Homes for Sale Near Winter Park High in Maitland - 38 homes

Remarks: Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property. Enjoy a short walk to the schools on a secluded sidewalk or take in the open sports fields across the street and Maitland Community park a few streets over.

Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC (407-252-5052)

Listing Agent: Garrett Mcginnis (321-278-9511)

Remarks: One or more photo(s) has been virtually staged. Nestled within the quiet, established community of Versailles, this exceptional residence invites you to slow down and savor the good life. Offering over 3,600 sq. ft., this home features 4 spacious bedrooms and 3 full baths, with a layout that is both functional and flexible. The PRIMARY SUITE is conveniently located on the MAIN FLOOR and features an EXPANSIVE ATTACHED OFFICE, CRAFT ROOM OR SITTING ROOM—perfect for today’s lifestyle. This generous space also presents a unique opportunity for reconfiguration, allowing you to expand the primary bedroom and/or create a truly luxurious bath retreat tailored to your vision. Upstairs, three additional BEDROOMS ARE IMPRESSIVELY SIZED, offering plenty of room for family or guests. A STANDOUT FEATURE of the home is the BONUS ROOM with its own private entrance, located just off the rear garage—ideal for a game room, media lounge, or entertainment hub complete with space for a pool table, ping pong table, and a large-screen TV. At the heart of the home, the EXPANSIVE 23 x14 kitchen is filled with potential and already equipped with premium appliances, including a SubZero refrigerator, separate SubZero freezer, and a Viking cooktop. Built-in desk space and charming banquet seating create a welcoming spot for casual dining and everyday moments. The inviting family room is designed for cozy evenings, featuring a wood-burning fireplace, beverage fridge, ice maker, and sink—perfect for entertaining or unwinding. For larger gatherings, the expansive living room and adjacent dining area provide an elegant backdrop, whether hosting dinner parties, game nights, or enjoying music by a grand piano. Step outside to your private oasis, set on NEARLY HALF OF AN ACRE of beautifully landscaped grounds. The generous deck surrounds a stunning 10-foot-deep SWIMMING POOL offering endless possibilities for outdoor entertaining, relaxation, and recreation. Life in Versailles extends beyond your front door. HOA Residents can enjoy PRIVATE ACCESS TO LAKE Minnehaha, complete with a dock—perfect for paddleboarding, kayaking, or soaking in breathtaking sunset views. Just beyond the back gate, Maitland Community Park offers an array of AMENITIES including playgrounds, tennis courts, basketball, racquetball, and scenic fitness trails. A convenient paved path even connects you to nearby shopping and dining, including Publix. Ideally located with easy access to Maitland Boulevard, SR 414, I-4, and 436, SUNRAIL station is close and ZONED IN TOP RATED SCHOOLS, this home offers both tranquility and convenience. With an optional HOA, you have the freedom to enjoy the community on your terms. This is more than a home—it’s a lifestyle waiting to be embraced. Make your appointment today to view this lovely home!

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

Listing Agent: Heather Frazee (321-689-9465)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.

Listing is courtesy of: CAPITAL EQUITY REAL ESTATE CO (321-300-4211)

Listing Agent: Christian Del Pino (407-925-9389)

Remarks: One or more photo(s) has been virtually staged. Priced below appraised value for a limited opportunity to capture instant equity. 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: Wake up to shimmering lake views and end your day with breathtaking Florida sunsets in this beautifully maintained 2 bedroom, 2 bathroom condo residence. The moment you step off the elevator and enter, you are welcomed by a bright open concept living space filled with natural light and oversized new glass sliding doors leading to your private enclosed patio. The kitchen features upgraded cabinetry, abundant natural light, a spacious eat in area, and a large island perfect for entertaining. Flooring was upgraded after purchase, new carpet was installed just six months ago, and the AC unit was replaced two years ago for added comfort and peace of mind. Custom tailored curtains add a polished finishing touch. The primary suite offers a private bath and peaceful retreat, while the split bedroom layout provides privacy for guests. Living in The Moorings means enjoying a serene lakeside lifestyle with a community pool, heated spa, clubhouse, beautifully landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Relax on the lakefront dock or entertain family and friends poolside. Walk across the street to Luke’s and Antonio’s or stroll to Maitland’s newly designed downtown area with open green space, farmers markets, movies in the park, and community events.

Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)

Listing Agent: Allison Hunter (407-221-4669)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1135 Thunder Trail, a beautifully updated pool home in Maitland, Florida, located in the highly desirable Dommerich Hills neighborhood. Situated on an oversized lot with no HOA, this property offers nearly 3,000 square feet of flexible living space, combining comfort, functionality, and the best of Florida outdoor living. Step inside to an open and inviting floor plan featuring a formal living room and dining area that flow seamlessly into a spacious family room, perfect for everyday living and entertaining. The heart of the home is the fully upgraded gourmet kitchen, complete with high-end appliances, double ovens, large cooktop, stone countertops, custom cabinetry, oversized refrigerator, and a massive center island designed for gathering. The family room is warm and stylish with a fireplace, custom feature wall, and a built-in wine bar with beverage coolers, bar sink, and coffee station. Large windows fill the home with natural light and provide views of the private backyard oasis. The first-floor primary suite offers a true retreat with dual walk-in closets, French doors leading to the pool, and a renovated ensuite bathroom featuring double vanities and a walk-in shower. Upstairs, you’ll find an expansive bonus room (26x17) with a half bath and built-in daybed, ideal as a media room, game room, home office, or guest suite, plus three additional bedrooms, a full bath with dual sinks, and custom built-ins throughout. Step outside to your private backyard paradise, featuring a sparkling in-ground pool, outdoor shower, fire pit area, multiple gazebo seating spaces, mature landscaping, and fruit trees. The fully fenced yard offers privacy and plenty of space for pets or play, while built-in gas lines make outdoor cooking effortless. Recent upgrades include: * New roof (2022) * New windows (2021) * New doors (2025) * HVAC (2019) * Fresh interior paint & updated landscaping Additional features include a two-car garage, large indoor laundry room with cabinetry, irrigation well, city sewer, and abundant storage throughout. Located just minutes from Maitland Social, Maitland City Centre, shopping, dining, and parks—and zoned for top-rated schools including Dommerich Elementary School, Maitland Middle School, and Winter Park High School—this home offers the perfect combination of location, lifestyle, and value. If you’ve been searching for a move-in ready pool home in Maitland with no HOA and top schools, this is the one.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Angela Worachek Pllc (503-381-1575)

Remarks: Under contract-accepting backup offers. 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: 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)

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: Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

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

Listing Agent: Angel Reyes (407-697-3313)

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: 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)

Remarks: Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)

Listing Agent: Beth Hathaway (407-314-1300)

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: Under contract-accepting backup offers. 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: This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: One or more photo(s) has been virtually staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in the bright sunroom overlooking the fully fenced backyard with a concrete wall for added privacy. A screened-in porch provides the perfect spot to enjoy Florida living year-round. This home’s prime location in Maitland provides easy access to top-rated schools, parks, shopping, dining, and major highways, making it both a peaceful retreat and a convenient base for daily living!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Blake Bolton (407-318-0361)

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: 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: Welcome to The Moorings on Lake Maitland, one of the most in-demand communities in the area. Consider this unit, 3-bedrooms and 2-1/2 baths, approximately 1700 square feet of living space with a 1-car garage, and overlooking the beautiful peaceful courtyard, to be your blank slate. Gleaming wood floors and fresh painted throughout, it is just waiting for you to make it your own. You'll love this comfortable living space, and there is so much to work with! From the entry foyer you'll find the eat-in kitchen immediately on your right. Head through the kitchen to the spacious dining room, and into the living room with vaulted ceiling and zen garden view. Half-bath and inviting screened lanai complete the ground floor living space. Upstairs you'll find the large primary suite, also overlooking the courtyard, and two more bedrooms, both front-facing, and a full bath in the hallway. The laundry room with washer, dryer and utility sink is in the garage. The grounds, pool and club house are maintained by the community, so all you have to so is enjoy the ambiance of the beautiful grounds and the lakefront. The many advantages to this convenient location include being on Lake Maitland, and, easy access to necessities like grocery and drug stores, and restaurants within walking distance. This one is priced to sell, so don't miss this opportunity!

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Sue Gilman (407-405-0108)