20 listings found
1640 E ADAMS DRIVE
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 5 Bath · 3 Half Baths · 8,174 SqFt · $1,340/SqFt
Days on Market: 230
County: Orange
Legal Subdivision Name: ADAMS GROVE
Year built: 1991
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.86
Behind private gates along the shores of Lake Maitland, this elegant Mizner-style Mediterranean estate offers an extraordinary opportunity to own a timeless lakefront masterpiece on the Winter Park Chain of Lakes. Encompassing approximately two acres of meticulously manicured grounds framed by soaring palms and mature live oaks, this exceptional property blends classic architecture with state-of-the-art amenities and modern luxury. Originally built with uncompromising craftsmanship and fully renovated in recent years, the home’s interiors, designed by Ted Maines, exude sophistication, featuring curated high-end finishes, custom built-ins, and designer lighting throughout. The main house offers 6,634 square feet while the detached media ... Read more....»
604 MINNEHAHA LANE
MAITLAND FL 32751
Residential / Single Family Residence
6 Bed · 5 Bath · 1 Half Bath · 6,163 SqFt · $470/SqFt
Days on Market: 147
County: Orange
Legal Subdivision Name: PACKWOODS PLAN/MAITLAND
Year built: 2006
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown ... Read more....»
105 TANGELO COURT
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,203 SqFt · $562/SqFt
Days on Market: 15
County: Orange
Legal Subdivision Name: HOLLIEANNA SHORES
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and ... Read more....»
255 W GEORGE AVENUE
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 4 Bath · 4,814 SqFt · $353/SqFt
Days on Market: 215
County: Orange
Legal Subdivision Name: REPLAT BLK B POORS ADD
Year built: 2007
Garage: Yes 2 vehicles
Private Pool: Yes
Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative stone accents, and a charming fountain, creating an inviting first impression. The grand foyer welcomes you with soaring ceilings, intricate wrought iron railings, and abundant natural light. The Great Room is designed for both comfort and style, featuring expansive windows, French doors that open to the backyard oasis, and concert speakers embedded in the ceiling ... Read more....»
755 CRANES COURT
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 4,566 SqFt · $311/SqFt
Days on Market: 249
County: Orange
Legal Subdivision Name: LAKE SYBELIA COVE
Year built: 2009
Garage: Yes 3 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. NEW PRICE! Discover your private oasis in the heart of Maitland, perfectly tucked away on a quiet cul-de-sac within an exclusive gated enclave of only 19 custom homes. Ideally positioned between Lake Sybelia and Lake Catherine, this one-owner estate blends timeless sophistication, modern comfort, and exceptional livability. With five spacious bedrooms, four-and-a-half baths, and a three-car garage, the home showcases soaring ceilings, elegant architectural details, and an open, flexible layout designed for today’s lifestyle. The gourmet kitchen features solid wood cabinetry, a large island, new refrigerator, walk-in pantry, and dual breakfast bars ... Read more....»
67 CYPRESS LANE
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 3 Bath · 2,292 SqFt · $584/SqFt
New Listing!!! Days on Market: 1
County: Orange
Legal Subdivision Name: MAITLAND SHORES
Year built: 1979
Garage: Yes 2 vehicles
Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the ... Read more....»
1421 SUNNYSIDE DRIVE
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,116 SqFt · $614/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: MAITLAND PARK SOUTH
Year built: 1966
Garage: Yes 2 vehicles
Private Pool: Yes
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 ... Read more....»
791 SEQUOIA TRAIL
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 4,144 SqFt · $313/SqFt
Days on Market: 53
County: Orange
Legal Subdivision Name: DOMMERICH WOODS
Year built: 1961
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, ... Read more....»
1619 DRUID ROAD
MAITLAND FL 32751
Residential / Single Family Residence
5 Bed · 4 Bath · 3,769 SqFt · $252/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: DRUID HILLS
Year built: 1958
Garage: Yes 2 vehicles
Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residence offers the kind of flexibility—and lifestyle—that’s hard to find and even harder to forget. With 5 bedrooms and 4 full baths, this meticulously cared-for property is designed to fit real life beautifully: a 4-bedroom, 3-bath main home, plus a private 1-bedroom, 1-bath apartment with a brand-new kitchen and its own separate entrance—perfect for guests, multi-generational living, a home office suite, or income potential. Step inside and feel the difference immediately. Freshly painted and thoughtfully updated, the home shines with new flooring, new lighting with sleek LEDs, and a layout ... Read more....»
1416 CARING COURT
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,451 SqFt · $268/SqFt
Days on Market: 56
County: Orange
Legal Subdivision Name: ENCLAVE/MAITLAND A-F
Year built: 2006
Garage: Yes 2 vehicles
Community Pool: Yes
Beautifully maintained Maitland home in the gated community of Montacino on Lake Charity. Conveniently located near Maitland City Center, Park Ave, Downtown Orlando, and RDV Sportsplex. Engineered hardwood floors lead from the entry to a formal living and dining room, powder bath, and into the great room with soaring ceilings open to the kitchen and patio. The gourmet kitchen features custom cabinetry, granite countertops, and stainless appliances. The first-floor owner’s suite offers French door access to the private patio, custom closets, and a spa-style bath with dual vanities, soaking tub, and walk-in shower. Upstairs, find three additional bedrooms (one ensuite) ... Read more....»
183 ORANGE PLACE
MAITLAND FL 32751
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,014 SqFt · $397/SqFt
Days on Market: 96
County: Orange
Legal Subdivision Name: ORANGEDALE PARK
Year built: 2018
Garage: Yes 2 vehicles
HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive, you’ll sense the refined lifestyle within. soaring ceilings, abundant natural light, and premium finishes throughout. The chef’s kitchen is a showpiece sleek cabinetry, stone countertops, and top-tier appliances. Entertain effortlessly with open living spaces that flow seamlessly to ... Read more....»
1100 WILLOWBROOK TRAIL
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 3 Bath · 2,964 SqFt · $236/SqFt
Days on Market: 76
County: Orange
Legal Subdivision Name: MAITLAND WOODS
Year built: 1966
Garage: Yes 2 vehicles
Incredible Opportunity to create your own dream home in the coveted Lake Sybelia / Maitland Woods neighborhood !! Spacious, One Story Living in this 4 bedroom, 3 bathroom home. Located just steps from Lake Sybelia Park. Convenient to I-4, Maitland Center, Winter Park, Altamonte Springs and downtown Orlando. After decades of being the stage for shared love and great family memories, this home is being offered to the market for the first time since 1974 - and offers the opportunity to make it your own for decades to come. Large living spaces including a kitchen with gas Viking range, additional ... Read more....»
1511 E HORATIO AVENUE
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 3 Bath · 2,676 SqFt · $262/SqFt
Days on Market: 31
County: Orange
Legal Subdivision Name: MINNEHAHA SHORES
Year built: 1957
Garage: No
Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Lease Purchase available with a downpayment. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept living area, featuring high ceilings and abundant natural light. The gourmet kitchen boasts quartz countertops, new appliances, and ample cabinet space, ideal for culinary enthusiasts. The adjoining dining area is perfect for entertaining guests or enjoying family meals. The master suite is a true ... Read more....»
708 THUNDER TRAIL
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 2 Bath · 1,907 SqFt · $333/SqFt
Days on Market: 59
County: Orange
Legal Subdivision Name: DOMMERICH HILLS SECOND ADD
Year built: 1964
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to 708 Thunder Trail in beautiful Maitland, Florida — a stunning 4-bedroom, 2-bath pool home nestled in the sought-after Dommerich neighborhood, with NO HOA! This charming single-story residence perfectly blends mid-century character with modern updates, featuring polished TERRAZZO FLOORS, an open and airy layout, and a bright living and dining area that flows seamlessly into a cozy family room with a wood-burning fireplace. The updated kitchen impresses with custom cabinetry, QUARTZ countertops, an LG Refrigerator, Bosch dishwasher, Bosch slide in glass top range with an island chimney vent hood, plus a Kohler farm sink. Both bathrooms have been tastefully ... Read more....»
1447 CARING COURT
MAITLAND FL 32751
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,110 SqFt · $296/SqFt
Days on Market: 25
County: Orange
Legal Subdivision Name: ENCLAVE/MAITLAND A-F
Year built: 2006
Garage: Yes 2 vehicles
Beautiful move-in ready home in the highly sought-after gated community of Montacino, located in the heart of Maitland. This single-story Mediterranean inspired home boasts three spacious bedrooms, including the grand Primary bedroom suite with its private spa-inspired bathroom with a jacuzzi tub, another inviting full bathroom, a convenient half bath, and a separate office or den great for remote work or hobbies. The split plan allows for plenty of privacy and includes a formal dining room, a chef's kitchen with a spacious eat-in area overlooking the gorgeous family room with a gas-ready fireplace, which leads to the peaceful screened-in back ... Read more....»
1024 KEWANNEE TRAIL
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 1,845 SqFt · $322/SqFt
Days on Market: 141
County: Orange
Legal Subdivision Name: DOMMERICH HILLS 3RD ADD
Year built: 1965
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Appliances and granite counters. Thoughtful upgrades at every turn. Currently zoned for Winter Park HS. Close to everything that Maitland and Winter Park known for, shopping dining and more. Don’t wait, come see today.
1695 E HORATIO AVENUE
MAITLAND FL 32751
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 1,939 SqFt · $273/SqFt
Days on Market: 175
County: Orange
Legal Subdivision Name: DOMMERICH ESTATES 1ST ADD
Year built: 1959
Garage: Yes 2 vehicles
Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, No HOA, Top Rated Shools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House is just revitalized with a new fresh interior Stone Eagle Color Paint, Roof replaced in 2024, AC replaced in 2022, Exterior repainted in 2022, and plumbing repipe in 2019. House had tile throughout interior floor. Schedule to view this wonderful home.
731 BUCHER ROAD
MAITLAND FL 32751
Residential / Single Family Residence
3 Bed · 1 Bath · 1 Half Bath · 1,523 SqFt · $279/SqFt
Days on Market: 103
County: Orange
Legal Subdivision Name: BUCHER HGTS
Year built: 1960
Garage: Yes 2 vehicles
Welcome! This well-maintained ranch-style home features a functional single-level design with a newer roof (2024) encompassing 1,523 square feet of living space, with an additional 255 square feet of expanded living space in the enclosed Florida Room to enjoy. The main living area includes three bedrooms and one and a half baths. a stunning kitchen (remodeled 2025), open floor plan, cozy Florida Room, and vinyl fenced backyard provide the perfect background to enjoy every day and a versatile space to accommodate your needs, and ideal for entertaining guests. Additional updates include a new HVAC system (2023), along with complete ... Read more....»
1033 HAMLET DRIVE
MAITLAND FL 32751
Residential / Single Family Residence
3 Bed · 2 Bath · 1,146 SqFt · $305/SqFt
Days on Market: 26
County: Orange
Complex/CommunityName: HAMLET AT MAITLAND
Legal Subdivision Name: HAMLET AT MAITLAND
Year built: 1994
Garage: Yes 1 vehicles
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 ... Read more....»
1074 HAMLET DRIVE
MAITLAND FL 32751
Residential / Single Family Residence
3 Bed · 2 Bath · 1,076 SqFt · $286/SqFt
Days on Market: 104
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: HAMLET AT MAITLAND
Year built: 1994
Garage: Yes 1 vehicles
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a fully fenced lot with durable vinyl fencing, offering both privacy and a secure space for pets or play. Just beyond your backyard, enjoy direct access to a public playground—an ideal setup for families or anyone who loves being outdoors without losing the comfort ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
