Maitland Houses for Sale

Welcome to Versailles, where timeless architecture meets everyday ease just steps from the shimmering waters of Lake Minnehaha. This beautifully updated home offers peace of mind with a NEWER ROOF, 4-year-old HVAC, NEW IRRIGATION SYSTEM and APPLIANCES approximately 5 years old. Inside, the thoughtfully designed split floor plan ensures privacy for the primary suite, while elegant formal living

Nicole Dege REDFIN CORPORATION

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

Brad Young HOMEVEST REALTY

One or more photo(s) has been virtually staged. Mortgage savings may be available for buyers of this listing. Welcome to this beautifully updated single-family home in the heart of Maitland, offering 3 bedrooms, 1 bathroom, and 1,848 square feet of comfortable living space. Set on over a quarter of an acre, this property blends modern upgrades with everyday functionality. From the moment you

David Zambrano REDFIN CORPORATION

Rates have DROPPED and with the FREE 1 year interest rate buy down, it's time to BUY. This four-bedroom, two-bath, split-floor plan home is move-in ready and ready for your personal touches. The home offers a large living room, open floor plan kitchen and den all with soaring ceilings. The fourth bedroom is in front of the house and is great for a home office or guest bedroom. The Winfield

Erik Baum PREMIER SOTHEBYS INT'L REALTY

Classic Colonial Brick Home on highly desired E Adama Drive across from Lake Maitland! 4 bedrooms, 4 Baths, 2 fireplaces-one in Primary bedroom! Full 2nd floor balcony porch with French doors! Terrific home for entertaining! Formal Dining room across from Formal Living room connected by large foyer! Family room/Library with built in shelves on both ends with wood burning fireplace! French

Carolann Flesch EXP REALTY LLC

Welcome to 1630 Chinook Trail, a fully renovated custom patio-style home making its market debut. Designed by builder Phil Kerr and architect Alan Berman, this home features French doors from nearly every room opening to a sparkling pool. Inside you’ll find 3 bedrooms plus a den, guest suite with walk-in closet and ensuite bath, and a 4th bedroom converted into a spacious master closet that can

Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

A fantastic 4-bedroom, 2.5-bath home with an office/flex space, located on a prime interior lot in the established Maitland Groves neighborhood. Major systems updated with a 40-year architectural roof (2013), Plumbing Re-pipe (2019); New windows and sliding doors (2023); Newer carpet in bedrooms; HVAC/AC (2006 with New Air Handler Blower Motor (Sept. 2025)), water heater (2008), and a whole-house

Vincent Scarlatos CORCORAN PREMIER REALTY

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 apeaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and

David Van Wormer VANWORMER REALTY & DEVELOPMENT

A mid century modern inspired ranch offers a special location just a block from the school with a walking path behind providing a unique lifestyle for this special home. Natural Coquina stone accents are the focal point of the exterior elevation with seamless windows that allow incredible light in and are in keeping with the architecture of the era. This 4-bedroom 2 bath home was thoughtfully

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

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

Richard Palmano PALMANO GROUP RE BROKERAGE LLC

Lakefront Dommerich pool home in one of Central Florida’s most coveted school zones! This 4-bedroom, 2.5-bath beauty offers nearly 3,000 sq. ft. of spacious living, zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Enjoy a private pool, stunning lake views, and plenty of space to gather, entertain, and relax—right in the heart of one of Maitland’s most desirable

TOM NOELKE EXP REALTY LLC

Nestled on a quiet, tree-lined cul-de-sac and a short walk to A rated Dommerich Elementary school, this well-maintained 4 bedroom, 3.5 bath pool home in the desired neighborhood of Cove Colony offers 3,115 sq ft of well-designed living space on a spacious .41-acre lot. From the moment you arrive, you are greeted by a vaulted entrance and sparkling fountain that sets a tone of elegance and

Megan Cross FANNIE HILLMAN & ASSOCIATES

One or more photo(s) has been virtually staged. Discover family living at its finest in one of Maitland’s most desirable neighborhoods. This renovated pool home sits on an oversized lot near Lake Sybelia, offering a spacious layout, designer upgrades, and a fenced backyard oasis. Walk to the Maitland Farmers Market and Lake Lily Park for community events and outdoor fun, with Winter Park and

Martha Leighton MIHOUSE REALTY LLC

Welcome to 1073 Hamlet Drive—an updated 3-bedroom, 2-bathroom block home with over 1,000 square feet of comfortable living space, a 1-cargarage, and a prime location in the highly sought-after community of Hamlet at Maitland. From the moment you step inside, you'll be greeted byvaulted ceilings, an abundance of natural light, and an open floor plan that’s ideal for entertaining. The

Wendy Jane MacAnthony ELEGANT REALTY LLC

Distinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcome to this truly unique residence in the highly desirable Dommerich Hills neighborhood, where character, thoughtful updates, and a versatile layout come together to create the ideal setting for modern living. Perfectly situated just minutes from Winter Park and Maitland—and zoned for Dommerich Elementary,

Brian Rotenberger COMPASS FLORIDA LLC

Welcome! This well-maintained ranch-style home features a functional single-level design with a newer roof (2024) encompassing 1,404 square feet of living space, including three bedrooms and one and a half baths. The 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

Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Build Your Dream Home in Prime Maitland Location! A rare opportunity awaits at 1550 Ridgewood Avenue — located just steps from the Enzian Theater, Park Maitland School, and minutes from Whole Foods Market. Zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High School, this property offers the perfect foundation for your next custom build. With a lot size of 77'

Justin Pekarek ORLANDO PROPERTY ADVISORS

Welcome to this beautifully renovated 3 bedroom, 2 bathroom home with 1,306 square feet of living space, perfectly situated on a spacious .15-acre lot in Maitland. From the moment you arrive, you’ll love the gorgeous curb appeal, manicured landscaping, and two-car garage. Step inside to find brand-new luxury vinyl plank flooring flowing throughout. The modern kitchen boasts stainless steel

Julian Jackson LOKATION

Showpiece Charles Clayton Home in Gated Lake Colony EstatesEvery detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort.Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek

David Plasencia COLDWELL BANKER RESIDENTIAL RE

Private setting within the exclusive Lake Maitland Owl Preserve, this spectacular five-bedroom contemporary residence was masterfully built in 2019 by award-winning E2 Homes. A dramatic 12-foot-tall wooden pivot-door makes a striking first impression, opening into a light-filled foyer, gathering, dining, and kitchen wide-open everyday living area with soaring two-story ceilings. A floating

Mick Night PREMIER SOTHEBY'S INTL. REALTY

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

Dominick Florio RE/MAX TOWN & COUNTRY REALTY

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.

Patrick D'Agostino GLORY INTL. REAL ESTATE CO

Nestled on a spacious corner lot in the highly sought-after Dommerich/Highland Park neighborhood, this distinctive two-story Mid-Century home offers both character and flexibility. With 5 bedrooms and 3 full baths, the layout is ideal for multigenerational living or accommodating guests with ease. Upstairs, the 5th bedroom serves as a private in-law suite, complete with a walk-in closet, full

John Forrester KELLER WILLIAMS REALTY AT THE PARKS

This 4-bedroom, 2-bath corner-lot home in the sought-after Dommerich neighborhood blends mid-century charm with thoughtful updates and room to grow. Set on a .27-acre lot with mature landscaping, a brick-paved walkway, and an oversized driveway, this home offers easy curb appeal and a warm welcome.Inside, vaulted ceilings, exposed beams, and large windows fill the living spaces with

Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

Welcome to your Lakefront Gem at Lake Lovely Estates!This fully remodeled 3 bedroom, 2 bathroom home on .54 acres is the epitome of modern lakefront living! Step directly into high-end finishes that elevate every corner of this privately fenced retreat. The newly updated kitchen dazzles with sleek quartz countertops, stainless steel appliances, and abundant cabinetry. Waterproof

Laura Heidrich COLDWELL BANKER RESIDENTIAL RE

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

Tuan Nguyen VISTA REALTY INVESTMENT

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

Mick Night PREMIER SOTHEBY'S INTL. REALTY

One or more photo(s) has been virtually staged. Welcome to 2171 Chippewa Trail—a beautifully maintained 4-bedroom, 3-bathroom pool home located in the highly sought-after Dommerich Hills neighborhood. This spacious residence offers 2,218 square feet of living space and features a brand-new roof and an abundance of natural light streaming through large windows throughout the home.Step into

Freddy DeCoster GOYAL & DECOSTER REALTY

One or more photo(s) has been virtually staged. Welcome to a private oasis in the heart of Maitland tucked away on a quiet cul-de-sac in an exclusive gated community of just 19 custom homes. This one-owner estate offers a blend of elegance, space and serenity between picturesque Lake Sybelia and Lake Catherine. This five-bedroom, four-and-a-half-bath pool home with a three-car garage sits on an

Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland.Blending classic

Maggie Walas FORTUNE INTERNATIONAL REALTY

This beautifully maintained three-bedroom, two-bath residence features an inviting open floor plan, perfect for both entertaining and everyday living. Recently painted with a fresh interior, the home radiates warmth and brightness throughout. Enjoy modern comforts with a brand-new air conditioning system installed just six months ago, ensuring a cool and comfortable atmosphere year-round. The

Bianca Botelho RE/MAX ASSURED

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

Peter Luu REAL BROKER, LLC

ACTIVE on the Market – Enhanced and Priced to Sell!Custom built in 2003 and secluded in an exclusive enclave of only six exquisite luxury homes, this 5-bedroom, 4.5-bath Mediterranean-style residence offers privacy, elegance, and an exceptional indoor-outdoor lifestyle. Designed around a stunning courtyard with sparkling pool, tropical landscaping, and outdoor lighting, almost every room on

Sandi Peery RE/MAX TOWN & COUNTRY REALTY

*2.99% Assumable Mortgage Rate Available* Welcome to 2031 Eaton Street, a modern haven with fresh exterior paint (Aug. 2025) just moments from the heart of Eatonville with no HOA! This renovated gem boasts 4 oversized bedrooms, 3 full bathrooms, and a sprawling 2518 square feet of living space on a 9,998 square foot double lot. Step inside to discover a spectacular open floor plan with new

Marcie Gumieny COMPASS FLORIDA LLC

Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests in Maitland bordering Winter Park. This home is a piece of history with character but in need of some TLC. Beautifully arched high ceiling along with a fireplace in the formal living room. The Florida room is surrounded by glass sliding doors that open to a wooden patio with French doors, countless windows,

Darryl Donkel HOME WISE REALTY GROUP, INC.

Under Construction. Exquisite One-Story Pool Home with Summer Kitchen | Over 3,200 SF of Luxury Living in beautiful Maitland on an oversized lot!Impeccably designed and ideally located, this stunning single-story estate offers luxurious and refined living space with 4 bedrooms, 3 full baths, 2 half baths, and a private study. The open floor plan showcases rich wood flooring throughout,

Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION