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$609,900
3 Beds 3 Baths Highland Park Estates SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. NEWLY sanded and stained Hardwood flooring, New Kitchen Flooring, freshly painted and ready to Welcome you to 2020 Geronimo Trail—an inviting 3-bedroom, 2.5-bath mid-century ranch-style pool home nestled in one of Maitland’s most beloved neighborhoods. Built in 1961, this home has been lovingly cared for by just three owners in its entire lifetime—a true testament to pride of ownership. Set on a .22-acre lot with mature trees and a spacious backyard, the home is ideally located just blocks from A-rated Dommerich Elementary and Maitland Middle, and zoned for Winter Park High School. A covered front porch welcomes you with classic charm, perfect for morning coffee or evening conversations in rocking chairs. Inside, you’ll find original hardwood floors, a bright living room with wainscoting, a dining room with French doors that open to the backyard, and an eat-in kitchen featuring solid wood Amish cabinetry—handcrafted in Indiana with extra-deep storage. A spacious laundry room with a half bath and backyard access makes for an ideal pool bath setup. The oversized garage offers high ceilings and attic storage, adding everyday functionality. The primary suite includes dual closets and an ensuite bath, while two additional bedrooms and a full hallway bath complete the thoughtfully designed floor plan. Additional features include multiple storage closets, a sparkling swimming pool, and a host of recent upgrades: new electrical panel, new plumbing, upgraded AC duct insulation, and a newer HVAC system. Located just minutes from the shops, dining, and cultural scene of downtown Winter Park, this home blends timeless architecture with modern comforts in a location that continues to grow in value and desirability. Don’t miss this rare opportunity to own a piece of Maitland history on a great street. Schedule your showing today!

2020 Geronimo Trail, Maitland

$465,000
4 Beds 3 Baths Maitland Village SubDv. 32751 Zip Code
Luxury Townhome located in Maitland within the gated community of Maitland Village Townhomes. This 4 Bedroom 2.5 Bath two story Townhome is original owner since built in 2012. This Townhome features Granite counters throughout to include the spacious kitchen and in all baths, Crown Molding throughout, inside laundry room and has a first floor Primary Bedroom with Primary bath and a private Lanai. For guests, the first floor also includes a half bath for convenience. The second floor includes 3 additional bedrooms, a full bath and a spacious loft. Off to the side of the loft is a small private office to maintain your personal bill paying and record keeping. Beautiful paver driveway and a 2 car garage. HOA Fee includes 250-channel cable television, 500 Mbps internet, water, sewer, trash, recycling, landscaping, streetlights, community pool, clubhouse, gate access and management services. Call today to and not miss this great opportunity to own a maintenance free living Townhome in a quiet area of Maitland!

1970 Michael Tiago Circle, Maitland

$530,000
3 Beds 2 Baths English Estates Unit 2 SubDv. 32751 Zip Code
Completely transformed with intention and precision, 1201 Manchester Road is a rare offering where style meets substance in one of Maitland’s most desirable residential pockets. Set on an oversized corner lot .26 Acres, just minutes from Lake Lily Park, Park Avenue in Winter Park, and the Enzian Theater, the location blends quiet neighborhood living with prime access to the city’s best. Step inside and experience a layout that feels natural, open, and deeply considered. Oak-toned luxury plank flooring flows throughout, anchored by smooth-finished walls, modern three-panel doors, custom trim work, and warm LED recessed lighting. The spaces feel bright but grounded, open yet purposeful. At the center, the kitchen stuns with a bold 8-foot quartz island, solid wood soft-close cabinetry, a custom-crafted blue range hood, marble backsplash, brushed brass finishes, and premium stainless appliances including a microwave drawer. The primary suite is private and polished, with detailed wall molding, a generous walk-in closet, and a spa-like bath featuring a 72-inch dual-sink vanity, marble-tiled walk-in shower, and matte black fixtures. Two additional bedrooms—each with new ceiling fans and built-in closets—share a second designer bath finished with striking tilework and wood vanity. Step outside through the French doors and into a backyard designed for both calm and celebration. The grand-size lap pool has been fully resurfaced and retiled, powered by a brand-new pump, and flanked by a custom Bali-style outdoor shower—a standout detail that elevates the space. The grounds have been completely overhauled with new sod, irrigation, sculpted landscaping, privacy fencing, and custom wood accents that give the exterior both structure and softness. The garage door and opener are brand new, and the driveway has been resurfaced for a clean, cohesive finish. 1201 Manchester isn’t just renovated—it’s meticulously refined. Turn the key and live well—your new home awaits. Schedule your tour today.

1201 Manchester Road, Maitland

$610,000
3 Beds 2 Baths English Estates Unit 3 SubDv. 32751 Zip Code
NEW PRICE!!! Stunning home in Maitland's English Estates neighborhood! PRE-INSPECTED - MOVE IN READY - HOME WARRANTY INCLUDED!!! Completely remodeled by Maru Design Studio, this beautiful 3-bedroom, 2 bath home features an open layout with high-end designer finishes throughout. Luxury vinyl plank flooring has been installed in every room of the home to create seamless transitions into each living space. The kitchen is absolutely gorgeous and features custom solid wood cabinetry, an island, brand-new stainless-steel appliances, and bright white Quartz countertops. A large living/dining room with decorative fireplace is adjacent to the kitchen and there’s a lovely multi-purpose room with built-in floor to ceiling shelving just off the foyer with French doors that open to the screened patio. Down the hall are two comfortably sized bedrooms and a gorgeous hall bath with a double sink vanity and optimum storage. The primary bedroom is spacious with a large walk-in closet and private en suite with shower. Each bathroom has been completely redone and include all new tile work, vanities, brass plumbing fixtures, new tub (hall bath), new toilets, and mirrors. Interior mudroom/laundry room off the 2-car garage has a new utility sink and room for additional storage. The backyard is a true oasis perfect for cookouts with family and friends or relaxing by the fire pit. New landscaping, including fresh sod and flowered garden beds complement the private backyard which showcases an array of pineapples, banana trees, and citrus trees. A large gazebo houses an all-new outdoor grill and is adorned with market lights and ceiling fan to keep you cool during the summer months. Other notable improvements include all new windows (2025), new roof (2021), new electrical panel (2021), water heater (2017), and copper plumbing. Located in the desirable English Estates neighborhood, residents enjoy quiet, walkable streets, close proximity to Kewannee Park with its waterfront boardwalk, playground, and wooded trails, and close proximity to major roadways, shops and dining. Homes in this neighborhood are zoned for English Estates Elementary, South Seminole Middle School, and Lake Howell High.

2460 Worthington Road, Maitland

$905,000
4 Beds 3 Baths Maitland Park South SubDv. 32751 Zip Code
Amazing opportunity to live in a ONE STORY home nestled between Winter Park and Maitland. This 4/2.5 is located in one of the best neighborhoods and just off of Park Avenue. Tons of natural light flows throughout the entire home. The cozy family room with beautiful built-ins opens up to the kitchen featuring light and bright cabinetry, granite countertops and a center island with room for barstools. Separate living room and dining room with wall to wall seagrass carpeting and a gorgeous brick wall plus an enclosed sunroom allows plenty of space to entertain. The split bedroom floor plan makes this the perfect place for any family with 3 bedrooms and 1.5 bathrooms separated from the primary bedroom. New windows throughout. Situated on a 0.30 acre lot, there is plenty of room to expand. Just a quick bike ride to Park Avenue and easy access to Winter Park Village and Downtown Maitland. Fantastic location right by The Enzian theater & Park Maitland school. Zoned for the highly coveted Dommerich Elementary, Maitland Middle and Winter Park High School! Welcome Home!

1441 Sunnyside Drive, Maitland

$2,250,000
6 Beds 8 Baths Terra Place SubDv. 32751 Zip Code
Presenting a stunning new construction residence located on a quiet cul-de-sac offering a seamless blend of luxury, functionality and modern design. The main home features four spacious bedroom suites, a dedicated office and a bonus/flex area, 4 full baths and 2 half baths, while the property also includes a rare-to-find one-level detached 1,143 sf 2BE/2BA guest house that includes a kitchen and a living area... *** ideal for for multi-generational living, spacious home office, live-ins or long term guests… Beautiful wood floors extend throughout the main house living spaces, complemented by designer porcelain tile in all baths. The open floor plan showcases soaring 21-foot ceilings in the great room and dining area, anchored by a beautiful chef’s kitchen complete with a dual-fuel range, quartz waterfall island, custom blended cabinetry and an adjacent walk-in pantry. A wall of sliding glass doors in the great room opens to the expansive covered lanai and new Pebble Tec pool with autofill and auto-drain features, all surrounded by travertine decking and a masonry and aluminum privacy fence. The first-floor primary suite offers a serene retreat with private pool courtyard views, a custom walk-in closet and a spa-inspired bath with marble floors, a spacious walk-in shower and a separate soaking tub. Upstairs, there are three additional bedroom suites and a versatile loft to provide ideal space for relaxation lounge area. The side-entry two-car garage includes epoxy floors, EV charging readiness and direct access to the mudroom, laundry, pantry and kitchen for everyday convenience. Designed for year-round entertainment, the covered lanai is stubbed and ready for a summer kitchen, with additional outdoor space available for expanded amenities. Both main and guest houses are bathed in natural light thanks to generous architecturally enhancing windows and glass doors. Modern comforts include smart lighting, exterior security cameras and a built-in audio system. On a quiet cul-de-sac, this property is within visiting or biking distance to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball, playgrounds, trails and pavilions! Enjoy easy access to other downtown Maitland amenities, 7-10 minute drive to Park Avenue in downtown Winter Park, quick access to major roadways & I-4, downtown Orlando, area hospitals, and both executive and international airports... Zoned for regarded Lake Sybelia Elementary, Maitland Middle and Winter Park High School, this exceptional home is a rare offering in a secluded, wonderful neighborhood.

734 Terra Place, Maitland

$8,925,000
5 Beds 8 Baths Adams Grove SubDv. 32751 Zip Code
Villa Serenata, a lakefront legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterranean estate on the renowned Winter Park Chain of Lakes. On approximately two acres of meticulously curated grounds, this extraordinary residence feels less like a home and more like a private resort, crafted for those who appreciate timeless architecture, thoughtful design and elevated lakefront living. A sweeping circular driveway welcomes you beneath a canopy of soaring royal palms and majestic live oaks, immediately setting the tone for what lies beyond. As the automated gate opens, the property reveals itself as a serene sanctuary where elegance and privacy coexist in harmony. The 6,634-square-foot main residence showcases interiors by acclaimed designer Ted Maines, unfolding across two levels of refined sophistication. The Mizner-inspired living room commands attention with dramatic 24-foot wood-beamed ceilings and twin walls of arched French doors, one framing sweeping views of Lake Maitland’s shimmering waters, the other opening to a sun-dappled courtyard where mornings naturally begin with coffee and quiet reflection. The upper level is devoted entirely to the primary suite, creating a private retreat complete with a heatless gas fireplace, spa-caliber bath with soaking tub and steam shower, a bespoke dressing room with custom built-ins, and a rooftop terrace with glass railings offering remarkable lake views. Three additional bedroom suites, each with an en-suite bath and generous walk-in closet, provide comfort and privacy for family and guests alike. At the heart of the home, the chef’s kitchen is equipped with Sub-Zero and Wolf appliances, custom cabinetry, and an expansive prep island designed to transition seamlessly from intimate family meals to catered gatherings of 50. The formal dining room features a dramatic curved wall of windows, turning every meal into a lakefront experience, while the richly paneled library and office offer a quiet space for focused work or relaxed reading. Complementing the main residence is a thoughtfully designed guest compound totaling 1,540 square feet. A private media pavilion delivers a state-of-the-art theater and listening room for film enthusiasts and audiophiles, while the one-bedroom guest apartment above provides a fully appointed living space with kitchen, living area and private entry, ideal for extended family, visiting guests or live-in staff. Outdoor living is equally exceptional. Resort-style travertine surrounds the pool amid lush tropical landscaping, creating a tranquil setting for sun-filled afternoons. A covered lanai with full summer kitchen flows effortlessly from the family room, while an expansive open-air terrace extends from the great room, an inviting backdrop for sunset cocktails overlooking the lake. Villa Serenata is more than a residence, it is a legacy estate, offering privacy, architectural distinction, and a lifestyle centered on one of Winter Park’s treasured waterfront settings.

1640 E Adams Drive, Maitland

$870,000
3 Beds 3 Baths Maitland Manor Subdivision SubDv. 32751 Zip Code
This beautiful home on a corner lot in Maitland features a new pool and a large backyard. Inside and out, it’s the perfect home to entertain friends and family. The home’s split floor plan and design maximize functionality. The living room, dining room and kitchen are all large spaces, and so are the three bedrooms. An extra room serves as a perfect office or nursery space. The primary suite boasts a huge closet and bathroom. Two driveways, and plenty of room for boat or RV parking add convenience. The meticulously designed landscaping adds beauty. Recent updates throughout, including a new roof, make this home move-in ready with flexible living and extra space inside and out. And it’s desirable, convenient location in a friendly, no HOA neighborhood make it the perfect place to call home.

446 Piney Croft Lane, Maitland

$2,535,000
5 Beds 4 Baths Sybelia Shores Second Add SubDv. 32751 Zip Code
Completed New Construction 2024 | Lakefront Luxury | Below Appraised Value: This extraordinary custom lakefront residence was built by Dave Konkol & is elevated on a 0.56-acre corner lot w/ approximately 112’ of lake frontage. Featuring a crisp stucco exterior, impact windows & remote-operated screened porches, the home is surrounded by professionally designed native landscaping & butterfly gardens which set the stage for a lifestyle defined by natural beauty, enduring materials, timeless design & everyday comfort. Once inside, the open floor plan showcases wide-plank, white oak engineered wood flooring & is filled w/ natural light from the large format windows that frame views of the backyard pool & serene Lake Sybelia out front. A formal dining space connects to a wet bar & opens to a functional yet casually elegant kitchen. Quartz countertops, custom soft-close cabinetry with pull-outs & a full suite of premium appliances lend functionality & refinement to the kitchen. A large walk-in pantry & adjacent drop zone add quality of life to the beautifully tailored design. The main-level primary suite is a sanctuary w/ lake views, remote-controlled blackout shades, decorative wood ceiling beams, a customized walk-in closet & a spa-like bathroom featuring Frank Lloyd Wright Brizo plumbing fixtures, a long vanity stained to match the fixtures, dual sinks, an oversized glass-enclosed shower with 21” rainhead, soaking tub & private water closet. A guest bedroom w/ adjacent full bath also functions as a pool and powder bath. The large laundry room w/ quartz countertops, GE Profile front-loading washer and dryer & a Laundry Jet Swift pneumatic laundry chute—connected to the primary suite & upstairs bedrooms and complete the main floor. Upstairs, two additional bedrooms with wide water views include customized closets & designer baths. The cozy loft and Bonus spaces flex easily for work, wellness, or play. Other interior features include built-in speakers, custom millwork, motorized blinds & smart-home wiring to enhance comfort and livability. Seamless indoor-outdoor transitions define the rear living experience, where a deep covered lanai includes recessed lighting, fans, speakers & motorized screens opening to a 7’ deep, heated, saltwater pool w/ sunshelf, outdoor shower & direct access to a full bathroom. The fenced backyard offers ample space for play, relaxation & a dog run. A custom dock w/ composite decking & covered boat lift sits on Lake Sybelia—offering year-round opportunities for boating, paddle-boarding, swimming & fishing on waters with no public access. Efficiency abounds thanks to a PES Solar system featuring 58 REC panels, four Enphase battery backups & real-time energy monitoring. Additional features include Trane HVAC systems, a commercial-grade water heater w/ recirculating pump & a new irrigation system w/ pump fed by lake water. The three-car garage includes modern paneled doors w/ openers and extra storage. Now unexpectedly available due to a change in the owners’ plans, this is a rare opportunity to purchase an almost-new custom home—combining advanced systems with timeless design—in one of Maitland’s most beloved neighborhoods, just minutes from Lake Lily Park, downtown Maitland, major thoroughfares and Winter Park’s shops and restaurants.

705 N Lake Sybelia Drive, Maitland

$323,000
3 Beds 2 Baths Sun Bay Club Condo SubDv. 32751 Zip Code
RARE and RENOVATED 3-BED / 2-BATH FIRST FLOOR Condo in GATED SUNBAY CLUB! Convenient and easy access from parking directly in front of the dedicated entryway and double entry door. Upon entry, experience the immediate openness of the living space. Living and Dining Area flank your path to the 2025 RENOVATED KITCHEN with eating nook with separate pantry and interior laundry closets. <br><br> KITCHEN/LIVING/DINING: Remodel includes SLEEK WOOD CABINETRY, GRANITE countertops, matching STAINLESS LG APPLIANCE package, an under-mount sink with high neck chrome faucet and balcony access are luxury features that make this cooking area a joy for every meal’s preparation. A NEW sheik dining room CHANDLIER hangs above an eating space and the mirrored wall doubles the feel of the room. The wood burning fireplace topped with opposing mirrors, and a sliding door leading to your large private balcony sets a mood you’ll love settling into every evening. <br><br> ENTIRE DWELLING: LUXURY VINYL PLANK flooring runs throughout the condo making cleaning and maintenance a breeze. Owner’s suite shares access to the private balcony overlooking the POND with FOUNTAIN. Primary bath features upgraded DUAL SINK VANITY topped with granite and a shower with retro glass block wall. WHITE PLANTATION SHUTTERS adorn every window and sliding door for privacy and elegance. The home has been FRESHLY PAINTED in a calming palette will perfectly compliment your own taste of décor and furnishing. Ample guest-bedrooms flank a JACK’N’JILL guest bathroom with DUAL REACH-IN CLOSETS providing all the storage you’ll ever need! HVAC (2021) with UV LIGHT will provide peace of mind. <br><br> SUNBAY CLUB: This small enclave of 68 condominiums offers a uniquely private living experience. Behind the iconic blue gates, you will find a beautiful community enhanced with fountains, open grassy areas, a tennis court, lakefront swimming pool and a boat launch perfect for your paddleboard. Sunbay Club replaced all tile roofs, gutters/downspouts, skylights in 2024. CONDO FEE INCLUDES: CABLE & HIGH-SPEED INTERNET (Spectrum). Fee also covers: Gated Entry, Exterior Maintenance (building/roof), Common-Areas, Landscaping/Irrigation, Lighting/Ponds Maintenance, Pool/Clubhouse Upkeep, Master Insurance Policy (buildings). Combined, these community services reduce your ownership costs tremendously!!<br><br> LOCATION: Access within minutes World-Class “RDV Sportsplex” (Genesis HealthClub), Interstate-4 (Express), Publix, shopping & dining options. Downtown Maitland, Winter Park and Orlando are only a minutes away. Come see why this is the address you will want to call YOUR NEXT HOME !!

1000 Winderley Place Unit 140, Maitland

$538,000
4 Beds 3 Baths English Woods SubDv. 32751 Zip Code
Perfectly positioned on a sprawling, nearly 1/3-acre corner lot in the heart of Maitland. Inside, the home unfolds into expansive, light-filled living areas where the great room, kitchen, and dining spaces connect effortlessly—designed for both stylish entertaining and relaxed family life. The kitchen is a true centerpiece, featuring solid wood white cabinetry, premium quartz countertops, a stainless steel appliance package with hood vent and microwave drawer oven, beautiful accent shelving, and a large island with eat-in counter seating—crafted for both function and beauty. This home strikes the perfect balance between expansive living spaces and tasteful, high-quality updates, creating a move-in-ready experience that's rare to find. A spacious two-car garage adds everyday convenience and storage. Step outside to a private, screen-enclosed lanai and patio, surrounded by mature landscaping and the peaceful privacy only a corner lot can provide — perfect for relaxing or entertaining year-round. Embracing the best of Maitland’s lifestyle- Publix Super Market at Maitland Place is just 1.5 miles away for everyday convenience. Lake Lily Park and the charming Maitland Farmers Market are only minutes from your doorstep. Downtown Winter Park’s award-winning Park Avenue is less than 10 minutes away, offering an unmatched mix of boutique shopping, acclaimed restaurants, art galleries, and year-round festivals. Quick access to I-4 makes commuting into Downtown Orlando a breeze. With top-rated schools, lush parks, and the very best of Central Florida at your fingertips, this location checks every box. Schedule your tour today.

2327 Fieldingwood Road, Maitland

$396,000
3 Beds 3 Baths Enclave At Maitland SubDv. 32751 Zip Code
Welcome to Montacino—a peaceful, gated oasis where style meets convenience. This 3-bedroom, 2.5-bath townhome offers timeless character and solid craftsmanship, with no rear neighbors and tranquil rear exposure. Designed with enduring finishes, the home features granite countertops, stainless steel appliances, and classic crown molding throughout the main living areas. Enjoy a functional layout with an open-concept living and dining space, a convenient downstairs powder room, and a covered back porch that provides a quiet retreat with peaceful views. Upstairs, the spacious primary suite offers a private balcony, generous closet space, and an en-suite bath. The upstairs laundry closet adds ease to daily routines. Perfectly situated just minutes from Downtown Orlando and the dining and culture of Winter Park, yet tucked away in a serene lakeside setting. The community features a resort-style pool and beautifully landscaped grounds, offering low-maintenance living in a truly charming location. Don’t miss the chance to own in one of the area's most desirable gated communities!

1379 Benevolent Street, Maitland

$1,820,000
4 Beds 3 Baths Delroy Park SubDv. 32751 Zip Code
Stunning Lakefront Pool Home on the Winter Park Chain of Lakes Welcome to your private oasis on the highly sought-after Winter Park Chain of Lakes. This beautifully updated home is nestled on a full acre along the tranquil shores of Lake Nina, ideally located between Lake Maitland and Lake Minnehaha. Nearly every room in the home offers panoramic lake views and spectacular sunsets, creating a peaceful and luxurious waterfront lifestyle. The light-filled interior features four bedrooms, two and one-half baths, a formal living room, a cozy breakfast room, and a spacious family room that opens into a separate game or playroom complete with a wet bar—perfect for entertaining. The recently updated kitchen is both elegant and functional, with a large granite island, farmhouse sink, classic subway tile backsplash, a gas range, and an LG stainless steel refrigerator. The master suite is a serene retreat with a tastefully remodeled bathroom that boasts marble countertops, dual sinks, and an impressive wet room that combines a soaking tub and walk-in shower. Throughout the home, you'll find rich hardwood and slate flooring, plantation shutters, insulated casement windows, and cathedral ceilings. Practical upgrades include a new HVAC system and roof installed in 2016, along with a tankless water heater. Step outside to enjoy the stunning backyard, complete with a resort-style pool area and two expansive decks—one just off the kitchen and another directly on the lake. The lush landscape includes four mature fruit trees: avocado, mango, lemon, and lime, adding to the tropical charm. For those who love the water, the refurbished boathouse and dock deck are ready for all your boating and waterfront activities. This home is a rare opportunity to live on the Winter Park Chain of Lakes with all the modern amenities and timeless style you could hope for. Located in a quiet, welcoming neighborhood, yet just minutes from downtown Winter Park’s boutique shops, top-rated restaurants, and highly regarded schools. Bonus: Be sure to ask about the owners’ expansion plans—an exceptional chance to personalize and enhance this already stunning lakefront gem.

251 W Trotters Drive, Maitland

$507,500
4 Beds 3 Baths Forest Brook SubDv. 32751 Zip Code
Tucked away on a quiet cul-de-sac in the coveted Forest Brook neighborhood, this one-of-a-kind, custom-built concrete block home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand foyer, elegant formal living and dining rooms, and a bright, open family room featuring a cozy fireplace — ideal for gatherings. The spacious kitchen is a chef’s delight, complete with a gas oven, ample cabinetry, an eat-in nook, and a built-in desk with shelving. Generous room sizes, recessed lighting, and tray ceilings add a touch of sophistication throughout, while the smart split-bedroom layout ensures privacy and comfort for all. Practical features abound, including a well-equipped laundry room with utility sink, extended counter space, and bonus cabinetry. Step outside into a lush backyard oasis, fully fenced and blooming with vibrant morning glories, a ginger tree, and a colorful array of seasonal plants. The large patio and deck — beautifully redone just 1.5 years ago — set the stage for effortless outdoor entertaining. Enjoy a sparkling 12-foot pool, resurfaced in 2020, with a 2022 pump replacement and premium pool sweep included. Additional upgrades provide peace of mind: hurricane-rated windows, a new roof in 2019, and a new A/C unit in 2020. This exceptional home is ideally situated near shopping, dining, and major roadways — ready to welcome its next owner with comfort, quality, and room to make it your own.

702 Green Meadow Avenue, Maitland

$1,395,500
5 Beds 5 Baths Lake Sybelia Cove SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the spacious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment and has a new sparkling finish, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience. A great canvas with many possibilities to create a space that truly reflects your modern vision and lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland home provides.

755 Cranes Court, Maitland

$432,500
3 Beds 2 Baths Oakland Shores 3rd Add Rep SubDv. 32751 Zip Code
*New roof is scheduled to be installed May 2025.* Welcome to this charming home located in the highly desired Oakland Shores neighborhood. This 3 bedroom, 2 bathroom home boasts comfort and tranquility inside and out. Stepping through the front door you are immediately greeted by the vast family room, featuring luxury vinyl plank flooring and beautiful tall ceilings. Lying just off the family room is a perfectly placed kitchen, featuring granite countertops, solid wood cabinetry, and stainless steel appliances. The spacious dining room accompanies the kitchen providing for wonderful entertainment space. Venturing down the center hallway you'll find one full bathroom and 3 bedrooms, all featuring beautifully maintained terrazzo flooring. The Master Bedroom lies at the end of the hallway providing the perfect space for you to relax in comfort. Leading your way to the lustrous backyard and porch area, you'll escape to your very own tropical oasis. The covered porch overlooks the beautiful pool, all featuring paver decking. There is a 16x12 shed located to the rear of the property, offering great storage or private office space, featuring electricity and AC. Additionally, the home features updated plumbing (2020), vinyl fencing (2021), new windows (2022), and new AC (2024). The covered carport provides ample space to park your vehicles to protect them from the elements. Attached to the carport is your interior laundry room and utility. Conveniently located providing access to Downtown Maitland, local restaurants and establishments, along with quick and easy access to and from I-4, this beautiful home awaits your presence!

605 Oranole Road, Maitland

$474,900
4 Beds 3 Baths Maitland Village SubDv. 32751 Zip Code
Welcome to this 4bed/2.5bath exquisite oversized, Mediterranean-style END-UNIT townhome nestled in the gated luxury community of Maitland Village, located less than 1 mile from I-4 and Maitland Blvd! This two-story gem offers 4 spacious bedrooms and 2.5 baths, featuring a thoughtfully designed open floor plan. The heart of the home is the modern kitchen, boasting stainless steel appliances, granite countertops, 42" cabinetry, a breakfast bar, and a generously sized walk-in pantry. The family room flows seamlessly into a covered outdoor lanai, creating additional living space perfect for entertaining or relaxation. The downstairs bedroom, adorned with bright corner windows and French doors, offers versatility as an office or guest room and has direct wired internet access. Upstairs, a spacious loft provides an ideal flex space for a play area or home office. The oversized master suite boasts a deluxe bath, dual vanity with granite countertops, a garden tub and shower, and an oversized walk-in closet. The second bedroom offers a walk-in closet and direct access to the second bathroom while the third bedroom offers a huge walk-in closet with a window. Enjoy maintenance-free living with amenities that include a barrel tile roof, double-pane windows, energy-efficient Carrier heat pump, R-30 roof insulation, and pre-wired security and surround sound systems. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, and sprinklers. This beautiful, gated community features a pool, clubhouse, and convenient access to Genesis Health Club (Former RDV), Winter Park, Downtown Orlando, and local favorites like Lake Lily Farmers Market or Uptown Altamonte & Altamonte Mall. This gem is near amazing jobs in the Maitland corporate and commerce centers. Discover modern living at its finest—comfort, style, and convenience awaits you at this beautiful END-UNIT townhouse.

1998 Michael Tiago Circle, Maitland

$3,385,000
4 Beds 5 Baths Ravndals Rep SubDv. 32751 Zip Code
Tucked away at the end of a quiet cul-de-sac, this serene lakefront retreat is sited on a lush 1.21-acre lot w/ 187 feet of shoreline on tranquil Lake Nina—part of the Winter Park Chain of Lakes—this 4-bedroom, 4.5-bathroom, 4,997-square-foot estate blends Santa Barbara-style charm w/ modern sophistication in one of Central Florida’s most desirable settings. A meandering drive leads you to a semi-circular paver driveway that welcomes you home. A deep, covered front porch provides a gracious entry, setting the tone for the calm, understated elegance found throughout. Once inside, nearly floor-to-ceiling windows span the entire rear elevation, offering breathtaking lake views from every angle & filling the home w/ natural light. To the right of the foyer, a cozy formal living room w/ a wood-burning fireplace invites quiet conversations or evening relaxation. To the left, the spacious dining room features a built-in buffet designed to preserve unobstructed views of the water. Just beyond, the newly renovated kitchen is a standout including a La Cornue French gas range, Monogram appliances, a concrete farmhouse sink, wide-plank oak flooring, luxury lighting & striking marble counters. A hidden scullery/laundry area offers practical overflow, connecting the kitchen to the oversized, air-conditioned 2-car, side-facing garage w/ built-in storage & a dedicated gym or flex room. Moving through the heart of the home, a large family room awaits—framed by soaring ceilings with cedar beam accents & outfitted w/ automated shades for comfort & privacy. The primary suite occupies its own wing & features a gas fireplace, dual walk-in closets, a spa-style bath, & 2 separate flex rooms currently used as an office & art studio. On the opposite side of the home, a tucked-away powder bath conveniently serves both guests & the pool area, while an additional en-suite bedroom downstairs offers privacy for guests or multi-generational living. Upstairs, two more bedrooms w/ en suite baths flank a generous loft w/ amazing lake views. Step outside & the setting is nothing short of spectacular. The resort-style backyard was designed for entertaining & unwinding alike, w/ multiple fire pits, a sparkling pool & raised spa & an outdoor kitchen complete with grill, pizza oven, built-in space for Green Egg, sink & refrigerator. The expansive lawn gently slopes toward the lake, leading to a rare, fully outfitted dock w/ a covered boathouse, lift, dual jet ski slips & utilities for water & electric—perfect for sunset cocktails or launching into the larger chain of lakes. Architectural details throughout the home include Mexican tile, natural wood & stone finishes, vaulted ceilings, metal accents, & custom lighting—thoughtfully layered to create a warm & inviting atmosphere. Major improvements include a home repipe (2020), updated electrical (2019), 3 new HVAC systems (2022), new garage doors (2021), & recently installed paver hardscape designed to accommodate ample parking for family & guests. In a sought-after Maitland lakefront enclave, this home pairs top schools w/ rare privacy & convenience. Lake Nina provides a quiet, scenic backdrop, yet a short, easily navigable canal offers direct access to the expansive waters of Lake Maitland & the greater Winter Park Chain—making it as ideal for tranquil mornings as it is for adventurous afternoons on the water. More than a home, this property is a lifestyle, a legacy & a front-row seat to the best of lakefront living.

645 Manor Road, Maitland

$410,000
3 Beds 3 Baths Enclave/Maitland A-F SubDv. 32751 Zip Code
Welcome to turnkey, modern living in the gated community of Montacino (Enclave at Maitland)! This upscale townhome has been beautifully renovated, with a stylish kitchen offering newer top-of-the-line GE Café appliances (2022) including an induction range, a brand-new dishwasher, and gorgeous white quartz countertops, plus neutral wood-like LVP flooring for durability (up the stairway and throughout the 2nd floor)…NO carpet! The open floorplan is ideal for entertaining, with a fresh and airy living/dining/kitchen combo enhanced by bright, custom Benjamin Moore paint. Upgraded lighting, mirrors, and hardware throughout add a luxurious, designer feel. Off the kitchen, a covered rear patio faces an expansive lawn wrapped in trees, providing outdoor enjoyment and completely maintained by the HOA. Upstairs, the spacious Primary Retreat awaits, with a large sitting area (also great for a desk or an exercise bike!), a balcony overlooking the lawn below, a custom walk-in closet by California Closets, and a modern en-suite bath featuring dual sinks and an upgraded TOTO Washlet bidet. Down the hall sits 2 more bedrooms, a full bath, and a laundry closet with storage shelves over the newer Whirlpool washer & dryer. Turnkey living is enhanced by the convenience of multiple storage closets, a downstairs powder room, and a 1-car garage with built-in cabinets and storage racks, plus plenty of guest parking right outside. Walk to the expansive resort-style pool or along the sidewalk overlooking Lake Charity, and drive just 10 minutes to the vibrant shops and eateries of downtown Winter Park or downtown Orlando. Experience the perfect blend of low-maintenance, luxury living in this charming, Montacino home!

1342 Benevolent Street, Maitland

$399,900
3 Beds 3 Baths Enclave At Maitland SubDv. 32751 Zip Code
Prime location in the gated community of Montecino! This beautifully updated 3-bedroom, 2.5-bath townhouse offers a bright and modern layout with new laminate flooring throughout the first floor. The fully renovated kitchen features granite countertops, a stylish backsplash, and newer stainless steel appliances, all overlooking the open porch and peaceful green space—ideal for relaxing or entertaining. Upstairs, the spacious master suite boasts a cozy sitting area, private balcony, walk-in closet, and an en-suite bath with dual granite vanities and a walk-in shower. Additional updates include new carpet upstairs, a remodeled half bath (2023), and a new water heater. Washer and dryer are included. The home also offers a one-car garage and is partially furnished for added convenience. Maintenance-free living in a beautiful community with access to a sparkling pool and scenic lake views. Conveniently located just minutes from I-4, shopping, dining, and Downtown Orlando!

1267 Blessing Street, Maitland

$725,000
3 Beds 2 Baths Hollieanna Shores SubDv. 32751 Zip Code
Renovated Maitland Gem with newer pool, move-In ready! Tucked away in a peaceful Maitland neighborhood, this beautifully updated one-story home offers a blend of style, comfort and convenience. With three bedrooms, two baths and 1,760 square feet of thoughtfully designed living space, this property is a hidden gem. Enjoy unbeatable curb appeal with lush landscaping, newer windows/doors, a lighted walkway to the front door, and a welcoming open front deck with a stylish, modern privacy wall. The oversized brick paver driveway adds charm and functionality. Inside, tile flooring flows seamlessly throughout the entire home, enhancing its clean, cohesive look. Plantation shutters and designer lighting add a refined touch to every room, while custom closet systems maximize storage in all bedrooms. The open-concept kitchen is a dream for everyday living and entertaining, featuring soft-close cabinets and drawers, bar seating and a cozy breakfast nook. It overlooks the spacious great room and dining area, both adorned with large picture windows that frame serene views of the backyard and pool. The primary suite offers a relaxing retreat with a walk-in closet and a beautifully updated en-suite bath with a large glass-enclosed shower. Two additional bedrooms and a spacious laundry room complete the smartly designed layout. Go outside to your private backyard oasis, fully fenced for privacy and beautifully landscaped to create a picturesque setting. A sparkling, heated/saltwater pool invites you to unwind or entertain, while the generous green space provides ample room for outdoor games, gardening, pets or future enhancements. The covered patio is ideal for alfresco dining, morning coffee or simply enjoying the Florida sunshine in your tranquil retreat. Additional features include a one-car garage with a large storage room and additional refrigerator. Just minutes from downtown Winter Park, top-rated public schools, and with easy access to major roadways, this home offers the best of comfort and convenience. Don’t miss your chance to own this move-in-ready home in one of Maitland’s desirable locations.

113 Tangelo Court, Maitland

$422,000
3 Beds 2 Baths Poors 2nd Add SubDv. 32751 Zip Code
The seller is ready to move quickly – this is a great opportunity for buyers! LOCATION! LOCATION! LOCATION! Nestled on a generous lot with beautiful mature landscaping, this charming Maitland home offers endless potential to create the modern living space you are looking for. Homes in this area move FAST, and with this unbeatable combination of location, convenience, and potential—this one won’t last long. Relax in the shaded backyard or take a leisurely walk to the lively weekend farmers market in downtown Maitland—just minutes away! Conveniently located near schools, parks, shopping, easy access to major highways, and a short walk to the Sunrail Station, it’s easy to see why this property is so desirable and sure to sell fast! Whether you’re craving a night out in Downtown Winter Park or catching a weekday game in Downtown Orlando, convenience is at your doorstep. The home also boasts a recently replaced roof (2018), and a standout feature you won’t find just anywhere—a 200 sq ft, air-conditioned, sound proof insulated office/studio space. So don't miss out—Schedule your private tour today before it’s gone!

410 Sandspur Road N, Maitland

$979,000
4 Beds 3 Baths Dommerich Woods SubDv. 32751 Zip Code
Welcome to this stunning move-in ready pool home in the highly sought after Dommerich neighborhood, known for its top-rated schools and wonderful community. Nestled on an over-sized corner lot in a quiet cul-de-sac, this beautifully maintained home boasts 4 bedrooms, 2 full bathrooms, plus a convenient half bath. The lush landscaping professionally designed by a certified Landscape Designer, exudes gorgeous curb appeal and surrounds the backyard pool and heated spa, creating a private oasis. A separate screened-in porch is connected by pavers providing another quiet retreat. Step inside to find a light-filled interior with elegant finishes and plenty of room to entertain. The heart of the home is the expansive chef's kitchen with modern appliances featuring a double oven, 2 gorgeous islands with plenty of barstool seating, room for a full dining table, plus an abundance of storage and pantry space. There are 2 large separate living rooms with gorgeous wood flooring and a full bedroom on the first floor, which also makes a perfect office. Upstairs is the huge Primary bedroom and walk-in closet with its completely renovated (2023) en-suite bathroom with quartz countertops, a lovely step-in shower and another closet for additional storage. There are 2 more beautiful bedrooms with good sized closets, another full bright bathroom with double sinks, and a huge laundry room. This worry free home makes getting insurance a breeze with a brand new A/C (2024) complete new roof installation, Hardie Board siding, and an in-ground pool and spa (all in 2015), plus a full home security system with pool security alarms on all of the downstairs doors. This perfectly located home allows for walking to Maitland Community Park, riding bikes to the A-rated public schools, and driving minutes to downtown Maitland with its restaurants, shops and grocery stores. Don't miss your chance to live in this fabulous home and join this welcoming community. Schedule your private showing today!

1621 Chippewa Trail, Maitland

$267,500
2 Beds 2 Baths Sun Bay Club Condo SubDv. 32751 Zip Code
RARE and RENOVATED 2-BED / 2-BATH Condo in GATED SUNBAY CLUB! Fall in love with the secluded placement of this remodeled condominium with its own staircase leading to a dedicated entryway and double entry door. Upon entry, experience the immediate openness of the living space. Volume ceilings, two large transom windows, open floorplan adjoining the living room, dining room and kitchen make this the most functional floorplan in the entire community. <br><br> DINING/LIVING: Remodel includes granite countertops, hardwood cabinetry with crown detailing, an under-mount sink, built-in trash receptacle and large window make this cooking area a joy for every meal’s preparation. A dining room large window creates an eating space where every meal will feel like a five-star experience. A wood burning fireplace flanked by built-in shelving, and a sliding door leading to your large private balcony sets a mood you’ll love settling into every evening. <br><br> ENTIRE DWELLING: Owner’s suite shares access to the private balcony. Additional upgrades include two renovated bathrooms, upgraded storage in owner’s walk-in closet, gorgeous shower with glass door and glass block wall. The entire home has been freshly carpeted and painted in a neutral palette will perfectly compliment your own taste of décor and furnishing. Ample guest-bedroom with dual reach-in closet provides all the storage you’ll ever need! HVAC (2023), WATER HEATER (2017) provide peace of mind. <br><br> SUNBAY CLUB: This small enclave of 68 condominiums offers a uniquely private living experience. Behind the iconic blue gates, you will find a beautiful community enhanced with fountains, open grassy areas, a tennis court, lakefront swimming pool and a boat launch perfect for your paddleboard. Sunbay Club replaced all tile roofs, gutters/downspouts, skylights in 2024. CONDO FEE INCLUDES: CABLE & HIGH-SPEED INTERNET (Spectrum). Fee also covers: Gated Entry, Exterior Maintenance (building/roof), Common-Areas, Landscaping/Irrigation, Lighting/Ponds Maintenance, Pool/Clubhouse Upkeep, Master Insurance Policy (buildings). Combined, these community services reduce your ownership costs tremendously!!<br><br> LOCATION: Access within minutes World-Class “RDV Sportsplex” (Genesis HealthClub), Interstate-4 (Express), Publix, shopping & dining options. Downtown Maitland, Winter Park and Orlando are only a minutes away. Come see why this is the address you will want to call YOUR NEXT HOME !!

1000 Winderley Place Unit 237, Maitland

$1,200,000
4 Beds 4 Baths Stonehill SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. This meticulously maintained home in the desirable Stonehill community offers an exceptional layout with thoughtful upgrades throughout. The freshly painted exterior and recently replaced tile roof give it standout curb appeal. Inside, the grand foyer, with soaring ceilings, leads into a formal living room with French doors overlooking the sparkling screened-in pool and covered patio. To the left, the formal dining room showcases elegant coffered ceilings, while the adjacent kitchen is a chef’s dream—featuring custom-built cabinetry, stunning granite countertops, a Viking double oven, built-in Sub-Zero refrigerator with a cabinet-matching front, Miele built-in coffee maker, built-in microwave, cooktop with a pot filler, and even two additional refrigerator drawers for extra storage. The kitchen opens to a spacious dinette and family room with a wood-burning fireplace and additional French doors leading outside. On the main floor, the primary suite offers high ceilings, French doors opening to the back patio, and a spa-like bath with dual walk-in closets, two vanities, a large walk-in shower with dual showerheads, and ample storage. A versatile additional room on this level, complete with a closet, is located across from a fully renovated pool bath, making it perfect for a home office or guest space. The large laundry room, featuring built-in cabinets and a sink, sits just off the kitchen near the entrance to the two-car garage. Upstairs, a spacious bonus room with a huge storage closet provides extra living space. Two generously sized bedrooms share a Jack-and-Jill bathroom with double vanities and a tub/shower combo, while another well-sized bedroom and an additional full bath complete the upper level. Beautiful wood floors run throughout the home, complemented by high baseboards and crown molding for a polished look. Outside, the screened-in patio and sparkling pool with a water feature offer a private retreat, while the fenced backyard adds both security and privacy. Located between Maitland Ave and 17-92, this home provides easy access to top dining, shopping, and entertainment in Maitland and Winter Park. Major roads including I-4, 17-92, and SR 436 are just minutes away, and the nearby SunRail station makes commuting downtown a breeze. Call today for a private showing!

142 Stone Hill Drive, Maitland

$3,193,000
5 Beds 5 Baths Northshore Estates SubDv. 32751 Zip Code
Welcome to this charming stately lakefront estate, a true gem straight from the pages of Southern Living—just minutes from Winter Park and the finest dining in Maitland, all on the serene shores of Lake Sybelia. From the moment you arrive, the large, inviting porch with it's charming swing beckons you into a home flooded with natural light and warm wood floors and a thoughtfully designed layout. The heart of this home is the expansive kitchen, seamlessly flowing into the family room and offering French doors that lead to a picturesque backyard. The downstairs primary suite provides a luxurious retreat, featuring large walk-in closets and a beautifully remodeled bathroom with a soaking tub and dual vanities. A private guest suite is conveniently located off the family room, offering its own entrance and separation from the rest of the home. Upstairs, you'll discover three generously-sized secondary bedrooms, a dedicated theater room, a private study, and a spacious bonus room complete with custom built-ins—perfect for play, work, or relaxation. Move right in as this home has not only been freshly repainted but all bathrooms have been remodeled and refreshed. Step outside to your personal private oasis, with no rear neighbors, where a newly remodeled pool with a sun shelf, stunning decking, and fire bowls set the perfect ambiance for both relaxation and entertaining. The lush side yard enhances the home's charm, while the boat dock provides the perfect spot to watch breathtaking sunsets or enjoy water sports on Lake Sybelia. This exceptional property offers the perfect blend of comfort, style, and lakeside living. Don’t miss the opportunity to make it your own!

571 N Lake Sybelia Drive, Maitland

$660,000
4 Beds 2 Baths Stonewood First Add SubDv. 32751 Zip Code
*PRISTINE NEIGHBORHOOD*HUGE FENCED IN YARD*SPARKLING POOL*RECENTLY UPDATED: ALL WINDOWS & ROOF* Welcome to this beautiful 4 bedroom, 2 bathroom, 2-car garage pool home, situated on a spacious 0.30 acre lot in the delightful Stonewood Neighborhood. This thoughtfully renovated and redesigned ranch home is move in ready for you and your family to begin enjoying life in your new house! Step inside and be greeted by the warm and inviting custom built kitchen featuring Bosch stainless steel appliances, custom solid wood soft close cabinets, quartz countertops with beveled edges, apron front cast iron sink overlooking your back patio, counter to ceiling subway tiling, an oversized island with bar seating and abundant storage, a wine cooler, and a cabinet front Thermador refrigerator all creating a luxurious touch. Off of the kitchen is a formal dining room with a stunning statement chandelier and french doors which lead out to the covered back patio. This split floor plan provides a serene atmosphere and privacy with the primary suite off of the dining room and separate from the rest of the home. The primary suite overlooks the pool with a set of french doors for easy access, his and hers closets, and a freshly renovated ensuite bathroom with glass enclosed walk-in, rainfall shower, double vanity, and custom frosted windows to allow ample natural lighting and privacy. Off of the kitchen, on the other side of the house, enjoy the charming living room space with built in shelves and a wood burning cozy brick fireplace and wooden mantel. As you step off the living room, walk down the hall with the additional 3 bedrooms and an additional bathroom. Hickory hardwood flooring can be seen throughout the home offering a seamless flow with tile flooring in both bathrooms, and carpet in the three additional bedrooms. Top rated windows (2019) throughout and three sets of french doors leading to the pool, custom vinyl shutters throughout common areas, new roof (2023) and high end finishes make the home turn key and create a worry-free living. Step outside into your outdoor oasis. This spacious backyard is a rare find- situated on 0.30 acre lot! The spacious covered paved back patio space allows you to enjoy being outside no matter the weather and the solar heated saltwater pool will have you enjoying the pool all year long! The new board-on-board privacy fence provides privacy for your family and the spacious backyard offers endless opportunities for enjoyment and play. The mulched playset area is perfect for a growing family or could have grass added in that area to extend the yard even further. This home is located in close proximity to I4 for easy commutes and only minutes away from Maitland Ave/Blvd exchange. This is truly is a rare find and won't last long! Schedule a private showing today and make this dream home your forever home!

460 Forestwood Lane, Maitland