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$795,550
3 Beds 3 Baths Maitland Woods Third Add SubDv. 32751 Zip Code
Nestled beneath a canopy of majestic oak trees in the highly sought after Maitland Woods neighborhood, this beautifully updated 3 bedroom, 2.5 bathroom pool home sits on an expansive .45 acre homesite, offering timeless charm, thoughtful updates, and the lifestyle you've been searching for. From the moment you arrive, you'll appreciate the instant curb appeal of this classic brick ranch home, framed by mature landscaping and one of Maitland Woods' picturesque tree lined streets. Inside, you're welcomed by a spacious formal living room that sets the tone for the warm and inviting spaces beyond. The beautifully renovated kitchen serves as the heart of the home, featuring stylish finishes, generous workspace, and an effortless flow into the family room, where a stunning brick fireplace creates the perfect place to gather with family and friends. The spacious primary suite offers a peaceful retreat complete with a custom walk in closet and an updated ensuite bath. Two additional bedrooms provide comfortable accommodations for family, guests, or a home office.' Designed for year round Florida living, the expansive screened lanai overlooks your own private backyard oasis featuring a saltwater pool, newer pergola, outdoor shower, and an oversized fenced backyard with plenty of room to entertain, play, or simply relax beneath the shade of mature oaks. Recent improvements include a new HVAC system (2025), complete replumbing, and updated electrical, offering peace of mind for years to come. Life in Maitland Woods is about more than just the home. Enjoy evening walks around the spring fed waters of Lake Sybelia, where neighbors gather to take in beautiful sunsets beneath the oak canopy. Just minutes away, charming downtown Maitland offers local restaurants, community events, the weekly farmers market, and beloved traditions like Movies in the Park. With Orangewood Christian School within walking distance and easy access to downtown Maitland, downtown Orlando, shopping, dining, and major roadways, this location perfectly blends small town charm with everyday convenience. This is more than a home. This is the sign you've been looking for. It's an opportunity to enjoy the timeless character, community, and lifestyle that have made Maitland Woods one of Central Florida's most cherished neighborhoods.

211 Talmeda Trail, Maitland

$875,000
5 Beds 4 Baths Dommerich/Maitland Highlands SubDv. 32751 Zip Code
Located on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary and Maitland Middle schools. This home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in kitchen opens to the cozy family room anchored by the wood-burning fireplace. Expanded in 2008, the attached 900 sq ft in-law suite has a bedroom, living room, kitchenette and bath - ideal for an elderly parent or returning college grad. This flex space would also be ideal as an exercise room or home office. Primary bedroom has screened patio access and a walk-in closet. Three secondary bedrooms with access to two additional baths. Living areas have wood and tile flooring and the bedrooms have luxury vinyl plank. Out back is a sparkling screened pool overlooking the wooded back yard. Recent improvements include all new interior paint throughout (7/26) and roof ('22). Conveniently located near I-4, several parks, and excellent neighborhood restaurants. Charming library with books to share. No HOA. Welcome home!

2051 Dyan Way, Maitland

$549,000
4 Beds 2 Baths Forest Brook Sec 2-A SubDv. 32751 Zip Code
Virtually Staged. Welcome home to this spacious 4-bedroom, 2-bath pool home in Maitland. From the moment you arrive, you'll appreciate the attractive brick exterior and inviting curb appeal. Inside, a welcoming foyer is flanked by a large formal living room with parquet flooring and abundant natural light, while the formal dining room features classic wainscoting and connects directly to the updated kitchen. The kitchen offers granite countertops, wood cabinetry, stainless steel appliances, a breakfast bar, and overlooks the generous family room with French doors leading to the backyard. The split-bedroom floor plan provides plenty of privacy. Two spacious secondary bedrooms with engineered hardwood flooring are located on one side of the home and share a hall bath. The primary suite is tucked away on the opposite side and features engineered hardwood floors, a walk-in closet and an ensuite bath with a walk-in shower. A fourth bedroom is centrally located, making it an ideal guest room, nursery, or home office. Just off the kitchen, you'll also find a large laundry room with built-in cabinetry for extra storage and access to the oversized two-car garage, which offers additional storage space. Step outside to a fully fenced backyard with an updated vinyl fence, a large pool ready for your personal finishing touches, and plenty of yard space for entertaining, pets, or play. Whether you choose to resurface the pool right away or customize it over time, this backyard offers great potential to create your own private outdoor retreat. Conveniently located just off Howell Branch Road, you're only minutes from I-4, Downtown Maitland, Winter Park, shopping, dining, and everyday conveniences. Call today to schedule your private showing!

564 Brookside Circle, Maitland

$699,000
3 Beds 2 Baths Dommerich Estates 1st Add Maitland SubDv. 32751 Zip Code
**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland

$925,000
4 Beds 4 Baths Serendipity Park SubDv. 32751 Zip Code
Ideally located in the heart of Maitland & built by Clarkson Concepts in 2017, this custom contemporary home offers 2,672 SF of thoughtfully designed living space w/ four bedrooms, three full bathrooms & one half bath. A covered paver front porch welcomes you inside, where high ceilings, recessed LED lighting, wood-like tile flooring, custom ceiling accents & oversized windows create a light-filled, contemporary interior. The living, dining, and kitchen areas flow seamlessly together and extend to an expansive wall of sliding glass doors that opens to the newly screened lanai with a tongue-and-groove ceiling, creating an effortless indoor-outdoor lifestyle. Designed to be the heart of the home, the kitchen showcases a dramatic 12’ island w/ seating for four or more, extensive shaker-style cabinetry including soft-close doors & drawers, granite countertops, stainless steel appliances, a slide-in gas range w/ vent hood, an under-counter drawer microwave, under-mount sink accompanied by a commercial-style pull-down faucet & a separate wet bar. Privately located on the first floor & thoughtfully separated from the alternate bedrooms, the spacious primary suite offers a tray ceiling, a modern ceiling fan w/ an integrated light kit, dual walk-in closets & a spa-inspired bath w/ white shaker cabinetry, granite countertops, a freestanding soaking tub, a frameless glass-enclosed shower w/ dual shower heads & an expansive vanity w/ dual faucets. Also on the main level & conveniently located for guest use, is a stylish powder bath appointed w/ a gray shaker vanity, quartz countertop, designer accent wall, contemporary mirror & lighting. Completing the first floor is a functional laundry/mudroom w/ shelving for storage above the washer/dryer, an optional gas hookup & direct access to the attached 2-car garage w/ an epoxy floor finish & open nook for storage. Upstairs, a versatile loft provides flexible space for a media room, home office, fitness area, or playroom. Three additional bedrooms are located on the second level. One enjoys the privacy of an en-suite bath with a tub/shower combination, white shaker vanity, granite countertop & contemporary lighting, while the remaining two bedrooms share a hall bath finished in a similar style, equipped with a walk-in shower. Additional home highlights include two-zone HVAC systems, an on-demand gas water heater, motorized shades throughout the main living areas, modern ceiling fans with integrated light kits, a security system, pre-wiring for surround sound, MI energy-efficient windows, contemporary five-panel interior doors, concrete block construction on the first floor, dimensional shingle roofing accented by a standing-seam metal roof over the front entry, a paver driveway and walkways & a private irrigation well to help reduce irrigation costs. The fully fenced backyard offers expansive green space w/ ample room for a future pool. Located in Serendipity Park, the home is within walking distance of the citywide bike trail, pedestrian boardwalk, SunRail, Publix, the library, post office, parks, restaurants & the new Maitland City Centre. Zoned for Lake Sybelia Elementary, Maitland Middle & Edgewater High School, the location also provides convenient access to Winter Park, Orlando, I-4 & more. With no HOA, quality construction, efficient systems & an exceptional walkable location, this home offers a rare opportunity to enjoy contemporary living in one of Maitland’s most desirable neighborhoods.

632 Gamewell Avenue, Maitland

$259,000
3 Beds 3 Baths Park Lake Twnhs SubDv. 32751 Zip Code
Gorgeous 3-bedroom, 3-bath, two-story townhome available now! This move-in-ready home features an updated kitchen with all appliances included, a convenient mudroom with washer and dryer hookups, fresh interior paint, and luxury vinyl plank (LVP) flooring throughout. Each spacious bedroom offers its own private bathroom and walk-in closet, providing comfort and privacy for everyone. It offers a 1-car garage and private courtyard, with plenty of guest parking. Enjoy maintenance-free living with the HOA handling exterior maintenance and lawn care. Conveniently located near I-4, shopping, dining, and everyday amenities, this property is ideal as a primary residence, investment property, or family home. Schedule your private showing today!

916 Park Lake Circle Unit 34, Maitland

$834,900
3 Beds 2 Baths Dommerich Hills Second Add SubDv. 32751 Zip Code
Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty. The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and living room, while cool and durable tile flooring extends throughout the remaining living areas. The family room features a wood-burning stone fireplace. Just outside, a lakeside fire pit is perfect for relaxing with family and friends while taking in peaceful water views and sunsets. The 12-foot-deep lanai overlooks the screened swimming pool and the 120 feet of lake frontage. Across the water lies a protected nature preserve, providing a backdrop of trees and nature. Whether hosting holiday gatherings, celebrating special occasions, or enjoying quiet evenings at home, the layout provides flexibility and comfort. Imagine your own pineapple patch and fruit trees! You’ll have seasonal oranges, Key limes, plums, and kumquats. Whether you're enjoying your morning coffee overlooking the lake or spending evenings under the stars, the outdoor spaces invite you to slow down and savor every season. The original 1968 home was replaced with a new home in 1997, incorporating the updated building codes that required hurricane-resistance structures. The home was connected to the new City of Maitland sewer system in 2025. New water heater 2026. This is more than just a home; it's a lifestyle. Here, families have room to grow, creating lasting memories, and nature is always just outside the door. This home has an exceptional waterfront setting and is situated very close to the Maitland and Winter Park Chain of Lakes. With a bright and inviting interior, thoughtful features, and an outstanding location, with A-rated schools, this property offers a rare opportunity to enjoy peaceful lakeside living without sacrificing convenience.

2624 Tuscarora Trail, Maitland

$420,000
2 Beds 2 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
Welcome to Lake Maitland Terrace, where this beautifully renovated condominium offers a rare opportunity to enjoy Chain of Lakes living. Included with the property is a leased boat dock on the Winter Park Chain of Lakes, paid through 7/31/2027, with the lease transferable to the new owner and renewable. This stunning 2-bedroom, 1.5-bath residence features picturesque lake views from both bedrooms as well as the screened front porch. The screened-in front porch is the perfect place to relax while overlooking the expansive lakefront campus, complete with a sparkling pool, fishing dock, putting green, and shuffleboard courts. From the moment you step inside, you'll appreciate the exceptional quality of the modern renovation, thoughtfully designed with both style and function in mind. The beautifully updated kitchen is ideal for entertaining, featuring premium finishes, generous workspace, and a party-size ice maker. It flows seamlessly into the dining area, where abundant built-in storage provides both convenience and organization. The spacious primary suite serves as a private retreat, complete with a walk-in closet, an updated half bath, and tranquil lake views to wake up to each morning. Whether you're looking for a full-time residence or a weekend escape, this move-in-ready home offers an exceptional lifestyle in one of Winter Park's most desirable waterfront communities. This is a rare opportunity you won't want to miss.

1140 S Orlando Avenue Unit K15, Maitland

$1,150,000
5 Beds 4 Baths Maitland Club Rep SubDv. 32751 Zip Code
Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.

900 Brightwater Circle, Maitland

$570,000
4 Beds 2 Baths English Woods SubDv. 32751 Zip Code
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

$615,000
4 Beds 2 Baths Forest Brook 5th Sec SubDv. 32751 Zip Code
Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.

741 Brookside Road, Maitland

$419,900
2 Beds 2 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!

1140 S Orlando Avenue Unit H3, Maitland

$295,000
2 Beds 2 Baths Sun Bay Club Condo Ut 1 SubDv. 32751 Zip Code
Ground-floor 2BR/2BA in the gated, lake-access community of Sun Bay Club in Maitland, FL — updated and move-in ready! The kitchen was renovated in 2023 with new cabinets, quartz countertops, and updated appliances (microwave 2024, dishwasher 2025). Both bathrooms were updated in 2026: the primary with a new double-sink vanity, modern lighting, and a pocket door for privacy, and the hall bath with a new vanity, mirror, and lighting. Durable wood-look tile and wood flooring throughout — no carpet. This is a two-story building, which falls outside Florida's SIRS and milestone inspection requirements that apply to condos three stories and taller. The open-concept living space extends through sliding glass doors to an enclosed sunroom overlooking the pond, ideal as a home office or morning coffee spot, and each bedroom opens to its own private screened patio. The primary suite adds a walk-in closet with built-in shelving; the second bedroom offers double closets with built-in shelving as well. HOA fee includes cable/internet, lake access for boats and jet skis, a large lakefront pool, a tennis court, and all exterior maintenance, including the roof. Minutes to Maitland and Winter Park shopping and dining, and easy access to highway I-4. Great option for low maintenance living as a primary residence or an investment opportunity. Schedule a viewing today!

1000 Winderley Place Unit 141, Maitland

$638,900
3 Beds 3 Baths Enclave At Maitland A-F SubDv. 32751 Zip Code
"PRICE IMPROVEMENT" 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 highly sought-after & 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 and all Central Florida has to offer. Call today for more info or schedule a private showing. This is Move-In Ready Perfection!

1404 Caring Court, Maitland

$1,095,000
4 Beds 4 Baths Maitland Club Rep SubDv. 32751 Zip Code
This elegant Mediterranean-inspired one-story residence is in the gated community of Maitland Club overlooking a tranquil pond. A well maintained 4 bedroom, 4 bath Plus home office with recent updates that include a new roof, hot water heater, pool heater, and a re-pipe. The home features a soft neutral interior palette throughout with an elegant formal living room filled with natural light featuring soaring ceilings and a dramatic wall of arched windows and French doors overlooking the outdoor living area. The dining room and home office are just off the entry foyer. The home office offers a warm workspace with hard wood flooring, custom bookcases and cabinetry. This room could be a temporary guest room it features a closet and is adjacent to the pool bath. The kitchen offers generous workspaces with extensive cabinetry, solid surface countertops, a center island, and a breakfast bar overlooking the family room. The open concept includes a planning desk and a casual dining space overlooking the pool. The spacious family room is designed for comfortable everyday living and effortless entertaining, featuring high ceilings, recessed lighting, and a fireplace framed by custom built-in audio-visual cabinetry. An oversized primary suite with a dramatic tray ceiling and expansive sitting area creates a true retreat-like atmosphere with an en-suite attached that features a large double vanity with dressing table, a relaxing garden tub and a large walk-in shower. On the opposite side of the home find three generous sized guest rooms and two full baths, laundry and hall to three car garage. The sparkling pool with tiered entry steps is surrounded by an expansive covered patio offering multiple seating and dining areas, all overlooking a lovely pond. Roof, Garage Floor and Pool heater warranties are available upon request.

1911 Belford Court, Maitland

$1,499,000
5 Beds 4 Baths Replat Blk B Poors Add SubDv. 32751 Zip Code
A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

255 W George Avenue, Maitland

$231,000
3 Beds 2 Baths Park Lake Villas Condo SubDv. 32751 Zip Code
Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sought-after school districts, zoned for Dommerich Elementary and Maitland Middle School. This move-in-ready home features significant recent upgrades, including a brand-new roof (2024) , new HVAC system (2024), and new Electrical panel (2026), providing peace of mind and energy efficiency for years to come. Inside, you'll find a functional floor plan with spacious living and dining areas, generous bedrooms, and abundant natural light throughout. Step outside to your large, private, fully fenced back patio, ideal for entertaining, relaxing, or enjoying outdoor living. The patio offers direct access to the community pool, making it easy to enjoy Florida's year-round sunshine. Ideally located near shopping, dining, and major roadways, this home combines low-maintenance living with top-rated schools and outstanding community amenities.

1507 Grove Street, Maitland

$325,000
2 Beds 2 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.

1140 S Orlando Avenue Unit I14, Maitland

$700,000
3 Beds 2 Baths Dommerich Hills SubDv. 32751 Zip Code
Located in the sought after Dommerich neighborhood, this beautifully maintained pool home is just a short walk to Dommerich Elementary and Maitland Middle School. Hardwood floors and an open floor plan create an easy flow for everyday living and entertaining, centered around a spacious kitchen with a gas range, breakfast bar, and generous gathering space. Additional features include a wood burning fireplace and an indoor laundry room. Major updates provide peace of mind, including a roof replaced four years ago, a six year old HVAC system, a water heater less than one year old, updated electrical and plumbing completed during the 2010 renovation, and a whole house generator powered by a 500 gallon propane tank. Outside, enjoy a large backyard with a pool, heated spa, and plenty of room to entertain, while a welcoming covered front porch with pavers and a tongue and groove ceiling adds warmth and curb appeal.

703 Nicoma Trail, Maitland

$204,950
1 Beds 1 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
PRICE IMPROVEMENT! Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.

1140 S Orlando Avenue Unit E2, Maitland

$899,000
5 Beds 4 Baths Forest Brook SubDv. 32751 Zip Code
JUST REDUCED - Welcome to this meticulously updated, one-story masterpiece situated on a sprawling, professionally landscaped 1/3-acre lot. This 5-bedroom, 3.5-bath sanctuary plus bonus room seamlessly blends high-end design with modern efficiency. At the heart of the home lies an extra-large gourmet kitchen designed for the serious chef, featuring double ovens, dual microwaves, and two dishwashers. The culinary space flows effortlessly into an impressively large dining room, while the living room offers a cozy retreat centered around a classic wood-burning fireplace, perfect for crisp winter mornings. The interior has been refreshed with a brand-new neutral paint palette that complements the fully updated bathrooms and high-end finishes found throughout. Outside, the large fully fenced backyard serves as a private oasis, boasting a stunning pool and ample space for grand-scale entertaining. A massive storage shed, equivalent in size to a full garage bay, conveys with the property to provide incredible storage or workshop potential. This home offers ultimate peace of mind with significant mechanical upgrades, including a 2021 AC unit, 2019 water heater, 2013 roof, and a new pool pump, new interior doors throughout and new door hardware as well Also Plantation Shutters throughout. Sustainability meets savings with a solar panel system that slashes the electric bill to approximately $50 a month for this expansive home. Whether you are seeking a fabulous primary residence, vacation home or a high-performing investment property, that can also be rented as a short -term rental/Airbnb this is the home for you. Available furnished or unfurnished. Garage was converted to a bonus room and laundry with a ½ bath and a small second kitchen. It can easily be converted back to a garage. HUGE STORAGE SHED IN SIDE YARD EQUAL TO A ONE CAR GARAGE. Well water used for in ground sprinklers, a huge savings on your water bill. This rare find delivers the space, privacy, and modern luxury today’s buyers demand. Near everything including Whole Foods, Trader Joes, Great Winter Park- Park Ave Shopping, Dining and galleries.

614 Brookwood Lane, Maitland

$1,199,000
4 Beds 4 Baths Lake Sybelia Cove Ph 01 SubDv. 32751 Zip Code
Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing.

873 Cranes Court, Maitland

$495,000
4 Beds 2 Baths Forest Brook 3rd Sec SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Seller Motivated. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook" This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand Foyer, Formal Living and Dinng rooms, open family room, ideal for gatherings. A new updated Chef's Kitchen, complete with a gas range, beautiful Cherry cabinets, new appliances, and new Quartz countertops. The spacious Florida Room has a fun step up bar with pass through access to the kitchen. Perfect for entertaining and offers its own AC/Heater unit. Step outside to the large wrap around Deck. Tons of space for outdoor entertaining. No neighbors behind you, just tons of conservation space. Additional upgrades include Roof-2021, AC-2023-Fl Room, AC-2025, Gas Water Heater-2010, Kitchen appliances 2023, Electrical panel- 2024. This home is ideally located just minutes from Winter Park, Casselberry, Winter Springs, Easy access to shopping, dining, and major commuter routes. Start living your Best Life.

653 Green Meadow Avenue, Maitland

$629,000
5 Beds 2 Baths Forest Brook 3rd Sec SubDv. 32751 Zip Code
Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 5 bedrooms, and 2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and storage. It's a canvas for your culinary creations. Whether you're a passionate collector or a lover of occasional indulgence, the built-in wine cooler transforms ordinary moments into extraordinary ones. Beyond elegant glass doors, unveil an expansive living room that is sure to captivate. Bathed in natural light, this grand space invites relaxation, entertainment, and cherished family moments. With 5 well-appointed bedrooms, there's ample space for everyone. The split floor plan ensures privacy and convenience for all members of the household. The master bedroom is a sanctuary of sophistication and comfort. With its spacious design and thoughtful layout, it provides an inviting escape from the world outside. The en-suite bathroom complements the master suite with its lavish features, double vanities, and a spa-like shower - experience the touch of rainfall from above and immerse yourself in the lap of luxury with the ceiling-mounted shower head. A dedicated bonus room adds an extra layer of versatility, it's ideal for a home office, playroom, or creative studio, the space adapts to your unique needs. Don't miss the chance to call this fully renovated gem your own. With its spacious layout, and modern finishes.

2642 Brookside Court, Maitland

$925,000
3 Beds 3 Baths Forest Brook 5th Sec SubDv. 32751 Zip Code
NEWLY PRICED TO SELL, UNDER APPRAISED VALUE, DO NOT MISS THIS OPPORTUNITY!! SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and just minutes from Winter Park. Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car garage on a .31 ACRE LOT is effortless Florida living.**SOLAR PANELS-(Avg. utilities $40/MONTH) From the moment you arrive you will be impressed with the mature, manicured landscaping and architectural features that sets the tone for the quality you will find inside. The EXPANSIVE OPEN FLOOR PLAN draws you in with an effortless flow between living, dining, and entertaining spaces. SLEEK MODERN CABINETRY, MARBLE FLOORING and DESIGNER FIXTURES elevate every room. The chef-inspired kitchen features a LARGE CENTER ISLAND perfect for casual dining, meal prep or gathering with guests. A stylish PASS THROUG BAR connects seamlessly to the Florida Room making entertaining a breeze. The OVERSIZED PRIMARY SUITE is a true retreat with MARBLE FLOORING, an abundance of natural light and CUSTOM SLIDING GLASS DOORS leading to the expansive pool deck. The en-suite bathroom features FLOATING VANITIES, MARBLE FLOORING and a SEAMLESS GLASS ENCLOSED SHOWER and STAND ALONE TUB that continues the modern aesthetic that feels like a five star hotel everyday. Laundry with sink and overhead cabinets is centrally located near the kitchen and primary suite. The focal point of the family room is the stunning MARBLE FACED FIREPLACE. Two generously sized secondary bedrooms are located off the family room, sharing a beautiful bathroom featuring marble floors, floating dual sink vanity and walk-in shower-consistent with the finishes throughout. The Florida Room is where the fun truly begins. Currently set up as the ultimate entertainment space, this incredible space offers endless possibilities- playroom, game room, movie room or the perfect indoor/outdoor lounge for hosting family and friends.NEW OVERSIZED WINDOWS frame spectacular views of the pool, floods the space with natural light and seamlessly connect the indoors to the out. The THIRD FULL BATH located off the Florida Room serves as the POOL BATH with walk-in shower, Jacuzzi, floating vanity and premium finishes. This homes outdoor spaces provide something for everyone. The large, screened-in pool deck features a Tiki Bar and dedicated PROJECTOR SCREEN AREA (Screen & Tiki Bar CONVEY IN THE SALE) perfect for entertaining pool side.The side yard with artificial turf is clean, low maintenance, and pet friendly. A charming brick paver seating area creates as cozy spot to relax, unwind or let the pets roam freely. Enjoy the tranquility of this homes beautiful backyard. ADDITIONAL LIST OF UPGRADES: 2020 HARDSCAPE & LANDSCAPING, 2021 NEW WATER HEATER & POOL PUMP, 2024/2025 REPLACED LARGE AC AND DUCTWORK, AC PRIMARY SIDE UNIT, 2025 NEW FLORIDA ROOM WINDOWS, ADDED RID-O-RUST SYSTEM TO WELL FOR IRRIGATION, SCREENED IN POOL/DECK, SOLAR PANELS (to be paid off at closing) ADDED DRY BAR WITH UPPER AND LOWER CABINETS IN DINING AREA. Conveniently located minutes away from boutique shopping, acclaimed dining and vibrant entertainment of the beautiful city of Winter Park with easy access to Orlando and surrounding communities. This home won't last long. Call your Agent to schedule a showing today!

755 Woodside Road, Maitland

$169,900
2 Beds 1 Baths Visconti West SubDv. 32751 Zip Code
Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

1375 Lake Shadow Circle Unit 11203, Maitland

$190,000
2 Beds 2 Baths Visconti West SubDv. 32751 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland