Circle Square Woods Homes for Sale in Ocala - 28 homes

Remarks: Modern Elegance Meets Serene Living in this Rare Sienna II Custom Model… Welcome to your “On Top of the World “sanctuary. This isn’t just a house: it’s a meticulously renovated, Furnished retreat designed for those who appreciate the finer things. From the moment you arrive, the charming covered front porch invites you to slow down and enjoy your morning coffee amidst beautiful curb appeal. Step inside to an airy, open-concept floor plan bathed in natural light. The heart of the home is chef-inspired kitchen featuring brand-new quartz countertops, custom cabinetry, and sleek tile backsplash. Whether you’re hosting friends around the center island or enjoying a quiet meal, the seamless flow into the Great Room—highlighted by a stunning new picture window – makes everyday living feel like a getaway. A thoughtful split-floor plan ensures peace for both the primary suite and guests. The Guest Room is on the left side with hallway to the Guest Bath with tub/shower, new countertop with vessel round sink and overflow drain and light fixture. At the end of the hallway is the guest bedroom providing comfort and convenience with a bi-fold deep closet with built-in shelves for storage. Moving on back into the Great Room you will see a door that opens to the private primary suite on the right side and opens to the dressing area with a new long vanity cabinet with plenty of storage below and quartz top with two vessels round sink w/overflow drain and light fixtures, walk-in customed closet creating a space where every item is effortlessly accessible and perfectly arranged. The en-suite bath offers a tiled step-in shower w/grab bar and bench, and comfort-height toilet. Connected off the Primary suite is the Florida Room to relax and enjoy the view of the rear paver patio overlooking the beautiful, landscaped backyard perfect for grilling out and having a nice cocktail. The 1.5 garage is located on the left side of the home. Plenty of space for a car and golf cart storage, hanging storage racks, new garage door opener and newer washer & dryer. Home Features: Roof (2014), A/C (2011), Front Door (2014), Back Door (2017), New Windows (2016). Your search ends here – come see why this home located in On Top of the World is where your next chapter awaits!

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

Listing Agent: Ron Viola (352-239-5851)

Remarks: PRICE IMPROVEMENT!! Seller is motivated. Welcome to the highly desirable On Top of the World 55+ community, where comfort, entertainment, and maintenance-free living come together! Situated on a desirable corner lot and within short distance to all the amazing amenities, this beautifully maintained home offers the perfect blend of convenience and active living. Enjoy resort-style amenities including a clubhouse, pickleball courts, swimming pools, fitness centers, bingo nights, and countless social activities. The monthly HOA covers lawn care, exterior house painting, sprinkler system maintenance, gate access, trash service, dumpsters, mailboxes, and even a golf cart sticker for added convenience. This move-in ready home features fresh interior paint completed in 2025, updated flooring, a new roof in 2025, A/C replaced in 2023, and a water heater installed in 2021. Enjoy peace of mind with Leaf Filter gutter protection throughout the home and annual pest control service. The spacious lanai includes beautiful plantation shutters installed in 2020, adding a versatile and elegant touch to the home while providing excellent natural light control and privacy. The renovated primary bedroom completed in 2021 adds a modern and comfortable touch, while the kitchen offers stainless steel appliances, tile flooring, and plenty of functionality. Bathrooms feature cozy carpeting for added comfort. If you are looking for an active 55 community with endless amenities, low-maintenance living, and a prime location, this home is a must-see!

Listing is courtesy of: PEPINE REALTY (352-226-8474)

Listing Agent: Marielena Petrucelli Moronta (352-745-5101)

Remarks: 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 and new garbage disposal. 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 volley ball courts. Steps away from the library and woodshop. Seller to include a 1 year home warranty valued up to $600.00 There are tons of amenities with 3 pools one of which is just completed!

Listing is courtesy of: RE/MAX PREMIER REALTY (352-732-3222)

Listing Agent: Beth Anthony (352-817-1212)

Remarks: PRICE SLASHED $15000!!! WOW!!! Nearly $30,000 in upgrades in the last 2 years! This well cared for Bostonian villa will give you peace of mind for many years to come with NEW ROOF, NEW HVAC and NEW Water HEATER in 2025, plus NEW FRONT WINDOWS and ADDED ATTIC INSULATION. Home features beautiful, durable laminate flooring throughout with tile kitchen and bath floors. NO CARPET anywhere! Huge, fully enclosed Florida room is open to the dining area and overlooks a spacious back yard. Come and look, and make it YOUR home!

Listing is courtesy of: LEGACY REALTY & ASSOCIATES (352-203-4801)

Listing Agent: Glen Schnicke (352-209-5811)

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: 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: 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: 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)