Homes for Sale Near Winter Park High in Maitland - 32 homes

Remarks: Under contract-accepting backup offers. Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the home features a thoughtfully curated interior with upgraded finishes, including laminate flooring, enhanced baseboards, wet bar in family room and a seamless, light-filled layout. The kitchen, enhanced with quality wood cabinetry, flows seamlessly into the main living areas, while generously sized split bedroom plan provides flexibility for family, guests or a home office. A comprehensive list of upgrades reflects pride of ownership such as a newer roof (2020), resurfaced pool (2020), advanced air-conditioning system with Enviracare Elite air purification (2019), updated electrical panels (2012), replumbing (2006) and a water heater (2022). More recent enhancements include full interior and exterior painting (2025), a newly installed wooden fence and a serviced sprinkler system with a new impeller (2026). Outdoors, enjoy a private retreat with a sparkling pool and covered deck with an outdoor entertainment area, ideal for year-round Florida living. Residents of Maitland Isle benefit from exclusive access to Lake Maitland, offering a rare opportunity for boating and waterfront recreation within one of Central Florida’s desirable communities. Ideally in a top-rated school district and just a short distance to the charm of downtown Maitland, this home delivers a lifestyle of convenience, prestige and tranquility. A rare offering where location, quality and lifestyle converge.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Maryanne Branner (321-377-3909)

Remarks: LOOK NO FURTHER! This completely remodeled POOL home boast a spacious 4 bedroom's and 2.5 bathroom's that are situated on an oversized corner lot (.26 acre). NEW plumbing, NEW fixtures, NEW kitchen, NEW bathrooms and more! From the moment you enter the front door, you can notice the large new tile floors, complimented by all custom cabinetry, high end light fixtures and a spacious floorplan. A gourmet kitchen with beautiful, light quartz counters to compliment the light and navy blue cabinetry. Retreat to the Master Suite with a stunning ensuite master bathroom featuring a glass enclosed shower with rain head, dual vanity and a modern garden tub great to soak away the stress from the day. Time to have some fun in the backyard! Jump right into the sparkling pool or lounge on the large open patio. The backyard is privacy fenced leaving a nice private space for entertaining and gathering with friends and family. This home is also in the perfect location just minutes from Park Avenue and many high end restaurants. Come check out you new home today!

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Jason Zinno (407-467-5631)

Remarks: To Buyer “Discover the advantage of owning one of Tuscarora Trail’s premier homesites—where space, privacy, and lifestyle come together, all within the highly sought-after Dommerich school district, supporting both today’s living and tomorrow’s resale value. ” Nestled on a serene lakeside setting in the heart of Maitland, this beautifully upgraded 4-bedroom, 2.5-bath home offers more than just square footage—it delivers a lifestyle steeped in comfort, elegance, and Florida charm. Spanning nearly 3,000 square feet on a generous 0.43-acre lot, this residence frames breathtaking lake and sunset views that greet you with every evening breeze. Sunlight dances through expansive glass doors, illuminating open living spaces that flow effortlessly into a resort-style outdoor oasis complete with a sparkling private pool, covered patio, and lush water-framed views—perfect for quiet mornings with coffee or lively gatherings under starlit skies. Inside, thoughtful updates—like fresh interior and exterior paint, major systems enhanced for modern living, and paid-off solar panels for incredibly low utility costs—blend timeless Florida living with smart sustainability. Situated in the highly sought-after Dommerich Elementary and Winter Park school districts, this home embodies both tranquil retreat and everyday convenience. You’re just minutes from the charming boutiques, world-class dining, and cultural attractions of Winter Park’s Park Avenue, and a comfortable drive to Orlando’s theme parks—including Walt Disney World® Resort—and the region’s major airports for effortless travel. Whether you’re hosting family by the pool, savoring sunset reflections on the lake, or enjoying the top-tier schools and vibrant local lifestyle, 2514 Tuscarora Trail is more than a house—it’s home. NO HOA

Listing is courtesy of: NOELKE REALTY (407-607-7166)

Listing Agent: Tom Noelke (407-607-7166)

Remarks: Experience turn-key living at its best in this beautifully renovated, designer-owned, lakefront condo, conveniently located in the sought-after Lake Maitland Terrace community on the Winter Park Chain of Lakes. This stunning 2-bedroom, 1-bath residence was thoughtfully redesigned with high-end finishes and an open, modern layout that maximizes both style and functionality. FURNITURE IS NEGOTIABLE! The completely updated interior features luxury “wood-like” vinyl plank flooring throughout, for enhanced durability. Enjoy a stylish kitchen with custom cabinetry, quartz countertops, tile backsplash, and newer appliances, and a beautifully remodeled bath with marble herringbone tile and designer fixtures. Additional upgrades include all new electrical, recessed lighting with dimmers, updated plumbing, custom closets, shiplap accents, new interior doors and trim, high-end Emtek door knobs throughout, and sound-reducing flooring underlayment for added comfort. Lake Maitland Terrace offers a true lakefront lifestyle, with private access to Lake Maitland, the largest lake on the Winter Park Chain. Residents enjoy a community dock and fishing pier, kayak & paddleboard racks, a sparkling pool, a clubhouse with lake views, shuffleboard courts, bike storage, and convenient on-site laundry....but this unit has it's OWN Washer and Dryer! Ideally located near shopping, dining, theaters, and just minutes from Park Avenue in Winter Park, this fresh and modern move-in ready condo offers effortless living in one of Maitland’s most desirable waterfront communities. Don't forget.... the FURNITURE IS NEGOTIABLE!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Marystuart Day (407-620-8683)

Remarks: 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 space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: 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 an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: 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 Mediterranean architecture with state-of-the-art modern enhancements, Maison du Lac is a stunning fusion of enduring charm and contemporary sophistication. Originally constructed with timeless materials – including stucco exteriors and expansive windows – the home has been meticulously transformed into an 11,668-square-foot architectural masterpiece. Clean lines and open-concept living harmonize with rich textures and refined details, resulting in an environment that is both stately and smart. Upon entering through the grand 14-foot custom iron door, you are greeted by soaring dual staircases and exquisite finishes in marble, granite, and intricate moldings that reflect the home’s bespoke craftsmanship. A showstopping, $250,000 crystal chandelier—custom-designed and operable at the touch of a button—crowns the expansive great room, setting a dazzling tone for the professionally curated interiors. A private elevator adds convenience and accessibility across all levels of the home. The fully reimagined kitchen is a culinary showpiece, featuring top-of-the-line Wolf appliances, gleaming Cambria countertops, a large walk-in pantry, and expansive prep space ideal for entertaining at any scale. Whether hosting a lavish dinner or a relaxed brunch, the kitchen delivers both impeccable style and everyday functionality. The private master wing is an indulgent retreat, complete with a cozy fireplace, executive office, sauna, fitness room, and dual custom walk-in closets. Five additional en-suite bedrooms are thoughtfully positioned for maximum privacy, offering luxurious accommodations for family and guests. With seven full bathrooms and three half baths, the residence is ideally equipped for both refined daily living and grand-scale entertaining. For effortless indoor-outdoor living, multiple entertainment spaces flow seamlessly onto a sprawling lakefront patio. The outdoor summer kitchen, complete with a powered screen enclosure, provides the perfect setting for alfresco dining while enjoying sunset views over the water. A brand-new dock with a boat lift invites leisurely days spent boating, fishing, or simply relaxing on the lake. Outside, the estate continues to impress. Two serene fishponds with fountains create a tranquil sense of arrival, while the fully fenced and gated grounds ensure ultimate privacy. The residence is equipped with a full-home LUTRON smart system, offering intuitive control of lighting, ambiance, and automation. Additional features include a six-car garage, a resort-style swimming pool, newly updated landscaping, and custom exterior lighting. Maison du Lac is more than a home, it’s a lifestyle of distinction, privacy, and effortless sophistication. This is the lakefront living at its finest.

Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)

Listing Agent: Maggie Walas (407-701-0144)

Remarks: Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath townhouse offers 1,734 square feet of thoughtfully designed space in one of Maitland's most sought-after communities. The open layout showcases soaring ceilings and gleaming engineered wood floors throughout, creating an inviting atmosphere filled with natural light. The heart of the home is a stunning galley-style kitchen featuring crisp white cabinetry with glass-front doors, stainless steel appliances, and a cozy breakfast nook—perfect for morning coffee or casual dining. The living room centers around a charming wood-burning fireplace, while elegant French doors lead to a private screened patio overlooking serene common green space dotted with majestic oak trees. Upstairs, the primary suite serves as a tranquil retreat with a generous walk-in closet and spa-inspired en suite bath complete with a walk-in shower and double sink vanity. Two additional spacious bedrooms and a full bath complete the upper level, with ample storage throughout. Plantation shutters and updated light fixtures add polish to every room, while an attached one-car garage provides convenient parking and additional storage. Living in The Moorings means enjoying an exceptional lifestyle with exclusive access to a private community dock on Lake Maitland, a sparkling pool, and a welcoming clubhouse. The location is truly unbeatable—just moments from the charm of Lake Lily Park and its beloved weekly farmer's market, five minutes from the upscale boutiques and dining of Park Avenue, and surrounded by Central Florida's finest shopping, restaurants, and entertainment.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light. The heart of the home is the stunning kitchen, showcasing white cabinetry, quartz countertops, stainless steel appliances, a decorative hood above the cooktop, and a classic subway tile backsplash. A charming bay window creates the perfect breakfast nook, while the open-concept living and dining areas provide ideal space for entertaining and everyday living. A wood-burning fireplace adds warmth and ambiance to the living room, creating a cozy focal point. Step through French doors into a sun-drenched sunroom with walls of windows overlooking tranquil community green space – your own private retreat for morning coffee or evening relaxation. Luxury vinyl plank flooring flows throughout the main level, complemented by plantation shutters and fresh paint. The second floor houses all three generously sized bedrooms, including a serene primary suite with a completely renovated en suite bathroom featuring a double sink vanity, walk-in shower, and spacious walk-in closet with custom built-ins. The updated hall bath offers a tub/shower combo and single-sink vanity. The second bedroom also features custom built-in closet organizers for added storage and convenience. Additional features include ceiling fans, interior laundry, and an attached one-car garage. Living in The Moorings means enjoying exclusive amenities, including a community dock on Lake Maitland, sparkling pool, and clubhouse. The location is unbeatable – just moments from Maitland's charming Lake Lily Park and its popular weekly farmer's market, five minutes from the upscale shops and dining of Park Avenue, and surrounded by the best of Central Florida's shopping, restaurants, and entertainment.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Mario Zendeli (407-325-3893)

Remarks: One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready residence features thoughtfully designed indoor and outdoor living spaces and is zoned for the top-rated Dommerich Elementary School. From the moment you arrive, manicured landscaping and an inviting covered front porch create a warm first impression. Inside, natural light fills the home through skylights and bay windows, highlighting hardwood floors and a wood-burning fireplace. The open layout provides a seamless flow between living spaces, ideal for everyday living and entertaining. The chef’s kitchen serves as the heart of the home and features custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. The kitchen opens to the main living areas, creating a functional and welcoming space. The primary suite offers a private retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom includes an oversized shower with spa-style jets and customized storage. Three additional bedrooms and a full bathroom are located down a terrazzo-finished hallway and include custom upgrades. The dining area captures beautiful morning light through the bay window, while the living room features French doors that open to the outdoor living space. The private backyard oasis is designed for year-round enjoyment and includes a heated pool enclosed by a full screened deck and patio, creating a true indoor-outdoor lifestyle. Additional features include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway with a 30-amp electrical hookup for an RV or boat. The home has been freshly painted inside and out, includes new carpet, and reflects quality craftsmanship throughout. Enjoy quick access to Winter Park’s shops, dining, parks, and cultural offerings, along with the conveniences of Maitland living, making this home an exceptional opportunity in a highly desirable Central Florida location.

Listing is courtesy of: STRICKLAND REALTY GROUP INC (407-448-5068)

Listing Agent: Amanda Binns (407-448-5068)

Remarks: Exclusive Dommerich opportunity to own a true 5 Bedroom, 3 Bath home PLUS a dedicated office—an almost impossible combination to find in this celebrated neighborhood. Situated on a quiet, private-feeling cul-de-sac on over 1/3 acre, this home offers space, function, and timeless charm to love for years to come. This enclave of Dommerich is special - with neighbors often gathering and enjoying afternoons in Adirondack chairs neatly situated in front lawns, thanks to the serene nature of the streets. Even more charm is found in the front exterior of this home, which includes a front courtyard, perfect for gardening or a cup of coffee in the morning. Inside, the flexible floorplan includes formal living and dining rooms on the same wing as the primary retreat, plus a spacious den/office overlooking the pool on the opposite side of the home. The cozy family room features a fireplace and built-ins, and opens to a well-designed kitchen with granite counters, stainless steel appliances, bar seating, and a functional breakfast nook. Durable wood-look tile runs through the kitchen, family room, and roomy den for easy maintenance and enjoyment for years to come! Newer sliders provide great views and access to the sparkling pool from the den that could also make a great office or play space. The split bedroom layout provides privacy, with the primary suite in its own wing featuring a large walk-in closet, dual sinks in the renovated bathroom, and a spacious size that makes this suite truly feel like a retreat. On the guest bedroom wing of the home, the first two bedrooms share a remodeled Jack-and-Jill bathroom with each also having walk-in closets (yes, WALK-IN CLOSETS in guest bedrooms!). Bedrooms 4 and 5 share the 3rd Bathroom (ALSO REMODELED) that can easily function as a pool bath thanks to the tile floors that seamlessly flow through the guest hall. Storage abounds in this home with multiple hall closets, an indoor laundry room, plus an oversized garage for any sports or recreation equipment.  Enjoy Florida living in the 20,000+ gallon pool with an expansive paver deck that extends along the side yard for additional entertaining space. This great backyard is low-maintenance thanks to the beautiful pavers, but a secluded yard space was saved for outdoor recreation or just enjoying the Dommerich neighborhood! Ideally located just across from top-rated Dommerich Elementary and Maitland Middle, savor a leisurely walk or bike ride to school daily. The home is also zoned for Winter Park High School! All easily accessible from Dommerich is Maitland Community Park featuring walking trails, fitness classes, and tennis; Maitland City Centre, known for its restaurants and festivals; renowned Winter Park and Park Avenue; and smooth access to all of Central Florida via nearby I-4. Move-in is easy thanks to major updates, including a full Roof Replacement in 2023, new exterior paint, an AC Replacement in 2021, a Replumb with PEX lines, sewer lines already connected with NO assestment fees, and no HOA. Don't miss this hard-to-find 5 Bedroom Dommerich home - you might be waiting YEARS for another chance like this!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Erin Baker (407-719-0030)

Remarks: Incredible location! This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. New windows! New electrical panels 2026, New water heater 2026. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share an updated bath with a glass enclosed tiled shower with rain shower fixtures. Laminate wood and tile flooring throughout! No carpet! Indoor laundry room with lots of storage with Maytag appliances. French doors lead you to a private fenced patio and one car garage! Step right outside the front door to the sparkling pool! Security system included. Zoned for sought-after schools, Dommerich Elementary, Maitland Middle, and Winter Park High. The neighborhood features a community pool, dock on Lake Gem and gorgeous landscaping and trees.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Ingrid Livingston (407-595-5972)

Remarks: Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Brian Rotenberger (407-948-8478)

Remarks: 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!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Maria Van Warner (407-256-8066)

Remarks: Dommerich Hills – Maitland Positioned in the heart of Maitland, this inviting single-story home in the highly desirable Dommerich Hills community combines comfort, character, and location. Offered for the first time in 60 years, this property reflects true pride of ownership and long-term care. Set on a spacious .24-acre lot, the home offers 4 bedrooms, 2.5 baths, and 2,265 sq. ft. of living space. A timeless brick exterior and side-entry two-car garage create strong curb appeal, while the single-level floor plan provides effortless everyday living. The kitchen flows naturally into the connected living and dining areas, promoting an open, comfortable layout perfect for gatherings or flexible work-from-home use. Enjoy a fully fenced backyard great for pets, gardening, play, or weekend entertaining in your own outdoor retreat. Recent updates include: roof (Nov 2021), HVAC (May 2023), garage door (Apr 2022), and now connected to the city sewer (Nov 2025). Dommerich Hills is a well-established, tree-lined neighborhood known for its spacious lots, mid-century architecture, and strong sense of community. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High, with the convenience of walking or biking to nearby schools. Minutes from Downtown Winter Park dining, boutique shopping, and easy access to major roadways and everyday conveniences. A rare opportunity to own a meticulously maintained home in one of Maitland’s most established and sought-after communities—offering the perfect blend of location, lifestyle, and long-term value.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)

Remarks: One or more photo(s) has been virtually staged. ONE OF A KIND for Dommerich Estates, this LAKE VIEW Home is designed for soaking in unforgettable sunsets and unwinding after a long day. Located directly across the street from the neighborhood lake lot, you will enjoy unobstructed views of the water, easy access to the boat ramp and fishing dock or launch your canoe or kayak for a peaceful paddle on the lake that also connects to the Winter Park Chain of Lakes! 4 generous bedrooms and 3 baths provide plenty of space for family and guests. Beautiful wood floors flow throughout and are complemented by crown molding for a classic touch. The spacious living room has a wood-burning fireplace and built-in cabinets to display all your treasures. It’s also large enough to be used for a combination living room/dining room and enjoy the lake views while you dine. The open kitchen and family room look out onto the screened patio and pool with a relaxing water feature. Feel secure during hurricane season with an installed and powerful Briggs and Stratton generator that will keep the power going to the kitchen, 4th bedroom and bath during the storm! Upgraded electrical system and the home has been replumbed for your peace of mind. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. Social events at the lake lot provide a fun opportunity for neighbors to meet neighbors and there is a boardwalk that connects you to Maitland Park with playgrounds, tennis courts, walking trails and basketball courts. The City of Maitland is vibrant with a small-town feel providing events designed to foster connections among residents with multiple parks and downtown events and concerts! Don’t pass on this opportunity to own this rare, lake view home in one of the best neighborhoods in the area!

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Shirley Welch (407-718-1450)

Remarks: Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized architect Jose Vengas, the home showcases dramatic ceiling heights, clean modern lines, and expansive glass walls that flood the interiors with natural light while blurring the line between indoor and outdoor living. The thoughtfully designed open-concept floor plan centers around a show-stopping chef’s kitchen featuring custom cabinetry, a statement marble backsplash, and a full suite of premium Sub-Zero and Wolf appliances perfect for both elevated entertaining and everyday living. Living and dining spaces flow effortlessly to a covered outdoor lounge with a fully equipped summer kitchen, overlooking a resort-style pool and spa designed for year-round enjoyment. Whether hosting guests or unwinding in private, this outdoor sanctuary is truly exceptional. All five bedrooms are generously sized private suites, each offering spa-inspired bathrooms with refined finishes and custom detailing. The primary suite is a true retreat, featuring a luxurious bath experience and expansive walk-in closets designed for both beauty and function. A first-floor owner’s suite provides exceptional flexibility for multi-generational living or guest accommodations, while the upper level reveals gallery-style walkways and an elegant terrace that highlights the home’s architectural artistry. With nearly 5,000 square feet of meticulously curated living space, this exceptional estate delivers modern sophistication in one of Central Florida’s most exclusive and private enclaves—just moments from Winter Park’s renowned dining, boutiques, and cultural destinations.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: Under contract-accepting backup offers. LONG AWAITED ARRIVAL IN DESIRABLE MAITLAND SUBDIVISION This beautiful, impeccably maintained and updated four bedroom three and a half bath pool home absolutely has it all! Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers four spacious bedrooms and three full baths on the first level and a bonus room/5th bedroom with half bath on the second level. The gorgeous kitchen boasts handsome, solid wood cabinets, granite countertops and stainless steel appliances with double ovens. The first floor open layout includes a large dining area with double fireplace leading into a wonderfully sized family room with fireplace and custom built-ins. Newly installed double pane, hurricane proof French doors brings in tons of natural light and leads out to your private oasis including newly resurfaced pool and brick paver deck, open patio and super fun gazebo with gas grill and nighttime lighting for entertaining! This home is fully supported by a full Generac system, never to be without power. Entire interior just freshly painted and new carpets installed in bedrooms and bonus room. Newer Roof (2021), HVAC (2020) and Tankless water heater. Samsung washer and dryer also included. Beautiful landscape and outdoor lighting add to its charm and warmth. THIS opportunity does not come along often. Look forward to meeting you there!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Laura Lane Heidrich (321-662-7491)

Remarks: Under contract-accepting backup offers. Under Construction. A striking blend of refined luxury and sleek contemporary architecture, this exceptional new construction residence is set to be completed in July 2026. Designed for effortless living and elevated entertaining, the home showcases 5 well-proportioned bedrooms, 4.5 designer bathrooms, and approximately 3,695 square feet of thoughtfully curated interiors. From the moment you enter, you’ll experience a bright, open layout that flows seamlessly from one space to the next. At the heart of the home is a culinary-inspired kitchen, complete with premium appliances, custom cabinetry, quartz surfaces, and a generous island that invites gathering and conversation. The living and dining areas are ideal for hosting, framed by expansive windows that capture views of the outdoor retreat. The private primary suite feels like a personal spa, featuring a serene bath with dual vanities, a freestanding soaking tub, a walk-in shower, and a spacious wardrobe closet. Each additional bedroom offers comfort, style, and ample storage—perfect for family, guests, or a dedicated office. Outside, the property transforms into an outdoor sanctuary with a shimmering pool, a covered lanai designed for year-round enjoyment, and a fully equipped summer kitchen ready for unforgettable weekends. A rare opportunity to own a remarkable residence where modern design meets everyday livability—a home you’ll never want to leave.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)