Location: Maitland
Keyword(s): Winter Park High
Keyword(s) High School: Winter Park High
Do Not Show Listings
223 QUAYSIDE CIR #C, MAITLAND, FL 32751
$575,000155 Days on yellowkey MLS ID: O6362370
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1734 Built: 1985Monthly Fee: $882 Tax: $4,185 (2024)Community: Moorings On Lake Maitland Condo Bldg 05Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,185
Elementary School: Lake Sybelia Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
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)
225 QUAYSIDE CIR, MAITLAND, FL 32751
$560,000205 Days on yellowkey MLS ID: O6338754
REDUCED by $35,000 (5.9%) on 04/03/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1734 Built: 1985 Tax: $3,080 (2024)Community: Moorings On Lake Maitland Condo Bldg 05Condo
Taxes:$3,080
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.
101 MARINER WAY, MAITLAND, FL 32751
$769,00016 Days on yellowkey MLS ID: O6396663
0 Days Off yellowkey (back on 4/16/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2413 Built: 1972Monthly Fee: $8 Tax: $3,528 (2025)Community: Maitland IsleSpa: NoSingle Family
Taxes:$3,528
Tax Year: 2025
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)
2514 TUSCARORA TRL, MAITLAND, FL 32751
$759,00077 Days on yellowkey MLS ID: O6380728
REDUCED by $20,000 (2.6%) on 04/16/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 3000 Built: 1971 Tax: $4,200 (2025)Community: Dommerich Hills 2 Nd AddSingle Family
Taxes:$4,200
Elementary School: Dommerich Elem
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)
1140 S ORLANDO AVE #H-13, MAITLAND, FL 32751
$449,00050 Days on yellowkey MLS ID: O6387926
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1964Monthly Fee: $546 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
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)
105 TANGELO CT, MAITLAND, FL 32751
$1,798,999142 Days on yellowkey MLS ID: O6364116
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026 Tax: $6,909 (2024)Community: Hollieanna ShoresSpa: YesSingle Family
Taxes:$6,909
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)
570 MANOR RD, MAITLAND, FL 32751
$12,500,000373 Days on yellowkey MLS ID: O6300040
Bed: 6 Bath: 8.5 Gar: 6 Liv Area Sq Ft: 11668 Built: 1996 Tax: $61,937 (2024)Community: Lake Maitland ManorSpa: YesSingle Family
Taxes:$61,937
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)
350 NORTHWIND RD, MAITLAND, FL 32751
$3,100,00085 Days on yellowkey MLS ID: O6377888
REDUCED by $199,000 (6.0%) on 04/11/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4819 Built: 2019 Tax: $18,531 (2025)Community: Lake Maitland Owl PreserveSpa: YesSingle Family
Taxes:$18,531
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)
103 WHITECAPS CIR, MAITLAND, FL 32751
$2,000,00040 Days on yellowkey MLS ID: O6382220
0 Days Off yellowkey (back on 3/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3695 Built: 2026 Tax: $3,439 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,439
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.
101 WHITECAPS CIR, MAITLAND, FL 32751
$2,150,00074 Days on yellowkey MLS ID: O6375435
1 Days Off yellowkey (back on 2/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4004 Built: 2026 Tax: $3,987 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,987
Remarks: Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic and refined. An impressive foyer sets the stage for the elegant interiors beyond, where high ceilings, natural light, and thoughtfully curated finishes create an atmosphere of sophistication and comfort. Designed for both effortless daily living and elevated entertaining, the open-concept layout flows beautifully from the expansive living room into the formal dining space, framed by a striking wall of oversized sliders that open up to the spacious backyard/pool area. The heart of the home is the show-stopping chef’s kitchen featuring stunning Chantilly quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry. The primary suite is designed to feel like a five-star retreat, featuring a spa-inspired bath offering a freestanding soaking tub, dual vanities, a glass-enclosed walk-in shower, and an expansive closet. Adding to the home’s rarity and versatility, the main level also features a true guest suite perfect for hosting in comfort, as well as a dedicated office. Outside, the backyard is the definition of resort-style living. The sparkling pool and spa anchor the space, surrounded by a generous covered lanai with a summer kitchen and abundant room for lounge seating and al fresco dining. And beyond the home itself, the lifestyle is exceptional. Residents of Hollieanna Shores enjoy access to a shared boat slip giving you access to the Winter Park Chain of Lakes, offering a level of exclusivity and lake-life convenience that takes this property to another level. All of this is just minutes from Maitland City Centre, beloved local parks, the iconic Enzian Theater, and the upscale dining, shopping, and charm of Park Avenue. This home redefines what luxury living looks like in Maitland, where location, design, and lifestyle come together in a home that feels truly unforgettable.
1695 E HORATIO AVE, MAITLAND, FL 32751
$529,000345 Days on yellowkey MLS ID: O6309191
0 Days Off yellowkey (back on 4/6/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1939 Built: 1959 Tax: $6,513 (2024)Community: Dommerich Estates 1St AddSingle Family
Taxes:$6,513
Remarks: Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, No HOA, Top Rated Shools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House is just revitalized with a new fresh interior Stone Eagle Color Paint, Roof replaced in 2024, AC replaced in 2022, Exterior repainted in 2022, and plumbing repipe in 2019. House had tile throughout interior floor. Schedule to view this wonderful home.
Listing is courtesy of: VISTA REALTY INVESTMENT (407-895-5757)
Listing Agent: Tuan Nguyen (407-446-3264)
1000 S ORLANDO AVE #B25, MAITLAND, FL 32751
$335,00037 Days on yellowkey MLS ID: O6391679
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 952 Built: 1964 Tax: $2,559 (2025)Community: Maitland Harbour AptsCondo
Taxes:$2,559
Remarks: Highly desirable Maitland Harbour, a boutique 38-residence lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.
Listing Agent: Padgett Mccormick (407-645-4321)
1732 RIDGEWOOD AVE #S, MAITLAND, FL 32751
$749,00081 Days on yellowkey MLS ID: O6378854
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2407 Built: 2016Monthly Fee: $425 Tax: $6,155 (2024)Community: Ridgewood Villas CondoTownhouse
Taxes:$6,155
Remarks: This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step inside and you immediately notice how expansive it feels. Soaring ceilings and abundant natural light make the home live far larger than a typical townhome. The first floor flows seamlessly, creating a true open-concept environment ideal for entertaining or everyday living. The oversized island anchors the space, perfect for hosting friends, casual dinners, or setting up a productive work-from-home station. Upstairs is where this home truly stands apart. Three full bedrooms, each with its own ensuite bath, a rare and highly desirable feature. The primary suite offers a private retreat with a spacious layout, generous walk-in closet, dual vanities, and a large walk-in shower that feels straight out of a luxury spa. The secondary suites provide comfort and privacy rarely found in townhome living. Step outside and enjoy a private side yard, a perfect extension of your living space. Whether you’re grilling on the weekend, setting up a small outdoor lounge, or simply enjoying the Florida sunshine, this added outdoor area gives you the flexibility most townhomes don’t offer. A private side-entry two-car garage adds both security and convenience while preserving the home’s clean curb appeal. If you’ve been searching for something near Winter Park that offers style, functionality, and location without compromise, this one checks every box.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
150 SENECA TRL, MAITLAND, FL 32751
$745,00037 Days on yellowkey MLS ID: O6389696
1 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2221 Built: 1957Monthly Fee: $8 Tax: $10,543 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$10,543
Remarks: Under contract-accepting backup offers. In the heart of Dommerich, this thoughtfully renovated mid-century pool home offers deeded access to the Winter Park Chain of Lakes & a well-executed floor plan designed for everyday living. Set on a .20-acre lot measuring 79’ x 111’, the home balances indoor comfort with outdoor livability, beginning with a welcoming front entry that opens to a casual foyer. To the left is a shared formal living and dining space filled with natural light from large-format windows. Wide plank engineered wood flooring, charming built-ins & updated finishes continue throughout the main living areas, creating a cohesive & visually consistent interior. Toward the back of the home, the layout transitions to a family room & adjoining Florida room, which, when used together, create a spacious secondary living area, or may function separately as a family room, casual dining area, office or reading room, all overlooking the pool and functionally connected to the kitchen. The kitchen is positioned at the center of the home & features white shaker cabinetry, grey quartz countertops, a large island with a butcher block countertop, seating and storage on all sides, a vent hood over the range, stainless steel appliances & a large white ceramic single-bowl farmhouse sink with a pull-down commercial-style faucet, along with windows overlooking the pool & backyard. The home offers an ideal split-bedroom plan, with the primary suite located on the back left side of the home and added in 2018 by Winter Brothers Construction. The suite includes a spacious bedroom with recessed lighting, separate closets with built-in organization & a well-appointed bath with dual vanities, a freestanding soaking tub, a glass-enclosed walk-in shower with rain shower head & a private water closet. On the opposite side of the home are three additional bedrooms, including one with an en-suite bath designed with a pedestal sink, wall-mounted storage & a glass-enclosed walk-in shower, along with a full hall-entry bath which comes with a tub/shower combination & new vanity (2026). Highlights of the backyard include a paver deck, saltwater swimming pool with a generous shallow shelf, child safety fence, play set, raised garden bed, lawn space for people and pets and a mature peach tree that produces fresh peaches. The home also features an attached two-car garage with a laundry area, professional landscaping and a newly installed white privacy fence with gated access on both sides. In addition to its charm & interior updates, the home offers meaningful system improvements, including electrical panels (2018), two HVAC systems (2018 and 2022), a full re-pipe to PVC/CPVC, roof replacement (2017–2018) & an electric water heater (2018). The property owner has the option to join the Dommerich Estates Beach Civic Association, which provides access to a private boat ramp, picnic area and lakefront amenities on Lake Minnehaha. Residents also enjoy convenient access via the neighborhood boardwalk to Maitland Community Park, offering tennis and basketball courts, trails, pavilions and year-round activities. Zoned for Dommerich Elementary, Maitland Middle and Winter Park High and located just minutes to Park Avenue, Lake Lily, the Maitland SunRail station and major roadways, this is an opportunity to own a move-in ready home in a well-established neighborhood with strong school zoning, a true sense of community and lake access to the Winter Park Chain of Lakes.
109 MINNEHAHA CIR, MAITLAND, FL 32751
$770,00094 Days on yellowkey MLS ID: O6374874
1 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2249 Built: 1976Monthly Fee: $13 Tax: $3,547 (2025)Community: Minnehaha ShoresSingle Family
Taxes:$3,547
Remarks: Under contract-accepting backup offers. RARE opportunity to own a Maitland Shores home offering access to Lake Minnehaha AND the Winter Park Chain of Lakes. Residents enjoy exclusive use of the HOA lakefront park with a fishing dock and paved boat ramp that creates quick access to the Nina Canal and Lake Maitland — the largest lake in the Winter Park Chain. The unique location of this home offers an oversized .34-acre homesite that is thoughtfully landscaped with rare tropical plants, rose gardens, and a peaceful front courtyard complete with a bubbling fountain. Ample driveway and garage space accommodate boat or vehicle storage, ideal for enjoying skiable Lake Minnehaha. Inside, this 3 bedroom, 2.5 bath home offers 2,249 square feet of living space in a split floorplan. A unique highlight of the floorplan is the dual primary suites, each with private access to the screened pool, making the home ideal for multi-generational living. Equally beautiful pool views are also visible from the kitchen, breakfast nook, and spacious family room. If you are staying inside, the family room features a large fireplace that creates a cozy focal point. Just off the family room is the remodeled kitchen that is both bright and functional with abundant cabinetry, granite counters, stainless steel appliances, breakfast bar seating, a built-in desk, and a breakfast nook with patio access. Beauty abounds from the patio with a resort-style screened pool, complete with decorative palms surrounding the pool. Steps from the pool begin the meandering gardens with colorful blooms. To aid the avid gardener is a covered and secure garden shed. With such an expansive homesite - more than 15,000 square feet - possibilities for adding a full workshop or even an Accessory Dwelling Unit/ADU could be explored. Adjacent to this estate is Minnehaha Park, a 7.5-acre City of Maitland park offering multiple tennis courts, pickleball courts, walking trails, picnic pavilions, and playgrounds. While the setting of this property is quiet and serene, the home is minutes from Winter Park shopping and dining; downtown Maitland and Maitland City Centre; I-4 access; and zoned Winter Park High School. Additional home updates include a full roof replacement and AC replacement in 2021, making move-in and insurance smooth and easy. Don't miss this chance to get Winter Park Chain of Lakes access for yourself at this exceptional price!
Listing Agent: Erin Baker (407-719-0030)
1024 KEWANNEE TRL, MAITLAND, FL 32751
$549,750270 Days on yellowkey MLS ID: O6331331
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1845 Built: 1965Monthly Fee: $8 Tax: $8,403 (2024)Community: Dommerich Hills 3Rd AddSingle Family
Taxes:$8,403
Remarks: One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Appliances and granite counters. Thoughtful upgrades at every turn. Currently zoned for Winter Park HS. Close to everything that Maitland and Winter Park known for, shopping dining and more. Don’t wait, come see today.
Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)
Listing Agent: Patrick D'Agostino (321-467-4555)
535 PAWNEE TRL, MAITLAND, FL 32751
$965,00045 Days on yellowkey MLS ID: O6389344
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2500 Built: 1957 Tax: $10,356 (2024)Community: Dommerich Estates 1St AddSingle Family
Taxes:$10,356
Remarks: Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one of the area's most desirable neighborhoods. Enjoy a perfect blend of comfort, style, and functionality, complete with modern renovations and exceptional outdoor living spaces. This corner lot home with multiple picturesque windows provides an abundance of natural light! Generously sized bedrooms provide ample space for family, guests, or a home office and include 2 master suites, both with 2 closets. Enjoy cooking and entertaining in the stunning, updated kitchen featuring modern appliances, sleek countertops, and plenty of storage. Luxury vinyl flooring throughout but still the charm of original wood floors in 3 of the bedrooms. Step outside to your own backyard oasis with a sparkling pool with a waterfall feature and paver patio, perfect for relaxing or hosting gatherings. Eco-friendly and convenient, the property includes an electric vehicle charging station. Tucked away yet ready in a moment’s notice is space for your boat, camper, or recreational vehicles. The attached one car garage offers secure storage for tools, bikes, toys, golf cart, hobbies or projects. You are just steps from the neighborhood lake lot where members can enjoy incredible sunsets, fishing, or launch your watercraft and enjoy a day on the lake. 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. The City of Maitland, despite its close proximity to Orlando, is vibrant with a small-town feel providing events designed to foster connections among residents with walkable neighborhoods, multiple parks and downtown street parties and concerts!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Shirley Welch (407-718-1450)
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