Circle Square Woods Homes for Sale in Ocala - 26 homes

Remarks: ***Price Adjustment - below market value*** The Florida Lifestyle awaits! Don't miss this End Unit villa, with an open, park-like setting around your home. Enjoy your mornings with coffee and the paper on the front porch, in the enclosed lanai or the back patio, all while enjoying the sounds of nature and lush landscaping. It's all laminate flooring throughout this 2 bedroom/2 bath home. The primary bedroom features a walk-in closet, and ensuite bathroom with a walk-in mobility tub with hydro jets for added relaxation. Utilize the multiple sitting spaces for a tv room, a craft room, or space to entertain. The long driveway leads to the oversized 2 car garage with tons of storage, golf cart parking and privacy screens to allow only the breeze inside! On Top of the World is a gated, golf cart, 55+ community - take a ride for groceries, to retail stores, dining out, or to meet friends at one of the pools! Enjoy activities for whatever meets your fancy! Make friends along the walking trails, at the dog park, on the greens or on the courts. Explore hobby's like RC flyers or cars, horseshoes, bocce ball or archery, stay healthy at the fitness and recreation centers, and so much more! Lawn care, tree trimming, exterior paint, yearly pressure washing, and trash pickup are included in the maintenance fee. The Roof and AC were replaced in 2017. There is nothing left to do - but move right in!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Nicole Garcia (352-229-3031)

Remarks: Cute and quaint 2bd/2ba villa located centrally close to shopping centers and a major highway for easy access.

Listing is courtesy of: WIN-WIN REAL ESTATE SERVICES LLC (407-271-3069)

Listing Agent: Lisa Manzo (407-271-3069)

Remarks: New price for quick sale! This home is clean and has been well maintained. Just needs some updating and is priced accordingly! Welcome to easy living in the heart of the highly sought-after On Top of the World 55+ active adult community! This well-maintained 2-bedroom, 2-bath Villa with a spacious 1409 square feet of living space, offering beautiful views and a peaceful, low-maintenance lifestyle — lawn care, trash, basic cable and exterior maintenance is included in your low monthly HOA fee! This home features a versatile bonus room perfect for a den, office, or hobby space, along with an ensuite primary suite providing privacy and convenience. Enjoy relaxing on both the front and back covered porches, ideal for year-round enjoyment. Additional highlights include a two-car garage, washer and dryer, and all appliances included. Thoughtfully designed with a functional layout and abundant natural light. A wonderful opportunity to enjoy an active lifestyle with easy living—schedule your showing today!Live your best life in this 55+ active community, loaded with amenities: Multiple community pools, fitness centers, tennis, raquetball, shuffleboard, cornhold, horseshoes, basketball and pickleball courts, softball field, dog parks, restaurants, entertainment, community center, numerous clubs and so much more! All included when you are a resident of On Top of the World. OTOW is a golfing community with wonderful golf courses. Golf course memberships are available if desired. All of this, and you're just minutes from shopping, dining, medical facilities, entertainment and more. This is Florida living made simple — schedule your showing today and come see why you will love living at On Top of the World!

Listing is courtesy of: CB/ELLISON RLTY WEST (352-854-9717)

Listing Agent: Vicki Whetsell (813-695-5295)

Remarks: Located in the Friendship Colony of On Top of the World, this end unit Bostonian model is a gem! Upon arrival you are greeted with the lovely exterior, large and welcoming front porch, beautiful landscaping and serene park-like views all around. This villa offers 2 bedrooms, 2 updated full bathrooms and 2 car garage. Also included are the updated kitchen with granite countertops and stainless steel appliances, three solar tubes for natural light and energy savings, crown molding throughout, functional and attractive built-ins, primary bedroom walk-in closet and an enclosed lanai under heat/air. Notable features include 2021 roof, 2022 HVAC and 2012 window replacements. So much to love about this home and community! On Top of the World is Ocala's desirable active 55+ community and a favorite of golf enthusiasts. Community amenities include 2 outdoor swimming pools & 1 indoor, 2 fitness centers, tennis, pickleball, bocce, shuffleboard, corn hole, horse shoes, billiards, archery range, library, dog parks, areas designated for remote control flying and race cars, restaurant and pub and over 100 clubs. HOA fee includes lawn care, trash/recycling, basic Spectrum Cable, roof repair, exterior painting every seven years, irrigation water, exterior maintenance and structure insurance, 24/7 monitored gates.

Listing is courtesy of: LAND TO SEA REALTY LLC (772-999-4504)

Listing Agent: Delisa Boling (772-999-4504)

Remarks: Presenting a meticulously renovated residence featuring new appliances that enhance both aesthetic appeal and functionality. This move-in ready Philadelphia Model includes two bedrooms, two bathrooms, and a one-and-a-half car garage, offering a spacious 1,411 square-foot living area designed for comfort. As an end unit, the property benefits from additional windows, providing abundant natural light to both bedrooms and the guest bathroom, thereby eliminating any sense of confinement. The comprehensive renovation encompasses 12 double-pane vinyl windows in the living areas, a reimagined kitchen with custom wood cabinetry (no pressed wood), and updated bathroom vanities as well as tiled shower and tub enclosures. The removal of popcorn ceilings further contributes to the unit’s contemporary feel. Luxury vinyl flooring extends throughout the main living spaces and is complemented by new tile in the kitchen and bathrooms. All drywall behind cabinets, tubs, and showers has been replaced with "Go Board," a closed-cell foam core system recognized for superior water and mold resistance, enhancing durability and peace of mind. The redesigned kitchen features floor-to-ceiling custom-built wood cabinetry, optimized for space and ergonomics, alongside granite countertops and brand-new Whirlpool appliances—including refrigerator, convection oven/air fryer, microwave, dishwasher, washer, dryer, and a reverse osmosis drinking water filter—ensuring modern convenience. Solar skylight tubes provide natural illumination to the living room and kitchen, creating a welcoming atmosphere. A climate-controlled sunroom ensures year-round relaxation. Exterior amenities include a fenced backyard with brick paver patio, privacy hedge, and artificial turf puppy potty area for added practicality and privacy. The attached garage accommodates both a vehicle and a golf cart, complete with a dedicated charging circuit, four-panel privacy screen, workbench, laundry sink, and ample shelving. Attic access via a pulldown ladder offers additional storage. I look forward to collaborating with the buyer’s agent.

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: PRICE REDUCTION! 2 bedroom 2 bath end unit in Top Of The World, Ocala's premier active 55+ gated community. New Roof 2021. Nicely landscaped front yard. Covered front porch to enjoy your morning coffee. Open floor plan. Storm door. Kitchen island with breakfast bar. Kitchen has extra counter space/cabinets and a large pantry. Primary bedroom has large walk in closet and en suite bath with walk in shower. Large screened lanai and a rear patio. 2 car garage with opener. Golf cart community. On site restaurant. Easy access to major highways. Near shopping and restaurants.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Tina Melichar (443-995-9013)

Remarks: JUST LIKE UP NORTH--DOWN HERE!! Beautiful wooded park setting for this exceptional expanded Bostonian, filled with LOTS OF NEW and loving touches throughout--HVAC 2025, ROOF 2024, REAR DECK 2024, SHOWER AND FAUCETS 2024, KITCHEN BACKSPLASH 2024, NEW KITCHEN LIGHT FIXTURES 2024, NEW KITCHEN BEVERAGE CENTER AND BENCH 2023, LUXURY VINYL PLANK FLOORING THROUGHOUT 2022, NEW CHAIR HEIGHT TOILETS IN BOTH BATHS 2022, NEW CEILING FANS 2022. Loads of counterspace with island and handy pantry. Well located within walking or golf cart access to all OTOW amenities. Close to the Pub and Recreation Center pool, plus pickle ball courts and miniature golf. Also close to the Rec Center workout gym and wallybalal courts. Steps away from the library and woodshop. Seller to include a 1 year home warranty valued up to $600.00

Listing is courtesy of: RE/MAX PREMIER REALTY HWY 200 (352-433-4449)

Listing Agent: Nancy Meininger (352-554-0757)

Remarks: OWNER MOTIVATED! Beautiful furnished 2/2 Montgomery model features granite countertops in the kitchen, a GLASS-ENCLOSED lanai, a 2017 roof, and a 2023 AC, offering comfort, value, and added space to make your own. Recently refreshed landscaping in the front yard and covered entry front porch welcome you inside to a spacious and flexible living area with room for both living and dining. The kitchen includes granite countertops and opens to a dual space that can be utilized for formal dining, office space, or living space perfect for everyday use. Just off the kitchen, the enclosed lanai provides another versatile bonus space. The primary suite offers ample room for furnishings, a deep walk-in closet, and an ensuite bath recently repainted with a tiled shower. The guest bedroom and bathroom are well-sized for visitors, with additional hallway storage for convenience. Enjoy low-maintenance living with an HOA that covers lawn care, exterior painting every 7 years, roof repairs if needed, basic cable, exterior insurance, and full access to all OTOW amenities, making it easy to enjoy the lifestyle this community is known for. Enjoy a true resort-style lifestyle year-round with an unmatched array of amenities designed for every interest. Residents have access to multiple state-of-the-art fitness centers, indoor and outdoor pools, pickleball, tennis, bocce ball, shuffleboard, billiards, and more, along with unique offerings like an on-site archery range, woodworking shop, and even a remote-control flying field. With three beautiful 18-hole golf courses and over 175 clubs and activities ranging from social gatherings to arts, dance, and theater, there’s always something to enjoy. Spend your evenings at the town square with live music and dancing, or take a quick golf cart ride to nearby shopping and dining. Plus, the World Equestrian Center is just a short 15-minute drive away. Additional highlights include a 2023 water heater, metal storage cabinets in the garage with wooden work benches, screen on garage door, and MORE! The owner wants this SOLD, call today to schedule your private showing!

Listing is courtesy of: WORTH CLARK REALTY (352-988-7777)

Listing Agent: Raena Ratcliff (352-461-3284)

Remarks: Look no further—step inside this beautifully maintained two-bedroom, two-bath villa with a two-car garage, located in the highly sought-after Premier 55+ community of On Top of the World. This home truly reflects pride of ownership. Gorgeous new luxury vinyl plank flooring throughout the living, dining, and bedroom areas creates a bright, airy, and welcoming atmosphere. The open-concept living space flows seamlessly into the kitchen, which features a large cooking island, stunning stone countertops, and a crisp white backsplash—perfect for both everyday living and entertaining. The guest bathroom is tastefully appointed with a stone-topped vanity and clean white tile surround with tub. The spacious primary suite offers a large walk-in closet and an en-suite bathroom complete with a walk-in shower. Enjoy relaxing on the cozy front porch or unwind in the enclosed Florida room at the rear, featuring all-new windows. Outside, the covered patio is ideal for barbecuing and extends further to accommodate all your outdoor cooking and entertaining needs. Additional highlights include a newer roof and appliances that have all been replaced since 2020, offering peace of mind for years to come. Schedule your showing today to begin your next chapter in this fun filled active community!!

Listing is courtesy of: CRYSTAL SNOOK REAL ESTATE (352-630-5270)

Listing Agent: Holly Vandeventer (352-572-8811)

Remarks: Welcome to this highly sought-after Birmingham Model in the premier 55+ community of On Top of the World! This beautifully maintained end-unit villa offers 2 bedrooms, 2 bathrooms, and 1,369 sq ft of comfortable, low-maintenance living. The desirable end-unit location provides added privacy and natural light throughout. Step inside to a functional and inviting layout, complemented by brand new carpet (2026) and an easy flow between living spaces. The home features a 1.5 tandem garage, perfect for extra storage, a golf cart, or workspace. Enjoy year-round relaxation in the screened lanai, ideal for morning coffee or unwinding in the evenings. Major updates provide peace of mind, including: New double-pane windows (2020) New A/C (2023) Located in the highly desirable On Top of the World community, residents enjoy resort-style amenities, golf, pools, fitness centers, and an active lifestyle. Move-in ready and perfectly positioned—this is Florida living at its best!

Listing is courtesy of: KELLER WILLIAMS CORNERSTONE RE (352-369-4044)

Listing Agent: Robin Brooks Schomp (352-427-4274)

Remarks: This Philadelphian is located in the much sought-after 55+ community of On Top of the World. It's on a pretty tree-lined street and ready for new owners. The front porch is the perfect spot for your morning coffee and to greet the day. Once inside you will see the beautiful, neutral tile flooring throughout the home. The kitchen has multiple updates such as stainless steel appliances, granite counter tops and white shaker cabinets with an eat in space. The enclosed lanai under heat and air gives extra living space. Primary bedroom has enough space for a king sized bed, and a spacious walk-in closet. The primary bath has a pretty, newer single sink vanity and step-in shower. The second bedroom is perfectly sized for guests and second bath features a step in shower and newer vanity. Roof replaced in 2022. This community has over 150 different clubs, golf cart access to grocery store, restaurants and shopping, multiple pools and recreation facilities, 3 golf courses and so much more. Don't wait to call for your appointment to view today!

Listing is courtesy of: RE/MAX FOXFIRE - HWY200/103 S (352-479-0123)

Listing Agent: Bonnie Ciesla (352-445-6572)

Remarks: Motivated Seller!! Bring an Offer!! Concrete block end-unit villa located next to open green space and convenient guest parking. Updates include 2016 roof, 2019 HVAC, 2019 windows, and a 2019 screened lanai. Home has no carpet. The updated kitchen features quartz countertops, new cabinetry, a breakfast bar, and a solar tube, Additionally all of the appliances are less than six months old, and it opens to the family room. Living and dining areas provide ample space. The primary bedroom includes a walk-in closet and an ensuite bathroom with a walk-in shower, Bathroom has been remodeled. The guest bedroom is comfortably sized, and the guest bath has an updated ceramic tile walk-in shower. The flooring in the bedrooms is vinyl wooden flooring. Outdoor living options include a front porch and a screened lanai. The garage includes a screen door. Conveniently located near shopping, dining, medical providers, and parks, with golf-cart access to nearby shopping centers. The HOA fee includes lawn care, trash and recycling, basic Spectrum cable, roof repair, exterior painting every seven years, irrigation water, exterior maintenance and insurance, 24/7 monitored gates, and use of community amenities, including pools, fitness centers, three golf courses, clubs, and more.

Listing is courtesy of: MAGNOLIA HOMES AND LAND LLC (352-807-1700)

Listing Agent: Brent Smith (352-355-6266)

Remarks: Enjoy the good life in On Top of The World, Ocala's best selling neighborhood. This charming townhome offers 1,688 square feet of open living space with a functional and flexible layout and HUGE Florida Room. The roof is only 2 years old and most of the appliances hav recently updated this home is move in ready. The living room features built-in shelving, storage, and a stylish focal point for displaying books, collections or decorations, and media systems. This home is very light and bright and has a good sized front and back porch living space. Both bedrooms are generously sized, each with convenient access to a full bathroom, making it the ideal layout. The spacious floor plan provides comfortable living areas with plenty of room to relax, work from home, or entertain. There is also a screened in garage door system already in place. Live the good life in the most sought after 55 + plus communities in Ocala.

Listing is courtesy of: THURMOND REALTY LLC (352-213-2413)

Listing Agent: Tiffany Moen (352-870-9414)

Remarks: Get ready to enjoy an amazing Florida lifestyle in this spacious 1,853-square-foot townhome offering 2 bedrooms, 2.5 bathrooms, and both a full-size family room and living room. Located in the Circle Square Woods neighborhood of On Top of the World, Ocala's premier, gated 55+ community known for top-of-the-line resort-style amenities, this home offers all of the living space you have been looking for. A tree-shaded front yard overlooks peaceful and beautifully manicured grounds with a park-like common area complete with a gazebo, providing a relaxing place to enjoy the outdoors. Golf cart access makes it easy to reach nearby shopping, dining, and essential services, and abundant community activities and amenities are only a short distance away. The versatile layout includes a full-size living room and a separate family room centered around a cozy stone-surround fireplace that adds warmth and character to gatherings with friends and family. The kitchen features stainless-steel appliances and a large center island overlooking the family room, perfect for meal prep and casual dining options. The stairway walls of this villa have also been constructed to allow for the installation of a motorized chair lift, making the upper level more easily accessible. The owner’s suite provides a generous retreat with plenty of room to unwind, along with an en suite bath that includes a spacious step-in shower with detailed tilework and a conveniently located linen closet. The guest bedroom also features its own private en-suite bath, while an additional half bath serves the main level. A covered rear patio and vinyl-fenced area create an inviting outdoor space ideal for pets, relaxation, or entertaining. Carefree living awaits as the monthly HOA fee includes basic cable, irrigation water, roof repair, exterior painting every seven years, exterior maintenance and insurance, landscaping, trash & recycling, and 24/7 monitored gates. Kick back and unwind, or head out and enjoy the endless activities available in this vibrant community overflowing with top-tier amenities. Residents have access to three golf courses, indoor and outdoor pools, recreation centers, clubs, concerts, dedicated RV parking, and Veterans’ Park, along with golf cart access to nearby shopping centers and beautiful Shalom Park. Ideally situated off Hwy 200, OTOW is close to banks, restaurants, and medical facilities, and just a short 10-mile drive south of the World Equestrian Center.

Listing is courtesy of: REAL BROKER LLC - OCALA (855-450-0442)

Listing Agent: Anthony Alfarone (352-897-0771)

Remarks: One or more photo(s) has been virtually staged. THE HIGHLY SOUGHT AFTER BOSTONIAN MODEL ON AN END UNIT IN ON TOP OF THE WORLD A 55+ COMMUNITY WITH INCREDIBLE AMENITIES IN OCALA FL! SPACIOUS FRONT PORCH FOR THAT SWING OR SWIVEL CHAIRS LEADS TO LARGE LIVING ROOM OVERLOOKING DINING AREA. TO THE LEFT ARE THE 2ND BEDROOM WITH CARPET AND 2ND BATH WITH WALK IN, EASY ACCESS JETTED TUB WITH SHOWER WAND. PRIMARY BEDROOM IN LEFT CORNER OF HOME WITH WALK IN CLOSET AND BATHROOM FEATURING WALK IN TILE SHOWER WITH GLASS SLIDING DOOR. BACK ACROSS HOME THROUGHT THE DINING ROOM YOU ARE GREETED WITH THE 2ND LIVING ROOM AND KITCHEN WITH ISLAND, PLENTY OF COUNTERTOP SPACE AND COFFEE BUTLER BAR AREA. 2 CAR GARAGE IS HOME TO THE LAUNDRY AREA. STEPPING OUT THE DOOR OF 2ND LIVING INTO ENCLOSED AND COVERED LANAI AND COVERED OUTDOOR PATIO, HOA IS $493.96 A MONTH AND INCLUDE EXTERIOR MAINTENANCE AND LAWN CARE.(ROOF REPLACEMENT THE OWNER RESPONSIBILITY AS NEEDED) REPAIRS OF ROOF HOA RESPONSIBLE. HOA INCLUDES ALL OF THE PHENOMENAL AMMENITIES AND GATED ENTRANCES. IF YOU LIVE A 55+ AND ITS MAINTENANCE FREE LIVING YOU WANT??? HERE IT IS!

Listing is courtesy of: GAILEY ENTERPRISES REAL ESTATE (770-733-2596)

Listing Agent: Richard Gailey (678-923-0007)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to Friendship Village in the highly sought-after community of On Top of the World. This charming 2-bedroom, 2-bath villa offers comfortable living on a beautiful tree-canopied street. The home features a spacious layout, and an oversized 1-car garage. Enjoy the large Florida room overlooking the backyard, creating a wonderful space to relax with your morning coffee or unwind in the evening. The home is also conveniently located close to Ocala’s shopping, restaurants, medical facilities, and everyday amenities. Major updates include a BRAND NEW roof and a BRAND NEW AC system (2026), offering peace of mind for the next owner. The sellers are also offering a $2,000 flooring allowance, giving the new owner the opportunity to select flooring that suits their style. A wonderful opportunity to make this villa your own while enjoying everything Friendship Village and On Top of the World has to offer.

Listing is courtesy of: NEXTHOME VISION REALTY (352-685-5005)

Listing Agent: Bre Martinez (352-426-1311)

Remarks: Welcome home to this beautifully maintained and inviting 2-bedroom, 2-bath villa nestled in a sought-after 55+ community in the heart of Ocala. From the moment you arrive, you’ll appreciate the charming covered front porch and serene green-space setting that create a peaceful, welcoming atmosphere with amazing privacy - no neighbors behind you. Inside, the home offers a bright and open layout with updated flooring throughout and generous natural light. The spacious kitchen is thoughtfully designed with ample cabinetry, solid surface countertops, perfect for both everyday living and entertaining. Adjacent living and dining areas provide comfortable flow and flexibility for gatherings or quiet evenings at home. The primary suite features abundant closet space and a private en-suite bath with a walk-in shower, while the guest bedroom and second full bath offer comfort and privacy for visitors. An attached one-car garage adds convenience and extra storage. Enjoy truly low-maintenance living with an HOA that covers exterior maintenance, lawn care, and community amenities. Residents enjoy access to a clubhouse, social activities, and beautifully maintained common areas, fostering an active and connected lifestyle. Ideally located near shopping, dining, medical facilities, and major roadways, this home offers the perfect blend of comfort, convenience, and community. Whether you’re looking for a full-time residence or a seasonal retreat, this move-in ready villa is a wonderful opportunity to enjoy relaxed Florida living at its finest.

Listing is courtesy of: ORLANDO HOME DEALER LLC (407-537-5353)

Listing Agent: Kristal Mason (208-547-7236)

Remarks: Welcome to 8830 SW 98th Pl, ideally located in the desirable southwest corridor of Ocala, Florida 34481. This inviting residence offers comfortable living in a peaceful, well-established community known for its convenient access to shopping, dining, medical facilities, and recreational opportunities. Inside, you’ll find a bright and functional floor plan designed for both everyday living and entertaining. The spacious living and dining areas flow seamlessly, creating an open and welcoming atmosphere filled with natural light. The kitchen provides ample cabinetry and workspace, making meal preparation easy and efficient. The primary suite serves as a relaxing retreat with generous closet space and a private bath. Additional bedrooms give flexibility for guests, hobbies, or a home office. Thoughtful layout and comfortable living spaces make this home ideal for full-time residents or seasonal owners. Step outside to enjoy a private outdoor area perfect for morning coffee, evening relaxation, or hosting friends and family. With its prime location and easy-care lifestyle, this property presents an excellent opportunity to enjoy all that Ocala has to offer.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Shane Sellers (352-820-9061)

Remarks: Under contract-accepting backup offers. Back on the market! Welcome to this charming 2-bedroom, 2-bath villa located in the highly desirable On Top of the World community in Ocala, Florida. Offering 1,204 square feet of comfortable living space, this well-maintained home features an open and functional layout ideal for relaxed Florida living. The home includes a convenient 1.5-car garage, providing extra space for storage, a golf cart, or hobbies. Enjoy low-maintenance living with access to world-class amenities including golf, swimming pools, fitness centers, walking trails, and countless social activities. Perfectly situated near shopping, dining, and medical facilities, this villa offers both comfort and an active lifestyle in one of Ocala’s premier 55+ communities

Listing is courtesy of: MOMENTUM REALTY - GAINESVILLE (904-903-1558)

Listing Agent: Kyle Hunziker (352-672-5668)

Remarks: Welcome to this beautifully refreshed 2-bedroom, 2.5-bath townhouse located in the charming Americana Village, known for its vintage European-inspired setting. Thoughtful cosmetic updates throughout provide a fresh, updated look while preserving the character that makes this community so admired. The inviting floor plan features a cozy living area with a fireplace, creating a warm connection between the family room and kitchen, ideal for everyday living or relaxing evenings at home. Each bedroom offers its own private bath, with an additional half bath conveniently located on the main level. Enjoy a peaceful lifestyle surrounded by manicured grounds, including a gazebo nestled within a park-like setting—perfect for enjoying Florida’s beautiful weather. This townhome offers easy access by golf cart to nearby shopping, dining, and community conveniences. Residents also enjoy access to a wide range of amenities designed to support an active, engaging lifestyle. A wonderful opportunity to own a low-maintenance home in a quiet, well-established community with timeless appeal.

Listing is courtesy of: NEXT GENERATION REALTY OF MARION COUNTY (352-342-9730)

Listing Agent: Patricia Mcleod (352-207-3162)