Downtown Maitland, FL homes for sale & real estate

Downtown Maitland, FL Homes for Sale

Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutique shopping, and local dining in one of the most desirable neighborhoods in the Maitland and Winter Park area. From the moment you arrive, the manicured landscaping and inviting covered front porch set the tone. Inside, natural light fills the home through skylights and bay windows, highlighting gleaming hardwood floors and a stunning wood-burning fireplace. The open layout connects each living s

Downtown Maitland, FL Homes for Sale

Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental income or private home office use. Designed by award-winning architect David Crabtree of Hive Workshop and constructed by Barefoot Brothers Construction, the home showcases vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork. The primary suite includes

Downtown Maitland, FL Homes for Sale

This 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space in a highly sought-after location. Enjoy a bright living area featuring a gorgeous tiled fireplace, built-in bookshelves, and two sets of French doors that open to your private patio and fenced backyard with brick pavers and turf grass. The home includes a spacious double vanity bathroom, custom shelving for extra storage, and a one-car garage with an additional air-conditioned room behind it. Recent updates include a 2021 roof, 2022 AC, and a transferable termite bond for added peace of mind. Located just 1.5 miles from Downtown Winter Park and Park Avenue, and only a mile from the newly renovated Wi

Downtown Maitland, FL Homes for Sale

Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private guest casita and a fully finished basement. Total area including outdoor spaces: 6,821 sq ft. The exterior showcases a stone façade, barrel-tile roof, wrought-iron detailing, and lush courtyards. A gated entry with outdoor fireplace leads to the guest casita with full bath, ideal for extended family, live-in support, or private office use. Inside, arched walkwa

Downtown Maitland, FL Homes for Sale

One or more photo(s) has been virtually staged. Experience classic Maitland charm with modern comfort in this beautifully updated 4-bed, 3-bath home just steps from Maitland City Center, Lake Sybelia, and top-rated schools. Surrounded by million-dollar homes, this property offers prime location near Winter Park, Rollins College, UCF, and leading medical centers. Enjoy nearby dining, trails, and lakes for kayaking or paddleboarding. Featuring a lighted pool, upgraded kitchen, double-pane windows, and two primary suites, this home blends style, convenience, and investment value. ? A rare Maitland gem— Roof 2024-New AC unit. schedule your private tour today!

Downtown Maitland, FL Homes for Sale

PRICE IMPROVEMENT! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and running water. Great Investment Opportunity! Reroofed in 2018.