Maitland FL Homes for Sale

4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

$258,500

3 Beds ⋅ 2 Baths ⋅ Clark Homes Acres SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a great opportunity for a first-time buyer or someone looking to downsize. According to the owner, the property was rehabilitated by the county in 2017, with updates that included the HVAC, plumbing, and electrical systems, and the roof was replaced approximately 10 years ago. Conveniently located near I-4 and Winter Park, this home is just minutes from local eateries, the library, and public transportation.

551 Ruffel Street, Maitland

$295,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away. This is a two-story building, which falls outside Florida's SIRS and milestone inspection requirements that apply to condos three stories and taller.

1000 Winderley Place Unit 239, Maitland

$824,900

5 Beds ⋅ 3 Baths ⋅ Dommerich Hills 6th Add SubDv. ⋅ 32751 Zip Code

Welcome to Dommerich Hills, where modern style meets everyday comfort. This beautifully renovated home offers the freedom of **NO HOA** and has been thoughtfully updated from top to bottom. From the paver driveway and elegant double-door entry to the bright, open-concept interior, every detail has been designed to make you feel at home. The heart of the home is a stunning chef-inspired kitchen featuring sleek custom cabinetry, stainless steel appliances, and a striking waterfall island with custom wood accents,perfect for entertaining family and friends. The spa like bathrooms has glass-enclosed showers, contemporary fixtures, and designer finishes that create a relaxing retreat. Step outside and discover your own private Florida oasis. A covered lanai overlooks the sparkling pool and expansive paver patio, creating the ideal space for outdoor dining, weekend gatherings, or simply unwinding in the sunshine. Conveniently located just minutes from major highways, shopping, dining, and entertainment, this beautifully renovated home combines modern design with everyday functionality. Schedule your private showing today and experience everything this exceptional property.

2801 Waumpi Trail, Maitland

$1,825,000

4 Beds ⋅ 4 Baths ⋅ Maitland Cove SubDv. ⋅ 32751 Zip Code

Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the living and family rooms, two fireplaces, and custom built-ins showcase quality rarely found today. The spacious layout features four bedrooms and 3.5 baths, including two primary suites ideal for multi-generational living. Generous walk-in closets and a blend of wood, tile, and carpet add comfort and function. A new A/C (Oct 2025) and a 6.5-year-old roof provide peace of mind. Living areas open to a bright rear sunroom with tranquil lake views. Whether you’re entertaining by the fire, enjoying coffee on the porch, or heading out onto the lake, this property delivers the Florida lifestyle at its finest.

1111 Audubon Way, Maitland

$2,150,000

5 Beds ⋅ 5 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic and refined. An impressive foyer sets the stage for the elegant interiors beyond, where high ceilings, natural light, and thoughtfully curated finishes create an atmosphere of sophistication and comfort. Designed for both effortless daily living and elevated entertaining, the open-concept layout flows beautifully from the expansive living room into the formal dining space, framed by a striking wall of oversized sliders that open up to the spacious backyard/pool area. The heart of the home is the show-stopping chef’s kitchen featuring stunning Chantilly quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry. The primary suite is designed to feel like a five-star retreat, featuring a spa-inspired bath offering a freestanding soaking tub, dual vanities, a glass-enclosed walk-in shower, and an expansive closet. Adding to the home’s rarity and versatility, the main level also features a true guest suite perfect for hosting in comfort, as well as a dedicated office. Outside, the backyard is the definition of resort-style living. The sparkling pool and spa anchor the space, surrounded by a generous covered lanai with a summer kitchen and abundant room for lounge seating and al fresco dining. And beyond the home itself, the lifestyle is exceptional. Residents of Hollieanna Shores enjoy access to a shared boat slip giving you access to the Winter Park Chain of Lakes, offering a level of exclusivity and lake-life convenience that takes this property to another level. All of this is just minutes from Maitland City Centre, beloved local parks, the iconic Enzian Theater, and the upscale dining, shopping, and charm of Park Avenue. This home redefines what luxury living looks like in Maitland, where location, design, and lifestyle come together in a home that feels truly unforgettable.

101 Whitecaps Circle, Maitland

$1,800,000

4 Beds ⋅ 5 Baths ⋅ Woodbridge SubDv. ⋅ 32751 Zip Code

Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland. This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre cleared lot surrounded by majestic oak trees, the home offers a rare sense of privacy and tranquility while still enjoying all the conveniences of city living. Designed for both comfort and entertaining, the home will include spacious living and dining areas, a gourmet kitchen, and generously sized bedrooms, plus a luxurious primary suite retreat. The outdoor space provides ample room to create your ideal backyard oasis, perfectly complementing the home’s modern design. Located less than a mile from Maitland Community Park, you’ll enjoy nearby sports courts, scenic trails, picnic pavilions, and playgrounds. Just a short walk away are Seminary Lake and the SunRail Maitland station, offering effortless access to recreation and commuting alike. This pre-construction opportunity is a rare chance to own a brand-new custom-style home in one of Maitland’s most desirable and well-connected neighborhoods.

1130 Mechanic Street, Maitland

$245,000

Woodbridge SubDv. ⋅ 32751 Zip Code

This 0.26 acre cleared lot is ready for you to create the home of your dreams! Nestled among majestic oak trees, it provides a serene and private setting while maintaining easy access to everything you need. Enjoy the perfect blend of a peaceful, country-like atmosphere right in the heart of the city. Located less than a mile from Maitland Community Park, you'll have access to sports courts, scenic trails, picnic pavilions, and two playgrounds. It's also a short walk to the Seminary Lake and the SunRail Maitland station. This lot offers a rare opportunity to build in a highly sought-after area surrounded by natural beauty and convenience.

1130 Mechanic Street, Maitland

$389,000

3 Beds ⋅ 4 Baths ⋅ Ultra Vista Condo SubDv. ⋅ 32751 Zip Code

Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a sense of privacy and comfort. The thoughtfully designed layout offers flexibility and convenience across two levels. The main floor features a spacious primary bedroom complete with a walk-in closet and private bathroom. Also on the first level is a welcoming living area with vaulted ceilings, creating an open and airy feel, along with a dining space that looks out through French doors. The kitchen is well-appointed with stainless steel appliances, stone countertops, and ample workspace, making it ideal for everyday living and entertaining. A screened rear porch extends the living space outdoors, perfect for relaxing or enjoying Florida evenings. Upstairs, you’ll find a second primary bedroom with an attached bathroom, offering a private retreat for guests or multi-generational living. A third bedroom, also with its own bathroom, is located just off a landing that overlooks the living area below, adding architectural interest and an open-concept feel. Significant updates completed in 2024 enhance both comfort and long-term value, including a new roof, upgraded air conditioning system with a 10-year manufacturer warranty, fully updated plumbing, and modern electrical improvements with new breaker boxes, switches, and receptacles. Interior finishes include wood flooring on the main level, luxury vinyl plank flooring upstairs, tile in wet areas, energy-efficient Low-E double-pane windows, recessed LED lighting throughout, and updated fixtures in the kitchen and closets. The exterior was freshly painted in 2025, adding to the home’s curb appeal and move-in-ready condition. With its low-maintenance design, versatile floor plan, and unbeatable location near Winter Park’s Park Avenue and the scenic Chain of Lakes, this home presents

1994 Kenaston Road Unit 1994, Maitland

$4,999,000

5 Beds ⋅ 8 Baths ⋅ Floridahaven SubDv. ⋅ 32751 Zip Code

Under Construction. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

360 Lake Seminary Circle, Maitland

$340,000

3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code

This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!

1033 Hamlet Drive, Maitland

$120,000

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

**ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!

2517 Caper Lane Unit 205, Maitland

$3,500,000

Coopers Sub SubDv. ⋅ 32751 Zip Code

Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building, adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St —offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023.

421 E Kennedy Boulevard, Maitland

$1,345,500

5 Beds ⋅ 5 Baths ⋅ Lake Sybelia Cove SubDv. ⋅ 32751 Zip Code

WOW! INTEREST RATE BUY DOWN FOR THE FIRST YEAR PAID FOR BY THE SELLER’S PREFERRED LENDER, REDUCING THE BUYERS INTEREST RATE AND MONTHLY PAYMENTS! CALL FOR DETAILS! AND $50,000 OFF - NEW PRICE !!!! A SUBSTANTIAL OPPORTUNITY WITH EXCEPTIONAL VALUE. This home has timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the spacious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment and has a new sparkling finish, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience. A great canvas with many possibilities to create a space that truly reflects your modern vision and lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Experience the extraordinary lifestyle this Maitland home provides, CALL TODAY TO SCHEDULE YOUR APPOINTMENT!

755 Cranes Court, Maitland

$229,000

Woodbridge SubDv. ⋅ 32751 Zip Code

Unlock the Potential of Your Dream Property in Maitland, Florida! Discover a prime opportunity to build your vision in the heart of Maitland, a charming and thriving community just minutes from downtown Orlando. This vacant land offers a blank canvas for your dream home or investment property. Nestled in a highly desirable area, you'll enjoy easy access to top-rated schools, tranquil parks, boutique shopping, and diverse dining options. With Maitland's rich history, vibrant arts scene, and scenic lakes, this location provides the perfect balance of serenity and urban convenience. Whether you're looking to create a modern masterpiece or a private retreat, this land is your gateway to endless possibilities. Don't miss your chance to secure a slice of one of Central Florida's most sought-after communities! Contact us today and take the first step toward making your vision a reality.

Mechanic Street, Maitland

$3,990,900

Woodbridge SubDv. ⋅ 32751 Zip Code

Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately ±8 acres of usable land comprising multiple contiguous parcels and rights-of-way. The property is designated as a Traditional Neighborhood and zoned RS-2. A previously submitted Planned Development application proposed a gated community with 28 single-family homes—featuring 13 conjoined duplex-style units and 9 lakeview single-family lots. A future buyer may choose to revive or revise this plan, offering a valuable head start on entitlements. This flexible property supports a variety of development options and may be subdivided for separate sale, presenting multiple investment paths. As one of the last remaining large infill tracts in the area, it offers approximately 766 feet of direct frontage on Lake Seminary. Don't miss this rare chance to acquire a high-potential property in a sought-after location.

1250 N Maitland Avenue, Maitland

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