Circle Square Woods Homes with Pool Community Features

Circle Square Woods Homes with Pool Community Features

Welcome to Circle Square Woods, a picturesque subdivision nestled in the heart of Ocala, Florida, in the scenic Marion County. This charming community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between. With its lush landscapes and beautifully designed homes, Circle Square Woods invites you to experience the best of Florida living.

One of the standout features of this delightful community is the abundance of homes with private pools. Imagine stepping out into your backyard oasis on a warm Florida afternoon, where you can relax by the poolside, entertain friends, or enjoy quiet moments with family. These homes are designed for leisure and comfort, allowing residents to fully embrace the outdoor lifestyle that Florida is known for.

Circle Square Woods is not just about stunning homes; it’s also about a vibrant community spirit. Residents enjoy a variety of amenities, including walking trails, parks, and recreational areas that promote an active lifestyle. The community is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that everything you need is just a stone's throw away.

Whether you are looking to invest in a new home or seeking a peaceful retreat, Circle Square Woods offers a welcoming atmosphere that feels like home. Come explore this enchanting subdivision and discover why so many people are proud to call Circle Square Woods their home sweet home in Ocala, Florida!

Newest Circle Square Woods Homes with Pool Community Features

$219,500
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Welcome to Easy Living in a Desirable 55+ Community! Enjoy comfort, convenience, and a relaxed lifestyle in this beautifully maintained home located in a sought-after 55+ community. Featuring a charming covered front porch, this inviting residence offers a spacious open-concept design that's perfect for both everyday living and entertaining. The heart of the home is the expansive kitchen, complete with abundant cabinetry, a large center island with seating, granite countertops, stainless steel appliances, and ample workspace for preparing your favorite meals. The kitchen flows seamlessly into the dining and living areas, creating a bright and welcoming atmosphere. The well-designed floor plan provides comfortable bedrooms, generous storage, and easy-maintenance tile flooring throughout the main living areas. Large windows fill the home with natural light, while neutral finishes make it easy to personalize your space. Outside, you'll appreciate the attractive landscaping, oversized corner lot, and peaceful setting—ideal for enjoying your morning coffee on the front porch or spending time outdoors with friends and neighbors. As a resident of this vibrant 55+ community, you'll enjoy a low-maintenance lifestyle with access to amenities and activities designed to keep you active, social, and engaged. Whether you're looking to downsize without compromising space or searching for the perfect place to enjoy retirement, this exceptional home offers the ideal combination of comfort, style, and community living. Schedule your private showing today and discover everything this wonderful home has for you!

Ocala
$189,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Welcome to this fully furnished, move-in-ready villa. This home has been completely remodeled with new flooring and new windows throughout. It features a stunning, brand-new kitchen equipped with new appliances, custom cabinets, elegant countertops, a stylish backsplash, and two convenient lazy susans. Both bathrooms have been updated with high vanities and walk-in tiled showers with built-in seating benches. Additional upgrades include a new Florida room, a private paver patio, a new garage door, and a new air conditioning system. With a 2018 roof and a 2022 water heater, this home offers stress-free living in an amenity-enriched community.

8891 Sw 96th Lane Unit B, Ocala
$159,900
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Welcome to this beautifully maintained Charlotte model villa in the sought-after Friendship Village of On Top of the World, Ocala's premier 55+ community. Offering 1,484 square feet of thoughtfully designed living space, this inviting 2-bedroom, 2-bath home combines comfort, convenience, and low-maintenance living. Step inside to discover luxury vinyl plank flooring in both bedrooms, while the main living areas, kitchen, bathrooms feature attractive ceramic tile for easy upkeep. The open-concept floor plan is bright and welcoming, creating the perfect setting for everyday living and entertaining. A standout feature of this home is the climate-controlled Florida room providing additional living space to enjoy year-round—ideal for relaxing with your morning coffee, entertaining guests, or pursuing your favorite hobbies in comfort.The oversized one-car garage offers plenty of room for your vehicle plus extra space for a golf cart, workshop, or storage. A built-in mezzanine provides even more storage, making it easy to keep everything organized. Enjoy the exceptional lifestyle that On Top of the World is known for, with amenities including golf, resort-style pools, fitness centers, pickleball and tennis courts, walking trails, clubs, restaurants, and endless social activities. Conveniently located near shopping, dining, medical facilities, and all that Ocala has to offer, this move-in-ready villa is ready for you to call home. Schedule your private showing today and experience the best of active adult living!

8711 Sw 96th Lane Unit C, Ocala
$199,900
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Welcome to this beautifully renovated Augusta model home located in the much sought after 55+ community of On Top of the World. Recent updates include fresh interior paint, modern lighting, ceiling fans, and ample storage—creating a clean, move-in-ready home. Community + Amenities. Enjoy resort-style living with access to multiple clubhouses, swimming pools, fitness centers, pickleball and tennis courts, racquetball, walking trails, and a hobby building. This fully renovated 2-bedroom, 2-bathroom villa offers 1,761 sq ft of thoughtfully designed, low-maintenance living with gorgeous finishes throughout. Step inside to engineered hardwood floors that are in the main living areas, giving a warm and inviting atmosphere. The spacious living room opens to a fully updated kitchen including granite countertops, a large center island, white cabinetry, and stainless steel appliances—perfect for everyday meals and entertaining with family and friends. A light and bright sunroom at the back of the home provides a great area for morning coffee. Just off the sunroom, a versatile bonus room offers flexibility—use it as a third bedroom as it is now or, a hobby space, home office, or den. The generous primary suite is a great retreat, highlighted by a barn door leading to the en-suite bath with dual granite vanities, double closets, a glass-enclosed shower with bench, and a linen closet. The second bedroom is nicely sized with carpet and there is a guest bath with a tub/shower combo and granite vanity. Recent updates include fresh interior paint, modern lighting, ceiling fans, and ample storage—creating a clean, move-in-ready home. Community + Amenities. Enjoy resort-style living with access to multiple clubhouses, swimming pools, fitness centers, pickleball and tennis courts, racquetball, walking trails etc. This golf cart–friendly community also offers a wide variety of social clubs and activities. The Bottom Line-Quality upgrades, flexible living space, and an unbeatable location in one of Ocala’s most vibrant 55+ communities—don’t miss it. Call for your appointment to view today!

8874 Sw 95th Street Unit E, Ocala
$234,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Completely Remodeled INSIDE. Roof 2022, A/C 2023, Hot Water Heater is new. This spacious open floor plan 2 Bed 2 Bath with a Bonus Room (office). Inside of home has been completely updated with stainless steel appliances. all floors replaced with beautiful hardwood floors matching throughout the home. Both bathrooms completely remodeled and all ceiling fans replaced. This home is move in ready. If you are looking for a 2/2 this one is worth taking a personal tour of today.

8743 Sw 90th Lane Unit A, Ocala
$198,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
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!

9820 Sw 89th Terrace Unit E, Ocala
$145,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Nestled down a quiet, tree-canopy lined road in On Top Of The World, you will find 9357 C SW 82nd Terrace, Ocala FL. This property sits at the front edge of the OTOW community- making it just 1 mile from Wawa, 1.4 miles from Publix, 0.8 miles from Sprouts, and so much more. It also backs up to a retention pond- so you can enjoy the view of mature, lush landscaping. The floors are new, the paint is fresh, and the price is right to bring your vision to life. There’s even a workbench already in the garage! A sky tube provides abundant natural light, and the plantation shutters are already in place to keep the light out when you don’t want it. An enclosed Florida Room faces the green back yard area. 2 spacious bedrooms and 2 bathrooms with stone tiling and walk in closets provide comfort and function. A breakfast nook off the kitchen provides a cozy place to read the news and sip your coffee, with a separate dining area to sit for dinners with friends. Move in ready, or update it to your hearts desire.

9357 Sw 82nd Terrace Unit C, Ocala
$139,900
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
END UNIT!! Welcome to one of the most desirable 55+ communities in Ocala, the highly sought after golf cart community of On Top of the World! This beautifully updated 2 bed, 2 bath Philadelphian villa offers 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. Schedule your showing today! 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!

8637 Sw 97th Lane Road Unit A, Ocala
$199,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
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.

8883 Sw 93rd Lane Unit F, Ocala
$169,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
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?

8556 Sw 90th Lane Unit F, Ocala
$159,999
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
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.

8868 Sw 97th Lane Road Unit G, Ocala
$126,000
2 Beds ⋅ 2 Baths ⋅ Circle Square Woods SubDv. ⋅ 34481 Zip Code
Welcome to carefree living in the highly sought-after On Top of the World community in beautiful Ocala, Florida! This charming 2-bedroom, 2-bath villa offers the perfect blend of comfort, space, and potential, ready for you to move in and make it your own! Step inside to find a bright, open living area that’s perfect for entertaining or relaxing in style. The neutral color palette throughout complements the ceramic tile and laminate flooring, creating a clean, inviting atmosphere. Enjoy your morning coffee or evening breeze from the screened-in back patio, ideal for year-round Florida living. The kitchen and bathrooms are functional and ready for your personal updates; a fantastic opportunity to add your own modern touch and build instant equity! The washer and dryer are included, and you’ll love the convenience of indoor laundry in the garage. Located in one of Ocala’s premier 55+ active lifestyle communities, you’ll enjoy world-class amenities including golf, swimming, fitness centers, clubs, and endless social activities. Schedule your private showing today before this gem is gone!

9331 Sw 84th Terrace Unit D, Ocala
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