Circle Square Woods Homes with Pool Community Features

Circle Square Woods Homes with Pool Community Features

Welcome to Circle Square Woods, a captivating subdivision nestled in the heart of Ocala, Florida, within the picturesque Marion County. This vibrant community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between.

Circle Square Woods boasts an array of stunning homes, many of which feature private pools, allowing residents to bask in the Florida sunshine year-round. Imagine lounging poolside in your own backyard oasis, hosting summer barbecues, or enjoying a refreshing dip after a long day. The allure of a home with a pool is undeniable, providing a perfect setting for relaxation and entertainment alike.

Beyond the beautiful homes, Circle Square Woods is designed with community in mind. Residents enjoy access to a wealth of amenities, including walking trails, parks, and recreational areas that encourage an active lifestyle. The community's lush landscaping and serene environment create a peaceful retreat while still being conveniently located near shopping, dining, and entertainment options in Ocala.

With its friendly atmosphere and engaging community events, Circle Square Woods fosters a sense of belonging that is hard to find elsewhere. Whether you’re taking a leisurely stroll with neighbors or participating in community gatherings, you’ll quickly feel at home.

Discover the charm of Circle Square Woods—where your dream home with a pool awaits! Experience the best of Ocala living, and make your move to this delightful community today.

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
$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
$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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