Caldwells Add Real Estate

Caldwells Add Real Estate

Welcome to Caldwell's Addition, a charming subdivision nestled in the heart of Ocala, Florida. Known for its serene atmosphere and friendly community, Caldwell's Addition offers a perfect blend of suburban tranquility and convenient access to urban amenities.

This delightful neighborhood boasts a variety of residential options, from cozy single-family homes to spacious properties with lush yards, making it an ideal place for families, retirees, and everyone in between. The tree-lined streets and well-maintained landscapes create a picturesque setting, inviting residents to take leisurely strolls or enjoy outdoor activities within the community.

Caldwell's Addition is strategically located near the vibrant downtown Ocala area, where you can explore an array of dining, shopping, and entertainment options. The rich cultural scene includes art galleries, theaters, and local events that foster a strong sense of community and belonging. For nature enthusiasts, the nearby parks and recreational facilities offer abundant opportunities for hiking, biking, and enjoying Florida's beautiful weather.

Families will appreciate the proximity to quality schools and educational institutions, ensuring that children receive a well-rounded education. Additionally, the area's easy access to major highways makes commuting to neighboring cities and attractions seamless.

Whether you’re looking to settle down or invest in a property, Caldwell's Addition is a hidden gem in Ocala that promises a warm, welcoming environment. Come and discover the charm of Caldwell's Addition, where community spirit and quality living converge!

Newest Listings in Caldwells Add

$649,900
3 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
Nestled in the walkable, golf cart–friendly Historic District of downtown Ocala, this beautifully renovated home blends timeless character with modern conveniences. Boasting three bedrooms, one full bath and one half bath, it’s the perfect balance of era-appropriate detailing and contemporary upgrades. The interior is completely renovated with new wiring and plumbing, a stylish new kitchen with modern appliances, and updated fixtures and finishes throughout, while preserving charming historic accents. Located in a golf cart and walking-friendly neighborhood, the home is just a short stroll or ride to shops, dining, and major medical facilities, with central access to Ocala’s vibrant downtown scene and parks. The exterior and interior balance preserved architectural details—moldings, trim, and vintage touches. The outdoor spaces are low-maintenance, with parking options available in a neighborhood known for its downtown charm. This property presents a strong move-in-ready option with turnkey updates and modern conveniences, plus solid investment potential for buyers seeking a historic, character-filled home in a coveted area. If you’re looking for a downtown Ocala residence that honors its history while delivering contemporary practicality, this renovated 3BR/1.5BA charmer in the Historic District is worth a look.

819 Se 2nd Street, Ocala
$410,000
3 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
Historic charm, an unbeatable location, and a front porch worth slowing down for! Located just a few short blocks from the Downtown Market, Ocala’s Historic Downtown Square, splash pad, award-winning restaurants, boutiques, special events, and so much more, this bungalow offers the best of downtown living. Pride of ownership is evident throughout this 3 bedroom, 1 1/2 bath home, where original wood trim, moldings, built-in shelving, and wood floors preserve the warmth and character of its historic roots. A light-filled bonus room adds flexible living space and is framed by oversized double-paned wood windows, creating the perfect spot for a reading nook, home office, art studio, or exercise space. Out back, the large deck provides ample room to relax, entertain, and soak up the Florida sunshine. Additional features include a carport with room for your golf cart — fitting for this golf cart-friendly neighborhood — plus storage and workshop space for hobbies, tools, or weekend projects. Classic bungalow character, thoughtful updates, and a downtown lifestyle come together in one truly special Ocala Historic District home. Roof 2022. HVAC 2021.

505 Se Sanchez Avenue, Ocala
$698,000
4 Beds ⋅ 4 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
****MOTIVATED SELLERS BRING WRITTEN CONTRACT OFFERS.**** STEP INTO A PIECE OF HISTORY WITH THIS ICONIC VICTORIAN PINK TWO-STORY TREASURE—WHERE TIMELESS CHARM MEETS MODERN OPPORTUNITY. PERFECTLY POSITIONED AND RICH WITH CHARACTER, THIS STANDOUT PROPERTY IS CURRENTLY ZONED HISTORIC RESIDENTIAL COMMERCIAL (RBH-3) AND OFFERS INCREDIBLE FLEXIBILITY, WITH ELIGIBILITY TO REZONE TO RBH-1, 2, OR 3 TO SUIT YOUR VISION. WHETHER YOU’RE DREAMING OF A DISTINCTIVE LIVE-WORK SPACE, BOUTIQUE PROFESSIONAL OFFICES, OR AN ENCHANTING BED & BREAKFAST, THE POSSIBILITIES HERE ARE AS EXPANSIVE AS THE HOME ITSELF. INSIDE, YOU’LL FIND A GENEROUS, ADAPTABLE FLOORPLAN READY TO BE TAILORED TO YOUR NEEDS—BLENDING VINTAGE ELEGANCE WITH FUNCTIONAL VERSATILITY. THIS IS MORE THAN A PROPERTY—IT’S AN EXPERIENCE. FROM ITS EYE-CATCHING EXTERIOR TO ITS INVITING INTERIOR SPACES, EVERY DETAIL INVITES YOU TO IMAGINE WHAT COULD BE. A TRUE MUST-SEE TO FULLY APPRECIATE. BE SURE TO EXPLORE THE IMMERSIVE 3D TOUR ATTACHED TO THE LISTING FOR A REAL-TO-LIFE PREVIEW. OPPORTUNITIES LIKE THIS ARE RARE—CALL TODAY TO SCHEDULE YOUR PRIVATE SHOWING AND BRING YOUR VISION TO LIFE.

805 E Fort King Street, Ocala
$299,000
2 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34470 Zip Code
Welcome to this beautifully preserved and thoughtfully updated 1948 vintage home, where timeless character meets modern functionality. Situated on a fully fenced 0.52-acre corner lot just minutes from downtown, this property offers a rare combination of space, privacy, and charm that is increasingly hard to find. The expansive grounds feature a storage shed, private garden, and a peaceful walking path with a small bridge, creating a setting that feels tucked away, yet connected to everything. From the moment you arrive, the mature trees and established landscaping set the tone for what’s inside. This home has been meticulously maintained and enhanced with key upgrades, including a new roof (2023), tankless water heater, 28 new windows, updated bathroom vanity, new stainless steel kitchen appliances, luxury vinyl plank flooring, updated light fixtures, and fresh interior and exterior paint. Inside, original details have been carefully preserved, including pristine original doors, doorknobs, and cabinetry with vintage hardware- all in excellent condition. These elements blend seamlessly with the home’s updates, offering both character and everyday livability. The finished Florida room is filled with natural light and overlooks the mature oak trees the area is known for, creating a calm and inviting space to start or end your day. With new windows and window treatments, this room is designed to stay comfortable year-round, and window treatments are included throughout the home. A rare feature in Florida homes, the semi-finished basement provides additional flexibility with a half bath and workbench—ideal for hobbies, storage, or a dedicated workspace. The guest bedroom includes a built-in Murphy bed with integrated storage, allowing the space to easily adapt to your needs. Outdoors, the combination of mature landscaping, no current rear or side neighbors, and thoughtfully designed outdoor features creates a setting that feels both private and usable. The recently redone brick paver driveway adds to the home’s curb appeal and overall quality. Located near downtown Ocala and close to new entertainment and dining options such as The Forge, Midtown Station, and the 1890 Tea House, this home is positioned within a growing and evolving part of the community while still offering a sense of retreat. This is a rare opportunity to own a vintage home that has been preserved, updated, and cared for with intention. Schedule your private showing today.

923 Ne 2nd Street, Ocala
$399,900
4 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
Located in Ocala’s Historic District and Golf Cart District, just 4 blocks from the Downtown Farm Market, this 2-story cottage is full of charm, character, and potential. The current floor plan configuration offers 3 bedrooms and 2 bathrooms, with the primary bedroom and both full baths on the first floor, plus 2 bedrooms and a bonus room upstairs. Original features include wood floors in many rooms, high ceilings, a fireplace in the formal living and dining area, and a double fireplace shared by the family room and primary bedroom. The cottage is positioned on the parcel with ample room for a future garage and/or pool. This home is ready for updates and restoration making it an exceptional opportunity for a buyer with vision to create a dream home in one of Ocala’s most sought-after historic neighborhoods.

721 Se 5th Street, Ocala
$569,000
Caldwells Add SubDv. ⋅ 34471 Zip Code
Prime downtown Ocala commercial property offering exceptional visibility, flexibility, and opportunity. This well-maintained 2,000+ square foot special-purpose building is ideally located in the heart of Ocala, just minutes from major hospitals, the Marion County courthouse, and thriving downtown dining, shopping, and business districts. Zoned RO (Residential Office), this versatile property supports a wide range of uses including medical office, professional services, boutique business, creative studio, or mixed-use workspace. The thoughtfully designed layout features a combination of climate-controlled and ventilated areas, allowing for seamless adaptability based on your business needs. Inside, a welcoming reception area creates a strong first impression for clients and visitors, while the interior offers a balance of open workspace and private offices, ideal for collaboration, consultations, or executive use. An upstairs loft provides additional flexibility—perfect for a private office, studio, or executive suite. Architectural character and a unique blend of indoor-outdoor design elements create an inspiring environment that sets this property apart from traditional office spaces. Positioned in one of Ocala’s most desirable and accessible locations, this property presents a rare opportunity for investors, business owners, or professionals seeking a strategic downtown location with strong long-term value and growth potential.

44 Se 9th Terrace, Ocala
$569,000
2 Beds ⋅ 3 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
Live, Work or Airbnb Downtown. Downtown Ocala | No Historic Restrictions | Airbnb Potential Fully updated property located just minutes from Downtown Ocala and the Historic District, offering rare flexibility for Airbnb, short-term rental, home office, or creative space without historic renovation restrictions. This golf-cart-friendly neighborhood provides easy access to Ocala’s restaurants, boutiques, and entertainment. The home features engineered hardwood and bamboo floors, granite countertops, (2025) smart stainless appliances, gas range, (2024) mini-split climate systems, fiber-optic internet, LED lighting, tankless water heater, and full smart-home integration. (2026) Gas Tankless Hot Water Heater, (2019) Roof. This home features tons of storage space under the home. A standout feature is the detached climate-controlled bonus building, ideal for a guest suite, office, studio, or gym. The fully fenced property with electric gate also includes gazebos, deck space, and outdoor shower, perfect for relaxing or entertaining. Move-in ready with location, flexibility, and income potential.

44 Se 9th Terrace, Ocala
$549,900
5 Beds ⋅ 4 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
HUGE PRICE REDUCTION!!! Ocala Historic District! Main House: 4 Br, 3 Ba. Guest House: 1 Br, 1 Ba, Full Kitchen. This beautifully preserved 1895 Victorian masterpiece invites you to step back into the Gilded Age, an era when quality, elegance, and craftsmanship were the standard, not the exception. The welcoming covered front porch with swing leads to a grand entry featuring an impressive, hand-crafted staircase, an ornate 29 ft. foyer, a Formal Parlor, and 1 full Bath, all highlighted by original hardwood floors and soaring ceilings. Beyond the foyer, the spacious Family Room flows seamlessly into the Dining Room, Kitchen, and Indoor Laundry Room, offering modern convenience while preserving timeless Victorian character. The main residence offers 2,606 sq. ft. The main level has a versatile Flex Room with closets that could make it a 4th bedroom. Upstairs, you’ll find 3 generously sized Bedrooms and 2 full Baths, including a stunning Primary Suite with a wood cathedral ceiling, an en suite Bath and a private spiral staircase to the ground floor. Step outside to a massive wooden deck and paver patio just off the back door, conveniently located near the garage/workshop. An exceptional bonus is the 592 sq.ft. Guesthouse featuring 1 Bedroom, 1 full Bath, a full Kitchen, and a Great Room, ideal for extended family, guests, or potential rental income. R3 zoning provides added flexibility for a variety of uses.  Main House HVAC 2023. Another Bonus: It's in the Golf Cart Zone as well as the Historic District.  Just a couple of blocks away from the Historic Downtown Square, Citizens' Circle and Farmers' Market.  Make your appointment today to see this rare beauty!

720 Se 3rd Street, Ocala
$499,000
4 Beds ⋅ 3 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code
Own a true Ocala landmark at 30 SE Wenona Avenue, a rare and beautifully restored 1887 Victorian located in the heart of Ocala’s coveted Historic District, just steps from the vibrant Downtown Square filled with art, dining, entertainment, and culture. Officially recognized by the City and proudly listed on the National Register of Historic Places, this iconic property offers timeless architecture paired with modern functionality. Thoughtfully restored in 2016, the home spans 3,120 square feet and features four bedrooms and three bathrooms beneath soaring 12-foot ceilings. Original details shine throughout, including meticulously stenciled and refinished hardwood floors, coffered ceilings, and four fireplaces that create warmth and character in every space. Generous walk-in closets and an inviting floor plan presents both elegance and comfort. The updated galley-style kitchen is equipped with stainless steel appliances, while the stylish, renovated bathrooms complement the home’s historic charm. A striking wrought-iron staircase adds architectural interest, and major system updates include a new roof and HVAC (2021) along with a two-car carport addition, providing peace of mind. Zoned B2, this exceptional property offers unmatched flexibility—ideal as a private residence, professional office, boutique retail space, bed-and-breakfast, Airbnb, art gallery, bookstore, or coffeehouse. Whether you envision living in history or creating a one-of-a-kind commercial presence in Downtown Ocala, this is a rare opportunity to own a truly irreplaceable property. Historic charm. Prime location. Endless potential.

30 Se Wenona Avenue, Ocala
$600,000
Caldwells Add SubDv. ⋅ 34470 Zip Code
Strategically positioned at the corner of NE 2nd Street & NE 9th Avenue W, this parcel sits just minutes from Historic Downtown Ocala. The site offers the perfect balance of proximity to downtown restaurants, retail, and cultural amenities. Surrounded by established neighborhoods and steady rental demand, this lot is one of the few remaining infill development opportunities in the Ocala core. **Lot Size: ±2.56 acres **Downtown-Adjacent Location: Less than 1 mile to Ocala’s Historic Square, restaurants, shops, and cultural venues - Infill Opportunity **Zoning: R-3 (Multi-Family Residential) **Density Allowed: 12 units/acre | ±30 units max by code **Permitted Uses: Multi-family dwellings, single-family homes, two-family and multi-family dwellings, residence-office and residence-galleries, bed & breakfast, assisted living facility **Special Exceptions Possible: Professional offices, day care, churches, recreation facilities, neighborhood wellness centers **Parking Requirement: 1.5 spaces/unit. Additional spaces may be required for amenities. **Utilities: City water and sewer are nearby **Neighborhood Context: Surrounded by long-standing homes, an opportunity for a well-positioned, modern infill product. **Corner Exposure: Frontage on both NE 2nd St & NE 9th Ave for easy access and design flexibility **Connectivity: Access to major corridors, including US 301/441 and SR 40 This site represents a rare chance to deliver new housing just outside the downtown core — close enough to enjoy the amenities. Ideal for an investor, builder, or developer looking to capture demand for modern apartments or townhomes close to downtown Ocala’s growing market.

9th Ave, Ocala
$995,900
Caldwells Add SubDv. ⋅ 34470 Zip Code
Location, Location, Location. This 2-story office building is located on the main 4 lane road in Ocala, Silver Springs BLVD, (HWY 40) with 114 ft of frontage! This parcel is over half an acre at .61 with ample parking. The front of the Victorian building is a grand entrance with the high columns and red brick porch. On the side of the building is the wood ramp for accessibility.  The inside of the office is full of historic charm, solid original wood floors on the staircase and upstairs, high ceilings, built-ins, solid wood trimmings, and a full kitchen. There are 6 total private offices, one office with full private bathroom, 4 bathrooms, 1 large conference room, 1 dedicated workspace downstairs, 2 lobby areas, and dedicated closed storage. There is 3120 sqft total under roof. There also is an already existing illuminated sign on Silver Springs BLVD. The building is not a registered historic building and can be removed. The zoning is B2. This is a great opportunity!

944 E Silver Springs Boulevard, Ocala
Start Your Search