Maitland Homes For Sale

Boasting modern Hacienda-style architecture and 280 feet of lakefront on Lake Maitland, this gorgeous 3.24 acre gated residence offers nearly 14,000 total square feet. An...

2019 NEW CONSTRUCTION MODERN FARMHOUSE LOCATED ON LAKE MAITLAND THE LARGEST OF ALL THE WINTER PARK CHAIN OF LAKES. THOUGHTFULLY DESIGNED WITH LUXURY ENTERTAINING AND WATE...

Lovely French Provincial estate on the Winter Park chain of lakes. This 5 BD/4 BA/2.5 BA home was extensively remodeled in 2013 by Posada Custom Homes. Beautiful well-e...

Just Reduced! Absolutely stunning, private lakefront estate on the shores of Lake Minnehaha. Tucked away, off a quiet street, this gated estate home features gorgeous pa...

Divine details in this stunning Coastal style home with exposed rafter tails & metal roof nestled on Lake Sybelia’s eastern shoreline. A completely new interior with luxu...

A rare gem in a private setting on the famed WINTER PARK CHAIN OF LAKES awaits your move! Situated on a no-outlet lane, this beautiful LAKEFRONT ESTATE boasts unexpected ...

Beautiful Winter Park Chain of Lakes Home on Lake Minnehaha - one of the best kept secrets on the Chain benefiting from less transient boaters & a slalom run! Almost 1-a...

Gracious Lakefront Home has 2 Master Suites, 5 additional bedrooms and 5 bathrooms, and a separate entrance to the IN-LAW/NANNY suite or Office! Large chef’s kitchen, gen...

ALMOST HALF ACRE (20823 sq ft) HIGH AND DRY featuring 180 ft of picturesque shoreline on Lake Maitland, largest of the Winter Park Chain of Lakes! This move in ready home...

Get to know Lake Sybelia Dr. Situated on 2.77 acres with private water frontage on Lake Sybelia. This house is set behind gates, with an oversized circular driveway in ...

Luxurious lakefront living is featured in this stunning, transitional style, well-maintained pool home with tile roof in the desirable & exclusive Stonehill neighborhood....

Introducing one of Maitland's HOTTEST & EXCLUSIVE properties. Driving into this premier gated community, you are welcomed by the enchanting canopy of trees that lead to y...

Elegance, style and sophistication! Stunning Custom Dave Cahill Homes Masterpiece! Gorgeous modern, light and bright with full in-law apartment and picturesque fountain g...

Traditional Dommerich Elementary home with an open floor plan has it all! Sitting on over 1/3 acre, the 4,110 SF home has large, open living spaces with a downstairs bonu...

One or more photo(s) has been virtually staged. Gorgeous new listing in Maitland’s gated community of Lake Colony Estates. This 3 bedroom, 3.5 bath home with office has b...

Price Improvement! Picturesque 5 bed / 6 bath plus office including media room, refrigerated wine room and 3 car garage! Highly sought Maitland Forest neighborhood pool h...

A Maitland home like no other in Dommerich on .37 acres, a lot and 1/2, and sidewalk to the schools - a truly perfect location. 5-bed split plan plus in-law suite, that c...

Under Construction. Under Construction / New construction – 2 townhouses in beautiful Maitland FL / Winter Park / Park Avenue. This first custom-built energy efficient lu...

Fantastic home seeks a new owner who has an appreciation for unique architecture, open floor plans, upgrades and loves entertaining. Step through the double entry doors t...

BEAUTIFULLY UPDATED 3 WAY SPLIT PLAN EXECUTIVE HOME IN KINGS ROW The owners spared no expense with the high-end renovations in this home. Entering the home through the ...

Price just reduced!!! Pam Niemann designed 2012 Parade of Homes "FIRST PLACE" winner for kitchen reno. Upon entering the open foyer you will note floating angular marble...

WELCOME TO KINGS ROW - One of Maitland’s most sought after neighborhoods. This spacious four bedroom, three full bath pool home is situated on an oversized lot. The large...

The quintessential lake house experience on 90' of refreshing, spring-fed, Lake of the Woods! Magnificent Lakefront Retreat that's been thoughtfully updated with the fine...

This Stunning Modern Traditional Estate Home is located in the Exclusive Hidden Estates Subdivision. Boasting over four thousand square feet, this Spacious Single Story H...

Don't miss out on this beautiful home in sought after Maitland/Winter Park area! This home with its charming coastal cottage exterior opens up to 2596 square feet and fee...

Gorgeous brick front home located in sought after Dommerich! Nestled on an oversized .35 acre lot, this 4 Bedroom 3 ½ Bath has it all! Step inside of this gorgeous home a...

This gorgeous, split plan, custom pool home is conveniently located in Maitland's best-kept-secret neighborhood where every street is a cul-de-sac and a community park is...

This beautiful four bedroom pool home is located in the exclusive Stonehill neighborhood just off Maitland Blvd. and minutes to I-4, Maitland Exchange, Winter Park Villag...

EXCELLENT LOCATION Beautiful spacious one story home on corner lot. All Floors, Bathrooms, and Bedrooms have been updated. New Air Conditioning Unit. Spacious Kitchen ...

MAITLAND LAKEFRONT OPPORTUNITY! BUILD NEW or REMODEL EXISTING RANCH with a SPLIT FLOOR PLAN. This property is located in a quiet neighborhood on a dead end street with ea...

Welcome Home to this Immaculate 4 bedroom/4 bath, Plus Office Pool Home Situated on a Beautiful Oversized Corner Lot! Located in Sought After Maitland Woods with just a ...

LAKE FRONT 4 bedroom, 2 bath home with character in the unique, established Maitland community of Bretton Woods!! This home is located in a beautiful, quiet neighborhood...

Call now... Just updated this June 2019. This stunning home boasts fresh interior paint plus NEW flooring throughout the home (2019), NEW roof (2019), NEW AC on 2nd floo...

Immaculate Executive home in the desired community of Hidden Estates. This 5 Bedroom, 3 full bath home has all the space you have been searching for to enjoy and enterta...

PRICE IMPROVEMENT!!!! on this Updated Dommerich beauty! Nothing left to do here- just bring the family and move right in! The antique brick driveway and new stacked ston...

Wonderful new listing in Dommerich! You must see this very large, 2,600+ SF home featuring 5 bedrooms, 4 full baths, plus an office and an oversized 20x40 pool! The home ...

Maitland Woods subdivision is nestled in the heart of Maitland between I-4 and Hwy 17-92 making it the perfect location with a small-town feel! This beautiful home is in ...

BACK ON THE MARKET! NEW A/C! NEW PRICE! This home has it all! There is a beautiful wrap around pool/patio area for entertaining. There is real brick on the patio and plen...

A Pristine Gem located in Maitland Woods! BIG savings, sprinkler system is on well! This house is very well maintained. With over 2,000 SqFt this Split floorpan offers ve...

This estate home is nestled on nearly a 3/4 acre lot shaded by mature trees, framed by pristinely manicured landscaping, and jeweled by the most luxurious WATERFALL, SALT...

In the heart of Maitland you will find a Quaint Gated Community where your new life begins. This single story residence boasts 3 Bedrooms / 2 Baths plus an Office/Den. An...

***PRICE REDUCED*** No HOA. New roof in 2018, all the bathrooms have been remodeled and the home has wood and tile throughout. This house is in move in condition. This be...

YOU WILL BE IN AWE AFTER SEEING THIS FABULOUS HOME! A GREAT BUY!!! RECENT APPRAISAL (4/21/18) IS $482k, SO LIST PRICE IS NOW $32,500 BELOW THAT APPRAISAL. ACT N...

Beautiful 4 bedroom 2 bath pool home in popular Maitland Woods. Split plan, hardwood floors, large newly refinished pool, new windows, plantation shutter, french doors, b...

Location! Location! Location! Beautiful Mediterranean house with quick access to highway I-4. Close to Winter Park, Downtown Maitland, and Downtown Orlando. Three bedroo...

Gorgeous updated Dommerich home! Shows like a model home! This 3 bedroom/2 Bath Pool/Spa home is MOVE_IN READY! Spectacular kitchen with wood cabinets, ample counter spac...

Mid-century Atomic Ranch home in Druid Hills. This home maintains its original character with re-finished terrazzo floors; stone 3-way fireplace; true-to-period kitchen d...

Beautiful spacious 4 bedroom/ 3 bath Dommerich Pool Home! This 2200 SF home has a three way split plan layout providing plenty of privacy. Large kitchen opens to the Fami...

Price reduction!!! A great opportunity to own in Maitland Woods! Spacious 4 bedroom, 2 & 1/2 bathroom single story pool home nestled in a quiet neighborhood and situated ...

Welcome to the sought-after Maitland Woods community. This 4 bedroom 2.5 bath POOL home offers a beautiful brick elevation giving the home the curb appeal you've been loo...

Amazing LAKEFRONT property in desirable MAITLAND! MILLION DOLLAR VIEWS from entire living area and kitchen! You will enjoy living in this mid-century retro remodeled home...

Now your home! This house is perfectly situated in Dommerich Estates and located on an oversized lot of over 1/3 of an acre. This 4 bedroom, 2.5 bath layout is perfect fo...

$30,000 PRICE REDUCTION...... Welcome to Dommerich Estates, located in Maitland's Historic District! Imagine yourself in this beautiful 3 bedroom 2 bath home that include...

Dommerich Estates charmer that is truly move in ready!! This is the perfect home for your family, located on a quiet street, a block from schools walk and close to Maitla...

Marvelous Maitland Woods beauty just steps from Lake Sybelia! This completely renovated 3-bedroom, 2-bath home features lots of natural light, enhancing its spacious ope...

Put your own spin on this perfectly placed home and make it your own! Located just down the road from Lake Sybelia Elementary. Featuring a spacious master bedroom, formal...

This is the one you have been waiting for located in the very sought after Dommerich area of Maitland! From the moment you get out of your car you can tell how well this...

Pleasant Ranch Style Home located in the beautiful Oakland Shores Neighborhood of Maitland. This 3 bed, 2 bath home boasts an expansive Living Room offering access to eve...

With quiet tree lined streets, we welcome you to this Clayton Custom Home filled with many built-in features such as a wood burning fireplace and large formal dining room...

This Mid-Century immaculately presented beauty is awaiting a family. The four bedroom and two bath, split plan home is ready for move in. This brilliant property, feature...

This meticulously maintained, single story residence in Maitland is detailed with quality finishes throughout. A split floor plan offering three bedrooms, two bathrooms, ...

Re-roof, remodel or rebuild in Maitland/Winter Park. Roof has leaks. Lot size is 85'x130'. Mature tree-lined street with little traffic. Best schools: Dommerich Elementar...

REDUCED DRASTICALLY!! This home is truly a diamond in the ruff nestled in the sought after area of Maitland. It has NO HOA and is COMPLETELY RENOVATED to reflect the lux...

This spacious 3 bed, 2 full bath 1,966 SqFt Dommerich pool home features formal living and dining rooms, a separate family room open to the kitchen, 2 wood burning firepl...

Huge price reduction! This 3 bedroom, 2.1 bathroom pool home is among the largest homes in the desirable Forest Brook community. The garage is converted into an office wi...

Enjoy maintenance free living in this stunning 3BR/2.5BA townhome! This townhome looks brand new, with one owner who has impeccably cared for and updated the home. It is ...

Gorgeous home in desirable Winfield community. You will feel welcomed from the moment you approach the front porch with the high arched window. Step inside and fall in lo...

This truly impressive 4 bedroom 2 bathroom home occupies a prime spot ideally located in the heart of Maitland. Boasting new paint inside and out, this home has an open ...

5 Full Bedrooms / 2 Bathrooms / 2000 sq ft / 2 Car Carport / Large Fenced Yard / 2 Storage Sheds / Beautiful Tree Lot Available For Immediate Occupancy.

Location, Location, Location! In sought after neighborhood of Stonewood. 4 bedrooms, 2 bath ranch includes formal living room, dining room and separate family room plus t...

Located in Maitland's highly sought after community of Forest Brook is this completely remodeled SINGLE STORY 3 bed 2 bath home. This move-in ready house is perfectly sit...

Fully upgraded luxury home. Brand new high end upgrades throughout include; Brand new granite countertops, brand new custom cabinets, brand new hardwood flooring, brand n...

Lovely 3 bedroom 2 bath home in the Dommerich/Highland Park Estates community. The kitchen has nice updates with Corian counter tops, updated light fixtures, breakfast ba...

Location is the first consideration...property is centrally located in Maitland 2-3 MINUTES FROM I-4! And it is in a PRIME LOCATION WITHIN THE COMMUNITY... END-UNIT situa...

Spacious (2337 s/f!) home in established neighborhood with NO HOA. The formal living and dining rooms feature wood parquet floors, crown molding and a wood burning firep...

Stop!! Look no further... This charming 4 bedroom, 2 bathroom Maitland POOL home situated on over a quarter acre lot is just what you have been searching for. As you driv...

Welcome to **English Estates** in Maitland!! Gorgeous, tastefully updated **pool home**. You will not have to do anything to this 3 bedroom 2 bath home. The kitchen opens...

Come and see this quaint, move in ready 3 bedroom 2 bath split floor plan home in the Heart of Maitland. If you want to live in walking distance to the commuter Sunrail S...

Location! Location! Location! This wonderfully established and highly sought after quiet community is centrally located to get to Orange and Seminole Counties easily wi...

Don't miss out on this thoughtfully renovated Maitland bungalow. From the craftsman touches and white brick fireplace sitting room & library to the spacious galley kitche...

New Price, Great home for Entertaining! This 3 bedroom, 2 bath home is located in the heart of English Estates in Maitland. The exterior was painted in 2015, a remodeled...

This home is upgraded with newly installed windows and HVAC system. As you enter the home there is a formal foyer w/seating area, formal dining and living room combo with...

Beautiful Mediterranean-style townhouse located in the gated community of Enclave at Maitland, situated with serene views of Lake Charity. The huge kitchen has granite an...

Don’t miss your opportunity to buy this beautiful block home! Hardwood floors throughout, 3 bedrooms, 2 full baths, 2 car garage, garden tub, and a bonus room. Ceramic ti...

Come see this beautiful family home in the desirable city of Maitland. This home boasts 4 bedrooms, 2 baths, a formal dining room, large family room, and a refreshing 12,...

This is a Beautiful Park Maitland Gated Townhome in a Very Sought after Community of Seminole County. This home has been UPGRADED throughout starting with Travertine tile...

Enjoy maintenance free living in this stunning 3 bedroom, 2 1/2 bath town home! The many interior features include plantation shutters, tile and wood floors, 42" Wood ca...

Mid-Century Modern with a Twist!PROPERTY: This is a fixer-upper in-progress property. Due to significant interest in property, Seller is willing to entertain offers prior...

CASH ONLY! Investor Special. BRING FLASHLIGHT - NO POWER ON - Double lot home with 3 bedroom 2 bath 2 car garage with large pool and tennis court. Lots of possibilities ...

What a CHARMER! A beautiful MID-CENTURY 3 bedroom 2 bathroom house in the heart of MAITLAND is ready for YOU to call it HOME! This home, situated on an oversized lot, h...

This lovely 3 bedroom 2 bath split plan home is designed for entertaining. It has a 25' x 14' Florida Room which overlooks a lush fenced back yard and has a custom swing...

Built in 2002, this Maitland two-story offers stainless steel appliances, pantry, breakfast bar, and a two-car garage. Upgraded features include new carpet in select room...

Built in 2002, this Maitland two-story offers a sunny courtyard and a two-car garage. Upgraded features include fresh interior paint. A community pool and common area mai...

This upgraded 3 Bedroom 2 bath townhome is located in Park Maitland. This home has a two car garage, ceramic tile throughout main floor & carpet throughout upper level. ...

Location! Location! Location! Come see this beautiful lakefront Mediterranean town home located in the heart of Maitland boasting amazing views of Lake Destiny! This 3 be...

AMAZING VILLA BOASTS LARGE BEDROOMS AND BATHROOMS AND LOTS OF STORAGE! INTERIOR BOASTS WARM WOOD FLOORS AND BRIGHT OPEN SPACES... MASTER BEDROOM IS DOWNSTAIRS! THE BACK...