Circle Square Woods Homes for Sale in Ocala - 17 homes

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: Welcome to a home that doesn’t whisper potential… it announces it. New roof installed by the association in 2021 and a high-efficiency HVAC system updated in 2019. This beautifully maintained end-unit villa offers 2 bedrooms, 2 bathrooms, and over 1,200 square feet of thoughtfully designed living space — all on one level for effortless flow and comfort. From the moment you arrive, you’ll appreciate the private feel of an end unit, the attached garage, and the clean architectural lines that make this residence feel both timeless and fresh. Step inside and you’re greeted by an expansive living and dining combination that feels open, bright, and incredibly livable. Natural light pours in, enhanced by skylights that elevate the space and create an airy, uplifting atmosphere. The luxury vinyl flooring adds a sleek, modern touch while offering durability for everyday life. The kitchen is perfectly positioned for connection and convenience, featuring a full suite of appliances including a range, refrigerator, microwave, dishwasher, disposal, plus washer and dryer. Whether you’re hosting friends for dinner or enjoying a quiet morning coffee, this layout makes everything feel seamless. The primary suite is generous in size, offering a spacious 14x14 bedroom retreat complete with a walk-in closet. It’s the kind of space that allows you to truly unwind at the end of the day. The second bedroom is ideal for guests, a home office, or a creative space — flexible and comfortable with built-in closet storage. One of the standout features? The Florida Room. That bonus space you didn’t know you needed but won’t want to live without. Morning sunlight, evening relaxation, reading, entertaining — this is where lifestyle happens. Add in the enclosed front and rear porch areas and sliding doors that blend indoor and outdoor living, and you have a home that truly embraces the Florida way of life. Built with solid block construction on a slab foundation and topped with a shingle roof, this residence offers peace of mind along with comfort. Central air and heat pump systems ensure year-round efficiency and comfort. The attached garage with opener and driveway parking add practicality to the lifestyle appeal. And here’s where it gets even better. This gated, guard-secured community delivers resort-style living every single day. Enjoy access to a clubhouse, fitness center, tennis courts, basketball court, park areas, restaurant, dog park, and a sparkling community pool. Golf carts are welcome, and golf course proximity adds to the elevated lifestyle experience. This isn’t just a villa. It’s ease. It’s light. It’s low-maintenance living with high-impact comfort. It’s waking up in a space that feels organized, flowing, and calm. It’s pulling into your garage after a long day and knowing everything you need is right here. If you’ve been waiting for a home that combines smart design, solid construction, flexible living space, and vibrant community amenities — this is it. Opportunities like this don’t sit still. They move. The question is… will you?

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: David Amerio, Jr (352-922-3667)

Remarks: Looking for your next investment property with a proven track record? This 2-bedroom, 2-bath villa is nestled in the highly sought-after gated 55+ community of On Top of the World, known for its vibrant lifestyle and abundant amenities. As you enter, you’ll be welcomed by a covered front porch leading into a spacious living room. The kitchen features ample cabinets and countertops, along with an eat-in area making it a functional space for everyday living. Large primary bedroom includes an en-suite bathroom with a tiled walk-in shower and a walk-in closet . A guest bedroom and an additional bathroom are conveniently located down the hall. Just off the kitchen is a lania area that’s under heat & air conditioning, providing a cozy additional space for year round enjoyment.Residents of On Top of the World enjoy a wide array of amenities, including multiple pools, restaurants, tennis courts, an RC field and more. Plus the community is golf cart-friendly with stores, restaurants and shopping just a short drive away. A 1-year home warranty will be provided at closing, and the roof was replaced in 2018 for added peace of mind. As a buyer incentive, the seller is providing a $5,000 credit at closing for flooring replacement. Schedule a showing today to explore this beautiful home and experience all that this wonderful community has to offer! (The seller is also offering the house for rent at $1,650 per month. Utilities are not included.)

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

Listing Agent: Alexus Macblain (740-255-3338)

Remarks: This 2 bedroom 2 bath home is located in the premier 55+ community voted one of the top places to retire in the United States in On Top Of World. Enter into the spacious open concept of the home with the living room/dining room combo. The primary bedroom will accommodate a king size suit and has a large shower with a good size walk-in closet. Guest bedroom will easily fit a queen set. The kitchen has plenty of cabinets and counter space with an area in the kitchen you could use as a small office for your computer or whatever you would like. And there is a separate room family room beside the kitchen. And still another glassed-in separate room by the family room to be used as you desire. The monthly HOA fee includes basic cable, roof repair, exterior painting every seven years, exterior maintenance and insurance, lawn service, 24/7 guarded gates and all the amenities that OTOW has; three pools (2 outside & 1 inside), two state of the art fitness centers, pickleball courts (COVERED & UNCOVERED), billiards, archery range, corn hole, bocce ball, tennis, shuffleboard, horse shoes, walking trails, dog park, remote control flying field and race cars, 175+ clubs, library, and much more! Let's don't forget 2 18 hole golf courses. A golf cart community with access to three shopping centers. Enjoy the resort-style amenities this active community features.

Listing is courtesy of: C/POWER REALTY LLC (352-598-7202)

Listing Agent: Lashunia Frazier (352-286-1071)

Remarks: Ready to enjoy the relaxed, sunny Florida lifestyle? This charming 2-bedroom, 2-bath villa offers the perfect blend of comfort, convenience, and low-maintenance living. Step inside and you’ll appreciate the spacious rooms and smart, efficient floor plan that make everyday living easy. The bright Florida room is a true highlight — ideal for morning coffee, reading, hobbies, or simply soaking in the sunshine. It opens right out to the patio, giving you a great spot for grilling or unwinding outdoors. The community offers a wide variety of amenities, so you’ll always have something fun and engaging to enjoy. Plus, shopping, restaurants, and parks are just a short golf-cart or car ride away, making this an ideal location for convenience and an active lifestyle. Come see this lovely villa and discover how effortless Florida living can be.

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

Listing Agent: Jenni Kennedy (352-775-0078)

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: This END UNIT villa at On Top of the World in Ocala's premiere 55+ Gated community. A spacious front porch perfect for enjoying your morning coffee or evening beverages welcomes you to this home. Step inside into the living room/dining room area and notice the laminate flooring throughout. The bedrooms are on the left side of the home with the guest/hall bath with tub and tile surround in between. The primary bedroom is in the back for privacy with an ensuite bath along with a step-in shower and large walk-in closet. The kitchen has been nicely updated with Granite countertops and newer appliances! The Florida Room is fully finished with heat/AC. Hello I just took a look at the listing. It has water filter/softener system for the whole house.The lanai has been converted into an all season room. With 1.5 Garage , the Washer/Dryer are in the garage. The monthly HOA fee includes basic Spectrum cable, irrigation water, roof maintenance & repair, exterior painting every seven years, exterior maintenance and insurance, landscaping, trash & recycling, 24/7 guarded gates and all the amenities that OTOW provides, three pools (2 outside & 1 inside & another under construction), two state of the art fitness centers, pickleball, billiards, archery range, corn hole, bocce ball, tennis, shuffleboard, horse shoes, remote control flying field and race cars, 175+ clubs, woodworking shop (extra fee), library, and much, much more! A golf cart community with access to three shopping centers. 2 years warranty is offered by the seller.

Listing is courtesy of: ENGEL & VOLKERS OCALA (352-820-4770)

Listing Agent: Escarlin Mancia (352-812-0645)

Remarks: 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: Enjoy comfortable, low maintenance living in On Top of the World, one of Ocala’s most sought after 55+ communities. This move in ready meticulously home features 2 bedrooms, 2 baths, 1,341 Sq.Ft. of living space, and a 1 car garage on a beautifully maintained lot. Tile flooring throughout creates a clean, cohesive look while keeping upkeep simple and convenient. As you enter, a spacious living room flows naturally into kitchen and dining area. Updated kitchen offers soft close cabinetry, granite countertops, pantry with pull out drawers and stainless steel appliances, combining style and functionality. Primary bedroom is generously sized and includes a large walk in closet and en suite bathroom featuring a walk in tile shower. Guest bedroom is also spacious with a bigger closet for extra storage. The guest bathroom is conveniently located nearby and features a tile tub/shower combination. Step outside to enjoy screened lanai and paver patio enclosed with vinyl fence, providing a private outdoor space perfect for relaxing, entertaining, or accommodating pets. Major recent updates include New Roof (2018) with architectural shingles and New HVAC system (2026) making this home truly move in ready. As a part of On Top of the World, residents enjoy an unmatched lifestyle with access to multiple pools, fitness centers, dog parks, tennis courts, shuffleboard, golf courses, RC Field, weekly activities and so much more, all within a community that also offers golf cart access to nearby restaurants, doctors and shopping. Schedule your private showing and see the possibilities this home has to offer!

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

Listing Agent: Chad Macblain (740-801-0071)

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: Owner says bring all offers! This home 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: 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: 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.

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

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

Remarks: Welcome to one of the most desirable 55+ communities in Ocala, the highly sought after golf cart community of On Top of the World! Located in the Americana neighborhood, this beautifully updated end unit Philadelphian villa offers 2 bedrooms and 2 bathrooms with the perfect blend of comfort, style, and low maintenance living. The home features fresh interior paint, newly painted garage walls and floors, updated trim, real wood interior doors, modern light fixtures, and stunning Pergo TimberCraft laminate flooring throughout. The guest bathroom includes a new toilet, and the primary bedroom offers brand new closet cabinets for added storage and organization. Enjoy year round comfort in the Florida room under heat and air, along with a spacious and inviting front porch perfect for morning coffee or evening relaxation. Major updates include a 2022 HVAC system and a 2015 roof, plus a brand new washing machine and like new dryer. The monthly HOA fee includes basic Spectrum cable, irrigation water, roof maintenance and repair, exterior painting every seven years, exterior maintenance, landscaping, trash and recycling, and 24/7 guarded gates, providing true peace of mind. Residents enjoy access to top of the line amenities including multiple pools, two fitness centers, pickleball, tennis, shuffleboard, bocce ball, billiards, an archery range, over 175 clubs, a woodworking shop (additional fee), a library, and so much more. This is more than a home, it’s a lifestyle!

Listing is courtesy of: COLDWELL REALTY SOLD GUARANTEE (352-209-0000)

Listing Agent: Scott Coldwell (352-209-0000)

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: Welcome to this exceptionally well-maintained and thoughtfully upgraded 2-bedroom, 2-bath residence located in the highly sought-after On Top of the World community. This move-in-ready home offers peace of mind and modern comfort with numerous recent improvements throughout. The newly renovated kitchen is a true centerpiece, featuring quartz countertops, a classic farmhouse sink, and stainless steel appliances that blend style and functionality. The open and efficient layout provides ample counter space and storage, making it ideal for both everyday use and entertaining. Major system upgrades include a brand-new electrical breaker box, brand-new water heater, and a new AC coil, ensuring reliability and energy efficiency. The home also includes all new window screens and rain gutters, adding to its overall durability and curb appeal. The spacious primary suite is a relaxing retreat, complete with an extra-large walk-in closet and a beautifully designed walk-in shower in the en-suite bath. The second bedroom and bathroom provide comfort and flexibility for guests, a home office, or hobbies. Outdoor living is just as inviting, with a charming front seating area perfect for morning coffee, an outdoor rear BBQ patio ideal for gatherings, and a rear enclosed lanai that provides additional year-round living space. These areas create multiple options for relaxing, entertaining, and enjoying the surroundings. On Top of the World is one of Central Florida’s most vibrant and sought-after active adult communities. Known for its resort-style lifestyle and exceptional amenities, this master-planned neighborhood offers residents endless opportunities to stay active, social, and engaged. With over 175 clubs and interest groups, multiple golf courses, fitness centers, tennis and pickleball courts, swimming pools, and community events, there’s always something to enjoy right at your doorstep. The community’s welcoming atmosphere, on-site dining, farmers market, and golf-cart-friendly layout create a truly connected and fulfilling way of life. On Top of the World continues to be celebrated as one of the nation’s premier 55+ communities, blending leisure, wellness, and neighborly spirit in a beautiful Florida setting. Truly move-in ready, this property is perfect for buyers seeking comfort, convenience, and a beautifully updated home in a desirable community.

Listing is courtesy of: CENTRAL CITY REALTY (352-456-1941)

Listing Agent: Nathaniel Suleiman (352-456-1941)

Remarks: This beautiful villa is in the On Top of the World, a Premiere 55+ Gated Golf Community! With 2 bedrooms, 2 baths, 1.5 car garage (sufficient for a car & golf cart), and finished FL room. This villa is centrally located within the community for easy access to the amenities. Cute front porch perfect for enjoying your morning coffee, or evening beverage, and meeting your neighbors! Step inside the spacious living room, To the left are the bedrooms with the guest bedroom in front with large-deep closet. Guest/hall bath divides the bedrooms. Guest/hall bath with tub, tile surround, and comfort height toilet. The primary bedroom is in the back right of the home for privacy and is large enough for king sized bed! There is also a large walk-in closet suite, the bath with step-in shower and comfort height toilet! The dining room has plenty of space. The eat-in kitchen is light and bright, with access to the 1.5 car garage, also where the laundry is located. The two finished Florida rooms are off the kitchen. Lots of space/potential out back for patio. The monthly HOA fee includes Basic Spectrum Cable, roof repair, exterior painting every seven years, irrigation water, exterior maintenance and insurance, landscaping, trash & recycling, 24/7 monitored gates and all the amenities that OTOW has to allow you to have a good time; three pools (2 outside & 1 inside & another under construction), two state of the art fitness centers, pickleball, billiards, archery range, corn hole, bocce ball, tennis, shuffleboard, horse shoes, remote control flying field and race cars, 175+ clubs, woodworking shop (extra fee), library, and much, much more! A golf cart community with access to three shopping centers. Centrally located 20 minutes from the World Equestrian Center, easy drive to 4 cruise ports and/or airports, and close proximity to entertainment complexes in Orlando.

Listing is courtesy of: ENGEL & VOLKERS OCALA (352-820-4770)

Listing Agent: Escarlin Mancia (352-812-0645)