Location: Maitland
Do Not Show Listings
1783 SUNNYSIDE DR, MAITLAND, FL 32751
$849,9009 Days on yellowkey MLS ID: O6420390
0 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2055 Built: 1986 Tax: $4,197 (2025)Community: Dixie TerraceSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,197
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
1750 POCAHONTAS PATH, MAITLAND, FL 32751
$599,000101 Days on yellowkey MLS ID: O6394358
REDUCED by $20,000 (3.2%) on 07/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1922 Built: 1957Monthly Fee: $17 Tax: $4,060 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$4,060
Remarks: Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brian Rotenberger (407-948-8478)
1404 CARING CT, MAITLAND, FL 32751
$639,00021 Days on yellowkey MLS ID: G5113516
REDUCED by $20,500 (3.1%) on 07/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2110 Built: 2005Monthly Fee: $285 Tax: $8,409 (2025)Community: Enclave At Maitland A-FSingle Family
Taxes:$8,409
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Remarks: "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!
Listing is courtesy of: ROCK SPRINGS REALTY, LLC (877-333-2811)
Listing Agent: Joel Bornstein (407-252-8092)
1511 GLASTONBERRY RD, MAITLAND, FL 32751
$549,00065 Days on yellowkey MLS ID: O6404282
REDUCED by $16,000 (2.8%) on 06/24/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2376 Built: 1969 Tax: $1,959 (2024)Community: NorthgateSingle Family
Taxes:$1,959
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include outdoor spa , updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Maydelin Munoz (407-485-4990)
726 FOREST GLEN CT, MAITLAND, FL 32751
$559,90011 Days on yellowkey MLS ID: O6420590
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1801 Built: 1973 Tax: $2,879 (2025)Community: Forest Brook 5Th SecSpa: NoSingle Family
Taxes:$2,879
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water heater, and French doors that open to a large backyard oasis. A bonus room with a mini split AC offers flexibility for an office or gym. Enjoy the private pool, patio, and proximity to top schools, shopping, and dining.
Listing is courtesy of: FLORIDA REALTY OF MIAMI CORP (305-598-5488)
Listing Agent: Janet Garay (786-355-7514)
823 WOODS COURT, MAITLAND, FL 32751
$950,0003 Days on yellowkey MLS ID: O6422384
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2145 Built: 1979 Tax: $7,742 (2025)Community: Dommerich WoodsSingle Family
Taxes:$7,742
Remarks: Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown molding, and an abundance of natural light. The versatile floor plan offers several inviting living spaces! At the front of the home, the formal living & dining rooms flow seamlessly into the beautifully updated kitchen, complete with a cozy breakfast nook, new cabinetry, quartz countertops, stainless steel appliances and an oversized breakfast bar overlooking bright family room. French doors open to the spectacular 28x11 sunroom with vaulted ceilings and a stunning wall of windows, providing breathtaking views of the manicured backyard, two private patios and the tranquil nature preserve- creating a peaceful retreat you'll enjoy year-round. The spacious primary suite features two closets and a generously sized en-suite bath with dual vanities and built-in storage. Two additional guest bedrooms and a large guest bathroom with built-in closets provide plenty of space for family and visitors. Additional updates and features include fresh interior paint, an inside laundry room, a two-car garage with new garage door, a new Trane HVAC system. new water heater. irrigation system with new well pump, & NO HOA! Excellent schools: Dommerich Elementary, Maitland Middle & Winter Park High! Residents enjoy access to the Dommerich boat ramp on Lake Minnehaha/Chain of Lakes, as well as a short stroll to the newly refurbished boardwalk leading to Maitland Community Park. This move-in ready home combines an exceptional location, thoughtful updates, and picturesque surroundings ...WELCOME HOME!
Listing Agent: Catherine D'Amico (407-252-3210)
200 MOSELEY AVE, MAITLAND, FL 32751
$410,00036 Days on yellowkey MLS ID: O6413652
0 Days Off yellowkey (back on 7/7/2026)
REDUCED by $10,000 (2.4%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 2026 Tax: $1,843 (2025)Community: Pindar SubSingle Family
Taxes:$1,843
Elementary School: Hungerford Elem
Remarks: Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind.
Listing is courtesy of: SYCHAR REALTY (407-921-0069)
Listing Agent: Brianna Grant (407-764-8436)
900 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,150,00010 Days on yellowkey MLS ID: O6420911
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3857 Built: 1999Monthly Fee: $395 Tax: $8,875 (2025)Community: Maitland Club RepSpa: NoSingle Family
Taxes:$8,875
Remarks: 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. 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.
Listing is courtesy of: ENGEL & VOLKERS ORLANDO DR PHILLIPS (407-905-6700)
Listing Agent: David Alderman (407-758-7358)
255 W GEORGE AVE, MAITLAND, FL 32751
$1,499,00027 Days on yellowkey MLS ID: O6415928
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4814 Built: 1957 Tax: $7,347 (2025)Community: Replat Blk B Poors AddSingle Family
Taxes:$7,347
Remarks: 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
755 WOODSIDE RD, MAITLAND, FL 32751
$925,00071 Days on yellowkey MLS ID: O6402797
REDUCED by $50,000 (5.1%) on 07/07/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3049 Built: 1974Monthly Fee: $8 Tax: $6,508 (2024)Community: Forest Brook 5Th SecSingle Family
Taxes:$6,508
Remarks: 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!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diane Heiken (407-920-4491)
1905 POINSETTA LN, MAITLAND, FL 32751
$499,00058 Days on yellowkey MLS ID: O6406934
0 Days Off yellowkey (back on 6/2/2026)
REDUCED by $11,900 (2.3%) on 06/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1864 Built: 1970 Tax: $3,353 (2025)Community: NorthgateSingle Family
Taxes:$3,353
Remarks: Under contract-accepting backup offers. Big vibes and even bigger possibilities! Say Hello to easy Florida living! This stylish 4-bedroom, 2-bath Maitland home delivers bright natural light, functional living spaces, and room for everyone to spread out. Whether you’re hosting game nights, working from home, or enjoying quiet mornings with coffee on the patio, this home checks all the boxes. A backyard perfect for entertaining and soaking up the sunshine! Prime location close to everything Central Florida has to offer! This one is ready to impress!
Listing is courtesy of: SYNCHRONICITY REAL ESTATE SOLUTIONS (407-617-2378)
Listing Agent: Michelle Terry (407-617-2378)
910 GAMEWELL AVE, MAITLAND, FL 32751
$645,00062 Days on yellowkey MLS ID: O6404438
0 Days Off yellowkey (back on 7/6/2026)
REDUCED by $10,000 (1.5%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2214 Built: 1964 Tax: $5,302 (2025)Community: Greenwood Gardens Sec 02 Rep 01Spa: YesSingle Family
Taxes:$5,302
Remarks: Under contract-accepting backup offers. Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of mind with a dedicated laundry room featuring a brand-new washer (2026) and newer dryer (2024). Major system updates have already been taken care of, including a new water heater (2025) and a recently installed HVAC system (April 2026), providing efficiency, reliability, and confidence from day one. Ideally located with close proximity to I-4 for easy commuting, and just a short walk to Maitland Community Park and Lake Lily, this home offers the perfect balance of convenience and lifestyle. A move-in-ready opportunity where the essential upgrades are already done for you.
Listing Agent: Sarah Tomlinson (407-721-7823)
541 MANOR RD, MAITLAND, FL 32751
$1,499,00049 Days on yellowkey MLS ID: O6406458
REDUCED by $100,000 (6.3%) on 06/25/2026
Bed: 5 Bath: 2.5 Liv Area Sq Ft: 3400 Built: 1956 Tax: $10,374 (2025)Community: Ravndals RepSingle Family
Taxes:$10,374
Remarks: Under contract-accepting backup offers. Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined California ranch blends modern design with effortless everyday living in one of Maitland’s most desirable locations. Completely remodeled in 2022, the home showcases a fresh, sophisticated aesthetic with thoughtfully curated finishes throughout. The light-filled interior offers seamless flow between living spaces, combining clean modern lines with warm, inviting character. The renovated kitchen features a brand-new range, oven, and microwave, creating a stylish and functional centerpiece for both entertaining and daily life. Custom closets throughout the home provide elevated organization and exceptional storage. In addition to the main living areas, a spacious bonus room offers incredible flexibility and can easily function as a second family room, home office, fitness studio, playroom, or media space to fit your lifestyle needs. Step outside to a private backyard retreat designed for entertaining, complete with a sparkling pool, expansive outdoor living space, and plenty of room for gatherings, dining, and relaxing under the Florida sunshine. The indoor-outdoor flow perfectly captures the essence of California-inspired living. Ideally positioned in a picturesque pocket of Maitland between two beautiful lakes, this home also benefits from zoning for top-rated schools while offering convenient access to dining, shopping, parks, and major roadways. A rare opportunity to enjoy modern California-inspired living in an exceptional location.
755 CRANES CT, MAITLAND, FL 32751
$1,395,500447 Days on yellowkey MLS ID: O6299581
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4566 Built: 2009Monthly Fee: $199 Tax: $10,895 (2024)Community: Lake Sybelia CoveSingle Family
Taxes:$10,895
Remarks: 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. The Saltwater pool has a brand new sparkling finish! 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 luxurious 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, 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, and endless possibilities to create a space that truly reflects your 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.
Listing Agent: Jo Ann Lamar (321-231-0052)
703 NICOMA TRAIL, MAITLAND, FL 32751
$735,00050 Days on yellowkey MLS ID: O6408335
REDUCED by $15,000 (2.0%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1842 Built: 1961 Tax: $4,767 (2025)Community: Dommerich HillsSpa: YesSingle Family
Taxes:$4,767
Remarks: Located in the sought-after Dommerich neighborhood, this pool home is just a short walk to top-rated Dommerich Elementary School 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 gas range, breakfast bar, and abundant gathering space. The home also features a wood-burning fireplace and indoor laundry room. Significant components have been updated and include the roof (4 years), HVAC (6 years), and water heater (less than 1 year), while the electrical and plumbing systems were updated in 2010 during the home’s cosmetic renovations. Outside, the large backyard is ready for summer with a pool, heated spa, and plenty of room to entertain. A welcoming covered front porch with pavers and tongue-and-groove ceiling adds to the home’s warmth and curb appeal.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
1065 GREGORY DR, MAITLAND, FL 32751
$519,00042 Days on yellowkey MLS ID: O6411336
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1929 Built: 1958 Tax: $5,684 (2025)Community: Druid Hills Estates 1St AddSingle Family
Taxes:$5,684
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cece Wong (407-809-1440)
1501 DRUID ISLE RD, MAITLAND, FL 32751
$799,900114 Days on yellowkey MLS ID: O6389520
REDUCED by $24,100 (2.9%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3000 Built: 1971 Tax: $11,716 (2025)Community: Druid IsleSingle Family
Taxes:$11,716
Remarks: Substantial price reduction for LAKESIDE LIVING in Maitland, Florida! LEASE OPTION CONSIDERED! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
499 JULIAN LN, MAITLAND, FL 32751
$455,00053 Days on yellowkey MLS ID: O6408583
REDUCED by $4,000 (0.9%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1596 Built: 1997Monthly Fee: $79 Tax: $2,495 (2025)Community: Brittany GardensSingle Family
Taxes:$2,495
Remarks: Location, Location, Location. Welcome to your new home in Maitland! This conviently located gated community home is a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The home benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The kitchen is a cook's paradise, complete with a natural gas range, a stunning accent backsplash that truly makes the room pop and new applicances. Enjoy the luxury of a generous walk-in closet in the primary bedroom, perfect for all your storage needs. The primary bathroom offers the convenience of double sinks, making morning routines smooth and efficient. The shower in the primary bathroom add an opulent touch to your personal spa-like retreat. Relax or entertain with ease with a patio for outdoor gatherings. The fenced-in backyard promises privacy for all your outdoor activities. The home benefits from a newer roof, new AC, new hot water tank, ensuring peace of mind for years to come. The appeal of the property is enhanced by fresh interior paint and fresh exterior paint to the entire home. The comfort features continue with new flooring throughout, ensuring all areas of the home are updated. Take advantage of this home's remarkable attributes and turn this dwelling place into your personal sanctuary. Some pictures virtually staged.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Charles Munk (407-417-7709)
140 E FAITH TER, MAITLAND, FL 32751
$500,000119 Days on yellowkey MLS ID: V4947849
REDUCED by $25,000 (4.8%) on 05/29/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2748 Built: 1956 Tax: $5,451 (2024)Community: Northwood HeightsSingle Family
Taxes:$5,451
Remarks: Virtually Staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite. Endless possibilities to maximize value and flexibility! The spacious single-level layout features 3 bedrooms, 2 bathrooms in the main house, plus an updated guest suite. Enjoy an open living and dining area with a stone fireplace, designer lighting, and luxury vinyl plank flooring. The upgraded kitchen includes wood cabinets, granite countertops, penny tile backsplash, and new stainless appliances. A bright family room leads to two outdoor seating areas, including a brick courtyard with a second fireplace. The oversized primary suite and additional bedrooms feature new plush carpet, while the bathrooms have been fully updated. The detached guest suite offers 1 bedroom, 1 bath, a sitting area, and a wet bar. Additional features include a washer and dryer, security cameras, and a Google/Nest doorbell, all conveying with the home. Double carport, oversized driveway, and a private lot on a quiet street. Conveniently located near downtown Maitland with easy access to I-4.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Greg Roberts, Llc (407-927-5303)
2494 CASTLEWOOD RD, MAITLAND, FL 32751
$570,00015 Days on yellowkey MLS ID: O6419597
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2482 Built: 1971 Tax: $3,375 (2025)Community: English WoodsSpa: NoSingle Family
Taxes:$3,375
Remarks: 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.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Neil Chetram (407-752-1597)
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