Top 25 Latest Maitland Real Estate Listings

Virtually Staged. Less than a ten-minute drive from downtown Winter Park, Park Avenue’s shops and restaurants, and Rollins College, this completely renovated home has upd...

Hidden Gem! This small community is quiet, independent, extremely well maintained and one of Maitland's most desirable communities. This unit is a spacious with two bedr...

An Inviting Retreat in a Prime Maitland Location!! Discover a home where comfort, charm, and convenience come together beautifully. This inviting 3-bedroom, 2-bathroom...

Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sou...

Step into easy, resort-style living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo offering 1,048 square feet of thoughtfully designed space in the ...

Virtually Staged. Welcome to 1605 Grove Street! This single story unit offers a spacious and versatile floor plan, comfortable living areas, and the convenience of low ma...

Welcome to this amazing opportunity to own inside the highly coveted Lake Maitland Terrace community. This second floor condo is two bedrooms and one bathroom and ready ...

This Winter Park Chain of Lakes condominium has been completely reimagined to the highest of standards with meticulous attention to detail, providing luxury living in the...

This residence exemplifies pride of ownership, boasting a beautifully appointed kitchen with high-quality, updated cabinetry and granite countertops, complemented by uppe...

Welcome to Winfield! This inviting home offers a thoughtful layout with comfortable spaces for relaxing, gathering, and entertaining. Step into a separate front living ro...

Welcome to modern elegance in the heart of Maitland! This beautifully renovated home offers the perfect blend of timeless charm, contemporary finishes, and inviting livin...

Virtually Staged. New to the market, this amazing 2 story 4 bedroom and 3 bath Maitland home has just finished a full remodel! This home has an open floor plan which fea...

Welcome to luxury, comfort, and convenience at this beautifully transformed ground-floor 1-bedroom, 1-bath condo in the gated community of Visconti West. Every square foo...

Welcome to 2514 Tuscarora Trail, a beautiful, fully renovated lakeview pool home nestled in the heart of Maitland, Florida! This spacious single-story residence offers 4 ...

Discover the charm and convenience of Maitland living in this four-bedroom home featuring two full bathrooms and one half bathroom. A large, beautiful patio creates an in...

Tucked inside The Moorings, one of Maitland's most charming lakeside enclaves, 219 Quayside Circle sets a new standard for the community, and it comes with its own DEEDED...

Exquisitely remodeled, from top to bottom, 2 bdrm 2 bath luxury condo on Lake Maitland, the largest of the Winter Park Chain of Lakes. Enjoy panoramic lake views and uni...

EXQUISITE CONDO WITH BOAT SLIP AND DOCK ON THE WINTER PARK CHAIN OF LAKES! This stunningly reimagined corner unit boasting extra windows for light/space and a limestone p...

Timeless Florida Charm in the Heart of Dommerich this classic ranch is ideally situated in Maitland's highly sought-after neighborhood. Combining the character of an esta...

Enjoy the charm of The Moorings on Lake Maitland in this inviting three-bedroom, two-and-a-half-bath townhome with an attached one-car garage. High ceilings, natural ligh...

Welcome Home! Check out this beautiful 3 bedroom 2 bathroom single family home with a beautiful pool in a NO HOA neighborhood! Take full advantage of the morning sunrise ...

Discover the best of Maitland living in this light and bright end-unit townhome in the gated, lakefront community of Lake Destiny. Offering 2 bedrooms, 2.5 bathrooms, and...

Welcome to this exceptional four-bedroom, two-and-a-half-bathroom pool home in the heart of Maitland, offering an ideal blend of comfort, privacy, and Florida-style livin...

Welcome to this beautiful 3-bedroom, 2.5-bath townhome offering approximately 2,100 square feet of comfortable living space in the gated community of Maitland Village. Th...

Virtually Staged. This mid-century ranch block home is ideally located in the heart of Maitland and features extensive improvements for a truly move-in-ready opportunity....