Luxury homes for sale & real estate in Maitland, FL

17 homes

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3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
One or more photo(s) has been virtually staged. Stately brick home in a premier Maitland neighborhood—set beneath a canopy of mature oaks on a lush 1/3-acre lot, this 4-bedroom, 2-bathroom home offers just under 2,500 SF of timeless elegance and modern comfort. A covered front porch perfect for rocking chairs, brick-paver walkway, double entry doors, and side-entry garage create an inviting first impression. The open layout makes everyday living and entertaining effortless. The heart of the home is the remodeled kitchen, featuring a large floating island with seating, pendant lighting, custom cabinetry, granite countertops, stainless steel appliances—including a built-in oven an

$869,000

4 beds2 baths2,500 sq ft

221 White Oak Cir, Maitland, FL 32751

Covered front porch • Custom cabinetry • Jetted heated tub

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
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

$1,300,000

4 beds2.5 baths2,116 sq ft

1421 Sunnyside Dr, Maitland, FL 32751

Covered front porch • Pool • Bay windows

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Pre-Construction. To be built. 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 wate

$4,999,000

5 beds7 baths6,466 sq ft

360 Lake Seminary Cir, Maitland, FL 32751

Floating staircase • Lakefront estate • Twenty-foot island

3D & VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. * The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes. ) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rusti

$1,836,000

4 beds3 baths3,142 sq ft

1016 Howell Branch Rd, Winter Park, FL 32789

Canal front oasis • New boathouse • Outdoor living area

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen Fre

$995,000

2 beds2.5 baths1,459 sq ft

219 Quayside Cir Unit B9, Maitland, FL 32751

Connected lakes • Historic canals • Dedicated boat slip

Property at 1745 E Adams Dr, Maitland, FL 32751, 4 beds, 3.5 baths

$1,200,000

4 beds3.5 baths2,378 sq ft

1745 E Adams Dr, Maitland, FL 32751

Property at 791 Sequoia Trl, Maitland, FL 32751, 5 beds, 3.5 baths

$1,299,000

5 beds3.5 baths4,144 sq ft

791 Sequoia Trl, Maitland, FL 32751

Property at 604 Minnehaha Ln, Maitland, FL 32751, 6 beds, 5.5 baths

$2,895,000

6 beds5.5 baths6,163 sq ft

604 Minnehaha Ln, Maitland, FL 32751

Property at 1525 Granville Dr, Winter Park, FL 32789, 5 beds, 5.5 baths

$4,750,000

5 beds5.5 baths5,211 sq ft

1525 Granville Dr, Winter Park, FL 32789

Property at 1640 E Adams Dr, Maitland, FL 32751, 5 beds, 6.5 baths

$10,950,000

5 beds6.5 baths8,174 sq ft

1640 E Adams Dr, Maitland, FL 32751

Property at 1416 Caring Ct, Maitland, FL 32751, 4 beds, 3.5 baths

$925,000

4 beds3.5 baths3,451 sq ft

1416 Caring Ct, Maitland, FL 32751

Property at 755 Cranes Ct, Maitland, FL 32751, 5 beds, 4.5 baths

$1,419,000

5 beds4.5 baths4,566 sq ft

755 Cranes Ct, Maitland, FL 32751

Property at 2550 Venetian Way, Winter Park, FL 32789, 4 beds, 4 baths

$2,499,000

4 beds4 baths4,875 sq ft

2550 Venetian Way, Winter Park, FL 32789

Property at 255 W George Ave, Maitland, FL 32751, 5 beds, 4 baths

$1,700,000

5 beds4 baths4,814 sq ft

255 W George Ave, Maitland, FL 32751

Property at 1451 Lyndale Blvd, Winter Park, FL 32789, 6 beds, 4 baths

$1,999,993

6 beds4 baths3,853 sq ft

1451 Lyndale Blvd, Winter Park, FL 32789

Property at 125 Whitecaps Cir, Maitland, FL 32751

$2,995,000

— beds— baths— sq ft

125 Whitecaps Cir, Maitland, FL 32751

Property at 1250 N Maitland Ave, Maitland, FL 32751

$3,990,900

— beds— baths— sq ft

1250 N Maitland Ave, Maitland, FL 32751

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NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Under Construction. Location, location, location! Nestled in Winter Park, this home is convenient to the best in shopping, dining and entertainment! The two-story Easterly design hosts four bedrooms, four full bathrooms, one half baths, study and sits on an oversized homesite. The open concept living area flows beautifully from the family room and dining room to the kitchen with laminate floors throughout. The owner’s retreat offers privacy, a HUGE walk-in closet with extra storage and a luxurious master bath with free standing tub, shower and dual sinks. The first floor also has a secondary bedroom and full bath that would serve perfectly as a private guest room. Upstairs features a

$1,450,000

4 beds4.5 baths3,565 sq ft

1807 Yorkshire Dr, Winter Park, FL 32792

Oversized homesite • Huge walk-in closet • Private guest room

3D & VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with its own bathroom and kitchenette. The home features original hardwood and vinyl flooring throughout, high vaulted ceilings, and an open floor plan designed for both comfort and entertaining. The family room and kitchen overlook the covered lanai, oversized pool, and spacious, private backyard. Fren

$2,490,000

5 beds4 baths3,948 sq ft

1205 Mayfield Ave, Winter Park, FL 32789

In-law suite • Open floor plan • Double lot

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Welcome to this stunning former Charles Rutenberg model home, perfectly situated on one of the largest lots in the highly desirable Prima Vera Cove enclave in the Spring Valley community. Set on . 83 acres, this beautifully maintained residence offers 5 bedrooms, 4 full baths, a dedicated office (or 6th bedroom), and a spacious upstairs great room, providing flexible living for today’s lifestyle. The gourmet kitchen features granite countertops, KitchenAid stainless steel appliances, a double oven, and a charming eat-in area overlooking the pool. Thoughtful upgrades include a propane fireplace, three Nest-controlled AC systems, PVC and copper plumbing, new water heaters, and ceiling f

$1,350,000

5 beds4 baths4,899 sq ft

354 Prima Vera Cv, Altamonte Springs, FL 32714

Screened pool • Gourmet kitchen • Rv pad

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets. " This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design elements with contemporary sophistication—indoors and out. Step into an open-concept layout bathed in natural light that highlights generous room sizes and thoughtful transitions from space to space. The welcoming foyer flows into a great living area and gourmet kitchen featuring a premium Thermador appliance package, including

$1,750,000

3 beds4.5 baths3,164 sq ft

1630 Chestnut Ave, Winter Park, FL 32789

Commercial gas range • Spa-inspired bath • Gourmet kitchen

NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
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

$975,000

3 beds3 baths1,875 sq ft

870 Carver St, Winter Park, FL 32789

Spa-style bath • Private entrance • Fully fenced yard

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Maitland, FL:
Experience resort-style living every day in this stunning Meritage Homes masterpiece, perfectly situated on a premium waterfront lot in the highly sought-after Water’s Edge section of Hawk’s Crest. This elegant home offers breathtaking pond and fountain views, especially enchanting at sunset, and an unparalleled combination of luxury, comfort, and energy efficiency. Step into your private outdoor oasis featuring a custom screened, saltwater, self-cleaning pool and spa with electric heat, LED color-changing lights, and an illuminated screen enclosure that creates an unforgettable nighttime ambiance. The expanded patio includes a custom outdoor kitchen complete with Quartz counter

$1,195,000

4 beds3 baths3,057 sq ft

1092 Wading Waters Cir, Winter Park, FL 32792

Custom screened pool • Waterfront lot • Dedicated office

Property at 2412 Chantilly Ave, Winter Park, FL 32789, 5 beds, 6.5 baths

$2,350,000

5 beds6.5 baths4,506 sq ft

2412 Chantilly Ave, Winter Park, FL 32789

Property at 1885 Temple Dr, Winter Park, FL 32789, 5 beds, 3.5 baths

$2,295,000

5 beds3.5 baths3,691 sq ft

1885 Temple Dr, Winter Park, FL 32789

Property at 1245 Wading Waters Cir, Winter Park, FL 32792, 4 beds, 3 baths

$1,065,000

4 beds3 baths3,050 sq ft

1245 Wading Waters Cir, Winter Park, FL 32792

Property at 210 Laurel Park Ct, Winter Park, FL 32792, 4 beds, 3 baths

$950,000

4 beds3 baths2,838 sq ft

210 Laurel Park Ct, Winter Park, FL 32792

Property at 1401 Green Cove Rd, Winter Park, FL 32789, 3 beds, 5.5 baths

$2,900,000

3 beds5.5 baths5,483 sq ft

1401 Green Cove Rd, Winter Park, FL 32789

Property at 2299 Via Tuscany, Winter Park, FL 32789, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,986 sq ft

2299 Via Tuscany, Winter Park, FL 32789

Property at 550 Palmer Ave, Winter Park, FL 32789, 5 beds, 6.5 baths

$7,200,000

5 beds6.5 baths5,939 sq ft

550 Palmer Ave, Winter Park, FL 32789

Property at 607 Ellen Dr, Winter Park, FL 32789, 4 beds, 4 baths

$1,630,000

4 beds4 baths2,812 sq ft

607 Ellen Dr, Winter Park, FL 32789

Property at 1861 Taylor Ave, Winter Park, FL 32789, 5 beds, 6 baths

$1,925,000

5 beds6 baths3,116 sq ft

1861 Taylor Ave, Winter Park, FL 32789

Property at 1302 Raintree Pl, Winter Park, FL 32789, 5 beds, 5.5 baths

$5,300,000

5 beds5.5 baths4,738 sq ft

1302 Raintree Pl, Winter Park, FL 32789

Property at 2001 Lake Dr, Winter Park, FL 32789, 5 beds, 4 baths

$2,165,000

5 beds4 baths4,798 sq ft

2001 Lake Dr, Winter Park, FL 32789

Property at 1540 Palm Ave, Winter Park, FL 32789, 5 beds, 3.5 baths

$1,999,000

5 beds3.5 baths3,423 sq ft

1540 Palm Ave, Winter Park, FL 32789

Property at 825 Palmer Ave, Winter Park, FL 32789, 3 beds, 3 baths

$1,799,000

3 beds3 baths3,297 sq ft

825 Palmer Ave, Winter Park, FL 32789

Property at 1166 Oaks Blvd, Winter Park, FL 32789, 4 beds, 3.5 baths

$1,649,999

4 beds3.5 baths2,860 sq ft

1166 Oaks Blvd, Winter Park, FL 32789

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Luxury Homes for Sale in Maitland

There are currently 17 luxury homes for sale in Maitland at a median listing price of $429K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Maitland stay on the market for 63 days and receive 3 offers. Popular neighborhoods include Spring Valley, Kingswood Manor, and Downtown Maitland. This map is refreshed with the newest listings in Maitland every 15 minutes.

In the past month, 26 homes have been sold in Maitland. In addition to houses in Maitland, there were also 44 condos, 9 townhouses, and 1 multi-family unit for sale in Maitland last month. Find your dream home in Maitland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Maitland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Maitland. Our Maitland real estate stats and trends will give you more information about home buying and selling trends in Maitland. If you're looking to sell your home in the Maitland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Maitland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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