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206 Quayside Cir Unit 203, Maitland
$950,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code
This Winter Park Chain of Lakes condominium has been completely reimagined to the highest of standards with meticulous attention to detail, providing luxury living in the perfect Maitland location. The sale includes a highly desirable, dedicated boat slip, giving you access to the entire Winter Park Chain of Lakes for year-round enjoyment and unparalleled lake views. A corner unit, the property is filled with beautiful natural light, creating a bright, fresh ambiance against the quintessential Florida backdrop of sunshine. The home has been entirely reconstructed from the ground up, featuring updated electrical, plumbing, HVAC, windows, sheetrock, an on-demand water heater, a whole-home water filter, in-floor heating, flooring, paint, lighting, kitchen, and bathrooms. Every interior detail showcases bespoke craftsmanship, including authentic oak chevron floors, designer wall and trim treatments, handcrafted base and crown moldings, and a Level 5 sheetrock finish with sprayed matte paint. Elevating the modern aesthetic are a double-sided Dimplex fireplace, integrated Lutron lighting and shades, handcrafted HVAC vents, and built-in Samsung Frame TVs. The home also offers brilliant storage solutions, featuring a large hidden storage closet concealed behind the entryway mirror alongside integrated hallway doors for seamless HVAC and closet access. The gourmet kitchen flows openly into the gathering space with direct views of the lake, centering around a seated island and an intimate eat-in area perfect for dining or entertaining. Designed to be efficient, sleek, and integrated with the formal living spaces, it boasts a restaurant-quality induction cooktop and speed oven, custom cabinetry with real brass inlays and brass doors, a Brizo touch faucet with on-demand hot water, and an integrated Thermador refrigerator with touch-sensitive doors. The luxurious owner's retreat enjoys stunning water views, upgraded lighting, a fully organized walk-in closet, and the ambiance of the double-sided fireplace. The primary bathroom offers an indulgent, spa-like experience with book-matched porcelain marble slabs, a shower with body sprays, in-floor heating, and a heated towel warmer. Thoughtful conveniences include a private water closet with a Kohler Veil intelligent toilet and bidet, seamless marble finishes, and double sinks paired with oversized medicine cabinets for ample storage. Perfectly positioned in a premier Lake Maitland location, the property is just across the street from hours of scenic trails weaving around the lakes of Maitland and Winter Park. Exceptional dining and coffee options like Luke’s, Francesco’s, Antonio’s, and Starbucks are just steps away, alongside numerous other local restaurants and bars. Daily conveniences are effortless with Whole Foods, Trader Joe's, Publix, Target, Home Depot, and REI all within a five-minute drive, while the historic Enzian Theater is close by for the perfect movie night.

206 Quayside Cir Unit 203, Maitland

140 Windglow Trail, Maitland
$910,000
4 Beds ⋅ 3 Baths ⋅ Windgrove SubDv. ⋅ 32751 Zip Code
Virtually Staged. New to the market, this amazing 2 story 4 bedroom and 3 bath Maitland home has just finished a full remodel! This home has an open floor plan which features classic elegant design style synonymous with Quarter Circle TO designs. Walking into the home, you will immediately notice the elegance. The whole home features luxurious wood style flooring, custom brick, and accent walls. All bathrooms feature waterfall showerheads and glass doors with gold finishes. The spacious and decked out kitchen features: White shaker cabinets, Quartz countertops, an island with a waterfall quartz counter top, double oven, modern cook top with stylish custom designed hood, farmhouse sink, touch screen WIFI refrigerator, wine rack, and gold hardware throughout. The spacious living room/dining room is great for hosting formal dinner parties or informal movie nights. The second living room is perfect for entertaining with a sliding glass door to the back yard and the bistro with 2 wine coolers nearby. The back yard boasts an oversized patio and a fire pit, which is fully fenced for privacy. There is an additional living room and space for an office on the second floor. This home showcases a beautiful staircase with tempered glass railings, motion sensor LED lighting up the stairs, and a 6 tier crystal chandelier. The Primary Suite features a walk-in closet and spa-like bathroom, highlights a modern bath tub, luxury shower containing waterfall and body shower heads. The fourth bedroom has French doors and its own entry to the incredible backyard. Easy access to lakes, restaurants, and shopping nearby. This home contains features of a million dollar home at this amazing price. This is a must see!

140 Windglow Trail, Maitland

2141 Falkner Road, Maitland
$515,000
4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Discover the charm and convenience of Maitland living in this four-bedroom home featuring two full bathrooms and one half bathroom. A large, beautiful patio creates an inviting setting for outdoor dining, entertaining, or simply relaxing, while the fenced yard adds privacy and space to enjoy the outdoors. Newer roof, brand new flooring throughout. New Bathroom cabinetry. Interior and exterior new paint. Located at 2141 Falkner Road, this home offers the added convenience of I-4 just around the corner, making travel throughout Central Florida easy. Everyday essentials and local attractions are within approximately a seven-mile radius, including Publix at Gateway Crossing, nearby gas stations, and the restaurants and cafés of downtown Maitland’s Independence Lane and City Centre. Enjoy nearby Fennell Park, scenic Lake Lily Park, fitness and recreation at Genesis Orlando Sportsplex, and movies and dining at Enzian Theater and Eden Bar. AdventHealth Altamonte Springs also provides nearby access to hospital care. Sent from my iPhone

2141 Falkner Road, Maitland

1931 Michael Tiago Circle, Maitland
$445,000
3 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code
Welcome to this beautiful 3-bedroom, 2.5-bath townhome offering approximately 2,100 square feet of comfortable living space in the gated community of Maitland Village. The open floor plan features spacious living and dining areas with abundant natural light, creating an inviting setting for everyday living and entertaining. The kitchen flows seamlessly into the main living areas, while all three bedrooms are located upstairs for added privacy. The generous primary suite provides a relaxing retreat with an en-suite bathroom and ample closet space. Additional features include an interior laundry area, a private outdoor patio, and an attached two-car garage. Maitland Village offers gated access, a community pool, clubhouse, sidewalks, and beautifully maintained surroundings, also includes water, Cable & internet . Conveniently located near I-4, Maitland Center, Winter Park, Downtown Orlando, shopping, dining, and entertainment. Schedule your private showing and discover the space, convenience, and lifestyle this Maitland townhome has to offer!

1931 Michael Tiago Circle, Maitland

161 White Oak Circle, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ Maitland Grove SubDv. ⋅ 32751 Zip Code
Finally, a home for sale in the desirable Maitland Grove! Step through the front door into bright, open living spaces, thoughtfully redesigned in 2024 to connect the great room, dining area, and kitchen. At the heart of the home, an oversized waterfall quartz island anchors a beautifully renovated kitchen with custom cabinetry, abundant pantry storage, and updated appliances. Continue into the family room, where an electric fireplace and custom storage create a comfortable place to gather. The four-bedroom layout includes two primary suites and three full bathrooms, offering flexibility for guests or a home office. Waterproof laminate flooring carries through the home, while the Florida room adds another inviting space with a custom bar overlooking the backyard. Outside, enjoy a 60-foot lap pool and room to relax or entertain. Major improvements include a 2022 roof and whole-house repiping, along with copper electrical rewiring in 2024. near Lake Sybelia and Lake Catherine, the home offers easy access to downtown Maitland, Winter Park, and Orlando. There are many more upgrades throughout—ask for the detailed list of improvements. Schedule your private showing today!

161 White Oak Circle, Maitland

790 S Lake Sybelia Drive, Maitland
$950,000
3 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32751 Zip Code
A truly unique opportunity to own well over half an acre of ultra-private property, set far back from the road, with 12 feet of deeded Lake Sybelia frontage and access. This charming, updated, cottage-style home offers 3 bedrooms plus a den, 2.5 bathrooms, and plenty of separate flex space for entertaining, both inside and out. The family room is light and bright with skylights, terracotta-look tile floors, a beamed ceiling, a window seat, and brick mantle. The inviting kitchen features smoky blue cabinetry, a farm sink, new refrigerator, tile counters and floors, and opens to the dining room and a light-filled sitting room with built-in wet bar, wine storage, and accordion doors opening to the backyard. The adjacent Florida room has walls of windows overlooking the yard and a door leading to the backyard. The split-bedroom floor plan offers two bedrooms sharing an updated hall bath with tile floors, quartz counters, dual sinks, and multiple showerheads, including a rain shower. The separate primary suite, part of the 2001 addition, is spacious with three closets and French doors opening to a brick patio. The primary bath features a single-sink vanity, built-in cabinetry, and shower. An attached den with a half bath and closet provides flexible space for an office, nursery, or additional sitting area. Additional features include wood floors in all bedrooms, ceiling fans, plantation shutters, a water softener, and interior laundry. Recent updates include roof (2019), AC (2023), insulation (2025), electric panel (2024), hot water heater (2026), lighting, fixtures, a new electric fence, and more. A long private driveway leads to a large circular drive at the rear of the property. A detached shed has electricity and running water. The fully fenced backyard offers mature landscaping, in-ground irrigation, and ample space and flexibility for outdoor living, entertaining, RV or boat storage, or for future improvements, additions, or to create a custom new build. The property includes a deeded 12-foot-wide strip of Lake Sybelia frontage, providing usable lake access and potential for an EZ floating dock; see survey/attachment for details. Ideally located near the new Maitland Public Library, currently under construction and expected to open in 2027, as well as the Enzian Theater, Maitland Art & History Center, and Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Assigned schools include Lake Sybelia Elementary, Maitland Middle, and Edgewater High. Lot size is approximately 0.65 acres per public record, including the portion of the parcel extending into Lake Sybelia; approximately 0.58 acres is dry land. Buyer to verify all measurements, property boundaries and lake access.

790 S Lake Sybelia Drive, Maitland

2362 Sierra Lane, Maitland
$339,000
3 Beds ⋅ 2 Baths ⋅ Sierra Condo Ph 2 SubDv. ⋅ 32751 Zip Code
A Hidden Gem in Sierra Condominium Association! Welcome to this beautifully maintained 3-bedroom, 2-bathroom condo with a private attached one-car garage, tucked away on peaceful Sierra Lane. With only one entrance and exit, Sierra offers a quiet, secluded atmosphere shaded by a canopy of majestic mature trees. Professionally maintained landscaping surrounds the community, creating a welcoming and well-kept setting. Inside, the spacious open living area features vaulted ceilings, abundant natural light, and four large glass-paneled doors overlooking the private paver patio, covered pergola, and peaceful creek beyond. Beautiful wood flooring extends through the main living areas, hallway, and primary bedroom, while durable porcelain tile flooring complements the entry, kitchen, and both bathrooms. The inviting family room features a wood-burning fireplace and a large walk-in storage closet, providing both warmth and functionality. The kitchen offers solid wood cabinetry, quartz countertops, ample storage, and newer appliances, including the stove and microwave. Its open connection to the dining and living areas creates an ideal layout for everyday living and entertaining. The split-bedroom floor plan provides excellent privacy, with the spacious primary suite positioned separately from the additional bedrooms. The primary bathroom features wood cabinetry, quartz countertops, porcelain tile flooring, and a convenient walk-in shower with a secure handrail. The second full bathroom also features wood cabinetry, porcelain tile flooring, and a convenient walk-in shower, providing comfort and functionality throughout the home. The entire home was re-piped in October 2026 with a new water heater October 2026. The HVAC system was replaced in 2020 and routinely serviced, while the washer and dryer are conveniently located in the private attached garage. Step outside to your own tranquil retreat overlooking the creek. The covered pergola and paver patio create the perfect setting for morning coffee, outdoor dining, entertaining, or simply unwinding at the end of the day. Sierra residents enjoy access to a community swimming pool and tennis courts, while Spectrum cable and internet are included with the association fees. The community has also benefited from professionally maintained common areas, ongoing tree care, updated roofs, exterior painting, and recent street repaving—providing added convenience and peace of mind for residents. Location is another standout feature, with Sierra offering convenient access to major shopping, entertainment, and dining, including many popular restaurants and shopping destinations within walking distance. Major roadways such as SR 436 are also nearby, providing easy access to Orlando and surrounding communities while allowing residents to enjoy a peaceful residential atmosphere. Combining low-maintenance living, thoughtful updates, abundant storage, a private garage, desirable community amenities, walkable dining and shopping, and a serene creekside setting, this truly is a hidden gem you won't want to miss!

2362 Sierra Lane, Maitland

1711 Grove Street Unit 519, Maitland
$239,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Villas Condo SubDv. ⋅ 32751 Zip Code
Virtually Staged. Rare updated 2/2 | | Top-Rated Schools Welcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High. Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced throughout Remodeled Kitchen with updated cabinets, appliances, paint, and a cozy dinette space Fully Remodeled Bathrooms (2024) including a private primary en-suite Private Outdoor Space: Second bedroom opens via slider to a fenced yard & patio Convenience: Indoor laundry room with washer/dryer included, pull-down attic storage, and designated parking right out front. Community & Location: Enjoy a tranquil, well-maintained neighborhood with a community pool just steps away. Walk or bike to Lake Lily Park & Farmers Market, Downtown Maitland, Enzian Theater, and local dining. Minutes to SunRail, I-4, Winter Park Village, and Park Ave!

1711 Grove Street Unit 519, Maitland

1241 Manchester Road, Maitland
$549,000
4 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Seller concessions or a mortgage rate buy-down are available. An absolutely stunning one-story home, ready for immediate occupancy as a primary residence or as a rental investment. Welcome to 1241 Manchester Road, a beautifully renovated home nestled in the heart of English Estates, one of Maitland's most sought-after and established neighborhoods. This exceptional 4-bedroom, 2-bath residence seamlessly blends timeless charm with modern updates, offering the perfect balance of comfort, style, and functionality. From the moment you step inside, you'll appreciate the bright open-concept floor plan, thoughtfully designed to maximize natural light and create an effortless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The beautifully updated kitchen serves as the heart of the home, complemented by tastefully renovated bathrooms and a versatile flex room that can easily function as a home office, fitness room, playroom, or media space. Step outside to enjoy the lanai overlooking a backyard, offering endless possibilities for weekend gatherings, outdoor entertaining, or simply relaxing in the privacy of your own backyard. Perfectly positioned in a quiet, tree-lined neighborhood, this home offers the ideal combination of tranquility and convenience. Just minutes from Winter Park, Downtown Maitland, and Downtown Orlando, you'll enjoy quick access to I-4, US-17/92, SR-436 (Semoran Boulevard), Howell Branch Road, and SR-434, making commuting throughout Central Florida effortless. Everyday conveniences are just around the corner, including Publix, Trader Joe's, Whole Foods Market, Costco, Target, Winter Park Village, Altamonte Mall, and an impressive selection of local favorites and acclaimed restaurants. Whether you're looking for your forever home or simply want to enjoy one of Central Florida's most desirable locations, 1241 Manchester Road offers an exceptional opportunity to experience the very best of Maitland living. Schedule your private showing today and discover why homes in English Estates are always in high demand.

1241 Manchester Road, Maitland

2494 Castlewood Road, Maitland
$545,000
4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code
Virtually Staged. Owner welcomes all offers! Seller is motivated and open to considering all reasonable offers. Schedule your showing today! Welcome to 2494 Castlewood Road, a beautifully updated pool home situated on a spacious corner lot in one of Maitland's most established neighborhoods. This move-in-ready residence offers peace of mind with a newer roof, solar panels, updated HVAC, and extensive interior renovations throughout. Inside, you'll find an open and inviting floor plan featuring luxury vinyl flooring, updated bathrooms, modern fixtures, quartz countertops, and custom cabinetry. The spacious primary suite includes a walk-in closet and renovated en-suite bath, while the additional bedrooms provide flexibility for family, guests, or a home office. A large screened Florida room overlooks the backyard and creates the perfect space for year-round entertaining. Outside, enjoy the oversized swimming pool, expansive patio deck, fully fenced yard, and storage shed, offering plenty of room for recreation and outdoor living. Conveniently located just minutes from Downtown Maitland, Winter Park, Park Avenue, AdventHealth, shopping, dining, and major roadways including I-4, this home combines modern updates, energy-efficient features, and an exceptional location in the heart of Central Florida.

2494 Castlewood Road, Maitland

1404 Caring Court, Maitland
$619,500
3 Beds ⋅ 3 Baths ⋅ Enclave At Maitland A-F SubDv. ⋅ 32751 Zip Code
"NEW PRICE" ON THIS MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY" OF ENCLAVE AT MAITLAND, FL 32751. Nestled within the private gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury interior footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded with high-end finishes, the triple split-plan layout features separate Formal Dining & Family Rooms that maximize both entertaining and day-to-day privacy. Enter through a HUGE 21' Long Foyer into the Large Family Room which boasts a 14' High Tray Ceiling and the Centerpiece of the home. Just off the Family Room is the Formal Dining room, perfect for entertaining & family dinners. The Kitchen is perfectly designed for the Serious Chef, boasting Level 3, 42" Maple Cabinetry with Upper Crown Molding, Premium Granite, Center Island with a (3) Person Breakfast Bar, Stainless Appliance Package including Double Built-In Ovens, French Style Refrigerator, Flat-Top Range, Tons of Counter & Storage Space, Dual Stainless Sink, Custom Tile Backsplash, Pendant & Recessed Lighting, Closet Pantry and an adjoining Sunlit Dinette that provides the perfect spot for casual morning coffee. The Primary Suite is the Perfect Couples Retreat! The Bedroom is generous in size and will accommodate all of your oversized furniture & features a HUGE Tray Ceiling, Crown Molding, Laminate flooring, and Dual Walk-In Closets outfitted w/Custom Storage Organizers. The En-Suite Bathroom offers His-and-Her Maple Vanities w/Undermount Sinks, Granite Counters, Deep Garden Soaking Tub wrapped in Custom Tile, Large Walk-In Shower engineered with Dual Shower heads at opposite ends, Under-Cabinet Accent Lighting and a Glass Block Window for lots of natural lighting. On the opposite side of the residence, Two Additional Bedrooms share a beautifully appointed Full Bathroom, offering an ideal setup for Children & Guests. If you work from home or just looking for a quiet space, you'll enjoy the Private Office/Den located just off the Family Room. The Interior Laundry Room is highly functional and included Front-Load Washer & Dryer, Integrated Wash Tub/Sink & Upper Storage Cabinets. Your living space effortlessly expands outdoors through a Triple-Slider to the 12'x16' Covered Back Porch w/Premium Slate Tile flooring. Here, you can unwind against the peaceful backdrop of an unobstructed Lake View & Conservation Area. Additional Features: Prestigious Maitland Lifestyle, Low-Maintenance Luxury, Directly Across from the Pool, Block & Stucco, Barrell Tile Roof, Freshly Painted Inside & Out, High Ceilings Throughout, Carrier HVAC (2021), Vacuflo Central Vac System, GE Hybrid 50 Gal Water Heater (2016), Double-Paned Windows, 18x18 Tile Flooring Flowing Diagonally, Premium 8" Crown Molding, Elegant Custom Arches, Tray Ceilings, 8’ High Doors, Upgraded 6" Baseboards, Surround Sound Speaker & Prewire, Security System, Ceiling Fans/Light, Pre Plumbing for Summer Kitchen, Epoxy Coated Garage Floor and (2) Garage Door Openers, Custom Garage Storage, Paver Driveway, Beautiful Palms, Magnolias & Ivy, Private Mailbox, Irrigation System and more. Incredible location close to I-4, Downtown Maitland, Altamonte & Orlando, Shopping, Dining, Theme Parks, Turnpike, Beaches, all Central Florida has to offer. Call for more info or schedule a private showing. MOVE-IN READY PERFECTION! ***SOME PICTURES VIRTUALLY STAGED***

1404 Caring Court, Maitland

1776 Bobtail Drive, Maitland
$519,999
4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

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