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$755,000
4 Beds ⋅ 2 Baths ⋅ Maitland Woods SubDv. ⋅ 32751 Zip Code
Don't miss this rare opportunity to purchase your dream home in the established Maitland Woods neighborhood. This charming 4-bedroom, 2-bath home has been meticulously maintained and contains premium finishes throughout. The open floor plan includes a large family/great room, dining room, and an enclosed patio, perfect for entertaining. The updated kitchen features a handmade subway tile backsplash, quartzite countertops, stainless steel appliances, a coffee bar, and a versatile indoor laundry/ second office or crafting room. The primary bathroom has been completely renovated, with a double-sink marble vanity, large shower, and walk-in closet. The second full bathroom is centrally located, with additional access to the enclosed patio, making it also an optional (future) pool bath. This home includes a large (0.29-acre) fully fenced backyard, ideal for children and/or pets to play. Some notable exterior improvements include: a new front brick patio, a new firepit area for entertaining, a vegetable/flower garden and beautiful landscaping. Maitland Woods is conveniently located near I-4, making commuting to either downtown Orlando or Lake Mary a breeze. In addition, the home is within walking distance to Orangewood Christian School, Lake Sybelia Elementary, the shops and restaurants of downtown Maitland (home of a weekly farmer’s market), city events at Lake Lily, and Lake Sybelia’s very own Homer Hough Park. Homer Hough Park is the area’s best-kept secret, with a playground, fishing, and pavilions for family events. This home will not last, call to schedule your private showing today! Age of major components includes water heater 2022; NEW front patio 2026; roof 2016; HVAC 2024/2025; Replumb CPVC 2020; inside and outside electrical panels 2025; and double-pane windows 2016-2023 – with lifetime warranty.

1191 Willowbrook Trail, Maitland
$725,000
3 Beds ⋅ 2 Baths ⋅ Highland Park Ests SubDv. ⋅ 32751 Zip Code
Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!

2040 Geronimo Trail, Maitland
$2,475,000
6 Beds ⋅ 6 Baths ⋅ Packwoods Plan/Maitland SubDv. ⋅ 32751 Zip Code
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 molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps.

604 Minnehaha Lane, Maitland
$1,575,000
5 Beds ⋅ 5 Baths ⋅ Maddon Cove 47/24 SubDv. ⋅ 32751 Zip Code
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 the main level has a door opening directly to this stunning outdoor space. The home delivers resort-style living every day. The main level features the primary suite with an extraordinary custom-built walk-thru closet, a separate nanny/in-law bedroom, a dedicated library/office with custom built-in bookcase, & an expansive laundry and storage room. Upstairs, you’ll find two more bedrooms connected by a jack-and-jill bath, and a separate bath ensuite bedroom, plus a versatile loft/flex space perfect for games, study hub, or media. Rich wood floors, a tile roof, owned solar panels, whole-house generator, irrigation well, and privacy fencing add comfort and efficiency to this remarkable home. The open gourmet kitchen and family room living spaces flow effortlessly to the pool and patio, ideal for both relaxed evenings and festive gatherings. Located on a quiet cul-de-sac with no through traffic, this home offers seclusion yet remains close to premier shopping, dining, and top-rated schools. Don't miss the chance to own this distinctive Central Florida retreat! Call today for your private showing.

135 James Place, Maitland
$902,000
3 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
Location, charm, and timeless style define this stunning 3-bedroom, 3-bath home in the highly sought-after Dommerich Estates of Maitland. Situated on an expansive corner lot and cul de-sac, this beautiful residence offers an exceptional blend of modern luxury and classic character. Step inside to rich wood floors, crown molding, and plantation shutters adorning every window. The spacious family room features a wood-burning fireplace, custom built-in bookshelves, and is wired for surround sound—perfect for cozy nights or entertaining guests. A sunroom/reading nook offers a bright and serene retreat and a bar area that seamlessly flows into the living space. The kitchen boasts granite countertops, and newly upgraded LG & Frigidaire Gallery stainless steel appliances (2023). French doors lead to your private backyard oasis, where a newly renovated pool and paved patio provide a perfect setting for outdoor entertaining. The expansive master suite offers a large walk-in closet and a sunken spa-inspired bath, ensuring a perfect escape at the end of the day. Additional recent upgrades include fresh interior and exterior paint. Newer windows, HVAC 2017 with 10-year warranty, updated plumbing lines, electrical panel updated 2023, and roof was installed 2010, making this home move-in ready. Outside, you'll find a front circular driveway with new pavers for added curb appeal and convenience, plus a rear cul-de-sac location that enhances privacy, accessibility, and outdoor fun for families. The location is unparalleled, close to shopping, restaurants, parks and major roadways. Located just 0.6 miles from Dommerich Elementary, this Dommerich Estates home is also zoned for Winter Park High School. Neighborhood amenities include lake access to Lake Minnehaha. Enjoy nearby attractions/ restaurants, Maitland Community Park, Minnehaha Park and downtown Maitland. This is more than just a home; it’s a lifestyle. Don't miss your chance to own in one of Maitland’s most coveted communities! Schedule your private tour today. *Info recorded in the MLS is intended to be accurate, but NOT GUARANTEED. Home square footage, room sizes and lot size should be independently verified. *

1591 Chippewa Trail, Maitland
$649,000
4 Beds ⋅ 3 Baths ⋅ English Estates Unit 1 SubDv. ⋅ 32751 Zip Code
MOVE IN READY! New Construction is a VERY rare find in Maitland especially in the English Estates neighborhood! Close to downtown Winter Park and 15 minutes away from Orlando. With 2,307 living square feet (3,186 total square feet) this home includes 4 bedrooms, 3 full bathrooms, 3 car garage, 10-foot ceilings, 8-foot interior doors, video doorbell camera, gutters installed outside, 2-inch blinds on all windows, Luxury Vinyl Plank throughout the home (no carpet), enormous 12-foot kitchen island ideal for guest seating, quartz throughout countertops, 5.25 inch baseboard, gourmet kitchen with GE appliances, triple sliding glass door, pavers in the driveway, open concept living and walk-in closets in all bedrooms. Designed with entertaining in mind, the gourmet kitchen has an expansive island with dining space and covered lanai for easy flow for family and guests. Stratford is hands down one of the best streets in the Estates, well established, and a short walk to English Estates Elementary School. Zoned for South Seminole Middle School and Lake Howell High School, and close to Lake Forrest Preparatory School. Maitland has been one of the most desirable towns in Central Florida for over 100 years with restaurants, shopping, arts center, the Enzian and more. Community is at the forefront for Maitland neighborhoods and one of the many reasons that make this area so special.

1231 Stratford Road, Maitland
$236,000
2 Beds ⋅ 2 Baths ⋅ Visconti West Condominium SubDv. ⋅ 32751 Zip Code
Enjoy resort-style living in this spacious third floor 2/2 split bedroom unit with vaulted ceilings and sweeping views of Lake Shadow. Seller recently installed new flooring and plantation shutters throughout. They have enjoyed many days sitting on the screen enclosed balcony reveling in the local wildlife and beautiful views of the lake. This unit comes with a single car garage, single carport and two separate storage rooms. Usually condominium living has limited storage, but not this one! The complex is gated and comes with amazing amenities, including a clubhouse, multiple pools, fitness center, playground, tennis/pickle ball and basketball courts. A secure trash receptacle is also provided, and trash is picked up at your unit. No walking it to a community dumpster, as is the case in some complexes. Water, sewer and trash are included in your HOA dues. Convenient to I-4 and just minutes from downtown it is considered a prime location.

1440 Lake Shadow Circle Unit 8302, Maitland
$239,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
This is a well-maintained Townhouse located in Maitland. The seller has resided in the property for 47 years and there are no deferred maintenance issues. Owner has upgraded the unit to include lifetime warranty (transferable) energy efficient windows in 2017. Solid surface countertops in kitchen and bathrooms along with complete kitchen remodel 10 years ago. May of 2024, owner had new electrical panel replaced both outside and in. Park Lake Townhouses is a well-maintained, quiet community close to I4, downtown Maitland and Winter Park, and Orlando. Community features include a private dock on Park Lake, a swimming pool for owners and guests, and beautiful oak tree ’ed courtyards. This Townhouse is truly something to see with freshly painted interior.

1019 Grove Street Unit 85, Maitland
$1,350,000
5 Beds ⋅ 4 Baths ⋅ Stonehill SubDv. ⋅ 32751 Zip Code
This stunning 5-bedroom, 4-bath pool home is located in the Stone Hill enclave. Upon entering, you will notice the abundance of natural light. The home features a three-way split plan with separate formal dining and living rooms. The primary bedroom includes walk-in closets, a separate bath and shower with dual sinks, as well as an additional private room ideal for a home office. The newly remodeled kitchen, open to the family room, boasts quartz countertops and stainless-steel appliances. Two fireplaces, one in the family room and one in the living room, add to the cozy atmosphere. Downstairs, there are three additional bedrooms and two full bathrooms. Upstairs, there is another bedroom and a full bathroom, along with a large gathering area suitable for a home gym, theater room or playroom. The home's outdoor space includes an enclosed pool and lanai, offering a perfect spot for morning coffee. The property features lush landscaping and pavers in the driveway, enhancing its curb appeal. Situated between Maitland Ave and 17-92, the Stone Hill community provides easy access to popular dining, shopping, and entertainment in Maitland and Winter Park. Major roads such as I-4, 17-92, and SR 436 are easily reachable, and the Sun Rail station is just half a mile away, offering convenient access for trips downtown.

138 Stone Hill Drive, Maitland
$2,875,000
5 Beds ⋅ 6 Baths ⋅ Backus & Gunion Add SubDv. ⋅ 32751 Zip Code
Stunning boat/ski lakefront home w 5,697sf on 1.5+- upland acres. 5 bed 4.5 bath w detached 1,100sf guest house over 3 car garage. Minutes from downtown Winter Park/Park Ave upscale shopping & dining. 10-minute drive to downtown Orlando. Features: gourmet kitchen, pool/spa, summer kitchen, expansive storage, lakefront views. The open concept kitchen is a true chef's delight featuring every accoutrement your heart would desire. A state-of-the-art refrigerator and freezer, double ovens, Ice maker, 2 wine/beverage fridges with a gourmet cook top, massive granite island and walk in pantry. This lovely kitchen is adjacent to the large family room and bonus room that each look out on to beautiful lake Sybelia. The downstairs flooring is a warm wide planked wood while the entrance and hall includes stunning large travertine tiles. The downstairs primary bedroom provides a private retreat of tranquility with breathtaking lake views as well as a large primary bathroom and walk in closet. You’ll find four substantial sized bedrooms and 2.5 baths upstairs with a bonus gamer room, study area and upstairs 2nd laundry room. The large front yard and lake views aren’t the only outdoor highlights the expansive property has to offer. You’ll enjoy entertaining and grilling in the large, covered summer kitchen or enjoy swimming in the beautiful crystal blue pool. It’s a gardeners delight with three large garden boxes and huge storage shed. There is also a large courtyard, half-court basketball court in addition to the shady large, grassed back yard. It’s truly a family home with tons of wonderful, usable and thoughtfully designed spaces with something for everyone to enjoy. Even your cars will be delighted with the oversized three car garage with extra space for a home gym as well. Come discover what living in Maitland is all about. This private and secluded street is a true gem as it offers privacy and an escape from bustling Orlando, yet minutes away from fine dining, top rated schools, parks and boutique shopping. This special home will provide the backdrop for many wonderful family memories to come. Schedule your private tour today and you’ll quickly see just what the epitome of luxury family living in gorgeous Maitland is all about.

1011 N Lake Sybelia Drive, Maitland
$795,000
4 Beds ⋅ 2 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
Welcome home to your 4 bed, 2 bath updated home with a pool, spa and creek flowing through your backyard, you will not be disappointed! This home is situated in a prime location within Dommerich, renowned for its charming fishing dock, Winter Park Chain of lake access, and legendary Halloween celebrations, this property offers an idyllic setting for family living. You will instantly be drawn in by its inviting curb appeal when you drive up as it has a spacious front yard, new exterior paint, picturesque front porch and paver driveway & sidewalk to greet you. When you walk in foyer you will notice the the beautiful hardwood floors throughout, natural light, crown moulding, new plantation shutters and custom shades on the windows and doors. To the right is your spacious formal living room, dining room combo. Then step into the kitchen and you will instantly notice stunning brick floors, the updated cabinets (6/2023), stainless Samsung appliances, under cabinet lighting, undermount large single sink, beautiful new quartz countertops (2023) and blue/gray backsplash (2023). Off of the kitchen is a great breakfast nook with more natural light from the above skylight which rolls into the welcoming, large family room. Off of this space you can enjoy your serene pool and patio view from the french doors as well as access to the oversized garage. To the left of the foyer is a hallway that leads to your 4 generously sized bedrooms, including the primary bedroom with remodeled en suite (2023) and hall bathroom. The primary bedroom features beautiful french doors with plantation shutters, custom walk-in closet and a beautiful updated ensuite bath. This bathroom features a newly installed tub, sophisticated marble top vanity and new light fixtures. Do not miss the view from your bedroom! In 2022, the pool was renovated featuring a diamond brite finish, pool lights, saltwater system, and a new pool heater. The property is further enhanced by a newer propane tank and updated lines, specifically designed for the Jacuzzi. Pavers have been recently cleaned and sealed in 2022, adding to the overall aesthetic appeal.The garage features a mini split HVAC, EV charging station and is used as another playroom. From the pool deck you can overlook your magical backyard with a stunning creek that flows to Lake Minnehaha, with a picturesque wood bridge which leads you to your own "island" and woods to play, put a fire pit or play-set to enjoy... nothing short of what your imagination desires! Not only is the home for you, the location is supreme due to deeded lake access to Lake Minniehaha to launch your boat and other nearby conveniences. Nearby Maitland Community Park, Kewannee Park, Seminole bike trail, and top-rated schools, including Dommerich Elementary, Maitland Middle, and Winter Park High. Homeowners had drawings completed to convert the oversized garage to another primary bedroom (5th bedroom) with en suite as well as add another garage at the end of the long driveway, available upon request. Roof: 2007, HVAC: 2019, Plumbing: 2008.

731 Sequoia Trail, Maitland