for your convenience. This 2-bedroom 2-bath is nicely sized with new laminate flooring, new tile in the bath, and a totally remodeled interior. The living area has an open-concept floor plan for the dining area and the kitchen, excellent for gatherings and entertainment. It overlooks the screened lanai that is perfect for that coffee in the morning or a cocktail at night overlooking the wooded area behind the condo. The kitchen is a remodeled work of art with tons of cabinets, endless quartz counters, new all-matching Samsung stainless steel appliances, and a pantry closet. Casual meals can be enjoyed at the breakfast bar, and gorgeous lighting and a cool fan finish the kitchen beautifully! The master bedroom is spacious with 2 large walk-in closets and a linen closet. In addition, the owner’s suite has its own entrance to the screened lanai. An amazingly remodeled and gorgeous bath with a walk-in shower, shower panel, and beautiful vanity completes the space! The 2nd bedroom has also been remodeled with a bathroom just a few feet away! The laundry closet is located on the lanai and has a full-size washer and dryer. This also provides extra storage. A carport for your car, which is directly in front of the unit. This won't last long. This is a beautiful unit. Come see it for yourself.
Listing is courtesy of: SANDPEAK REALTY (727-232-2192)
Listing Agent: Bedsy Renwanz (727-259-3357)
161 LAKESIDE DR, OLDSMAR, FL 34677
$2,00015 Days on yellowkey MLS ID: TB8511614
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981Community: East Lake Woodlands CondoSpa: NoCondo
Remarks: Call Fonda Dillard 813-514-5222 to Discover your perfect getaway! This inviting, fully furnished 2-bedroom, 2-bath condo awaits your arrival. Simply bring your essentials to enjoy a comfortable, updated living space, complete with in-unit washer and dryer. 2 bedrooms and they are seperated by closet space and bathrooms for privacy. Embrace tranquility on the back patio, offering serene lake views and glimpses of local wildlife. Located in a golf community for that well maintained and clean looks, you're moments away from shopping, dining, and entertainment. Available for a 3-month minimum stay from June 1 to October 31. Please note, pets are not permitted. Make this your home away from home; call now to secure your retreat!
107 WINDWARD PL #107, OLDSMAR, FL 34677
$2,00019 Days on yellowkey MLS ID: TB8508465
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984Community: Meadows Condo At East Lake WoodlandsCondo
Elementary School: Cypress Woods Elementary-PN
Remarks: Available June 1 though October 31. Rest and relaxation are the 'key' to this beautifully decorated first floor condo in The Meadows of gated East Lake Woodlands Country Club community. Tile flooring thru out the living area with comfortable setting to watch your flat screen tv or out to the glass enclosed lanai to enjoy your new book! Dining area to set up a more formal table or grab a bite in the eat in kitchen area. Kitchen has stainless appliances, breakfast bar overlooking the dining/living area. Split bedroom plan. Primary bedroom with queen size bed, tv, walk in closet and sliders out to the lanai (where the washer and dryer are located in the utility closet). Primary ensuite bath with tiled walk in shower and linen closet. Guest bedroom with twin beds, tv and guest bath with tub/shower combination. This is a non-smoking/vaping residence, and all short term rentals are subject to a 13% sales/tourist tax. Water, sewer, trash, basic cable, internet and up to $100 in electric included in the rent. Please call for availability.
Listing is courtesy of: PREFERRED REALTY GROUP, LLC (727-418-1020)
Listing Agent: Sandy Harris (727-365-3930)
135 W CYPRESS CT, OLDSMAR, FL 34677
$2,10095 Days on yellowkey MLS ID: TB8471216
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Community: East Lake Woodlands Cypress EstatesSpa: NoCondo
Remarks: Call to see this East Lake Woodlands Finest 2 Bedroom 2 Bath cute downstairs corner condo with almost everything new. Including most of the windows. Treat yourself to elegance in this remodeled Kitchen with LOTS of cupboard space and Quartz counters. New cabinets and lighting. Walk in to see the beautiful flooring throughout the condo. The large Master Bedroom has 3 closets and room for a King size bed. The guest room is separated by the closets and both baths. A small Pet is welcome under 20 lbs. Reserved space right in front of the building. Close to all kinds of shopping in the Eastlake corridor. Great Schools and gated community. Usually commute 25 minutes to airport or 20 to the beach.
207 PALMETTO CT, OLDSMAR, FL 34677
$1,700182 Days on yellowkey MLS ID: TB8452612
Remarks: Updated 2-Bedroom, 2-Bath Ground Floor Condo with Patio in Gated East Lake Woodlands! This beautifully updated 2-bedroom, 2-bath condo is located in the desirable gated community of East Lake Woodlands. Featuring newer HVAC and a hot water heater (just 3 years old), this home offers modern comfort with luxury vinyl flooring throughout, including the screened lanai. The open-concept great room features sliding glass doors that lead to the lanai, while the primary bedroom also boasts sliders for easy access. The spacious primary suite includes two large walk-in closets, a linen closet, and a lovely ensuite bath. The second bedroom offers a full wall of closets and is conveniently located near the hall bath. For added convenience, the lanai houses a washer and dryer in a dedicated laundry closet. Enjoy outdoor living with a separate patio perfect for grilling, or take advantage of the community amenities, which include a pool and tennis courts. Nature abounds with meandering walking trails throughout ELW! This condo offers the perfect blend of style, comfort, and leisure in a secure, gated environment, close to all amenities and our famous Gulf Beaches and 2 airports!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nicole Harmon (727-385-1357)
108 NINA WAY #3, OLDSMAR, FL 34677
$1,69566 Days on yellowkey MLS ID: TB8493205
REDUCED by $100 (5.6%) on 05/05/2026
Remarks: Located in East Lake Woodlands, the popular golf course community, this two-bedroom, two-bath condo was totally updated in 2017 with flooring, A/C, hurricane shutters on balcony, stainless look appliances, refrigerated wine rack, additional kitchen storage besides custom pantry with pull out drawers, and granite counters with tile backsplash. New hot water heater was installed in 2020 and so was the new roof fully funded by HOA. Screened balcony has a courtyard style rear view and a nice side view of included community pool. Master Bedroom has 2 walk-in closets and a private bath with shower. Securely gated East Lake Woodlands offers a beautiful lifestyle with lakes, ponds, trees, walkways for fitness and many other community amenities. Optionally, you may join the Country Club for golf, restaurant, drinks, outdoor fire pits, tennis, heated community pools and so many other social activities. Centrally located between Pinellas, Pasco, and Hillsborough counties, a 5-minutewalk to Publix, Walmart, Target, and AMC Plaza, and 20-25 minutes to both airports, the location provides easy access to parks, restaurants, beaches and other entertainment venues.
Listing is courtesy of: PINNACLE REALTY GROUP (813-996-4000)
Listing Agent: Ameer Lakhani (727-776-6200)
218 CARYL WAY, OLDSMAR, FL 34677
$1,74058 Days on yellowkey MLS ID: TB8495651
Remarks: Welcome home to this beautifully updated second-floor condo located in the highly sought-after, gated community of East Lake Woodlands with golf course views. Known for its peaceful surroundings and resort-style living, this community offers both comfort and convenience in an ideal setting. Step inside to discover a bright and airy interior filled with natural light. This move-in-ready residence has been thoughtfully upgraded with a brand-new eat-in kitchen, featuring new white wood cabinetry, quartz countertops, and new appliances—perfect for everyday living and entertaining alike with pass thru window into the dining area. Fresh interior paint and new flooring flow seamlessly throughout the home, complemented by energy-efficient LED lighting and updated bathroom vanities for a clean, modern, and cohesive design. Primary bedroom with two walk in closets, separate dressing area and walk in shower in primary bathroom. Guest bedroom with wall closets. Washer and dryer are located in closet off hall near guest quarters. Generous storage and ample closet space add to the home’s functionality and overall comfort. Enjoy the added privacy of a second-floor location while taking advantage of the exceptional lifestyle within the East Lake community. Rent includes water, trash, basic cable, and internet, providing outstanding value and ease of living. Conveniently located near shopping, dining, parks, beaches! This is a non-smoking residence. A small pet may be considered with owner approval.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Karen Sewell (727-542-4467)
109 PINE CT, OLDSMAR, FL 34677
$2,30073 Days on yellowkey MLS ID: TB8490609
REDUCED by $200 (8.0%) on 04/08/2026
Remarks: OFFERING FIRST MONTH FREE WITH A ONE YEAR LEASE! Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo located in East Lake Woodlands, a sought-after gated and guarded golf community in Oldsmar. This inviting home features an open floor plan that seamlessly connects the living, dining, and kitchen areas—perfect for both relaxing and entertaining. The spacious primary bedroom offers a walk-in closet and a cozy alcove ideal for a home office or reading nook. Both bedrooms feature brand new vinyl flooring, adding a fresh, modern touch along with durability and easy maintenance. A second bedroom and full bathroom provide comfort and flexibility for guests or additional living space. Step out back to enjoy your private screened-in patio, perfect for morning coffee or unwinding in the evenings while taking in the peaceful surroundings. Enjoy the security, serenity, and lifestyle that come with living in a well-maintained golf community—conveniently located near shopping, dining, and beautiful Gulf Coast beaches. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (813-977-3500)
Listing Agent: Scott Corr (631-992-1927)
111 E CYPRESS CT #111, OLDSMAR, FL 34677
$1,90047 Days on yellowkey MLS ID: TB8499374
Remarks: Off Season Condo Available May 1st through December 30th. Cypress Estates of East Lake Woodlands Country Club Community This two-bedroom, two-bathroom condo on the first floor has eat-in kitchen, screen enclosed patio and split bedroom plan. Livingroom/dining room combination with leather furniture, dining table close to open kitchen and enclosed patio where washer and dryer are located in closet. Queen bed in primary and bedroom shower in primary bathroom. Twin beds in quest bedroom with tub in guest bathroom. Rent includes water, sewer, trash, basic cable, local phone service and up to $100 per month of electric. Rates are subject to 13% sales/tourist tax. Please call for availability.
270 WOODLAKE WYNDE #270, OLDSMAR, FL 34677
$1,625110 Days on yellowkey MLS ID: TB8476906
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 674 Built: 1985Community: East Lake Woodlands Woodlake RunCondo
Remarks: AVAILABLE MARCH 1st - FULLY FURNISHED, second floor condo with vaulted ceilings in the Woodlake Run area of gated East Lake Woodlands Country Club community. Private foyer tiled entrance takes you to the dining/living area with vaulted ceilings and clear view windows to keep it light and bright. Efficient kitchen with window has built in microwave, wall pantry and pass thru window into the living area. Sliders from the living area and the bedroom out to the screen enclosed wrap around lanai has storage closet, ceiling fan, and utility closet where the washer and dryer are located. Bedroom with king size bed, ceiling fan, walk in closet and large linen closet. Bathroom offers large vanity area and shower/tub combination. Flat screen tv's in living area and bedroom. The community offers two heated pools and private membership to the golfing Country Club. This is a nonsmoking/vaping residence with water, sewer, trash, basic cable and internet included in the rent. No pets please.
207 WOODLAKE WYNDE #207, OLDSMAR, FL 34677
$2,10055 Days on yellowkey MLS ID: TB8496771
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 924 Built: 1984Community: East Lake Woodlands Woodlake RunCondo
Remarks: Available May 1st through November 15th! Woodlake Run of gated East Lake Woodlands Country Club Community.......Beautiful sunsets over the pond in this first floor condo. Entrance foyer takes you to tiled living area with comfortable leather couch complete with electric reclining, remote mood lighting tv cabinet (with Roku and Spectrum cable) into dining area and breakfast bar to open kitchen with stainless appliances and granite counter tops. Sliding glass doors from kitchen (and guest bedroom) to screen enclosed patio in the front where the washer and dryer are located in the utility closet. Sliders from the living room and master bedroom will take you to the oversized glass enclosed lanai in the back overlooking the two acre pond. The condo has a split bedroom plan with primary bedroom having king size bed, walk in closet, shower/tub combination in the primary bath with oversized vanity and linen closet. The guest bedroom has twin trundle bed, guest bath with shower only and linen closet. This is a non smoking residence with nearby community pools, assigned parking and prefer no pets please. The rent includes water, sewer, trash, basic cable, internet and up to $100 of electric. All short term rentals are subject to a 13% sales/tourist tax. Please call for availability. .
244 CYPRESS LN #244, OLDSMAR, FL 34677
$2,000364 Days on yellowkey MLS ID: TB8394650
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1053 Built: 1980Community: East Lake Woodlands Cypress EstatesCondo
Remarks: 2nd Floor Condo with Lake View in Cypress Estates of gated East Lake Woodlands......... Comfortable lifestyle in this second-floor condo with wonderful pond view of 2-acre lake in Cypress Estates of East Lake Woodlands Country Club Community. Walk into living room/dining room combination with sliders out to screen enclosed lanai overlooking pond. Spacious kitchen with breakfast bar to living area. Split bedroom plan. Primary bedroom with queen bed and guest bedroom with twin beds. Primary bath with walk in shower, guest bath with shower/tub combination. Community pool and covered parking nearby. This is a non-smoking residence. Water, sewer, trash, basic cable and up to $100 per month of electric is included in the rent. All short-term rentals are subject to a 13% sales/tourist tax. Please call for availability
212 CYPRESS LN, OLDSMAR, FL 34677
$1,65059 Days on yellowkey MLS ID: TB8485274
Remarks: This condo is located in the gated community of East Lake Woodlands. The property features a Newly renovated Kitchen with an open floor plan, split bedrooms, eat in kitchen. Primary bedroom has two walk-in closets, a linen closet and en suite bathroom with shower, a guest room with the bathroom steps away, a screened lanai includes a laundry closet with new washer dryer for tenant use. This condo overlooks the community lake. Water, sewer, trash, basic cable, and Internet/Wi-Fi included in the rental rate.. one covered assigned parking space, guest space is available. Maximum two cars per unit. Community pool is a quick walk away.. This location is close to medical, shopping, dining, entertainment, and A rated schools.
Listing is courtesy of: TAMPA BAY SIGNATURE PROPERTIES, LLC (727-692-2847)
Listing Agent: Christi Watson (727-692-2847)
284 WOODLAKE WYNDE, OLDSMAR, FL 34677
$2,00061 Days on yellowkey MLS ID: TB8494637
Remarks: Call to see this stunning East Lake Woodlands furnished short-term rental! This updated 2-bedroom, 2-bathroom upstairs unit boasts vaulted ceilings and two relaxing balconies. Enjoy the serene view of the large pond from one balcony and watch the lively activity at the pool from the other. Simply bring your clothes, food, and a great attitude. Everything else is provided. The bedrooms are split for added privacy, and reserved parking is conveniently located right up front. A washer and dryer are also included, and all utilities, internet, and cable are covered. This beautiful property is close to shopping, theaters, and numerous restaurants on Tampa Road and East Lake Business. Plus, it's just a short drive to the airport and the beaches. We will consider a small pet. Available now through December 2026 only. Don't miss out on this fantastic opportunity!
106 MEADOW LN, OLDSMAR, FL 34677
$1,695139 Days on yellowkey MLS ID: TB8465265
0 Days Off yellowkey (back on 3/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1985Community: East Lake WoodlandsCondo
Remarks: Welcome home to this updated unfurnished second-floor condo located in the desirable Gated community of East Lake Woodlands. This two bedroom, two bath condo features an open floor plan with a split bedroom layout, offering privacy and flexibility. The condo has a nice eat in Kitchen with pantry. The Kitchen overlooks the bright living and dining areas. Sliders flow seamlessly out to a screened lanai overlooking a green belt, perfect for relaxing or enjoying your morning coffee. A laundry closet including a washer/dryer for use is located on the lanai & adds every day convenience. Both bedrooms are well sized and the updated interiors provide a clean modern feel throughout. You will find the primary bedroom has a walk-in closet and two additional closets. Also an ensuite bath featuring a walk-in shower. The guest bath has a tub/shower & is steps away from guest room. Water, sewer, trash, basic cable, and Internet are included in the rental rate! This adds Great value! The community pool is a short walk away. Newer Hurricane rated Windows & and Doors adds thermal & sound barrier protection. East Lake Woodlands is conveniently located near Shopping, Dining, Medical, Entertainment, Parks, Beautiful Beaches and easy access to Clearwater, Tampa, St Pete Airports.
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