Maitland Single Family Homes For Sale - 85 homes

Remarks: Under contract-accepting backup offers. Villa Serenata, a lakefront legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterranean estate on the renowned Winter Park Chain of Lakes. On approximately two acres of meticulously curated grounds, this extraordinary residence feels less like a home and more like a private resort, crafted for those who appreciate timeless architecture, thoughtful design and elevated lakefront living. A sweeping circular driveway welcomes you beneath a canopy of soaring royal palms and majestic live oaks, immediately setting the tone for what lies beyond. As the automated gate opens, the property reveals itself as a serene sanctuary where elegance and privacy coexist in harmony. The 6,634-square-foot main residence showcases interiors by acclaimed designer Ted Maines, unfolding across two levels of refined sophistication. The Mizner-inspired living room commands attention with dramatic 24-foot wood-beamed ceilings and twin walls of arched French doors, one framing sweeping views of Lake Maitland’s shimmering waters, the other opening to a sun-dappled courtyard where mornings naturally begin with coffee and quiet reflection. The upper level is devoted entirely to the primary suite, creating a private retreat complete with a heatless gas fireplace, spa-caliber bath with soaking tub and steam shower, a bespoke dressing room with custom built-ins, and a rooftop terrace with glass railings offering remarkable lake views. Three additional bedroom suites, each with an en-suite bath and generous walk-in closet, provide comfort and privacy for family and guests alike. At the heart of the home, the chef’s kitchen is equipped with Sub-Zero and Wolf appliances, custom cabinetry, and an expansive prep island designed to transition seamlessly from intimate family meals to catered gatherings of 50. The formal dining room features a dramatic curved wall of windows, turning every meal into a lakefront experience, while the richly paneled library and office offer a quiet space for focused work or relaxed reading. Complementing the main residence is a thoughtfully designed guest compound totaling 1,540 square feet. A private media pavilion delivers a state-of-the-art theater and listening room for film enthusiasts and audiophiles, while the one-bedroom guest apartment above provides a fully appointed living space with kitchen, living area and private entry, ideal for extended family, visiting guests or live-in staff. Outdoor living is equally exceptional. Resort-style travertine surrounds the pool amid lush tropical landscaping, creating a tranquil setting for sun-filled afternoons. A covered lanai with full summer kitchen flows effortlessly from the family room, while an expansive open-air terrace extends from the great room, an inviting backdrop for sunset cocktails overlooking the lake. Villa Serenata is more than a residence, it is a legacy estate, offering privacy, architectural distinction, and a lifestyle centered on one of Winter Park’s treasured waterfront settings.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Priced to Sell | Renovated Pool Home in Prime Maitland Location This thoughtfully refreshed 4-bedroom, 2-bath concrete block home offers comfort, flexibility, and lasting value in one of Maitland’s most convenient locations. Move-in ready and well priced, it presents an excellent opportunity for buyers seeking a home with major updates already completed. Inside, modern finishes blend seamlessly with timeless design, creating a bright, neutral space ready for your personal style. The updated kitchen features stainless KitchenAid appliances, new granite countertops, and easy flow into the main living area. Bathrooms have been refreshed, seamless luxury vinyl plank flooring runs throughout the home, and fresh interior paint enhances the clean, contemporary feel. Significant system upgrades provide added confidence and peace of mind, including interior and exterior electrical panels with surge protection (2024), new HVAC (2023), fully permitted roof (2020), complete CPVC re-pipe, and a newly replaced pool pump (2025). The front yard was enhanced with Provista sod and irrigation in 2025, adding curb appeal and ease of maintenance. A voluntary $50 annual HOA payment helps maintain the neighborhood’s front entrance and enhances overall community appeal. The open-concept layout overlooks a spacious pool deck, creating an inviting setting for entertaining or everyday living. The outdoor space is ready for the next owner to design and customize to their preferences. A versatile floor plan allows for a true four-bedroom configuration or the option to convert to three bedrooms with expanded living space. There is also strong potential to enlarge the primary suite within the existing footprint or through a future addition. Ideally located just half a mile from English Estates Elementary and minutes from Kewannee Park, shopping, dining, scenic trails, I-4, and the airport, this home combines everyday convenience with established neighborhood charm.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential! Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while sitting in a sought-after neighborhood where many properties are being transformed into spacious, high-end residences. It's an ideal opportunity to enjoy modern luxury today and customize further tomorrow in one of Maitland's most desirable areas. Step into a bright, open floor plan where the family room integrates effortlessly with the dining area, anchored by a cozy fireplace – perfect for gatherings. The heart of the home is the fully renovated kitchen, featuring abundant cabinetry, sleek quartz countertops, and a large kitchen island with seating for four at the breakfast bar – ideal for casual meals or entertaining. Spacious primary suite with a custom walk-in closet and sliding doors opening to the back patio and fire pit area – your private oasis for relaxing in the backyard. The en-suite primary bathroom boasts dual sinks, quartz counters, and a walk-in shower with a nice rain showerhead. Two generously sized secondary bedrooms with ample closet space, sharing a beautifully updated hall bathroom with another walk-in shower and rain showerhead. Brand-new Jeld-Wen windows, updated water and electrical systems, new tankless water heater, and new efficient central A/C system. Luxury vinyl plank flooring flows seamlessly through the entire home, delivering durability and style. Nestled in a peaceful, family-friendly neighborhood, this home offers quick access to top-rated Orange County schools including nearby Dommerich Elementary and strong feeders to Maitland Middle and Winter Park High. Enjoy a short drive or easy stroll to Scenic Lake Lily Park, with walking trails, picnic spots, playgrounds, and charming events; Maitland's vibrant cultural scene; excellent dining options; Premier golf courses, boutique shopping, and the upscale charm of Park Avenue in Winter Park; and convenient proximity to major Orlando attractions, theme parks, airports, and employment hubs – all while enjoying Maitland's quiet, tree-lined streets. This move-in-ready gem combines modern finishes with tremendous upside in a location that's rapidly appreciating. Don't miss your chance to own in one of Central Florida's most desirable pockets!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Matias Ugarte Palacios (689-253-4778)

Remarks: Under contract-accepting backup offers. Welcome to this stunning home in Maitland, located at 1817 Braeloch Ct. A welcoming foyer opens to elegant formal living and dining rooms featuring gorgeous fixtures, plantation shutters throughout, 5½-inch baseboards, and beautiful manufactured wood flooring. Vaulted ceilings and skylights fill the home with natural light, while a cozy wood-burning fireplace and stylish wet bar create the perfect setting for entertaining. The completely renovated kitchen by Braden Kitchens offers abundant cabinetry and storage, with even more storage available in the spacious laundry room. The luxurious primary suite has been fully updated and features a beautifully redone bathroom and a custom built-in closet system. Step outside to a private screened pool and an impressive redesigned porch with pavers, vaulted ceilings, and skylights—perfect for relaxing or hosting guests. The home also includes a convenient half bath, two additional bedrooms with walk-in closets, a second bathroom that serves as a pool bath with a shower and linen closet, and a third bedroom with French doors leading directly to the pool area. Additional highlights include a central vacuum system, an oversized two-car garage, a shingle roof installed in 2021, A/C (2018), and a newer water heater for peace of mind. Residents also enjoy HOA community access to a private boat ramp and dock on the lake, which features a private skiing and slalom course. Boat storage at the private dock may also be available for an additional $100 per year, offering even more convenience for enjoying the Florida waterfront lifestyle.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Abby Nelson (407-571-1445)

Remarks: Welcome to this thoughtfully updated one-story home in the established community of English Estates, where timeless design and everyday comfort come together. A brick paver driveway leads to the front porch creating an inviting first impression. Inside, the light-filled living room opens effortlessly into the heart of the home. The updated kitchen features granite countertops, beautiful 42-inch cabinets, stainless steel appliances, and a convenient breakfast bar perfectly positioned to flow into the dining area. A separate family room offers additional living space and opens to a covered, screened porch which is an ideal setting for relaxed evenings or casual outdoor dining. Back inside, two secondary bedrooms share a beautifully updated full bath, while the primary bedroom offers a peaceful retreat complete with its own private en suite bathroom. Step outside to a spacious, fenced backyard with plenty of room for entertaining, gardening, or simply enjoying the Florida sunshine. Recent improvements that add both value and peace of mind, include a new roof (2024) with transferable five-year warranty, A/C (2021), whole house replumbed (2021), irrigation system (2022), septic drain field (2018) and updated double paned windows. You will love how close you will be to to Winter Park with their great farmers markets, Park Ave and so much more! Conveniently located with easy access to major roadways, shopping, and restaurants, this move in ready home offers a wonderful blend of comfort, updates, and location. A home that is easy to enjoy and well worth seeing in person. Schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Barrett Spray (407-927-3650)