Maitland Homes For Sale

Private 2-acre gated estate on Lake Maitland "6-lake chain of lakes", gorgeous timeless architecture with magnificent manicured grounds! This fabulous residence is extrem...

Lovely French Provincial estate on the north shore of Lake Maitland. This 5 BD/4 BA/2.5 BA home was extensively remodeled in 2013 by Posada Custom Homes. Beautiful well-...

LUXURIOUS LAKEFRONT ESTATE! Appraised at $4 Million Dollars. This Winter Park Chain of Lakes Custom 3 car garage home has panoramic views of Lake Minnehaha w/ 110' of wat...

New construction featured in this year’s Parade of Homes. Get swept away by this stunning, waterfront estate thoughtfully designed by Michael Wenrich Architects. Located ...

*PRE-CONSTRUCTION - TO BE BUILT* Build the home of your dreams! The opportunity is yours on this vacant waterfront lot. A private boardwalk with boat dock on a canal lead...

Magnificent Mediterranean on the Winter Park Chain of Lakes. The house sits on 3/4 acre of land 17’ above the lake. The soaring foyer features a sweeping staircase, limes...

Incredible home for sale in Maitland located in a tucked back oasis that most don't know about. This home features some of the most ornate and lavish finishes one could o...

Gorgeous 1.67 acre lakefront property on Lake Maitland… the largest lake on the Winter Park Chain of Lakes. This is a wonderful opportunity to make this 6 bed/6.5 bath po...

Situated on pristine Lake Seminary in Maitland (Orlando), this custom lake front home is spacious, gracious, and a solid fortress. This location is near everything. This ...

You will feel like you have traveled back in time to “Old Florida” as you meander down the long, private drive to this Lake Maitland home that sits on 1.45 acres. This is...

This fabulous contemporary estate is situated on a half acre lot in an established neighborhood between Lake Catherine & Lake Lilly Park. This custom home built by Maroo...

Located on Lake Nina, one of the Maitland/ Winter Park Chain of Lakes best kept secrets sits this 3 bedroom 2 full bath 2 half bath home. Home boasts over 3,100 Htd. Sq.F...

This beautiful four-bedroom, three-bath home boasts 4,780 square feet under air and 5,606 total square feet. Once inside, you will find an open living room and dining roo...

STUNNING 5 bed/5.5 bath PLUS office including media/bonus room. Maitland Forest pool home tucked away on quiet cul-de-sac across from Lake Minnehaha. Entertain on your ba...

Prestigious Maitland Lakefront Pool Home nestled between 2 lakes. Enjoy Sunrise every morning from your screened lanai with spectacular views over Lake Charity. The ult...

Enjoy magnificent sunsets on Lake Minnehaha, on the Winter Park Chain of Lakes. Do you like to ski, boat and fish? Look no further...bring your boat, skis and fishing pol...

To enter this beautiful Maitland neigborhood by water you enter a short canal that opens up like a waterfront cul-de-sac. Most of this home has been updated. It feature...

This custom pool home is located in a small gated community in Maitland..The home features bedrooms 4 bedrooms 3.5 bathrooms plus an office and oversized 3 car garage....

Beautiful custom Cahill-built home in Lake Colony Estates, the top gated neighborhood in Maitland. The quality finishes and features of this home are extraordinary. The b...

NO HOA! Come & enjoy all that Winter Park has to offer when you move into the the SPECTACULAR DOMMERICH ESTATES community. With access to the Winter Park Chain of Lakes &...

This Remodeled Dommerich Estates modern farmhouse is an open floor plan 4 bedrooms 4 bathrooms that sits on a .30-acre lot in "A" rated school district. As you enter, you...

Lakefront living awaits! Come tour this elegant French-provincial estate located in the popular, guard-gated community of Maitland Club.  With nearly 90 feet of frontage ...

Well-maintained custom built two-story pool home with gorgeous lake view in the highly desirable Maitland neighborhood of Stonehill. Lushly landscaped front and back yard...

Within the growing suburb of Maitland, the intimate Stonehill community holds a home near I-4 that is walking distance to a community center and places of worship. First ...

Magnificent 5bedroom 5bath home on private cul de sac in desirable Gated Maitland Club. Entering through 8 Ft Honduras Mahagony Front doors into 16ft ceilings, beautiful ...

Stonehill is a charming community of just 30 homes. With easy access to I-4, the RDV sports complex, Winter Park boutiques and restaurants and short walk to Lake Lilly an...

Your waterfront paradise awaits! This private spring fed 55-acre lake ensures minimal boat traffic and maximum privacy while still being able to waterski and watersport o...

This is your opportunity to own a beautiful one of a kind single story custom home in Dommerich Estates. This home features 4 bedrooms and 3.5 baths, with a 3 way split f...

Beautifully, fully remodeled executive home in an upscale neighborhood. Expect to be impressed. Minutes from Winter Park, Lake Sybelia, the Maitland Business Center and m...

Dommerich Estates gem on one of the best streets, lined with mature Oaks and landscaping with an ambling creek that runs through back and connects to Winter Park Chain of...

This fantastic four bedroom home is located on a tree lined street in the quiet community of Stone Hill conveniently located to everything that Maitland/Winter Park has t...

Lakefront living at its finest! Don’t miss your chance to own this immaculate 4 Bed-3 Bath home located on the private, spring fed Lake Sybelia in the heart of Maitland! ...

BRAND NEW CUSTOM HOME - MOVE IN READY, centrally located in Maitland! REAR FACING GARAGE. No detail overlooked – The open floor plan encompasses volume ceilings, design i...

Lovely 4 bedroom, 3 bath family home with large in-law suite overlooking gorgeous back yard with large pool!! This home sits on a .51 acre sized lot with an absolute pa...

Take a second look - new pics for this stunning lakefront home in desirable Druid Isle community. Completely updated in 2017-2018, this gorgeous home features open-concep...

Fabulous Maitland home in Dommerich on beautiful quiet oak-lined street, and spacious yard and walking to schools. This 2,900 square feet home is a rare find and truly sp...

Have you been looking for an AFFORDABLE LAKEFRONT home with your own PRIVATE DOCK near Winter Park? LOOK NO FURTHER! Welcome to Audubon Way, located on the south shore of...

LUXURIOUS, EXECUTIVE HOME WITH A SPARKLING SALT WATER SWIMMING POOL! This immaculate home was ***COMPLETELY REMODELED IN 2007*** ALL NEW WINDOWS with a HUGE ADDITION and ...

Rare Opportunity to purchase in this highly sought after neighborhood! Immaculately renovated custom 4 bedroom POOL (salt water) home offers stunning curb appeal with lus...

Located on a quiet cul-du-sac, off Lake Catherine, this fabulous 1-story home has been renovated and recently expanded. The split floorplan is ideal with a large master s...

Beautiful updated Dommerich pool home is located in a family friendly Maitland neighborhood. This 1 story home underwent a total renovation in 2008 to an open floor plan ...

Gorgeous Lake Sybelia lakefront bungalow on a nice size lot. Boat dock on private Lake Sybelia. Two bedrooms, two full baths cottage style home with breath-taking views...

Beautiful home situated on an oversized lot in desired Kings Row neighborhood, within strolling distance to park and playground. "A" rated schools. Updated eat-in kitchen...

Druid Hills – Maitland! Outstanding 3 bedroom 2 bath home, with a HUGE FAMILY ROOM boasting a pristine lake view. Come home and enjoy an exclusive living area with a WOOD...

Recently updated home located within Maitland Club is ready for you to move right in! This bright and open split plan home contains neutral colors and vaulted ceilings th...

Newer home in Dommerich Woods built in 2009 by custom builder Shawn Wolfe with Native Homes! Situated on a double wooded lot, this three bedroom, three bath home with be...

A jewel in the crown of Maitland! Just a little under half an acre with lush landscape and a perfectly manicured lawn. This well cared for four bedroom, two and one half ...

This beautiful Maitland home is located in the desirable "Hidden Estates" and is perfect for a family of any size. Tucked away under majestic oaks, this "Hidden" large 1....

This Druid Isle lakefront home offers spectacular views of Lake Charity. This charming home is located on a private cul de sac on a beautiful tree lined street and welcom...

Welcome home to this beautiful 4/3.5 in coveted Maitland Club. The flexible three-way floor plan is wonderful for entertaining and family living. The first floor has a ...

THIS IS THE DOMMERICH ESTATES HOME YOU HAVE BEEN LOOKING FOR!!! Priced below recent appraisal! WALK TO Dommerich Elementary & Maitland Middle!! FABULOUS curb appeal welc...

BACK ON MARKET 8/03/18 - Seller made some repairs and had the home freshly painted inside and out! - Spacious and Bright Split Floor Plan Pool Home tucked back in Maitlan...

Wonderful & spacious home situated on large corner lot in charming Maitland Woods neighborhood. Large formal living & dining rooms with wood floors, family room with wood...

Beautifully remodeled family home in Maitland Grove. This property sits on an oversized corner lot and has been fully renovated including brand new wide plank floors, kit...

Stunning Maitland Home in desirable gated community! Former model home in Montacino - Enclave at Maitland. Minutes from the new Adventist hospital and Downtown Orlando, w...

Now Vacant. Wonderful Mediterranean house in a stellar location close to Winter Park and downtown Maitland. Gorgeous views of the lake as soon as you enter the Gated Comm...

Back on market. Deal fell through due to buyer being victimized by a Ponzi scheme having nothing to do with this property at all. RECENT APPRAISAL (4/21/18) IS $482k, S...

This spacious home needs a family to make it theirs! The split bedroom plan and two distinct living areas provide even the busiest of households plenty of space for priva...

Gorgeous, meticulously maintained beauty on one of the most desirable and quiet streets in Dommerich! The charming curb appeal with long paver driveway and front porch w...

Interior freshly painted throughout! Beautiful home, perfectly maintained. 4 generous bedrooms, split plan, huge island in kitchen, granite countertops, all appliances,...

A Florida classic, Clayton home with crown molding, 2 fireplaces & ceiling fans throughout. French doors open to backyard that features 26,000 gallon, kidney shaped pool,...

Dommerich Beauty on coveted Cheyenne Trail, walking distance to Lake Minnehaha. Move in ready to this updated spacious open floor plan home. Granite countertops, stainl...

Beautiful and move-in ready home in Maitland! Totally remodeled kitchen and bathrooms, fresh interior paint, and great curb appeal. Wonderful open floor plan, the brand n...

Lovely home in desirable Dommerich Estates, this 3 bedroom, 2 1/2 bath home is in move-in condition. The lanai, pool, 24,000 gallons resurfaced 6 years ago, and built in ...

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...

Welcome home to this gorgeous 3bdrm, 2.5 bath Mediterranean style CORNER unit townhome with 2305 sq.ft in Maitland's award winning gated subdivision - Montacino. The upsc...

Charming and well maintained 4 bedroom 2 bath home in Dommerich Estates! Privately located near the end of Mojave trail. As you enter this home, you walk under 1 of 2 sky...

Great Maitland Location!! This gorgeous home in highly desirable Stonewood neighborhood is located on a large .35 acre fenced in lot with an oversized screen enclosed h...

Dommerich Estates renovated home with room to grow on a gorgeous corner lot and a short walk to schools and Maitland Community Park. This home has been opened up and has ...

Here is your chance to own a beautiful well maintained home in the sought after neighborhood of Dommerich Hills. This home boasts an open floor plan with sightlines from...

Great opportunity to own in Maitland Woods! Spacious 4 bedroom, 2 bathroom single story pool home nestled in a quiet neighborhood and situationed on a large corner lot wi...

Located Brittany Gardens, a Quaint Gated Community in Maitland. Upon arrival you will be impressed with the lush landscaping and pristine condition. Your new home feature...

It's not often that you can get a split plan, 3-car garage and over 2500 square feet in Dommerich and the best schools in Orange County – about 10 blocks to grade school ...

LOCATION + LAKE ACCESS! Just a short walk to Community Park and Lake Sybelia dock for lake activities! Situated on a large corner lot in the quiet section of the much sou...

Pride of ownership is evident in every aspect of this spectacular home located in desirable Dommerich Estates in Maitland! Spacious 4 bedroom and 2 bath home offers a ve...

Wow! Maitland! Here is your chance to own a beautifully updated MID CENTURY MODERN home in the sought after neighborhood of Oakland Shores. Kitchen is a designer's dream ...

Location, Location, Location. Charming 4 bedroom/2 bath pool home located in highly desirable Dommerich Hills in Maitland. Upon entry you will notice the beautiful cherry...

Well appointed Traditional pool home in desirable well established community of Stonewood. Upon entering find to either side of the hallway the separate formal living and...

This 4 bedroom 2 bath home is located in Dommerich Hills close to Dommerich Elementary and Maitland Middle . Fireplace located in the formal living room great for gatheri...

Located in the sought after community DOMMERICH HILLS!! This charming 3 bed 2 bath pool home on an OVERSIZED lot with huge backyard is ready to be called home! Gorgeous w...

Nestled in the established neighborhood of Oakland Shores, this beautifully remodeled 4 bedroom, 2 bath home is waiting for you! Lovely polished travertine floors flow th...

Beautiful, almost new luxury, end unit townhome in the gated community of Maitland Village. Modern kitchen with 42 inch wood cabinets, granite countertops and stainless s...

Walk the cemented pathway leading to the covered entryway of this traditional single story home. The home welcomes you with an open concept floorplan and a bright living ...

Spectacular, like-new townhome in the exclusive gated community of Maitland Village. Can’t be beat location and convenient low-maintenance living. This townhome features ...

Amazing upgrades and a private pool! Located in a highly sought after area in Maitland, this 5 bed/3 bath two-story pool home has so much to offer and is move-in ready. T...

Stunning 4 bedroom, 2 bath REMODELED pool home in a quaint neighborhood of Maitland. The home sits on an oversized corner lot and has been updated with new plumbing, elec...

Very in demand neighborhood! Dommerich Estates has an impeccable reputation. This is your chance to pick up a fixer upper for below market value. This is the perfect opp...

Great NEW PRICE IMPROVEMENT. New roof April 2018. Forest Brook: Voted one of Maitland's most desirable communities. You have found your hidden Spanish Mediterranean oas...

This lovely move-in ready home is in the English Estates neighborhood, on a street lined with beautiful mature trees and is conveniently located between Maitland and Cass...

Value is in the lot. Home is not in safe condition for occupying. .44 lot size. Calling all builders! See pics of new construction on Sandspur

Beautiful four bedroom pool home available in the desirable English Woods community of Maitland. The master bedroom has three closets, full private bath, and sliding door...

English Estates Gem conveniently located in desirable Maitland. This home is upgraded with newly installed windows and HVAC system. As you enter the home there is a forma...

This three-bedroom home is located in Maitland and features a screened patio in the backyard with a few large trees. The master bathroom features dual sinks, separate tub...

A beautiful 4 bedroom 2.5 bath in a Gated Community with views on Lake Charity. A beautifull large Pool. An open Kitchen with Crown Molding & Granite Upgraded Tiles. Open...

Immaculate home in a No HOA community. Park like setting and Cul de Sac street with boat ramp. Ski access to Lake of the Woods Lake. Home is presently used as a 3BDR a...

Updated 3/2 home in Maitland near the RDV. The vaulted ceilings, unique structural accents, and open floor plan create an airy yet cozy space. This house features a brand...

MAITLAND TOWNHOME-THE ENCLAVE AT MONTACINO-Gated Mediterranean Luxury (3) Bedroom, (2.5) Bath located on quiet street with park like mature tree view behind property. Kit...

Come and get it! New Listing! New Home! Built 2018... 3 Bedrooms, 2 Baths, large Great Room and Granite counter tops in Kitchen and both Baths.

Water Front, Maitland Location! Three story Townhome, with foyer and entry level just off the over-sized two car garage brings you to the second level entering the large ...

Three bedroom, 3 bath townhouse in desirable Park Lake in Maitland with one bedroom & bath downstairs with sliders to the patio and two large master suites upstairs each ...

Well maintained 2 bedrooms 2 bath townhouse, kitchen, living, office, two full car garage, conveniently located in an excellent and quiet gated community (Visonti), few m...

Maitland's Best Kept Secret! Centrally located in this fantastic, secluded community tucked away on Park Lake close to Winter Park, Orlando and Maitland, ideal for the in...

Corner lot property with 2 bedrooms and 1 bathroom,low property taxes and there is no HOA (Homeowner Association).